sunset tours martha's vineyard

Sunset Sail Shared Tour

• We include a variety of sodas on all of our sails.
• We included bottled water on all of our sails.
• We include a nibbles plate with a variety of cheeses, fruits and charcuterie.
• If you choose to bring additional beverages, we have an ice chest on board to keep them cold.
• All guests of legal drinking age will receive a welcome Captain's cocktail served with their hors d'oeuvre plate. Additional alcohol is not included.
• Crew Gratuity is not included. The industry standard for sailing excursions is 15-25%
• 99 Water St, Vineyard Haven, MA 02568, USA We meet guests at the end of the wooden dinghy dock that is attached to the Steamship Ferry Dock. From the roundabout and facing the water, look for the black lamppost to the left of the Steamship ferry boarding dock. Walk towards the lamppost and down the small wooden dock to the end.
• Not wheelchair accessible
• Near public transportation
• Infants must sit on laps
• Confirmation will be received at time of booking
• Most travelers can participate
• This tour is for adults age 21+ (Or 16+ if traveling with a parent or guardian.)
• Not recommended for travelers with severe mobility issues. Climbing and walking on uneven surfaces is necessary to board the boat.
• Guests must be of legal drinking age to consume alcohol on board.
• This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
• This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund
• This tour/activity will have a maximum of 6 travelers
• All sales are final and incur 100% cancellation penalties.
• You'll start at 99 Water St 99 Water St, Vineyard Haven, MA 02568, USA We meet guests at the end of the wooden dinghy dock that is attached to the Steamship Ferry Dock. From the roundabout and facing the water, look for the black lamppost to the left of the Steamship ferry boarding dock. Walk towards the lamppost and down the small wooden dock to the end. See address & details
• Pass by East Chop Lighthouse West Chop Lighthouse Martha's Vineyard Vineyard Haven Marina
• You'll return to the starting point

• Trek813875 0 contributions 5.0 of 5 bubbles Fun in the Sun Captain Wendy and crew are fun and engaging. Great knowledge of the area. Beautiful boat. Exactly what we’d hoped it would be. Read more Written September 3, 2023
• dawnbY3818HP 0 contributions 5.0 of 5 bubbles We loved it! This was our second trip with Captain Wendy and it was even better than the last! The crew is so friendly, the views are spectacular and the music and vibes were amazing! We will continue to come back every year! Read more Written August 29, 2023
• Julia W 0 contributions 5.0 of 5 bubbles Personal Tour of the Harbor. Captain Wendy was a delight. She was very friendly and willing to share her love of sailing with our group. We enjoyed our sunset cruise very much. Read more Written September 20, 2022
• 22Patricia_Ann 0 contributions 5.0 of 5 bubbles Amazing sunset cruise! Great sunset cruise with an excellent captain! Captain Wendy is experienced, professional and friendly (plays great music) and provided us with an amazing sailing cruise! Would definitely join her again! Read more Written September 20, 2022
• J5029IJscotts 0 contributions 5.0 of 5 bubbles Captain Wendy u The last 10 minutes as we coasted in as the sun set over the harbor we’re magnificent. Wendy handled our group as a kind professional, knowing when to allow us some space and when to engage us. She let our 84 yo mother take the wheel and allowed us to raise the sails. She is so pleasant and accommodating. Read more Written September 16, 2022
• jamestV3232VD 0 contributions 5.0 of 5 bubbles Wonderful late summer sail! We sailed right out of Vineyard Harbor and caught a wonderful fresh wind. Sailed down towards Edgartown with lots of sights and landmarks along the way. Captain Wendy was most accommodating . She is so knowledgeable and handled the boat like it was nothing. We brought wine with us, so asked to sail a little more level and she kept us all dry. I would highly recommend sailing with her. Read more Written September 16, 2022
• Mcs1025 0 contributions 5.0 of 5 bubbles A perfect day on the perfect charter ! Thanks Captain Wendy for a great charter for me and my family this past week. We ended up with the perfect day on the perfect sailboat with the perfect captain ! You're the best! Thanks for making this first time sailing experience for my nieces memorable and fun ! See you next time ! Cheers ! Michele Read more Written September 11, 2022
• plm124 0 contributions 5.0 of 5 bubbles Captain Wendy is the Best! What a glorious way to spend our last day at Martha’s Vineyard! Captain Wendy took our family on a beautiful and relaxing 2-hour sail around the the island and although our two young grandchildren were a bit hesitant at first, by the time we returned to dock, they were ready to set sail again! Wendy was the greatest - we felt safe and in good hands - like sailing with a good friend! I highly and strongly recommend you set sail aboard Captain Wendy’s lovely ship - I plan on a longer sail on my next trip! Read more Written September 11, 2022
• jaykay50 0 contributions 5.0 of 5 bubbles Wonderful Sunset Sail Captain Wendy was great! Provided us with good information as we sailed to see a beautiful sunset. Very chill environment - perfect way to wrap up a great day. Read more Written September 4, 2022
• lindsaymA5121ZJ 0 contributions 5.0 of 5 bubbles Sailing with friends My girlfriends and I went to Martha’s Vineyard for our 45th birthday celebration and enjoyed the sail the vineyard excursion so much! Our captain and co-captain was an all female team and they were amazing! It’s a definite must if you are in the area. Read more Written August 30, 2022
• yaseminw2015 0 contributions 5.0 of 5 bubbles Stop Debating - Choose Sail the Vineyard! We had an excellent sail with Captain Wendy! I was overwhelmed by the various groups/charters offering sails on the Vineyard. Tripadvisor reviews, a call answered in real time by her, and the added bonus of supporting a female owned business landed us with Captain Wendy. She, her crew and her boat are all amazing! Our family of 5 was celebrating my husband's 50th birthday and the Sail The Vineyard team made sure it was extra special. We've been summer visitors for decades yet had never done a private sail. Perfect way to see Vineyard Haven Harbor - East Chop, West Chop and more! Captain Wendy had stories to share and even answered our random questions. We chose the 2 hour sail not knowing how we'd fare. Now we know to do longer. Can't wait to go again next season! Highly recommend Sail the Vineyard for a safe, personable, and extraordinary outing. No need to stress over the options - choose Captain Wendy! Read more Written August 28, 2022
• mykiyaas 0 contributions 5.0 of 5 bubbles Amazing time ! Had an amazing time with family and friends. Can’t wait to come back for another sailing experience! Read more Written August 21, 2022
• X43MAericm 0 contributions 5.0 of 5 bubbles Highly recommend Our family had a great time with Captain Wendy and Lana. Fantastic way to see Vineyard Haven. It was definitely one of the highlights of our trip! Read more Written August 18, 2022
• gabbyf248 0 contributions 5.0 of 5 bubbles Amazing! Must do! Captain Wendy and Lana are so awesome! The boat was such a cool experience and definitely big enough for 6 people. There’s a bathroom on the boat too! Definitely will be doing this every year. Read more Written August 16, 2022
• 892arianao 0 contributions 5.0 of 5 bubbles Amazing!! Absolutely amazing sunset with Captain Wendy!! Her and Lana were so helpful and welcoming, one of the best cruises here! 10/10 would recommend! Read more Written August 16, 2022

More to explore in Martha's Vineyard

Sunset Sail Shared Tour provided by Sail The Vineyard

Ranked #1 on TripAdvisor 4 years in a row PLUS: Traveler's Choice Award Recipient

(508) 493-8767

• New Excursions
• Vineyard Day Sails
• Special Events
• Off The Vineyard
• Photo Gallery
• The Vineyard
• Policies & FAQ
• News & Updates
• Job Opportunities

Sail With Us

"life is either a daring adventure or nothing".

 Helen Keller coined the phrase and we totally agree. At Sail The Vineyard, we take life on as a daring adventure and embrace all that means. We are a unique all-female crew, led by an adventurous, accomplished female captain who splits her time between Martha’s Vineyard and The Caribbean. Our captain is not only a US Coast Guard Master Mariner and Royal Yachting Association Yachtmaster, she is the only Certified instructor on Martha’s Vineyard, credentialed by the American Sailing Association. She takes great pride in mentoring sailors and particularly enjoys mentoring other female sailors.

The thrill of sailing aboard our sleek, fast classic sloop-rigged sailboat is the perfect adventure for your vacation to the Martha's Vineyard. Exploring the beauty & history of the Vineyard by sea is a special experience you won't forget.  The picturesque coastline of lighthouses, historic homes, and beautiful beaches are just a few of the beloved sights of the area. Embrace adventure yourself and feel the thrill of the wind in your hair, find your inner mermaid, and maybe learn the art and science of sailing.  

"The Sea, once it casts its spell, holds one in its net of wonder forever"

Let us show you the magic of the sea on one of our sailing excursions. Breathe in the salt air and find your inner mermaid!  Enjoy snacks or a picnic lunch while under way, listen to the ocean as it swooshes by and feel the wonder of the vessel as the wind fills the sails and carries you away.

To some, it's just water. For us, it's a place to regain sanity

We all need a little help regaining sanity now and then.  The constant pull of technology - cell phones, email, social media - often prevent us from living in the moment.  Unplug with us.  Unwind for a few hours or an afternoon and regain your sanity.

For Your Safety

We are fully compliant with all current regulations for charter boats and carry a maximum of 6 guests per the U.S. Coast Guard Code of Federal Regulations, Subchapter C. 

Traveler's Choice Award plus #1 on TripAdvisor 3 years In A

Guests love our captain no matter where she's sailing see what they're saying, join our mailing list.

Be the first to hear about upcoming course registration and special events.

Copyright © 2018 Sail The Vineyard - All Rights Reserved.

Ahoy, sailors!

Please make note of our new phone number:

508.493.8767

 Martha's  Vineyard

• Which ferry should I take to get to Martha's Vineyard? There are 5 ferries to get to Martha's Vineyard - depending on where you are traveling from and whether you are taking your car or not. Nantucket & Martha’s Vineyard High Speed & Car Ferry | The Steamship Authority - this is the most popular and the only ferry you can take your car on - although you WILL need a reservation - standby can take all day, (some days no standby), Thousands of people are traveling on this ferry - it is best to leave your car in the parking lot in Falmouth and walk on. PLEASE BE ADVISED THAT YOU CANNOT PARK IN WOODSHOLE WHERE THE FERRY IS.... they WILL tow you .... parking is located at two different spots - the closest is approx. 15 min away and they offer a free shuttle back and forth. For Martha's Vineyard Travelers While there is no dockside parking available at our Woods Hole terminal, there are several off-site lots in Falmouth. We encourage you to arrive an hour before your departure time, so you have the time you need to park your car and ride our free shuttle service to the terminal. For your convenience, all shuttle buses have bike racks, capable of accommodating two bikes during daylight hours. A bike shuttle bus is available every day throughout the summer season. Current/real-time parking lot information is readily available by logging onto our mobile website at SteamshipAuthority.com, by calling our parking information line at (508) 457-7275 (PARK) or tuning into 1610 AM on your radio. This ferry ride is 45 minutes to the Vineyard. Island Queen Ferry • Martha's Vineyard Ferry - Second most popular, especially for those staying closer to Falmouth and the parking lot is right next door... makes getting to and from the ferry much easier... The drawback - compared to the Steamship Authority is there are fewer trips available. The trip takes approximately 35 minutes and offers an enclosed lounge or outside decks for passengers to relax and enjoy the scenic views of Vineyard Sound. The ferry is located at 75 Falmouth Heights Rd, Falmouth, MA, 02540 Hy-Line Cruises: Nantucket and Martha's Vineyard High-Speed Ferries (hylinecruises.com) - This ferry is especially convenient for those staying in the lower cape area (Hyannis, Yarmouth, etc). This link is perfect for your many questions: FAQs | Hy-Line Cruises (hylinecruises.com) New York City | New Jersey | Martha's Vineyard Getaway By Seastreak Ferry -- THIS FERRY ALSO HAS YEARROUND SERVICE FROM NEW BEDFORD, MA Seastreak is a leader in revitalizing fast passenger ferry services in the New York metropolitan area. We proudly offer high-speed catamaran services to points in Manhattan, central New Jersey, Nantucket, Martha’s Vineyard, and more with a fleet of robust vessels. In addition to commuter services to and from Manhattan and New Jersey, we offer an array of special events, sightseeing cruises and tours, daytrips, and getaways year round. In addition to our New York operations, we operate a seasonal ferry service (May through October) between New Bedford, Massachusetts and the port of Oak Bluffs on Martha’s Vineyard. The Martha’s Vineyard division operates daily service utilizing two high-speed catamaran ferries with capacity of up to 149 passengers. Martha’s Vineyard Fast Ferry – Rhode Island Fast Ferry -- a High-Speed Ferry to Martha's Vineyard, operating between Quonset Point, RI and Oak Bluffs, MV Rhode Island Fast Ferry is a water transportation company that provides ferry services to Martha’s Vineyard and Block Island. The company operates the largest and most luxurious fast ferry to Martha’s Vineyard, which departs from Quonset Point in North Kingstown, Rhode Island. The ferry ride takes approximately 95 minutes and offers stunning views of Narragansett Bay and Vineyard Sound. The company also offers sightseeing cruises, offshore wind support, and lighthouse cruises.
• Can I park at the Steamship Authority? NO!!!! Please be advised that you CAN NOT park in Woodshole at the Steamship Authority.... You WILL be towed.... Please park in one of the Steamship Authority Parking Lots available and take the FREE shuttle to the ferry (and back) Click on this link for directions, phone number and info: Nantucket & Martha’s Vineyard High Speed & Car Ferry | The Steamship Authority 286 Palmer Ave - Google Maps
• What if the ferry is diverted to Vineyard Haven because of weather?? Do you pick us up in Vineyard Haven?? No..... All tours leave Oak Bluffs at 1 Seaview Ave If the ferry is diverted, we will know ahead of time and we will delay the tour until 11am... to give time to passengers to make their way to Oak Bluffs via the Martha's Vineyard Transit Authority, Uber, or Taxi It takes approx 10-15 minutes to get to Oak Bluffs (depending on traffic) We will be contacting reservations the night before for a pretrip check in.... we will also be keeping an eye on the weather for such delays or diversions. Thank you for your attention to this matter.
• If we would like to get back to other areas we already toured, what is the best way? Vineyard Transit Authority tip: if getting on and off more than once, buy an all day pass (approx $9), you will save $$$
• If the tour is canceled due to weather, is there a refund? Yes, a partial refund. We have a weather policy put in place to also protect ourselves... IF THE FERRIES ARE RUNNING, WE ARE RUNNING if the ferries are canceled due to the weather, and an alternative date cannot be made then a 50% refund will be made. If HomeGrown Tours cancels due to the weather a FULL refund will be made. example: it may be thundering and lightening and heavy down pours, but the ferry is running: we will not be touring due to the bad weather.... we will then refund fully! we keep a close eye on the weather daily and if bad weather is predicted, we stay in close contact with you to discuss what options you have. all refunds will be made on the 11th of each month
• What is your cancellation policy? 24 hour notice
• How many times do we get off the bus? We have 2 scheduled step offs for dining, restroom, shopping and sightseeing There is another stop we try to make as long as there is availability for parking.... a lil hole in the wall Native American bakery .... very small area, most times available - but alot of times no parking.... and cannot turn around - its always a luck of the draw! keep your fingers crossed.... :) We have several stops along the way to learn more in depth history and photo ops.
• How long are the step off stops and where?? The first step off stop is in Menemsha, Chilmark A quaint lil fishing village 15 minutes The second stop (could be, as described in the other faqs) at the Orange Peel Bakery in Aquinnah 10 minutes The Second (or third) stop is The Gay Head Clay Cliffs and Lighthouse in Aquinnah 30 minutes
• What type of vehicle do we tour in? And is Air Conditioned? We are the only tour company on Martha's Vineyard that has small shuttles Our cute lil shuttles offer a small group of 14 people There are huge windows which are great for sightseeing You can sit in comfy touring chairs without being cramped in small seats Ability to stand and walk around Our shuttles are definitely air conditioned
• What makes you different than the other tour companies? HomeGrown Tours is the only interactive tour company on Martha's Vineyard. HomeGrown Tours is the only Wheelchair Accessible Tour Company on Martha's Vineyard We are the only tour company mostly anywhere that offers a screen at the front of the bus that shows what certain sites looked like in the days or yore AND we have a new digital sound system that will surprise you at the local JAWS sites on tour. We are the only Wheelchair Accessible Tour company! (probably anywhere that I can find.) We have successfully helped make Martha's Vineyard a more accessible place to visit Please contact us to let us know in advance if you need a wheelchair lift - thank you for your attention to this matter. AND WE LOVE TO HAVE FUN..... we share a ton of history, personal stories and so many photos to help you see how we grew as an island and as a community. When you leave us, you will have learned something new and exciting... our stories will make you laugh or maybe cry, but that's what makes us unique and very family oriented.
• Are there private tours? Yes, we offer private tours for those that would rather not do a shared tour with others. We customize YOUR tour to what your desires are and what you would like to do most. Remember: our private tours are very laid back and relaxed. We also go where others don't go.... example: we will take you to the highest point on Martha's Vineyard - peaked hill - used to be a Laran station during the war to watch for boats and planes. Peaked Hill is 350 feet above sea level and overlooks all of Aquinnah.... It's a most beautiful spot.... or we take you on different roads to secret spots so fun to visit Most private tours are at least 4 hours and can be done at whatever time you choose, and we pick you up at your place of residence (hotel, private home, etc.) and drop you off where you choose.
• Do you do other things than just tours? Yes!! We have a clamming gig - clients dig for clams (quahogs) and learn about how to collect (dig)or (rake), keep and cook and eat (some raw) We take photos and videos for your own lil album of clamming fun Kids LOVE this gig We provide the permits and all equipment This event is primarily for those that are staying in residences with cooking facilities... Lets chat.... 7743278192 We do transportation for Weddings, Bachelor/ Bachelorette parties, Bar Crawls, Kids Summer outings, Beach parties and Scavenger hunts.
• Military Discount? Yes, we offer a military discount: You must provide an ID
• Do we a need a ticket to get on?? YES!!!!! you must provide a ticket whether its from your phone or you printed it out.... IF YOU DO NOT HAVE A TICKET, YOU CANNOT GET ON.... PLEASE BE AWARE OF THIS For those that cannot get the ticket printed or other trouble acquiring it, please contact us immediately and we will help you.

MOST POPULAR

This is the most popular tour to get an overall feeling of what MV is all about. Experience all the towns, rolling hills with ancient stone walls, beautiful vistas and breathtaking views. Fully narrated.  Please understand that besides our 24 hour cancelation policy, we also have a 50% weather policy to ensure our protection as well...  Thank you for your understanding ....

THE BUS TOUR  $65

Best Rated Martha's Vineyard Bus Tours And Sightseeing Packages

ULTIMATE JAWSOME JAWS TOUR

Sunset Tours

 HomeGrown Tours KidZ

Homegrown's

New  Mascot

SPECIALTY TOURS

Arranged by our team, romantic sunset, all island taster, here for the day, weekend excursion, august showdown.

HomeGrown Tours KidZ

   Sunshine Therapy

   farm to table,    hiking at the neck,    time with the animals,    historical curiosities,     fishing expedition.

HomeGrown Tours is the most unique tour company on Martha's Vineyard. Your tour is not only narrated by a 3rd generation Islander but it is also a hands on learning experience. I pass around items that relate to the Vineyard to get a feel of how we live here, I have a screen that shows what certain sites looked like in the 1800s, I offer cold bottled water and lite snacks and rain ponchos for those wet days. Our bus tours are fun, safe and full of history! Book privately and we go where other tours buses dont go. I treasure Martha's Vineyard and the history and beauty. Book a tour with us and make it the highlight of your vacation. Thank you for letting me show you where I live, you wont be disappointed.

NAUTI GIRL EXCURSIONS

Day and sunset cruises we have a nauti excursion that is perfect for everyone ​edgartown boat tours ~ captain angie fisher 15th generation islander and commercial fisherman.

PRIVATE  EDGARTOWN CRUISES & EXCURSIONS

ALL OF OUR EXCURSIONS ARE PRIVATE AND FULLY CUSTOMIZABLE 

ALL EXCURSIONS INCLUDE 

USCG LICENSED MASTER CAPTAIN

FULLY FUELED 24' BENNINGTON DOUBLE-DECKER PONTOON BOAT WITH BLUETOOTH STEREO

A COOLER STOCKED WITH ICE FOR YOUR USE (BYOB)

ICE COLD BOTTLED WATER

TOWELS FOR DAYTIME EXCURSIONS

BLANKETS FOR SUNSET EXCURSIONS

WATER TOYS & FLOATS

Whether you're looking for a short adventure or a full day of fun, we have something for everyone.

EXCURSIONS OFFERED

2 HOUR EXCURSION

4 HOUR EXCURSION

8 HOUR EXCURSION

SUNSET EXCURSION

SUCLUDED BEACH EXCURSION

Captain Angie Fisher

Captain Angie Fisher is a native of Martha's Vineyard. She comes from a long bloodline of Fishermen. Her ancestors were whalers on Martha's Vineyard in the 1800s and her family has never left.  She has lived in Edgartown her entire life. Edgartown is and forever will be her home. Growing up as a fisherman's daughter she spent most of her childhood in or on the water in Katama Bay, Sengekontacket Pond,  Edgartown Great Pond, and Cape Pouge.  Almost Everyday day in the summer her parents (Francis and Lori Fisher) would pack up the 1972 4x4 van and head to the beach. Grills, coolers, tables, horseshoes, Boogey boards, masks, and snorkels. Don't forget the Quahog rakes and baskets!  Every day was a beach party to her, while her father was clamming and quahogging she would swim out and "help" her dad looking for little necks with her feet. It was the best childhood she could ask for. She is her father's daughter! And Angie felt at a young age she wanted to work on the water. She has been a commercial fisherman in Edgartown for 20+ years, she also helped out on her father's oyster farm in Katama Bay for 3 years. For over a decade she has dreamed about owning her own charter business, doing leisure cruises/excursions in Edgartown but as a mother of 2, she couldn't find the time or the resources. Now that her children are practically adults she found the time and accomplished getting her USCG Masters (Captains) License and dove in! She is the true definition of an Island Nauti Girl!

   Wanted to say a huge Thank You for an Awesome charter a few weeks back. Angie is so friendly! I had a great time learning about MV from her. Her knowledge and experience on the water made the experience! Everything from private settings to comfy blankets and extra towels to information on oystering makes the her chapter one of a kind,  personal and top-notch! Can't wait to be able to do it again sometime soon!

Reviews .

I booked the Nauti Girl 8 hour excursion which ended with the sunset excursion for a girl's weekend! What a blast!! We will be back!!! She is the real deal! Her ease and professionalism at the helm speak to Angie’s deep experience. 

 I recently took this charter with Angie and a group of friends. It was amazing!!!! Meeting Captain Angie was like meeting an old friend. Angie flawlessly ran that boat with an ease like no other. Nothing but laughs and good times. Cannot wait to do it again! You rock Angie and Nauti Girl Excursions!

What an unforgettable excursion. Captain Angie flawlessly navigated the boat and made sure everyone was having a great time. We made memories that will last a lifetime! Will book again! THANK YOU CAPTAIN ANGIE!  

Feelin' nauti d ay and sunset cruises we have a nauti excursion that is perfect for everyone ​edgartown boat tours ~ captain angie fisher 15th generation islander and commercial fisherman.

• Skip to main content
• Skip to footer

Vineyard Square Hotel & Suites

4 Favorite Spots to Watch a Martha’s Vineyard Sunset

There’s no need to boost the saturation in these vacation snapshots — nature’s paintbrush gifts us sunsets that are nothing short of vibrant. You only have so long to enjoy the show, so if you have your heart set on catching this classic island photo op then you need to be in the right place at the right time. Whether that place is perched atop a lighthouse or out on the water, these Martha’s Vineyard sunset spots are guaranteed to set your sights ablaze on either side of the island.  

Four Ways to Set Your Sights on a Martha’s Vineyard Sunset

Menemsha Public Beach

Between a charming village vibe and unobstructed water views, Menemsha is easily the most favored haven for enjoying end-of-day colors between locals and visitors alike. Stop by Larsen’s Fish Market or Menemsha Fish Market to grab some succulent seafood to-go before you claim your front-row seat on the shoreline. No matter how many people begin to pack up, be sure to stick around after the sun sinks below the horizon. Trust us, this is when the most vivid colors show their cards and you won’t want to catch them from your rearview mirror.

Aquinnah Cliffs

An already Instagram-famous photo location by day, the red clay Aquinnah Cliffs are even more beautiful when a blue sky is swapped out for a multicolored one. For one fail-proof vantage point, head to the Aquinnah Cliffs Overlook for a full sunset viewing package of the water, cliffs, and lighthouse. If you happen to swing by on a Thursday evening, opt for an even better view overlooking the beach from within the Gay Head Lighthouse itself.

East Chop Lighthouse

If you can’t squeeze a trip to the Wild West (as far as the Vineyard is concerned), stick closer to our corner for equally pleasing Martha’s Vineyard sunset sightings. Pay a visit to our neighbor, Oak Bluffs, to watch the colorful gradient from the East Chop Lighthouse . Sunday evening visitors have the advantage of viewing the sky from the lighthouse interior, but the views are just as grand if you’re watching them surround the stoic structure.

By Water on Edgartown Harbor

To truly feel like you’re right in the center of the action, set sail on a sunset cruise with Plan Sea .  Bring aboard supper on-the-fly from your favorite Edgartown restaurant — this crew happily invites you to pack a snap and drink of your choosing. While you watch the purples, pinks, and oranges reflect off the water, the chatty cruise crew will drop fun facts and tales about the buildings and scenic views that the boat passes by.

Want to catch the sunset but only have five minutes? For Vineyard Square Hotel guests, it’s as easy as running up to our shared fourth-floor harbor view veranda for an exclusive viewing of the radiant sky set above Edgartown’s rooftops. Be sure to swing by the front desk for even more sunset spot secrets or to share your own discoveries. We never get sick of a good sunset photo on this island!

Related Articles

Plan a Visit to the Martha’s Vineyard Food and Wine Festival

Despite its small size, Martha’s Vineyard is home to an incredible food scene. Whether craving cheesy pizza or looking for the perfect place to grab lunch, there’s something for everyone and every meal. The region’s culinary scene is celebrated annually during the Martha’s Vineyard Food and Wine Festival (MVFW).  This is perhaps one of the […]

Where to Get the Best Pizza on Martha’s Vineyard Near Edgartown

When you plan a stay at Vineyard Square Hotel & Suites, there are two things you never have to worry about: being bored or going hungry. Our Edgartown hotel is close to countless adventures like exploring West Tisbury or going on guided tours. It’s also close to endless dining options, including some of the best […]

Explore Memorable Things to Do & See in West Tisbury

Planning a relaxing vacation doesn’t mean it has to be boring. Known for its laid-back atmosphere, Martha’s Vineyard is the best of both worlds. You can enjoy memorable adventures while also enjoying the slower pace of life. For anyone staying at Vineyard Square Hotel & Suites, there are things to do from sunrise to sunset. […]

Spend a Day at the Manuel F. Correllus State Forest

For anyone looking to escape the hustle and bustle of life for a little while, there’s no better destination than Martha’s Vineyard. This charming New England island is known for its laid-back atmosphere. However, that doesn’t mean your trip will be boring by any means. For anyone staying at Vineyard Square Hotel & Suites, it […]

See the Next Big Thing at a Martha’s Vineyard Film Festival

Sometimes, there’s nothing better than curling up and watching a movie. Take this pastime to the next level by planning your visit to a Martha’s Vineyard film festival. Each festival is unique, but they all have something in common. They showcase incredible talent both in front of and behind the camera. Anyone planning to visit […]

A Guide on How to Get to Martha’s Vineyard

If you’re looking for a vacation filled with charm and adventure, look no further than Martha’s Vineyard. The New England island is home to numerous charming towns, including Edgartown. Home to Vineyard Square Hotel & Suites, the seaport village has countless things to do and see. However, before you can enjoy all the fun, you […]

A Look at the History of Our Edgartown Hotel

Situated in the heart of downtown Edgartown rests Vineyard Square Hotel & Suites. Located close to charming shops and world-class restaurants, the charming Edgartown hotel is a top option for anyone looking to enjoy a relaxing Martha’s Vineyard getaway for a reason. In honor of our many years serving vacationers, we wanted to take a […]

Celebrate the Season | A Guide to Christmas in Edgartown

As temperatures continue to drop and fall settles in, many people start looking ahead and working on their holiday plans. For families trying to get away this year and make the season extra special, consider packing your bags and staying at Vineyard Square Hotel & Suites. Our charming boutique hotel is the perfect home base […]

• Give A Gift Certificate
• Privacy Policy
• Accessibility

Online bookings will be available starting April 1, 2024. But you can always buy your gift card now!

The Black Dog Tall Ships

Sailing charter on martha's vineyard, ma.

Choose your Sail!

• MOST POPULAR!
• Hour Glass 3 Hours
• User All Ages

Day or Sunset Sails

Scheduled regularly throughout the season, the Alabama sets sail from the Black Dog Wharf on three-hour long cruises. Join us onboard for an unforgettable afternoon or evening sail, help the crew in the raising of the sails, manning the wheel with the captain or just relaxing!

• Hour Glass 5 Hours

Edgartown Fireworks Cruise

Enjoy the fireworks in Edgartown, MA aboard the Schooner Alabama! The most sought after cruise of the season. Guests are shuttled out to the schooner on a harbor launch and treated to a sail in Edgartown Harbor and front row tickets to the fireworks while anchored near the lighthouse.

• Hour Glass 4 Hours

Oak Bluffs Fireworks Cruise

Board the schooner and enjoy a sunset sail aboard the Alabama as she transits from her mooring to the fireworks venue off of Oak Bluff’s village. After the sunset sail the Alabama will anchor in close proximity to the fireworks so that guests are treated to a fantastic vantage point.

• User Ages 13+

John Cruz Concert Cruise

Sail with us as we welcome back our friend singer / songwriter John Cruz!

The schooner Alabama is a living piece of America’s maritime history. Built in 1926 for the Mobile, Alabama Bar Pilots, she served until her retirement in 1966. Never fitted out as a sailing vessel by the Mobile Pilots, she was finally given this opportunity thirty years later when it was decided to put her back to work in 1994.

Visit The Black Dog Tavern

Full service, year-round waterfront dining in our legendary Tavern on Vineyard Haven Harbor.

Tie-up at The Black Dog Wharf

Services ranging from hourly tie-ups to long-term transient professional care and service.

Shop The Black Dog Brand

Out of one sailing Captain’s love for the sea, his island home, and of course, his dog, The Black Dog Brand was born.

See why our customers love sailing with us!

"Really awesome sail with a super cool captain and crew! The Alabama has a ton of character and she really made it an enjoyable experience :) Have a chowder at the inn with a beer and set sail!!!!!"

"My family had a wonderful time on the Alabama! The Captain and crew were so hospitable. We all helped hoist the sails and then enjoyed a beautiful relaxing sail. Do this while on the Vineyard, you won’t be disappointed!!"

"Spent a great afternoon on the water with Capt. Douglas and the crew- highly recommend! Can’t believe it took us this long to take advantage of this local gem!"

"Such a treat to get out on the Sound on a beautifully crafted Tall Ship for a fresh perspective of this special island! Knowledgeable & friendly crew engaged guests to the extent guests could choose."

"had a great outing on the Alabama with our family. it was rather windy but the crew handled it well — beautiful trip. we did byo which worked ni key. enjoyed nice conversations with the crew and with other guests. Recommend!"

sunset paddle board

Learn paddle.

Many of our guests are first time paddlers.  Our tours accommodate all levels of skill and ability.  We ask only that you bring your spirit of adventure and a healthy sense of humor.  Before each kayak tour there is an instructional session to familiarize you with your equipment and paddling techniques!

Spot Marine

Kayak tours.

Cost: $105 a person

Kayak glow tour, when: mon, wed, fri, sat where: little b ridge,ob time: starts at sunset length: 1.5 hours ages: min. 7 years old what: new this year join us at sunset to enjoy the water at dark. hop into your glass bottom kayak and take off for a paddle around the pond, where wildlife beneath the water will be visible from the glow of your li ghts bonus: solar powered tour.

Cost: $55 kids $75 adults

Sunset kayak tour, when:  mon, wed, fri, sat where: little bridge,ob time: changes length:  2 hours ages: any age what:  p addle out in the calm, colorful waters of dusk, enjoying the wildlife & beauty of the coast. land for a beach picnic as the sun sets  we use the moonlight to explore the pond on our return trip. good for all ages.

Cost: $45 kids $65 adults

2 hour kayak adventure, when: 7 days a week, where: little bridge,ob, time:  10am & 1pm, length: 2 hours, ages: any age, what:  paddle during the day in sengekontacket pond with our experienced tour guides common tour activities include wildlife sightings, oceanside kayaking, various games, and jumping off jaws bridge.

Sunrise tour

When: tuesday s where: little bridge,ob time: 45 min before sunrise length:  2  hours ages: min. 10 years old what: watch the sun’s reflection on the water’s glassy surface and the gentle ripples from your wake as the sun slowly rises over the water. breakfast and coffee provided.  this is chick’s favorite time on the water, owner recommended trip + private tour option.

Cost: $140 a person

Full day tours.

Our full day  Kayak Adventure is available  seven days a week  at 9 am .  Lunch picnic, and snacks provided, a true sea kayaking experience.  Departure locations based on wind & tides.  Full Day locations: Aquinnah loop around the cliffs, Edgartown to the Chappaquiddick ‘Gut’, one-way Tashmoo to Menemsha drift or East & West Chop day in the rip! 

Cost: $125 a person

Pedal .

The bike tour begins & ends in the center of Oak Bluffs town, making it easy to find! The tour pedals around many beautiful sites and will be determined based on the guide and group. Surrounded by water an d the sea air we park our bikes for a snack break on State Beach and fuel up for next adventure- a kayak tour! All equipment, guides and snack break included! Minimum party of 3.

Paddle board Tours

paddle board Glow Tour

When:   mon, wed, fri, sat where: little bridge,ob time: starts at sunset length: 1.5 hours ages: min. 7 years old what: new this year join us at sunset to enjoy the water at dark. hop into your glass bottom paddle board and take off for a paddle around the pond, where wildlife beneath the water will be visible from the glow of your lights   bonus: solar powered tour.

Cost: $55  kids $75 adults

Sunset paddle board tour, when:  mon, wed, fri, sat where: little bridge,ob time: changes length: 2 hours ages: any age what:  p addle out in the calm, colorful waters of dusk, enjoying the wildlife & beauty of the coast. raft up for a beach picnic as the sun sets  we use the moonlight to explore the pond on our return trip. good for all ages.

Cost: $55 for each paddler

Paddle board tour, time: 9am & 11am, length:  1.5 hours, what:   whether you have never been on a paddle board or you're a pro, we have a tour that will be perfect for you. our tour guides are on hand to give lessons, help people up, and maybe even push people over.

Cost: $40 for each paddler

Paddle board yoga, when: tuesday & sat(privates only) where: little bridge,ob time: 9am length:  1.5 hours ages: any age what:  our relaxing paddle board flow is the best way to start your morning. our instructor will be there to guide you through a peaceful flow on the water.

Paddle Board fitness

When:   thursday where: little bridge,ob time: 9am length:  1  hour ages: any age what:  whether you have never been on a paddle board or you're a pro, our paddle board fitness class is for you. our instructor will be ther e to guide you through stretching, paddling, and fun activities that get you moving, paddle board or kayak.

Cost: min $300

Private tour, when: 7 days a week where: little bridge,ob time: any time 5 am to 10pm length:  2 hours ages: any age what: day time kayak or paddle board tour, but private  set off with your own guide who will customize the tour to your groups interests paddle around the pond or head out into the ocean. spot wildlife along the way and relax while improving your paddle skills. $300 min..

When: TBD Where: little Bridge,OB Time: 7pm Length:  1.5 hours Ages: any age What: Paddle out to a protected cove and anchor down to the bottom for a soulful experience underneath the stars. Your guide will lead you in beginner yoga while the sun sets around you and the full moon rises. Regular and clear kayaks and SUPs available!

The 2024 Season is Available | Book Online NOW!

The Premier Boat Tours and Rentals in Martha’s Vineyard, & Cape Cod

Choose a category.

• Sunset Cruises
• Day Time Cruises

Bachelor/Bachelorette Cruises

Special events, cape cod to martha’s vineyard bachelorette party cruise.

All aboard the Party Ferry for a truly memorable event. Go from Falmouth Cape Cod and spend 2-3 hours having a blast aboard the boat cruising the beautiful shoreline of Woods Hole, stop in a secluded cove for a quick swim and on to Oak Bluffs to continue the party onshore. Return to Cape Cod.

• Globe Daytime cruise, sightsee, swim , Go somewhere - transport
• Users Bachelor / Bachelorette
• Info Bachelor/Bachelorette Cruises
• Hour Glass 5+ hours

Cruise Aboard Our Sea Adventure Charters

Are you searching for large boat cruises and memories to last a lifetime? Look no further than Plan Sea Adventure Charters ! Operating out of Cape Cod and Martha’s Vineyard , our 18-passenger boat rentals are available for tours, transport, and parties to and from Falmouth and Cotuit in Cape Cod &  Edgartown  and Oak Bluffs on Martha’s Vineyard . Ranging from 2 to 8 hours in length, our private cruise packages are offered in four categories:

• Special Event Cruises
• Bachelorette Party Cruises

Our boat cruises are perfect for family outings, bachelorette parties, team building, and chasing the sunset with your loved ones. Whether you’re looking to host group events or tour the local area more privately, our boat tours will leave you relaxed, inspired, and enticed to explore more of New England . Each vessel is safely chartered by Captains with U.S. Coast Guard Masters Licenses , while our professional staff ensures guests are comfortable and boats are maintained, clean, and running smoothly.

Climb aboard beautifully furnished, classic New England motor vessels for amazing coastal views and luxurious rides along Nantucket and Vineyard Sounds – featuring indoor and outdoor heated seating, a bathroom, and a wet bar. Open weekends, Friday through Monday, our cruises can be booked with a 48-hour booking notice. Grab your group and experience aquatic adventures today!

Cruise Aboard an Authentic New England Lobster Boat

Your Martha’s Vineyard and Cape Cod getaway offers a peaceful and relaxing respite from daily life. Complement your idyllic vacation with a private luxury boating experience aboard Plan Sea.

We provide unrivaled customer service and put your mind at ease by taking care of everything and offering flexible and customizable itineraries aboard our extraordinary vessel.

Whether you’re looking for a relaxing day on the water with a private boat charter in Cape Cod, or private trips to Martha’s Vineyard , trust Plan Sea to plan your perfect day at sea. Plan Sea is a 40-foot U.S. Coast Guard inspected motor vessel ( photos ). Our boat can take large groups of up to 18 passengers. She is a beautifully furnished, classic New England motor vessel with comfortable heated indoor and outdoor seating, a bathroom, and a wet bar. Our Captains are U.S. Coast Guard-licensed Masters.

Let our expert and professional staff create a memorable sea-faring experience , from Cape Cod to Martha’s Vineyard , with our private two to eight-hour cruises. Our Cape Cod boat tours leave you inspired, relaxed, and enticed to explore New England.

Make Plan Sea your Plan A!

Shannon Shipman

Bringing Joy to Your Home Through Art

Top 11 Places to Photograph at Sunrise and Sunset on Martha’s Vineyard

Contributor: john montes jr.

All Images Provided by John Montes Jr.

I met John on one of my excursions to the Vineyard and had the most delightful time shooting with him. John’s personality is bigger than life and he had me laughing the entire time we were together. He is such a talented photographer and an incredibly kind person who loves the New England Photography Community , and has some EPIC shots of sunrise and sunset on Martha’s Vineyard. John has shot probably every corner of Martha’s Vineyard so I asked him to give me his top 10 – John gave me 11! So be sure to check these beautiful locations out next time your visiting the Vineyard, and give John a follow on IG – @jmontesphotography !

1. Edgartown Harbor Light –

Without a doubt, Edgartown Harbor Light is the most photogenic lighthouse on Martha’s Vineyard.  This iconic lighthouse offers everything that a photographer could want. Sunrise and sunset from every angle with a ton of space, plus the added option of seriously good astro-photography.  It hosts a beautiful red light that looks outstanding in your nighttime photos. If you have a drone, the view is extra special.

2. South Beach –

South Beach is one of the more popular beaches on Martha’s Vineyard.  A public beach that offers free parking is a welcome spot on a resort island where most things aren’t so cheap.  When the weather is calm, the waves come up very smooth on the beach. If smooth water across the sand photos are your thing, this is THE go to spot on Martha’s Vineyard.  The waves come up very consistent and you can make magic with the camera. I think it’s important to note that the sunrise and sunset on South Beach occur between early October through mid March each year.  Outside of this timeframe the sunrise and sunset will occur over land, not on the water.

3. Lucy Vincent Beach –

This is really something you need to see sooner rather than later.  This amazing structure has seen terrible erosion over the last 5-6 years, and if we have a few more years of bad winter storms it will be gone.  If you are going to get one beach photo on Martha’s Vineyard, this is the one you want. You will hold a photo of an iconic structure that future generations will only know existed from pictures.

4. Moshup Beach –

I can’t say enough great things about this place.  If you are a beach scene fanatic, this is the only place on Martha’s Vineyard that you need to go, specifically for all the rocks!  You can get the most amazing sunset scenes at Moshup, it has scenery like no other place on island. You definitely can’t shy away from the clay cliffs.  It’s important to note that you will only get sunset shots here, and you can get them year round.

5. Menemsha –

Menemsha will always be one of the biggest names on Martha’s Vineyard.  I can’t tell you how many times I go there and drop in to see Stanley at the Menemsha Fish Market.  Stanley has the best chowder and lobster bisque. You eat there and then you jump over to the jetty for some of the best sunsets you will see on Martha’s Vineyard.  To see the sunset over the water on Menemsha, you need to drop in between April 15 th and September 1 st .

6. Great Rock Bight –

This is one of the best kept secrets on Martha’s Vineyard.  Most people don’t know about it, and most people don’t visit it. When you park, you have about a ¾ mile walk down to the ocean.  Please keep in mind that you have a major walk back to your car! This spot is not handicap friendly, it’s downhill all the way and a major uphill hike all the way back.  All that aside, the sunset view here is incredible. You can view this sunset onMartha’s Vineyard ALL YEAR LONG. You will lose some view early and later in the year, but the sun always sets over the water at Great Rock Bight.

7. West Chop –

I really love West Chop on Martha’s Vineyard.  This spot offers so much shooting it’s absolutely ridiculous.  Let’s start with the shooting months – You can get the sunset over the water from February 1 st through November 1 st .  Outside this range you won’t get a sunset over the water.  West Chop offers so many different views depending on where you are.  You can go high from the overlook or down low on the beach looking across the dock.  This is definitely a spot you can’t miss. I hope you can use some of these images for inspiration.

8. Sengekontacket Pond –

I think subconsciously this is probably my favorite spot to shoot on Martha’s Vineyard.  “Senge” is not a sunrise location to shoot, but it’s an incredible sunset location that offers more shots than you will know what to do with.  If you want a water sunset on Martha’s Vineyard, Sengekontacket offers ridiculous views, especially when the water is calm. The best reflections I get on MV are on Senge.  Your shots can span through Edgartown down to the Jaws Bridge, then all the way into Oak Bluffs. What an iconic spot.

9. Nashaquitsa Pond –

I have to believe this is the most underrated spot to shoot photos on all of Martha’s Vineyard.  This is a really quick view as you cross a bridge through Chilmark. 99% of the people drive right on through. The other 1% see this absolutely incredible view, and the smart ones take out their camera.  Some of my best photos have occurred here and you will only get them in the summer months. You need to shoot for April 1 st through October 1 st for the best photos across the magic spot.  If we narrow it down make it 07/01-09/01.

10. Vineyard Haven Harbor –

I love this spot so much.   There are several spots to shoot for VH: Eastville Point Beach is one of the more popular spots that is accessible to everyone and free.  Other spots along Beach Road are not free, but they offer some good stuff. 

11. Lambert’s Cove Beach –

I have gotten beautiful sunset photos at Lambert’s Cove.  Don’t go there for sunrise, there are no water views. There is somewhat of a walk to get to the beach, but you will find that it’s absolutely worth it.  If you can play the tides right or if the water is warm enough, you can cross the inlet to James’ Pond and go further down the beach for some even more unique views for your sunset on Martha’s Vineyard.  Note – In the summer months the parking is “resident only” until 6pm. Lucky for you the sunset in the summer isn’t until 8pm. The parking lot is fairly small so if you can have someone drop you off that would be best as it’s very crowded in the summer.  The views for sunset across the water are available year round.

Pin For Later

Check out these blog posts

Leave a reply cancel reply.

Your email address will not be published. Required fields are marked *

Notify me of follow-up comments by email.

Notify me of new posts by email.

take a look at the

Travel guides.

the Newsletter

Keep up to date with the latest print releases, photography tips, and travel guides.

• Small Business Resources
• Core Values 1.
• Shop My Prints 2.
• New England 3.
• Contact Me 6.

@shannon.m.shipman

• Privacy Overview
• Strictly Necessary Cookies

This website uses cookies so that we can provide you with the best user experience possible. Cookie information is stored in your browser and performs functions such as recognising you when you return to our website and helping our team to understand which sections of the website you find most interesting and useful.

Strictly Necessary Cookie should be enabled at all times so that we can save your preferences for cookie settings.

If you disable this cookie, we will not be able to save your preferences. This means that every time you visit this website you will need to enable or disable cookies again.

• Transportation

508-654-0381

Tripadvisor's #1 MARTHA'S VINEYARD TOURS 2016 thru 2024 $55 Group Tours

 The Perfect sightseeing tours to see Martha's Vineyard!

Photo Gallery

Martha's vineyard tours and excursions, join us.

Powered by GoDaddy

Martha's Vineyard, MA

Top 10 Martha’s Vineyard Sunsets

A Martha’s Vineyard vacation is a bucket-list item that provides a host of exceptional experiences, be they sailing, kayaking, farm-to-table food, hiking, art events, film festivals or celebrity spotting. But one of our favourites is the stunning sunsets that are visible here from land and sea. A perfect way to end a perfect day on this magical New England island.

So that begs the question of where to head to get the best sunset!

• Menemsha Hills or Cedar Tree Neck Take one of these lovely and simple hikes out to the overlook or beach and watch the sunset away from the crowds.
• West Chop Drive out past the lighthouse and rub shoulders with the old money of the Vineyard out on pretty West Chop in Vineyard Haven. The sun sets out over the Elizabeth Islands.

Safe Travels, Simon

Availability

Adults (18+) 1 2

Kids (16+) 0 1

Check Availability

• Girlfriends Getaway
• Romance Package
• No Car & Go Green – Martha’s Vineyard Eco Package

Get Directions

5 things to do on Martha’s Vineyard

S even miles off the coast of Massachusetts is an island full of unspoiled landscape and plenty of fun, according to Carol Ward, information specialist for the Martha’s Vineyard Chamber of Commerce.

A New York Times best-selling author shares her favorite Martha’s Vineyard spots

Martha’s Vineyard, with 124 miles of coastline across six towns — Aquinnah, Chilmark, Edgartown, Oak Bluffs, Vineyard Haven, and West Tisbury — is a vacation destination with a year-round population of about 23,000 that balloons to 200,000 during the summer months, according to the chamber.

The Massachusetts escape has been called one of the most magical island getaways in the U.S. by Country Living and served as a backdrop for New York Times best-selling author E. Lockhart’s books. Boston.com readers recently named Edgartown the most picturesque small town in Massachusetts .

“It is a really, very, very unique place,” Ward said. “It’s a beautiful place on a very human scale that allows you to really connect with what you are seeing and what you are doing.”

The island’s diversity means visitors of all ages and interests can customize a day of fun, Ward said, by choosing from activities such as historic sites, shopping, dining, beaches, hiking, biking, museums, art galleries, farms, lighthouses, following the African American Heritage Trail , and more.

Whether strolling down island through bustling Oak Bluffs or visiting the unspoiled landscape up island at places such as the famous Aquinnah Cliffs , there’s a “sense of timelessness” on the island, Ward said.

“It’s just magic,” she said.

Ward offered the following tips for what to see and do during a day trip to Martha’s Vineyard this season.

1. Head to the Gingerbread Cottages

A neighborhood full of 19th-century “Gingerbread Cottages” is as well-known as the island’s beaches and lighthouses. The 318 pastel-colored homes are located at the  Martha’s Vineyard Camp Meeting Association , a National Historic Landmark.

“It’s lovely,” Ward said about the famous neighborhood.

The Tabernacle , located on the grounds, is the largest covered outdoor performance space on the island and hosts a sunset concert series in the summer. The cottages are privately owned, so visitors must stay on the public pathways.

“They do have a little museum that’s open in July and August where you can see what the inside of the cottages look like,” Ward said.

Summer visitors can also take guided walking tours of the neighborhood on Tuesdays and Thursdays during the months of July and August, and private tours are available by appointment.

2. Head to the beach

“Because we are an island, you are never very far from the beach ,” Ward said.

The island offers many beaches, some public and others reserved for residents and town visitors with a parking or beach permit.

Joseph Sylvia State Beach in Oak Bluffs, which runs along the eastern side of the island facing Nantucket Sound, is great for families due to its “gentle child-friendly waves,” according to Ward.

Katama Beach , also called South Beach, in Edgartown offers three miles of barrier beach on the south shore. The public beach is one of the island’s most popular ocean-facing beaches, Ward said, and vehicles with permits are allowed on marked trails.

For a more remote experience, Ward recommends heading to Menemsha Public Beach in Chilmark or Lobsterville Beach in Aquinnah.

Menemsha Public Beach, next to Menemsha Harbor, is popular for its sunsets, Ward said (author E. Lockhart called them “ magical “). Lobsterville Beach in Aquinnah offers two miles of Vineyard Sound beach and dunes and is a favorite fishing spot.

3. Explore a museum and view art

There are several fantastic museums on the island, according to Ward.

Martha’s Vineyard Museum in Vineyard Haven, just a 10-minute walk from the ferry terminal, houses more than 100,000 items, and current exhibits include “Unfreedom: Stories of enslavement, indenture, and incarceration on Martha’s Vineyard” and “Jaws: Creating Amity Island.” The movie “Jaws” was, of course, filmed on the island in 1974.

“It is very comprehensive,” Ward said about the museum. “It has a little area for kids and it really gives an overview of the island and how it has evolved over the years.”

The Carnegie Heritage Center in Edgartown is “a wonderful little gem of a museum,” Ward said. The restored landmark includes reading rooms, a gift shop, a library, and a revolving exhibition called “Living Landmarks.” Visitors can learn the history of the Wampanoag people at the Aquinnah Cultural Center .

Travelers can also walk through an outdoor sculpture garden in West Tisbury at The Field Gallery , Ward said, which features contemporary art by both emerging and established artists.

4. Enjoy dinner with a view

There are so many fabulous restaurants across the island, Ward said, and some serve up incredible waterfront views.

The Lookout Tavern in Oak Bluffs is a waterfront restaurant with a festive atmosphere and good food, Ward said. The restaurant, which does not take reservations, serves seafood, burgers, and sushi. It has a raw bar, too.

“It just puts you in that vacation frame of mind,” she said.

Bettini at the Harbor View Hotel on Edgartown Harbor and across from the Edgartown Lighthouse serves American cuisine with an “island farm-and-sea-to-table philosophy,” according to its website.

“It is an excellent place for dinner and has an excellent view,” Ward said.

The Dunes , a restaurant at Winnetu Oceanside Resort in Edgartown, recently named among the best family-friendly resorts in the U.S. by Tripadvisor, is also well worth dining at, Ward said.

“They have a wonderful deck,” Ward said. “The view is stunning. The grounds are stunning. The food is delicious. It’s really very special.”

During the summer months, guests can arrive at the restaurant via water taxi from downtown Edgartown.

5. Check out a farm — or a farmers market

A lot of Martha’s Vineyard is rural and the island’s many farms are great places to check out, Ward said.

Grey Barn & Farm is a certified organic farm, creamery, and bakery in Chilmark, which was established in 2009 and offers tours followed by cheese tastings in the garden.

“They have the most extraordinary cheese that they make in-house,” Ward said.

Another excellent island farm is Morning Glory Farm in Edgartown, Ward said, a family farm established in 1975 that grows 60 acres of vegetables and fruits and offers a farm stand and bakery.

“They do a great job with their baked goods and other things that they produce,” she said.

The West Tisbury Farmers Market , which has been feeding islanders since 1974, is open from June to October on Wednesdays and Saturdays from 9 a.m. to noon.

“That’s definitely something worth checking out,” Ward said.

Getting there

Travelers can get to Martha’s Vineyard by ferry or by plane.

“There’s something very magical about a ferry trip,” Ward said. “It is certainly part of the experience.”

Visitors can take the Steamship Authority , which is a year-round ferry service that also carries cars, or seasonal ferry service out of Hyannis, Falmouth, and New Bedford.

Once there, guests can take advantage of an all-island bus system that generates from Vineyard Haven, Ward said.

“You can take buses to other parts of the island, which is wonderful if you are here for a day trip and don’t have a vehicle,” she said. “You can easily pick up a bus to Oak Bluffs and Edgartown and West Tisbury, and from those points you can continue on to other parts of the island such as Aquinnah and Menemsha.”

Guests can also rent cars and bicycles for the day, and use a ride share service.

Reader recommendations:

Food and beverages:

Back Door Donuts — @kimaustinpowers

Larsen’s Fish Market — @noahvanschalkwyk

Nomans — @kerryemooney , @billykeane96

West Tisbury Farmers Market — @whattheheckner

Activities:

Aquinnah Cliffs — @bostown66 , @mandygrayy , @12numberkejoote

Beaches — @melissam.driscoll

Bicycling — @suzsen , @chrism051901 , @pallavikolambkar , @amacattack12

Edgartown shopping — @shophappy

Gay Head Lighthouse — @metal_head_ralfi_ralf

Lucy Vincent Beach — @cryandancebeast

Oak Bluffs — @addisonprimm

Old Sculpin Gallery — @sydcaroline

South Beach — @kbry2000 , @colleen_williams

Yoga on the Vine — @sydcaroline

Need weekend plans?

The best things to do around the city, delivered to your inbox.

The post 5 things to do on Martha’s Vineyard appeared first on Boston.com .

• News & Sports
• Home & Garden
• Eat & Drink
• Things to Do
• Classifieds
• Real Estate
• Subscriptions FAQs

The strange afterlife of Christopher Gray

"My Dead Dad," a documentary about a Vineyard man’s odd return, screens on-Island in July.

Mike Creato of Classic Aviators has led bird’s eye tours of the Vineyard from his cherry red, open cockpit bi-planes at Katama Airfield for more than 20 summers.

Most passengers sign up for tranquil sightseeing over fields and beaches. Those willing to pay extra endure barrel rolls, free falls, and other aerial stunts one might consider death defying. 

One sunny afternoon last June, Creato himself came face-to-face with death when a woman showed up with a complete human skeleton as her plus-one.

Olivia Gray Konrath, a Chicago resident who spends summers on the Vineyard, wanted Creato to fly her and the carefully mounted, fully articulated skeleton of her father, Christopher Gray, around the island. 

“We strapped them in,” Creato recalled, “and she handled her dad’s skeleton, pretty much. He didn’t fall out, luckily.”

“We expected it to be just the strangest thing ever,” Creato says, “and that Olivia would be a certified nut. But actually she was very nice. Aside from traveling with her dad’s skeleton, she couldn’t have been more normal.”

Mrs. Gray Konrath had flown on Creato’s flights before, but this was her first time with her father — an architectural historian and longtime summer resident of Vineyard Haven who died in 2017 — dead or alive.

“He always wanted to go with me on the biplane,” she said in a telephone interview. “And I was a teenager, and I thought I was too cool, and I never went with him.”

Their flight together was only part of a strange, arguably morbid, journey for Mrs. Gray Konrath and her father’s skeleton last summer. 

She took the skeleton to his favorite haunts in Washington, where they posed for pictures at the Lincoln Memorial, and in New York City, where they posed at the Manhattan Bridge. They then drove to Woods Hole in a van and boarded the ferry. 

They spent three days with a film crew on the Island. In addition to the flight, she took her dad’s remains out kayaking, and perched him in chairs in their backyard and on the beach. Her two young children, born after he died, were able to meet their grandfather’s skeleton. Photos show it seated in a place of honor at a crowded family dinner table.

She finally dropped him off at a boarding school in New Hampshire, his chosen final resting place.

A tall, rumpled, garrulous figure, Christopher Gray wrote the popular Streetscapes column each Sunday in the New York Times from 1987 to 2014. Each column was a quirky rumination on the city’s little known buildings and byways, usually enlivened with mordant humor. 

He and his wife, Erin Drake Gray, spent summers at Pond House, off Lambert’s Cove Road, with their children Peter and Olivia.

He was “always pretty open about his own mortality,” and what he wanted after he died, Mrs. Gray Konrath recalled. 

He once asked his family to consider putting him to rest with a Viking-style funeral pyre on the Mississippi River. 

In 2017, Gray told his family that he had decided he wanted his skeleton to be cleaned, mounted and displayed at St. Paul’s School, the college prep boarding school he had attended decades earlier in Concord, N.H. 

“It was so common for him to talk about stuff like this,” she said. “‘Alright dad, pass the butter.'”

“You never think that your parents are going to die, right?” she added.

Mrs. Gray Konrath later discovered that her father had donated $25,000 to St. Paul’s, and had offered to double the amount if they displayed his skeleton for ten years, or until it was stolen by the senior class.

Six weeks later, her father fell ill with complications from pneumonia, and was admitted to palliative care. He was 66 when he died. 

The family knew they wanted to honor his last wish, although they knew almost nothing about turning his remains into a display-quality skeleton. In her father’s last days, his daughter couldn’t help but laugh.

“I found myself in that moment sitting there watching my favorite person in the world die, while simultaneously having to start going down these weird rabbit holes of Google to try to figure out this last wish for him, and laughing to myself about it while crying,” she recalled. “I thought to myself, this just feels like a movie. And I don’t make movies.”

Her thoughts of a film – and early steps to fulfill her father’s wishes – would soon be delayed by another tragedy. A year and a half later, her mother Erin passed away from cancer.

Mrs. Gray Konrath says that after her parents’ deaths, she combined her grieving as best as she could with trying to fulfill her father’s dying wish. 

This meant calls to research facilities that study decomposition and assemble human skeletons. She finally made an arrangement with the Smithsonian Institution in Washington and a facility known as a body farm at the University of Tennessee, which had agreed to help since the skeleton would be used for educational purposes at St. Paul’s.

It took six months of natural decomposition at the body farm to produce a brown-stained skeleton. One year later, the bones were transported to and logged at the Smithsonian. 

In 2020, the family was told that the skeleton was finally being assembled in an anthropologist’s basement.

“It was another sort of reminder to me of, ‘Hey, this is the film. I need to make a film about this,” Mrs. Gray Konrath said. 

Obtaining her father’s skeleton is where “My Dead Dad,” her documentary about her father’s death wish and and her own decision to take his bones on a final journey, begins. 

She quickly decided she wanted to spend time with her dad’s skeleton before dropping it off at school, she said. 

“‘You know what, I’m not just going to pick up this skeleton and deliver it straight-shot from D.C. to New Hampshire,'” she recalled thinking. “‘I need to make stops along the way.'”

Her road trip pitch made some family members uncomfortable, including her brother Peter, who appears in scenes in New York City. Mrs. Gray Konrath said she understands their concerns, but she did what she felt was right. 

“I’ve learned in my grief that you need to lean into whatever feels right, because grief is [bad] enough, you know?,” she said. 

Taking his remains back to the Vineyard was especially bittersweet. 

“The Island has always been my favorite place in the entire world,” she said. “Since my parents have died I’ve always felt very close to [them], especially on the Island.”

“It is a feeling of home whenever I get off the ferry and drive down our long dirt road to the house. I kind of … feel [my father] in the trees almost, as the leaves are rustling in the wind.”

Her final journey with her father also led to an unexpected surprise at the Lambert’s Cove house.

When she was a young girl, she says, her parents set out the remaining pieces of a china set so she and her brother could entertain themselves by throwing rocks at it.

“I remember that to the point that every time I walk over that part of my driveway,” she said. “I instinctively look down at the ground to see if I see any blue and white china pieces… I never see anything.” 

“And while I was on the Island for… filming with the skeleton, I was walking to the beach and I looked down. And there were three big pieces of blue and white china.”  

She said her parents’ deaths have led her toward personal growth, because she has been able to honor them in her own life. 

“I’ve always struggled with my own confidence and believing in myself to follow through on something,” she said. “And my dad always wanted me to believe in myself and my capabilities.”

“There’s something to be said for losing the two most important people in my life and becoming a mother after that happens,” she added.  “There is a motivation there that I want to show my children that I will do anything for my family, and also that if they have a dream, they can do it.”

Since her parents’ deaths, Mrs. Gray Konrath has become a death doula, a non-medical professional who provides emotional, physical and educational support for someone nearing death. She hopes her film can help make death and grief easier on families.

“If someone sees the film or hears my story, my biggest goal would be to inspire you … to feel less alone in your grief,” she said.

“My Dead Dad” shows for free at the Martha’s Vineyard Film Center on July 21 at 4 pm, and Mrs. Gray Konrath will appear for a Q&A session afterwards. The film was made with filmmaker Erik Osterholm (“Anthony Bourdain: Parts Unknown”), her former colleagu e at Plum TV on the Vineyard.

Mrs. Gray Konrath documented her road trip on Instagram at the account @deaddaddytrip.

RELATED ARTICLES MORE FROM AUTHOR

SSA bracing for summertime crew shortage

Student newspaper takes top awards

Tisbury School exploring Portuguese program

Strangely morbid and yet enticing story. Maybe there is “life after death”. I loved it. Think of all the things not accomplished on ones bucket list that might well be done “later”.

LEAVE A REPLY Cancel reply

Save my name, email, and website in this browser for the next time I comment.

Latest Posts

Marilyn fish, deurward l. hughes, popular categories.

• Community 9987
• Letters to the Editor 5625
• Arts & Entertainment 4444
• Sports 4007
• Obituaries 3902
• Things to Do 2327
• Town Columns 1792
• Community Notes 1557
• Eat & Drink 1469
• Opinion 1459
• Visual Arts 1360
• Chilmark 733
• Editorial 726
• West Tisbury 714
• Oak Bluffs 709
• Privacy Policy
• User Agreement