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Explore Portland with a REAL local!

Portland, maine's #1 city & lighthouses historical tour.

Welcome to The Real Portland Tour!

Hop aboard for a fun and authentic Historical Sightseeing Tour of Portland, Maine and 3 lighthouses with a guide who is a REAL local, born and raised right here in Portland! Let me take you for an insider’s look at the rich history and current happenings of this charming and highly acclaimed city. We’ll go where other tours go, and then I'll take you places other tours don't - you'll see hidden gems and learn little known facts about Portland and the great state of Maine that only a REAL local knows! 

The Real Portland Tour is the only tour of Portland that includes a full city historical tour and a trip to 3 lighthouses! I've been a tour guide since 2001, and I'm also a college librarian. I've spent years researching the hidden history of Portland, and I take pride in being the most informative, entertaining, and experienced guide in town! 

The Real Portland Tour has been featured in American Libraries magazine, named the #1 Thing to Do in Portland, Maine by The Abundant Traveler , and is the top rated City & Lighthouses Tour of Portland on TripAdvisor and Viator!

"Been to Portland 100 times...never knew most of the info shared. This guy needs his own tv show."

The real portland tour named the #1 thing to do in portland, me by the abundant traveler.

Check out the video !

The Real Portland Tour is featured in American Libraries magazine!

Read "The Man with a Van" here !

The Real Portland Tour Portland, Maine Spoken Word Poem/Rap recently published!

I'm honored to say my Real Portland Tour spoken word poem/rap about Portland, Maine history was published in the Longfellow Days Anthology titled "Read To Me Some Poem" 

Over 99% 5-Star Reviews on TripAdvisor & Viator!

The real deal..

I've been giving tours of my hometown of Portland, Maine for over 20 years, and in the offseason I'm a librarian at Southern Maine Community College. I have a Master's degree in Library Science, and I'm always digging into Portland’s history to find something new and interesting, while at the same time keeping on top of current happenings and making sure to visit as many local establishments (especially our world class restaurants and bars) that I can. I take pride in representing this city, and providing an authentic tour delivered with a true Mainer's sense of humor! 

In addition to being a tour guide, I am a featured poet for the annual Longfellow Days festival where I perform my Portland history spoken word poem/rap (you'll hear some of my rap on the tour)!

I've given more than 10,000 tours over the years to hundreds of thousands of people from across the country and the world. It has been an absolute honor to tell so many people the unique history of my hometown! I'm thankful every day to be able to do what I love to do. I hope to see you soon!

 *Tour length is approximately 1 hour and 45 minutes. Most tours sell out in advance, so make sure to book ahead of time directly on my website.

"Derek was a wealth of knowledge! So much personality! A driving/talking teaching/rapping librarian"

Important booking notice.

  *I strongly recommend booking directly on my website. Booking directly on my website brings you to FareHarbor, which is my preferred booking processor. Bookings processed via FareHarbor have full refunds for cancellations made up to 24 hours before your tour time.

If you decide to book on a different 3rd party site such as TripAdvisor, Viator, Groupon, etc, you are subject to their terms, conditions, and refund policies which may differ from FareHarbor.

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Copyright © 2018 The Real Portland Tour - All Rights Reserved.                                                              

96 Commercial St, Portland, ME 207-329-7401

THE 10 BEST Portland Sightseeing Tours

Sightseeing tours in portland.

• Historical & Heritage Tours
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• Cultural Tours
• Walking Tours
• Beer Tastings & Tours
• Archaeology Tours
• Private Tours
• Wine Tours & Tastings
• Ports of Call Tours
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• Up to 1 hour
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• 4 hours to 1 day
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• The ranking of tours, activities, and experiences available on Tripadvisor is determined by several factors including the revenue generated by Tripadvisor from these bookings, the frequency of user clicks, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.

1. The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

2. Portland Tall Ship Cruise on Casco Bay

3. Central Coastal Maine Private Day Tour

4. Lighthouse Lovers Cruise in Portland

5. Sunset Lighthouse Harbor Cruise from Portland's Old Port

6. Maine Whale Watching Tour in Portland

7. Acadia National Park and More Private Day Trip from Portland

8. Seven Portland Lighthouses Tour

9. Private Lighthouse Sightseeing Charter on a Vintage Lobster Boat

10. Guided RIB Boat Adventure of Casco Bay

11. Audio Guided Walking Tour from Old Port of Portland, Maine

12. Ultimate Portland Self-Guided Driving GPS Audio Tour

13. Portland Bicycle Tour with 5 Lighthouse Stops and XL Lobster Roll

14. Self-Guided Driving & Walking Bundle of Portland Maine Tours

15. Private Sunset Charter on a Vintage Lobster Boat

16. Private Day Tour to Salem MA, Kennebunkport, Kittery

17. Peek at Portland Sightseeing Trolley Tour

18. New Hampshire White Mountains Autumn Foliage Tour from Portland

19. Half Day Private Boat Charter from Portland

20. Southern Coastal Maine (York, Ogunquit) Private Day Tour

21. New England Fall Foliage Private Lobster Boat Cruise

22. Self-Guided Driving & Walking Bundle of Maine Tours

23. 1-Day Tour to Portland-Maine from Boston

24. Portland, Maine Private Custom Tour

25. Portland Maine Self-Guided Walking Audio Tour

26. Lighthouses in Time Sunrise or Sunset Cruise in Portland, Maine

27. Portland Maine City and Lighthouse EBike Tour

What travelers are saying.

• Sail Portland Maine
• Schooner Glory
• The Real Portland Tour
• Portland Explorer
• Maine Brews Cruise
• Portland Fire Engine Co. Tours
• Maine Day Trips & Tours
• Old Port Historic Tours

The Scenic Route Maine Tours

Portland, maine lighthouse tours.

We are outside the ship terminal

Featured Tours

• Most Popular!
• Clock 2 hours

City & Lighthouse Tour

The best way to get a taste of what our great city of Portland has to offer! A must do!

• Clock 3 hours 30 minutes

Kennebunkport Tour

Enjoy the scenic drive to the lovely seaside village of Kennebunkport; incredibly picturesque and quaint.

Scenic Route Maine Tours is a LOCAL, family-owned and operated Maine Lighthouse tour company sharing what we love about our charming city of Portland and great state of Maine!

Operating since 2012, our stellar Tripadvisor reviews prove that small groups and excellent value combined with premium quality  is a great mix.

Our friendly, fun, and knowledgeable guides love what they do and want to share their excitement with you!

Praise For Our Maine Tours From Tripadvisor

"Well run tour. Guide was excellent with many facts and stories about the area. Great communication from owner leading up to the tour. Would highly recommend"

"Excellent knowledge of area, easy to understand, small and intimate! Fun! Picked up right at pier from cruise line, she had great recommendations for downtown lunch spots too!"

"Great tour. Guide was knowledgeable about the area & shared some fun facts. Kennebunkport area is very quaint & shopping fun. Recommend this tour."

"In Portland for one day on a cruise and took this bus tour to Kennebunkport. It was a very pleasant drive-through with a great overview of a beautiful coastal town and just the right amount of time to walk around the downtown and/or eat lunch. We hope to return to Kennebunkport."

Maine Tour Company

The best tours and activities in maine, planning your maine vacation just got easier our directory of tours and activities in maine lets you browse and buy entry to incredible experiences curated by locals.

We are the home of the best tours, activities, and things to do in Maine. We travel the Pine Tree State from north to south, east to west and everywhere in between to bring to you the widest range of experiences for your next Maine adventure!

Featured Tours & Activities

All-inclusive lighthouse & sightseeing charter.

Embark on an unforgettable adventure with our all-inclusive sightseeing excursion in Portland!

• Private Groups Only
• Activity , Tour

Portland’s Best Craft Beverages Bus Tour

This afternoon bus tour is a look at many different craft alcohol products that are being made here in the city of Portland.

Private Island Fort Tour

Board the Elizabeth Grace for this exclusive one-of-a-kind experience. Whether you are a local or visiting from away, the stone fortresses built in the early 19th century in Portland Harbor are always captivating.

Providing 5-Star Maine Experiences!

Portland, ME   Travel Guide

Courtesy of Joe Potato Photo | Getty Images

23 Best Things to Do in Portland, Maine

Portland, Maine, is a tough little city. A large part of it burned down in the Great Fire of 1866. But in the following years, Mainers and architects and builders from nearby cities like Boston came together to rebuild using the less-flammible brick

• All Things To Do

Old Port Old Port free

U.S. News Insider Tip: Don't miss Wharf Street in Old Port, which has an eclectic mix of bars and restaurants along its pedestrian-only cobblestone street. Try Street & Co.'s upscale seafood, The Independent Ice Co.'s fine whiskeys and the Bar of Chocolate's specialty martinis and sweets. – Mariya Greeley

This downtown neighborhood is considered the city's center and bustles with things to do left and right, all the while gracefully maintaining its historical facade. The area is lined with cobblestone streets and 19th-century warehouses, and with the wharf just steps away on Commercial Street, the city's heyday as a world-renowned port town is easily felt. Tourists can benefit from ferries and cruise experiences, as well as the delectable catches aboard the lobster boats that dock there daily.

Portland, Maine, Brewery Tours Portland, Maine, Brewery Tours

U.S. News Insider Tip: For nondrinkers or those looking to take a booze break, check out places like Root Wild Kombucha and Urban Farm Fermentory . They offer a range of nonalcoholic and alcoholic drinks with atmospheres comparable to the breweries nearby. – Mariya Greeley

Beer is to Portland is what lobster is to Maine. If you visit without sampling some brew, you're missing out. Portland is considered by experts to be one of America's best beer cities thanks to its large crop of local brewers as well as its role in the microbrew movement. For a city with a population of a little more than 68,000, its nearly 20 breweries offer plenty of choices for both residents and visiting beer enthusiasts.

Portland Museum of Art Portland Museum of Art

U.S. News Insider Tip: Consider aligning your visit with a First Friday Art Walk. The first Friday evening of every month, the Arts District comes alive with art lovers taking self-guided tours of local art galleries and venues. Meanwhile, musicians, performers and artists of all types display their art in the streets. – Mariya Greeley

For such a small city, Portland houses some pretty big names in its art museum. Andy Warhol, Claude Monet and Winslow Homer are among the icons showcased within the Portland Museum of Art. Along with some of the greats, the museum features an extensive collection of American, European and contemporary works, as well as pieces from Maine artists. Paintings abound, but you'll also find photographs, sketches, pottery, furniture, ornate silverware, sculptures and so much more. With more than 18,000 pieces in its collection, visitors are bound to see something new each time they browse the museum’s galleries. Additionally, the museum hosts regular events, including movie showings, curator talks and family-focused activities.

Popular Tours

The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

(1031 reviews)

from $ 65.00

Downtown Portland, Maine City and Lighthouse Tour-2. 5 hour Land Tour

(655 reviews)

from $ 70.00

Portland Tall Ship Cruise on Casco Bay

(195 reviews)

from $ 93.17

Portland-area Beaches Portland-area Beaches

Maine's Atlantic beaches might be known for relatively chilly waters (peak is approximately 65 degrees Fahrenheit), even in the summer months, but Mainers will tell you how refreshing a dip in the ocean is on a hot summer day. If that doesn't sound like your idea of fun, you’ll still find plenty of activities and atmospheres to enjoy on Portland-area beaches.

Although East End Beach is the only public beach in Portland (located off Eastern Promenade ), there are more than a half-dozen others within 20 miles of downtown, each with distinct characteristics and benefits. Every summer, they’re host to families and friends laying out or playing on the sand and kayakers, sailors, surfers, paddleboarders, swimmers and more enjoying the water. Maine beaches are beautiful year-round, and ideal places for quiet walks in the offseason. 

Casco Bay Islands Casco Bay Islands

Though there is only one public beach in the town of Portland ( East End Beach ), shorelines abound in the nearby Casco Bay Islands. The Casco Bay Islands are a group of islands located off the coast of Portland, six of which are accessible by ferry year-round. Each island has its own personality, history, attractions and activities.

Cliff Island is the smallest Casco Bay Island that's accessible year-round by ferry and is home to only 60 full-time residents. All roads are unpaved here, and as such cars are seldom used. The island doesn't offer many attractions, but does provide a tranquil, secluded atmosphere.

Eastern Promenade Eastern Promenade free

Portland's waterfront is at its most picturesque at the Eastern Promenade. Beloved by locals, the Eastern Promenade is a 78-acre waterfront park located on a stretch of land separating Back Cove from the Fore River. The park offers trails, a beach, and plenty of grassy areas to simply kick back and unwind. To make the most of your visit, take a stroll along the 2-mile Eastern Promenade Trail, which starts in the heart of the Old Port .

Once an old rail line, the Eastern Promenade Trail takes visitors away from the excitement of the city's center by the rocky banks of Fort Allen Park and small yet charming East End Beach (Portland's only public beach), where you'll find plenty of locals soaking up the sun or embarking on bay adventures. To continue the coastal trek, the trail connects directly to the Back Cove Trail, which snakes for about 3.5 miles along Back Cove with picturesque views of the water and downtown skyline. There are plenty of other shorter trails and paths located in the park that bring hikers to various points of interest. Once you've gotten your fill of scenic strolls, consider a climb up the park's grassy hills for sweeping views of the bay, as well as the islands and boats that dot its deep blue waters.

Fort Williams Park Fort Williams Park free

Located adjacent to Portland Head Light in Cape Elizabeth is the 90-acre Fort Williams Park. Fort Williams was a U.S. Army fort from 1872 to 1962. A few years later, residents of Cape Elizabeth bought the land to later turn it into a park. Visitors today can picnic, tour an arboretum, hike or walk along the park's trails or visit the park's other historical sites, including Battery Keyes (one of the last batteries built on the old fort site) and Goddard Mansion (the ruins of a grand home built in the 1850s). Travelers should note there are no trash receptacles around the park so you must take your trash with you when you leave.

There's also natural and recreational amenities to explore, including tennis and pickleball courts, athletic fields and a garden designed specifically to let children explore their relationship with nature.

Portland Observatory Portland Observatory

For some of the best views of the harbor, head to the historic Portland Observatory, the country's last standing maritime signal tower. Built in 1807, the octagonal, 86-foot-tall tower was commissioned by Captain Lemuel Moody as a communication station for Portland's harbor, but it wasn't built as an altruistic measure. Moody charged ship owners an annual fee of $5 to alert merchants (who he also charged) of ships arriving. He could spot them from as far as 30 miles away with his telescope. Before the observatory was built, ships couldn't be seen from town until they came around a point of land and were practically in the harbor. Moody offered an advantage to both paying captains and merchants, while also making a tidy profit for himself.

Eventually, the two-way radio replaced the tower's function, but the Moody family operated the tower until 1923. After some years of neglect the observatory was donated to Portland and in 1984, Greater Portland Landmarks took over and restored it. Recent visitors said the views from the observatory are not-to-be missed and its history is fascinating. Reviewers also advise allowing 45 minutes for the observatory tour. There is no elevator, so you'll have to climb the stairs to the top to take in the views, but past travelers say the pace is manageable.

Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour

(8 reviews)

from $ 90.00

Harbor Lights and Sights Cruise

(226 reviews)

from $ 48.00

Vintage Fire Truck Sightseeing Tour of Portland Maine

(610 reviews)

from $ 36.00

Victoria Mansion (Morse-Libby House) Victoria Mansion (Morse-Libby House)

Architecture buffs and lovers of interior design will be swept up by the opulence of the Victoria Mansion (aka the Morse-Libby House or Morse-Libby Mansion). This National Historic Landmark was originally built in the mid-1800s as a summer house for hotelier Ruggles Sylvester Morse. In 1940, William Holmes, a New York educator visiting Portland, purchased the home. He and his sister (an interior design instructor) turned it into a museum named in honor of Queen Victoria.

What makes the Victoria Mansion so important in the eyes of historians is that it's seen as an exemplary illustration of pre-Civil War grandeur. The exterior of the house was modeled after an Italian villa and features an ornate square tower, numerous balconies and piazzas. Inside, prepare to be even more amazed. Ninety percent of the original interiors are still intact, with carved wood paneled walls, gas light fixtures, cherub-clad crown molds, and ornate draperies and carpeting throughout. Designed by Gustave Herter of Herter Brothers, one of the most popular design firms of the day, it is the only work of his kind in the U.S. that remains intact.

Peaks Island Peaks Island free

Portland doesn't end at the waterfront. Peaks Island, one of the Casco Bay Islands , is 3 miles east of downtown's shore and about a 15-minute boat ride away. Peaks Island was known as the Coney Island of Maine in the 19th century (it was home to amusement parks, theaters and more), but nowadays it feels more like a quaint neighborhood with roughly 1,000 year-round residents.

Peaks is a perfect low-key day trip for history buffs, art lovers and outdoor enthusiasts. When you arrive, rent a bike or golf cart, the preferred modes of transportation on the island. Head to Baba's Cafe, Inn on Peaks or Island Lobster Company to fuel up for the day while overlooking the ocean. From there, explore the galleries and shops along the harbor side. Cool off at Sandy Beach or trek the nearly 4-mile loop trail that takes you around the island, passing scenic views and the remnants of historic Battery Steele — an important coastal defense battery constructed during World War II to protect the entrance to Casco Bay. For more Peaks Island history, stop by Fifth Maine Museum, or for something playful head to the world's only Umbrella Cover Museum, a quirky collection that is dedicated to the appreciation of the mundane.

Hadlock Field Hadlock Field

U.S. News Insider Tip: Special activities, like fireworks or "Bark in the Park" games, which allow you to bring a four-legged friend and sit in a designated pets area, make the experience extra special. Look for them when booking tickets. – Mariya Greeley

For Portland pride, look no further than Hadlock Field. In the summer, the field hosts regular games for the beloved Portland Sea Dogs, the local minor league baseball team. The field was named after Edson Hadlock Jr., who coached baseball at Portland High School from 1950 to 1978.

Portland Head Light Portland Head Light

Commissioned by George Washington in 1787, this lighthouse project was provided $750 by the General Court of Massachusetts when Maine was still a part of Massachusetts. When the U.S. government took control in 1790, the lighthouse was given an additional $1,500 for its completion. The lighthouse got its name from being situated at the entrance for ships at Portland Harbor. Portland Head Light was first lit in 1791, making it the oldest lighthouse in Maine.

Located about 5 miles southeast of Portland in Cape Elizabeth's Fort Williams Park , the tower provided navigation to ships for almost 200 years. The lighthouse was decommissioned by the U.S. Coast Guard in 1989 when it became an automated tower.

The Holy Donut The Holy Donut

In 2010, Leigh Kellis felt the Portland food scene was missing great doughnuts. So she decided to make them. After months of experimenting with different recipes in her kitchen on Portland's Munjoy Hill , Kellis landed on a mix that met her standards. Her variation on a northern Maine recipe included a type of food you might not expect in doughnuts: potatoes. Riced potatoes added a unique flavor, texture and consistency that set Kellis' doughnuts apart, and orders from local shops started coming in. With her family's support, Kellis soon opened the first Holy Donut retail location. Now, the family-owned business is a bonafide doughnut destination with four Maine locations: two in Portland, one in Scarborough and one in Arundel.

With about 20 rotating imaginative doughnut flavors – including seasonal, gluten-free and vegan options – you have a good chance of finding a flavor that you'll love. Though potato doughnuts aren't for everyone, many recent customers rave about unique flavors like dark chocolate sea salt, maple bacon and pomegranate. They describe the doughnuts as dense, filling and delicious. Reviewers also tend to mention the friendly service adding to their positive experiences.

Discover Portland City and Lighthouse Tour

(243 reviews)

Private Lighthouse Sightseeing Charter on a Vintage Lobster Boat

(42 reviews)

from $ 307.50

Private Sunset Charter on a Vintage Lobster Boat

(33 reviews)

from $ 332.50

Two Lights Lighthouses Two Lights Lighthouses free

Built in 1828, these two Cape Elizabeth lighthouses were the first twin lighthouses on the coast of Maine. They may look familiar: One of them was featured in Edward Hopper's well-known "The Lighthouse at Two Lights," a painting housed in the  Metropolitan Museum of Art in New York City . Today, the eastern lighthouse on Lighthouse Point Road is an active, automated station, shining 17 miles out to sea, while the western lighthouse is a private residence. Neither lighthouse is open to the public.

You can still get lighthouse views at On the Rocks at Two Lights, a lookout at Dyer Cove where recent visitors praised the natural beauty and recommend sunrise and sunset trips. While you’re there, stop for a bite at the Lobster Shack at Two Lights, a seasonal award-winning restaurant that dates back to the 1920s. The area is 6 miles south of Portland Head Light if you're in the mood for a lighthouse road trip.

Wadsworth-Longfellow House Wadsworth-Longfellow House

Built after the Revolutionary War, the Wadsworth-Longfellow House was home to four generations of the esteemed family whose contributions to American culture are now celebrated in this museum. The most famous person in this family was 19th-century poet Henry Wadsworth Longfellow, who grew up in the home.

Along with its esteemed namesake, the home is also important to Portland and U.S. history. The building is the oldest standing structure on the Portland peninsula, the first brick dwelling in the area and the first home museum in Maine. The site is operated by the Maine Historical Society.

Children's Museum and Theatre of Maine Children's Museum and Theatre of Maine

U.S. News Insider tip: Children's Museum and Theatre of Maine is next to Thompson's Point, a venue that hosts big name music acts for outdoor concerts and weekly events during the summer. The museum is also steps from the International Cryptozoology Museum where you can explore BigFoot mythology and more. – Mariya Greeley

If you're looking for something to do with the kids in Portland, the Children's Museum and Theatre of Maine is a must-see attraction. With more than 30,000 square feet of space, this museum provides interactive learning and fun for the entire family.

Coastal Maine Botanical Gardens Coastal Maine Botanical Gardens

U.S. News Insider Tip: Visiting during the holiday season? The garden creates a mile of spectacular light displays , called Gardens Aglow, open a few nights a week to brighten the winter darkness. – Mariya Greeley

The Coastal Maine Botanical Gardens is an attraction that took 16 years to create. What started as a dream for a public garden became the largest botanical garden in New England. Located about 60 miles northeast of Portland, the gardens consist of more than 300 acres of land, 17 of which feature plants native to the state. Each garden at the facility has a specific theme, including dahlias, bees and rhododendron, among others.

Munjoy Hill Munjoy Hill free

U.S. News Insider Tip: Munjoy Hill's Duckfat Frites Shack, a little sister location to downtown's Duckfat, has a limited menu, but shorter wait times than its popular sibling. You'll find the order window down an alley beside Oxbow Blending & Bottling. – Mariya Greeley

If someone mentions happenings on "the Hill" in Portland, they're likely not referring to Washington, D.C. politics but to the Munjoy Hill neighborhood of the city. Munjoy Hill is Portland's easternmost neighborhood and lies between Washington Avenue and Mountfort Street on one side and Casco Bay on the three others.

A Walk Through Time Tour in Portland

(365 reviews)

from $ 48.99

2 Hours | Portland, Maine Hidden Histories Walking Tour

(298 reviews)

from $ 49.00

Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine

(99 reviews)

from $ 150.00

Tate House Museum Tate House Museum

Tate House was built in 1755 for Captain George Tate and his family. Tate was a senior mast agent for the British Royal Navy, a role which meant he was responsible for the transport of white pines — now Maine’s state tree — from Maine to England. During hourly site tours, visitors should expect to see artifacts, furnishings and the grounds, which not only tell the story of how the Tate family lived in the 18th century, but also the importance of mast trade during this period.

Located about 4 miles west of downtown, the Tate House is the only pre-Revolutionary home in Portland that is open to the public. Past visitors say that the tour is an educational experience.

Portland Fire Engine Co. Tour Portland Fire Engine Co. Tour

Looking for a unique way to explore Portland? The Portland Fire Engine Co. sightseeing tour takes travelers on a ride around town in a vintage fire truck.

Expect to see scenic coastal views of Portland, along with historical sights, lighthouses and Civil War forts. During the 50-minute tour, you'll also enjoy a live narration of Portland history and view historical images provided by the Maine Historical Society on the truck's LED TV. Past tourgoers describe this as a fun outing and applaud the insightful guides.

Maine Narrow Gauge Railroad Co. and Museum Maine Narrow Gauge Railroad Co. and Museum

U.S. News Insider Tip: Look out for special events like Ice Cream Trains and Sunset Express rides on weekend evenings during the warmer months and special "Polar Express" rides during the holiday season. – Mariya Greeley

Located about 1.5 miles from the Portland Museum of Art , the Maine Narrow Gauge Railroad Co. and Museum teaches travelers about train preservation and Maine's narrow gauge railway history. The state's two-foot gauge railway system was made of tracks less than half the width of standard gauge railways. These narrow tracks were cheaper and easier to build while allowing trains to navigate Maine’s tough terrain of forests, rocky hills and mountains. A unique system, these rails helped to connect rural areas with larger cities and made travel and transportation of goods more accessible. From the 1870s until the 1940s, about 200 miles of narrow gauge railroads served many small communities in Maine.

Palace Playland Palace Playland

Situated about 20 miles south of Portland in the town of Old Orchard Beach, this 5-acre amusement park is New England's only beachfront amusement park. Past visitors say Palace Playland is an awesome place to take the family.

The park has a 24,000-square-foot arcade and features more than 200 games like Skee Ball and air hockey. And no amusement park would be complete without rides. Younger visitors can enjoy kiddie rides like a carousel and spinning tea cups, while older kids and adults test their bravery on the park's thrill rides like the Sea Viper roller coaster.

Funtown Splashtown USA Funtown Splashtown USA

Located about 15 miles south of Portland in Saco, Maine, Funtown Splashtown USA is a family-owned amusement park. The park is home to about 50 rides, water slides, pools and games for travelers to enjoy. Past visitors said the park is particularly fun for families with a variety of rides and clean facilities. However, some caution that lines can be quite long depending on the day and on-site food can be pricey.

Standout rides include Excalibur, Maine's only wooden roller coaster, and the Thunder Falls Log Flume, the longest and tallest log flume ride in Maine. The facility has several water slides, rides and pools at its Splashtown Water Park. And when your stomach starts to rumble, there are a variety of different eateries on-site (outside food and drinks are also allowed). 

New England Fall Foliage Private Lobster Boat Cruise

Portland's Best Craft Beverages Bus Tour

(16 reviews)

from $ 99.00

Portland Pubs Walking Beer Tour

(24 reviews)

from $ 89.00

Things to Do in Portland, ME FAQs

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16 Awesome Walking Tours in Portland, Maine

Portland, Maine is a beautiful city that’s perfect for taking a walking tour. With its historic architecture, coastal views, and delicious fine dining restaurants , diners , and cafes, there are plenty of sights to take in.

It also happens to be Maine’s largest city, so you get all the energy of a city without all the crowds (well, some places can be kind of crowded).

From a cultural exploration of the city to a jaunt along the waterfront in Old Port, each of the walking tours offers something unique. Whether you’re looking for a leisurely walk around town or an in-depth look at local history and culture, there are tours to suit all interests.

You can choose from a variety of walking tours, including learning about Portland’s cool history , a culinary journey through some of the best eateries in town, or even a craft beer tour .

Whether you’re an architecture buff, a foodie, or just looking for some fresh air and exercise, there’s something for everyone on these fun Portland Maine walking tours.

If you know you are coming to Portland but aren’t sure where to stay, why not opt for a place with an indoor pool? Here are the top-rated hotels in Portland that have indoor pools .

No matter which tour you choose, you can be sure to get an unforgettable experience while exploring the best of Portland Maine on foot. So lace up your shoes, grab your camera or phone, and get ready to experience a wonderful walking tour of the city!

Walking Tours Portland Maine

✅ Walking Tours: Portland, Maine’s History

Exploring the history of Portland, Maine is a great way to really get to know this vibrant city. For those looking for an in-depth look into the past, guided walking tours offer a unique opportunity to explore the historic sites, culture, and stories of the area.

Whether you’re interested in learning about the city’s founding fathers or seeing the grandeur of its post-Industrial Revolution architecture, there’s something for everyone on these informative, educational tours.

With an engaging, and often locally-raised tour guide who shares their passion and knowledge of Portland’s past, visitors will learn about everything from the city’s maritime history to its vibrant food culture.

So put on your walking shoes and get ready to explore the past of this beautiful city!

Walking Tours Portland Maine: History Tours

1. a walk through time tour in portland.

~$50/two ppl

If you’re looking to explore Portland’s history, join this captivating walking tour. You’ll have the opportunity to view many amazing attractions throughout the historic cobblestone streets of Old Port, downtown, and the waterfront area.

Your experienced guide will share intriguing stories of Portland’s rich past. Snacks are provided for all participants and group sizes are capped at 20 people!

Book, or Learn More About A Walk Through Time Here

2. Portland Hidden Histories Walking Tour

~$49/Two ppl

Discover Portland’s unique culture as you explore the city with a local guide. Learn about the tenacious souls who have shaped Portland’s identity through centuries of rebuilding, uncovering stories both inspiring and awe-inspiring.

As you wander down historic avenues, your curiosity for this vibrant destination will be sure to grow! Explore the eons of history in Portland’s historic Old Port and working waterfront on this Hidden Histories Tour!

Feel the palpable presence of Indigenous Wabanaki leaders’ earliest relationships with European colonizers as you are taken through a 1.5-mile route along historic streets like Congress Street, The Old Port, and Commercial Street.

This tour offers an exclusive collection of hidden histories over the course of the 2-hour walking tour that are not offered in other tours. It is sure to be entertaining and informative all at once!

Book, or Learn More About Hidden Histories Tour Here

3. Portland Black History Walking Tour

~$49/two adults

Step back in time and see the journey of the Black Portlanders who strived to move our city, state, and nation toward freedom, democracy, opportunity, and equality.

The success of Maine’s early settlements was propelled by Black labor, expertise and intelligence – all while they continually fought against oppression in order to gain power. Join this guided tour that will walk you through these monumental moments!

Explore the incredible history of Maine and some legendary people of the area with the Portland Black History Tour. With two hours of captivating narration, you will journey 1.5 miles through the Old Port and East End neighborhoods.

You’ll discover stories that are often overlooked in traditional tours- such as those who founded local communities, overturned slavery statewide, drove maritime industries, gained political influence, and fought for equal rights.

Created by uncovering piles of research and historic documents, this tour will open your eyes to a different, and unexpected, history.

Book, or Learn More About Black History Walking Tour Here

4. Portland Women’s History Walking Tour

Portland women have served as driving forces of the city’s culture and national progress toward equality.

Listen to the stories of incredible women, such as the Indigenous Penobscot performer who shifted immigration policy, a Chinese immigrant laundress named American Mother of the Year, a white tavern keeper confronting British Navy ships, and an enslaved Black maid abolishing slavery in her state!

Their indomitable spirit shines through their outstanding accomplishments both within factories and on ballots. Unlock the captivating charm and rich history of a city that was almost lost had it not been for the substantial power of women.

Hear stories told with humor, heart, and abundant enthusiasm by your guide, a Portland native. Explore museums, grand row houses, noble churches, and flawless Federal-style mansions on this two-hour walking tour across 1.3 miles through Portland’s Arts District and West End neighborhood!

Book, or Learn More About Portland Women’s History Walking Tour Here

5. Downtown Portland: Coastal Vibe and Old Mansions

During this self-guided tour, you’ll embark on an enlightening journey as you go back in time to the City Hall, where a rich history awaits.

You’ll be in good hands with your tour guide who will then lead you down Congress Street – Portland’s most celebrated thoroughfare – and introduce you to iconic and historic landmarks such as Monument Square, the Wadsworth-Longfellow House, and the Museum of Art.

Afterward, explore the city’s architectural masterpiece: Victoria Mansion. Boasting an impressive and intricate Italianate design, it is one of the area’s prized attractions. Then, make your way to Old Port, an amazing port district with plenty of historical charm.

Wander through its antique stores, art galleries, and picturesque buildings for hours on end, or enjoy some delicious seafood in any one of its top-rated restaurants! Old Port is one of the best places in Portland to do all those things all within a short distance of each other.

When you return to Congress Street, prepare to be awestruck by the grandeur of the Gothic Cathedral of the Immaculate Conception. You’ll also have an opportunity to climb up the Portland Observatory for unbeatable 360-degree scenic views!

To top it off, the tour will conclude at the Eastern Promenade where spectacular ocean vistas and a myriad of historical monuments await—it’s sure to create lasting memories of your stay in Portland.

Book, or Learn More About Coastal Vibes & Old Mansions Here

Walking Tours Portland Maine: Culinary Tours

✅ Walking Tours: Portland, Maine’s Culinary Scene

If you’re a foodie, then Portland, Maine is the perfect destination for you! With its abundance of delicious eateries and unique culinary experiences, it’s no surprise that many people flock to this city to sample its cuisine-it’s definitely home to the hottest restaurants in the state.

(While Portland restaurants might dominate, there are amazing fine dining spots around the state as well. )

Now, you’ll have the chance to explore the best restaurants in town on foot – with walking tours of Portland Maine’s culinary scene. From enticing seafood restaurants to mouthwatering bakeries, these guided tours offer a tasty exploration of the city’s best eateries.

Learn about the area’s unique food culture as you sample local specialties and get behind-the-scenes looks at some of Portland, Maine’s best restaurants. So grab your appetite and get ready for an unforgettable foodie adventure!

6. Old Port Culinary Walking Tour from Portland

~$140/two ppl

Aspiring epicures can wander through Portland’s picturesque Old Port on their own, but to expose the city’s hidden gems and authentic culinary delights, a Maine foodie tour with a reliable guide is the best bet.

Uncover all that Portland has to offer with this guided foodie tour. You’ll visit up to six eateries and tantalize your taste buds with enough samples for an entire meal! With one exciting tour, you get an unforgettable experience of some of Maine’s finest fare.

With no more than 14 travelers, you’ll get familiar with the local food as your guide regales stories about Portland’s lively culinary scene. Visit five to six eateries along Commercial Street in the heart of Old Port and savor delicious Maine-inspired cuisine!

Book, or Learn More About The Old Port Culinary Walking Tour Here

7. Donut Tasting Walking Tour: Portland’s Old Port

~$45/two ppl

Portland, Maine has made a name for itself as one of the top culinary hotspots nationwide. Okay, so you might not think of donuts when you think culinary tour, but that would be a mistake!

On this tour, you’ll get an awesome opportunity to savor some of the city’s best donuts while also gaining insight into its remarkable history! Your guide will take you to The Holy Donut (famed everywhere!), and you won’t have to wait in line!

You’ll also visit other local favorites that are equally delicious. What an awesome memory–an unforgettable journey through Portland’s delectable doughnut scene!

Book, or Learn More About Donut Tasting Walking Tour Here

✅ Walking Tours: Portland, Maine’s Beer Scene

Portland, Maine is becoming a well-known destination for its craft beer scene. With so many breweries to choose from, it can be hard to know where to start. But now, visitors can explore the city’s best beer offerings on foot!

Guided walking tours of Portland Maine’s beer scene offer a unique opportunity to get in some craft beer tastings while learning about its history. Get an insider look at the area’s breweries as you sip your way through this beautiful city.

So grab a map and get ready for an adventure that takes you to the best beer spots in Portland!

8. Old Port Walk, Talk, and Taste Brewery Tour

~$87/two people

Take a guided, leisurely, walking tour and discover the storied past of Portland’s waterfront.

Explore prohibition-era landmarks as you learn about importing goods to the area while sampling delicious beer from three iconic local breweries: Shipyard Brewing Company, Gritty McDuff’s, and Liquid Riot Bottling Company.

Travel in small groups with an experienced local guide on comfortable minibuses (though you are walking for the tour of the breweries) for maximum enjoyment. Snacks and beverages are included throughout your journey, plus convenient pickup services at our centrally located meeting point!

Book, or Learn More About Old Port, Walk, Talk, and Taste Tour Here

Walking Tours Portland Maine: Scavenger Hunts

✅ Walking Tours (sort of): Do a Portland, Maine Scavenger Hunt

Like a self-guided tour but better, because you get to experience the sights and sounds of Portland, Maine like never before – by taking part in a fun-filled scavenger hunt at your own pace! Guided scavenger hunts are a really fun way to explore this charming city.

As you wander through the streets of Portland, you’ll get to experience its vibrant culture while discovering hidden gems tucked away in unlikely places. With exciting tasks to complete and interesting facts about the city to uncover, you’ll have a blast as you make your way through town.

Portland is full of surprises, so take part in this unique activity and explore the city like a local. With the help of your friendly (remote) guide, you’ll get to experience Portland from a new perspective and gain a better understanding of its culture and history.

And with fun tasks to complete along the way, you’re sure to have an adventure you won’t soon forget. So grab your map, pick up a few clues, and get ready for an unforgettable scavenger hunt in Portland, Maine!

9. Portland Scavenger Hunt: The Maine Event

~$12/ two ppl

Are you craving a thrilling outdoor activity in Portland? The Let’s Roam scavenger hunt app has the answer! Whether you’re from here or somewhere else, this is sure to make a fun afternoon of wandering the city.

Get ready for some exploration on foot and discover what Portland has to offer. See if you have what it takes by taking pictures, racing against time limits, and navigating your way through locations like Congress Street and Old Port with The Maine Event Scavenger Hunt!

Book, or Learn More About The Maine Event Scavenger Hunt Here

10. Portland, Maine Madness Scavenger Hunt

~$28/two ppl

Unlike with most scavenger hunts, guests get their own remote host to help and motivate them along the way. These specially crafted adventures blend tour-like elements with creative challenges and detective hunts that the whole family can enjoy.

You’ll uncover off-the-beaten-path gems and creatively interpret clues related to art, history, and culture – all for points! Ready to take your talents global and make a name for yourself? You can compete with teams from all over the world for international fame and glory!

Plus, even if there’s no competition in sight near where you live, it doesn’t mean that fun should be out of reach. You’ll still get a chance to shine by showcasing your favorite hangouts or uncovering unusual oddities along the way.

Book, or Learn More About Maine Madness Here

11. Scavenger Hunt in Portland, Maine by Zombie Scavengers

Are you ready to face the ultimate challenge? Portland is calling and it needs your help! With Zombie Scavengers, you will have the opportunity to explore this city in search of essential items required for surviving a zombie apocalypse.

You’ll earn points each time you find something – but that’s not all: complete some thrilling zombie-themed challenges on the app for extra points! Strategize carefully if you want to amass as many points as possible and avoid becoming a victim of this merciless apocalypse.

Don’t worry; they’ve got your back with their remote host available through chat in case anything goes wrong. So, can YOU survive an epic battle against zombies in Portland?

Book, or Learn More About Zombie Scavengers Here

12. Unique Wacky Walks Scavenger Hunt

~$10/two ppl

Join Wacky Walks on an exciting scavenger hunt around Portland and become the King or Queen of your group as you compete with others. The app-based game will lead you to locate hidden items in the city while also completing fun tasks along the way.

As a reward for finding each item and finishing these missions, points are awarded to players. Gain the highest possible score and be crowned King or Queen of Portland for a day by playing Wacky Walks!

With no time limit, take your time exploring the city as you play. Not to worry if you need assistance – the host will always be on hand through chat support.

Book, or Learn More About Wacky Walks Scavenger Hunt Here

13. Crazy Dash Scavenger Hunt Adventure

Discover Portland like never before with Crazy Dash! The app and the remote host provide a checklist of thrilling tasks to complete and exciting locations to explore. You are free to visit them in any order you choose, earning points along the way for each challenge completed or object found.

Best of all, there is no time limit on this laid-back adventure, so you can take your time exploring the fantastic city that is Portland! In addition, the helpful remote host will be available throughout your game if assistance is ever needed.

Book, or Learn More About Crazy Dash Scavenger Hunt Here

14. Operation City Quest Scavenger Hunt

Ready to discover Portland? Look no further than Operation City Quest! Download the app and complete tasks all around the city for points. Whether you decide to start with an item or challenge is completely up to you!

Track your progress on the leaderboard, and don’t forget about the helpful remote host ready via chat if problems occur during your journey.

Book, or Learn More About Operation City Quest Scavenger Hunt Here

15. 3Quest Challenge Scavenger Hunt

Take a tour of Portland in an entirely unique way, with the 3Quest Challenge! Download the app and explore the city following clues written as riddles. As you complete tasks, collect points to check your ranking on the leaderboard.

Whether competing with friends or colleagues, find out who will be crowned victor at this exciting scavenger hunt! Take on three quests and explore the city of Portland in just two hours! All you need is your wits, and a remote host to assist virtually along the way.

Divide up objects and tasks into 3 different excursions: first quest, second quest, and third quest; finish them one by one to complete the game. Set yourself a time limit if you want more of a challenge!

Book, or Learn More About 3Quest Challenge Scavenger Hunt Here

16. Portland Freedom Trail

$0/Self-guided

Experience Portland, Maine’s history and culture like never before with a self-guided walking tour on the Freedom Trail. This exciting journey takes visitors through some of the city’s most significant locations and attractions, highlighting important stops along the Underground Railroad.

Learn about this powerful movement as you explore churches, schools, homes, and businesses that played a role in helping thousands of enslaved African Americans find freedom. You’ll also gain a better understanding of the city’s past.

Get The Self-Guided Portland Freedom Trail Map Here

Conclusion: Walking Tours in Portland Maine

As you can tell, there are many Portland walking tours for you to choose from–Maine foodie tours, brewery tours, educational tours about the (surprising stories) and people who made Portland what it is today, and some plain old fun tours like the scavenger hunts.

If walking tours of Portland aren’t your thing, maybe a boat tour of Casco Bay, or a bus tour of local breweries is more your style.

No matter what you choose, you’re sure to have a great time sightseeing and learning something new on any of these Portland tours. It’s an amazing city, and experiencing it on foot is really the best way to tour Portland.

If you’re not from the area and want to avoid having to take a car at all, here are some great Portland hotels with free airport shuttles . Several of the hotels are right downtown, too! This means you could spend all your time without the hassle of renting a car.

If you want to venture a little further away, in the winter, why not try some great skiing just a couple of hours away? During the other seasons, Portland is still close enough that you could take a day trip to Acadia National Park !

Get Your Guide To 7 Beautiful Sandy Beaches In Maine

Meet the heart and soul behind Wandering Through Maine – a true New Englander at heart, originally from NH, who found their forever home in the beautiful state of Maine. Maine called to them like a lighthouse beacon, and they've embraced it wholeheartedly ever since. This blog isn't just a guide; it's a heartfelt invitation from someone who's walked the trails, sailed the waters, and knows Maine not just as a place on the map, but as a vibrant community and an adventurer's paradise that they call home.

Private Sightseeing Tours and Travel Planning

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Enjoy a Private Tour & Travel Planning Experience in Maine

Experience the scenic beauty of natural Maine. Participate in the exciting discovery of nearby day trip tours and getaway excursions by creating your own customized adventure activities that fit your style and interests. Lighthouses and scenic coastal tours with lobster lunch stops or oyster adventures will delight you and your family or group of any size. Maine is natural, with over 3,000 miles of coastline and forests that cover 90% of the state, where you will always find quiet beauty. Our private driver guided tours are done by local guides in most areas along the coast from York, Maine in the southern part to Bar Harbor / Acadia National Park along the northern coast. We also offer complete travel planning assistance booking accommodations, transportation, activities and even dining with our local Maine partners. Spend less time planning your Maine travel experience and more time enjoying it.

Lighthouses

From world renowned lighthouses to our award winning lobster, and everything in between - here are the key sites to see when you tour with us.

Coastal Maine

Beauty, flavor, people, and places. There are more than just a few reasons why so many people return year after year.

This is the best way to experience Maine. You can sit back and relax as we explore Maine together. Welcome to Vacationland.

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Maine day trips & tours.

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Visit Portland

The Official Site for the Greater Portland Region of Maine

Greater Portland Region of Maine

With its heady mixture of artistic and outdoor adventure, our region is stylish and sophisticated, genuine and welcoming—a place where grey flannel and plaid flannel can coexist. Modern marvels mingling with maritime history. And underlying the latest art, fashion, music, and culinary scene is a deep sense of continuity.

We invite you to experience the character of a region that blends the present with a very special past.

The Lay of the land

Experience the Best of both worlds

In Portland, Maine you’ll find a metro hub with cobblestone streets, nationally-lauded eats, and a scenic working waterfront in the heart of the Old Port. Go from the middle of the action to the middle of just about anywhere with neighborhoods + nearby towns boasting beaches, arts + culture, shops/boutiques, lighthouses, outdoor adventures, and world-class accommodations.

Dive deep and uncover hidden gems in every charming corner of Greater Portland, Maine…

Featured Upcoming Events

There’s always something to do in Greater Portland, Maine.

From daily tours to cruises, art exhibitions, music, and live performances.

Browse our Events Calendar and save your favorites.

Always cross-check event time/date with organizer’s website before booking. 

Join us in celebrating Maine’s kelp harvest across the state for its sixth year this April!

Join us for a free monthly cultural event in Portland.

Come enjoy the Kentucky Derby with Batson River!

An Expansive Trail of Maine Art, Crafts, and Food

Kick off summer with a week of wine in Portland!

Celebrate the change of seasons overlooking the Saco River.

Visitor Information

When you’re in town, stop by one of our Visitor Information Centers to pick-up brochures, Visitor’s Guides, maps of the region, and plenty of pro-tips to help make the most of your stay in Greater Portland.

Beginner's Guide to Greater Portland

Ready, Set, Explore. Let’s unpack essential tips for your upcoming trip to Maine. Portland is a vibrant coastal city brimming with history, culture, and natural beauty.

Packages + Deals

Browse through the special packages and deals offered by participating businesses. Find special deals on tours and attractions to maximize your visit. Enhance your shopping experience and find that perfect gift or souvenir. Don’t forget to enjoy the food scene. Find discounts and happy hour specials.

On The Blog

Keep up with the constantly changing landscape of the Greater Portland region. We will be bringing you ongoing articles about quintessential Maine as well as the cutting-edge sophistication of our world-class food, craft brews, and upscale art scene that’s creating quite a stir among travelers.

If you haven’t been, maybe it’s time to see what all the buzz is about yourself…

Summer is here, and so is the heat! Whether you’re visiting or a born and bred Mainer, the question isn’t if you’ll cool off, but where!

Have you recently gotten engaged? Planning a wedding for your best friend? It’s never too soon to start thinking about bachelorette and bachelor parties!

Join lifelong Mainers, Amy + Dan, as they make their way down the coast for seven days of fun in the sun—exploring a bit of everything Maine has to offer.

Meet in Maine

Welcome to Maine—the ultimate backdrop your next meeting or event. Perfect for outdoor retreats and small group meetings. Rich in culture and history, Maine will keep your attendees entertained every season, while our natural beauty inspires and refreshes. 

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Marry in Maine

Searching for your dream wedding destination? Whether plans for your big day include an ocean view, a stay in luxury resort, or an authentic barn venue—stunning Greater Portland locations and activities will exceed expectations for every style and budget. 

DISCOVER SPRING

Plan your ultimate vacation getaway where you can unwind and savor life at a leisurely pace. Whether you prefer to relax along Maine’s rugged coastline or immerse yourself in the excitement of upcoming fairs, festivals, and seasonal delights, there’s something for everyone to enjoy in Portland and its charming neighboring towns.

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INTERNATIONAL LANGUAGE BROCHURES

A good travel plan has a steady pace so you see the sites, but allow enough time to stop and soak up local culture. Find hotels that specialize in Foreign Independent Travel  and will help make an enjoyable experience when traveling to Greater Portland Maine on your own.

Chinese | Mandarin

AREA METROPOLITANA DI PORTLAND

Autentica – Per la sua natura

RÉGION DE PORTLAND

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Book 2024 Tour Tickets Here!

Unique Portland Maine Tours

The best sightseeing and lighthouse tours in portland, maine.

Quick Details

• Checkered Flag Tour Starting Point: 180 Commercial St. Portland, Maine
• Clock Tour Times: 9:30 am. 10:00 am, 10:30 am, 11:00 am, 11:30 am, 12:00 pm, 1:00 pm, 1:30 pm, 2:00 pm, 2:30 pm, 3:00 pm. 3:30 pm and 4:00 pm

Users Capacity: Groups of up to 13

Clock Duration: 50 minutes

Portland, Maine Sightseeing Tours Information

Explore the BEST sightseeing and lighthouse tours in Portland, Maine with Portland Fire Engine Co. Tours! Our Portland tours offer a unique opportunity to discover the beauty and history of Portland, Maine aboard a Vintage Fire Engine. Join us as we traverse the cobblestoned streets of Portland’s peninsula, passing by iconic landmarks including lighthouses, civil war forts, and the captivating historical architectural buildings that define our wonderful Maine city. With our 50-minute Portland tours aboard our Vintage Fire Engine, you’ll have the chance to experience so much of Portland, Maine’s rich heritage.

Here is a list of some of the sites you will see on our tour.

• Portland Old Port
• Portland Custom House
• Casco Bay Lines
• Portland Cruise Ship Terminals
• Longfellow Birth Place
• Shipyard Brewery
• Maine Narrow Gauge Railroad
• Fort Allen Park
• Fort Gorges
• Spring Point Ledge Lighthouse
• Portland Headlight
• House Island
• Eastern Promenade
• Macworth Island
• Percival Baxter Pet Cemetery
• Fort Sumner (Casco Bay)
• Portland Observatory
• Portland Eastern Cemetery
• Maine Jewish Museum
• St. Paul’s Anglican Church
• Cathedral of the Immaculate Conception
• Central Fire Station
• Portland City Hall
• First Parish Church
• Monument Square
• Henry Longfellow House
• Portland Museum of Art
• Hay Building
• Baxter Building
• Longfellow Square
• Neil Dow House
• Maine Medical Center
• West Mansion
• Western Cemetery
• Irish Heritage Center
• Victoria Mansion

Led by our knowledgeable local guides, our lighthouse tour showcases high-resolution photographs from the Maine Historical Society through our onboard multimedia system. With a maximum capacity of 13 people per tour, be sure to book early as our tours sell out quickly!

Join us for an unforgettable adventure and uncover Portland’s hidden gems as we explore the city’s rich history and culture. Book your Portland tour today and experience the magic of our Vintage Fire Engine tours!

Interested in booking a Private Charter for your group?

Which Portland, Maine Trolley Tour Should You Take?

If you are mapping out your first trip to Portland, Maine, you may be overwhelmed with the number of destinations there are to see. While this is arguably a good thing, logistics often prevent you from being able to visit all the sights on your list. After all, when you factor in driving time, finding parking spots, and navigating directions through unfamiliar roads, you could end up spending more time in your car than visiting a Maine landmark! Fortunately, with Portland Discovery Land and Sea Tours, you can visit the most beautiful (and historically significant) places in Portland without the logistical headaches. As Portland’s #1 sightseeing tour company, we offer tours to fit every guest.

Portland Discovery Land and Sea Tours is well known in the industry for our commitment to 100% customer satisfaction and for our Certificate of Excellence from Trip Advisor. Our trolleys meet exceptionally high standards, are fully updated and impeccably clean. We have comfortable open-air seating with unobstructed views and a top-notch sound system that makes the narration crystal clear.

On one of our most popular tours, the Portland City & Lighthouse Tour by trolley, our guests enjoy a 105 minute fully narrated tour of Portland’s diverse history and architecture. This trolley tour also visits the Portland Headlight, an icon of the Maine coast. This lighthouse has been standing tall and helping vessels find safe passage since it was first lit on January 10, 1791. The Portland Headlight is also visible from our Lighthouse Lovers Cruise. Another option for those who don’t have a lot of time to spend but who wish to get a taste of what our little city has to offer is the 60 minute Peek at Portland tour . This fully narrated trolley tour of the Portland peninsula explores Portland’s rich history and explores highlights that include The Portland Observatory, The Longfellow House, and Victoria Mansion.

Portland Headlight is adjacent to the historic Fort Williams Park, a fort that was once used during World War II to protect the Cape Elizabeth shoreline and contribute to Harbor Defense in Portland. While the fort was closed and deactivated on June 30, 1963, the 90-acre park is now home to residents and tourists alike for recreational activities. In addition to seeing the Portland Headlight up close (with plenty of time for pictures), our Portland, Maine trolley tour also brings our guests to these other unique destinations:

The Old Port

You can’t visit Portland without a proper introduction to the Old Port district. Recognized for its authentic cobblestone streets, comfy taverns, and working waterfront, this unique dockside community is known for its foodie restaurants and eclectic shopping opportunities. There are countless places to eat, satisfying every craving from Maine lobsters and Maine whoopie pies to escargot and filet mignon.

The Victoria Mansion

This famous mansion (also known as the Morse-Libby House) was built between 1858 and 1860 as a summer home for Ruggles Sylvester Morse, a Maine native who made his fortune as the proprietor of luxury hotels in New Orleans. Henry Austin, a famous New Haven, Connecticut-based architect, built this home. True to his style, the Victoria Mansion is recognized as one of the most prominent (and important) examples of the Italian villa style within our American domestic architecture. Gustave Herter, a famous interior designer and furniture maker, designed the interiors of the Mansion. Today, ninety percent of the Mansion’s original furnishings still remain intact.

The Wadsworth–Longfellow House

Housing three generations of a family that made important contributions to the political, literary, and cultural life of New England, this house is an important stop on the trolley tour. One of the most famous men in this family, if not all of

America, poet Henry Wadsworth Longfellow (1807–1882), grew up here. Almost all of the artifacts and household items found on the property are original to the Wadsworth and Longfellow families. Longfellow Garden is located behind the home, and its beautiful landscaped grounds and paths are open to the public in seasonal weather.

Booking Your Portland, Maine Trolley Tour Today

For your convenience you may book your reservation online. If you have a very important event, like a wedding, corporate event, or another private group function, consider a trolley charter for your transportation or shuttle service needs. Please contact us if we can help you coordinate this service; it’s one of the best ways to travel in Portland.

When you travel with us, our tour guides will be happy to help you maximize your Maine experience by giving you the “insider scoop” on all the best places to dine and shop in Portland. Portland is a city that’s meant to be fully enjoyed and Portland Discovery Land and Sea Tours can make that happen for you! We invite you to be our guest – and experience the best Portland has to offer for yourself