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Enjoy the best days of the year with a clear conscience and positive feeling: For more than 40 years, we have been pursuing the principle of sustainable tourism. Traveling with a small number of guests creates space for great things. Meeting people at eye-level in the countries you visit, experiencing cultures, appreciating regional values and creating added value for the region. This is pointing the way ahead because it is in keeping with the times. Because we are firmly convinced that traveling in harmony with nature is possible and necessary.

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Small Cruise Yachts

The best of small ship cruises.

Windstar's 148 to 342-guest small ships and personalized approach bring you closer to each destination and every port, so you can see the world from new perspectives. Share intimate moments away from the crowds, and immerse yourself in local, exotic cultures, all on a small cruise ship where surprise and delight are constant companions.

The Wind and the Stars Know the Way

You can slip past the crowds to discover smaller ports and get to know the local culture on more intimate excursions. Windstar's 148 to 342-guest small ships and personalized approach bring you closer to each destination and every port, so you can see the world from new perspectives. We offer two different yacht styles — the iconic sailing Wind Class and all-suite Star Plus Class — with custom-crafted journeys that highlight their unique attributes, whether island-hopping in Tahiti or cruising the Norwegian fjords. No wonder Windstar was voted the World’s Best midsize-ship ocean cruise line by the readers of Travel + Leisure in 2022.  

Iconic Wind Class

Windstar's flagship, Wind Surf sails with just 342 guests in 171 total staterooms: 18 Ocean View Suites with his and her bathrooms, 2 Bridge Suites, 1 Officer's Suite, and 150 Ocean View Staterooms.

Wind Star sails with just 148 pampered guests in 74 total staterooms: 73 deluxe, ocean-view staterooms and 1 deluxe Owner’s Suite with queen beds and a dining/sitting area.

Wind Spirit sails with just 148 pampered guests in 74 total staterooms: 73 deluxe, ocean-view staterooms and 1 deluxe Owner’s Suite with queen beds and a dining/sitting area.

All-suite Star Plus Class

Star Pride welcomes 312 guests in 156 suites, including 4 Owners' Suites, 2 beautiful Classic Suites, 3 Deluxe Suites, 79 Ocean View Suites, 58 Balcony suites, and 10 Star Porthole Suites.

Star Breeze welcomes 312 guests in 156 suites, including 4 Owners' Suites, 2 beautiful Classic Suites, 3 Deluxe Suites, 79 Ocean View Suites, 58 Balcony suites, and 10 Star Porthole Suites.

Star Legend welcomes 312 guests in 156 suites, including 4 Owners' Suites, 2 beautiful Classic Suites, 3 Deluxe Suites, 79 Ocean View Suites, 58 Balcony suites, and 10 Star Porthole Suites.

Caribbean Small Ship Cruises

10 best caribbean small ship cruises for 2024-2025, sailing the caribbean, windward islands, pearls of the caribbean, barbados to panama, classic yachtsman caribbean, panama to antigua, cruising the leeward islands, enjoy caribbean rhythms at the turn of the year, the essential of the caribbean, grenadine islands, top 10 luxury caribbean small ship cruises for 2024-2025, caribbean cruise destinations, virgin islands, lesser antilles, st. vincent des grenadines, 8 best small caribbean cruise ships & sailboats for 2024-2025, caribbean sailing cruise video.

Caribbean Small Ship Cruising Guide & Travel Tips

Caribbean island overview, discover the top 10 places to visit in the caribbean, caribbean cruise: when to go, top sites to visit in the caribbean.

• The Blue Hole of Belize: Nestled in the Lighthouse Reef, the Great Blue Hole is a massive underwater sinkhole. This natural wonder, over 300 meters in diameter and 125 meters deep, showcases stunning marine life and geological formations, making it a world-renowned dive site.
• Piton Mountains in Saint Lucia: The iconic Pitons, two volcanic spires rising dramatically from the Caribbean Sea, are a UNESCO World Heritage Site. Gros Piton and Petit Piton offer breathtaking views and hiking opportunities, showcasing the unique geological features of the region.
• Pristine Tobago Cays Marine Park: This protected marine reserve in the Grenadines is a haven for marine life. Snorkelers and divers can explore vibrant coral reefs, swim with sea turtles, and enjoy the crystal-clear waters of this idyllic Caribbean destination.
• Historic Sites of San Juan, Puerto Rico : San Juan's Old Town, a UNESCO World Heritage Site, boasts colorful Spanish colonial architecture. El Castillo San Felipe del Morro and Castillo San Cristóbal, historic fortresses, reflect the city's strategic importance in the region's history.
• Dominican Republic 's Pico Duarte: As the highest peak in the Caribbean, Pico Duarte stands at 3,087 meters above sea level. Hikers can embark on an adventure through dense forests to reach the summit, where panoramic views of the island await.
• The Baths, Virgin Gorda : This geological wonder in the British Virgin Islands features colossal granite boulders creating stunning grottoes and pools along the beach. It's a natural playground for exploration, swimming, and photography.
• Morne Trois Pitons National Park, Dominica : Dominica's UNESCO-listed national park is a treasure trove of natural wonders. Boiling Lake, the second-largest hot spring in the world, and Trafalgar Falls, with its twin cascades, highlight the island's geothermal activity.
• Cuba's Viñales Valley : Known for its picturesque tobacco fields and limestone karst formations, Viñales Valley is a UNESCO site. The vibrant landscapes and traditional agricultural practices offer a glimpse into rural Cuban life.

Our Favorite Caribbean Cruise Ports for Small Ships

Windjammer cruises in the caribbean, fun facts about the caribbean.

• Diverse Coral Reefs: The Caribbean is home to some of the most diverse coral reefs globally, with an array of marine life inhabiting its crystal-clear waters.
• Multilingual Region: The Caribbean is a linguistically diverse region, with English, Spanish, French, Dutch, and various Creole languages spoken across its islands.
• Pirates' Haven: The Caribbean was a notorious haven for pirates during the 17th and 18th centuries, with legendary figures like Blackbeard and Calico Jack roaming its waters.
• World's First Rum Distillery: Mount Gay Rum Distillery in Barbados claims to be the world's oldest, dating back to 1703, showcasing the region's historical ties to the production of rum.
• Birthplace of Salsa and Merengue: The Caribbean has played a pivotal role in the development of music genres, including the birthplace of salsa in Cuba and merengue in the Dominican Republic.
• Blue Flag Beaches: The Caribbean hosts numerous Blue Flag beaches, recognized for their environmental management, cleanliness, and safety standards.
• Hurricane Alley: The Caribbean experiences a hurricane season from June to November, with a higher likelihood of hurricanes and tropical storms during these months.
• Biodiversity Hotspot: The Caribbean is a biodiversity hotspot, hosting a vast array of plant and animal species, including the endangered Hawksbill turtle and the colorful Queen Angelfish.
• Cricket Craze: Cricket is a popular sport in the Caribbean, and the West Indies cricket team is one of the most successful in international competitions.
• Arawak and Taino Indigenous Peoples: The Caribbean was originally inhabited by indigenous peoples, including the Arawak and Taino, whose influences are still visible in the region's culture and traditions.
• Cayman Islands' Stingray City: Grand Cayman's Stingray City allows visitors to interact with friendly southern stingrays in their natural habitat, creating a unique and unforgettable experience.
• Jamaica's Blue Mountain Coffee: Jamaica is renowned for its Blue Mountain Coffee, one of the most sought-after and expensive coffees globally, grown in the Blue Mountains region.

Caribbean Cruises

10 must-see attractions and things to do in the dominican republic - top experiences & activities, wildside of the virgin islands, top tips to know when traveling to the caribbean.

• Diverse Currency: Be aware that the Caribbean is a region with diverse currencies. While some islands use the Eastern Caribbean Dollar (XCD), others, like Jamaica, use the Jamaican Dollar (JMD), and some, including Puerto Rico, use the United States Dollar (USD).
• Hurricane Preparedness: During the hurricane season (June to November), stay informed about weather conditions and consider travel insurance that covers unforeseen disruptions. Check local advisories and be flexible with your plans. Prices tend to be lower during this season.
• Island Time: Embrace the laid-back lifestyle known as "island time." Things may move at a slower pace, so plan accordingly and savor the relaxed atmosphere.
• Water Safety: Exercise caution with water activities. While the Caribbean boasts stunning beaches, currents and tides can be strong. Pay attention to warning flags, and only swim in designated safe areas.
• Local Cuisine Exploration: Dive into the local cuisine. Each island offers unique flavors, so try traditional dishes and street food. Don't miss specialties like jerk chicken in Jamaica or conch fritters in The Bahamas.
• Bargaining Skills: Brush up on your bargaining skills, especially in local markets. Haggling is common, and you may score better deals on souvenirs or goods by negotiating with local vendors.
• Transportation Options: Explore various transportation options. Some islands have well-developed public transportation, while others may require renting a car. Consider your destination's infrastructure for the best travel experience.
• Language Variation: English is widely spoken, but many islands have their own dialects or languages. Familiarize yourself with local phrases, especially if English is not the primary language spoken.
• Health Precautions: Be cautious about food and water hygiene. Stick to bottled water, avoid consuming raw or undercooked seafood, and use insect repellent to guard against mosquito-borne illnesses.
• Sun Protection: The Caribbean sun can be intense. Pack sunscreen, a hat, and lightweight clothing to protect yourself from sunburn. Stay hydrated, especially in warmer months.
• Cash vs. Cards: While larger establishments accept credit cards, it's advisable to carry some cash for smaller businesses or markets. ATMs are available, but check for fees and notify your bank of your travel plans.

Video: Sailing the Caribbean on a Small Ship Cruise

Caribbean Adventure Cruise Stories

Sailing the bahamas on the liberty clipper, our spanish virgin islands cruise, top caribbean travel destinations, caribbean trips by departure date.

• 2024 Caribbean trips (26)
• 2025 Caribbean trips (12)
• May 2024 (6)
• October 2024 (9)
• November 2024 (15)
• December 2024 (14)
• January 2025 (8)
• February 2025 (8)
• March 2025 (10)

Top Experiences in Caribbean

• Caribbean Cruises (25)
• Caribbean Beaches (10)
• Caribbean Cultural (7)
• Caribbean Active (5)
• Caribbean Land Tours (5)
• Caribbean Luxury (4)

Caribbean Trips by Duration

• 8 day trips (11)
• 15 day trips (6)

Caribbean Trips by Activity

• Caribbean small ship cruises (24)
• Caribbean snorkeling (17)
• Caribbean small ship sailing (14)
• Caribbean wildlife viewing (9)
• Caribbean hiking (8)
• Caribbean homestays (4)
• Caribbean kayaking (3)

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Liberty Fleet of Tall Ships

Boston harbor sailing cruises, featured boston sailing experiences.

• Most Popular!
• Hour Glass 1.5 Hours

Boston Harbor Day Sail

Come out for a day sail adventure in Boston Harbor aboard our classic schooner, the Liberty Star.

• Hour Glass 2 Hours

Boston Harbor Sunset Sail

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic Boston tall ship!

Read what guests are saying about their sailing experience with Liberty Fleet in Boston!

The view of the harbor was amazing and the experience of the tall ship was one of a kind. The crew was friendly, knowledgeable, and always available to help. We also loved the relaxing pace of the sail.

It was just wonderful. My husband got to help raise the two large sails. I really enjoyed that we actually sailed around the harbor. The engine was only used for leaving and returning to the wharf. The crew was awesome.

We danced with strangers, sang, laughed and had a wonderful time! I don't plan on having another bachelorette party, but if I do, I'd do this again! 6/5 stars!

We loved seeing Boston this way. The sunset was beautiful and the crew was friendly. My only regret is that we didn’t do the longer cruise.

These 3 lesser-known cruise lines offer amazing voyages on sail-powered ships

There is nothing quite as magical — or romantic — as a cruise on a sailing ship.

To stand on the deck of a vessel topped with dozens of billowing sails, propelled through the waves by the power of the wind alone, is to go back in time to an earlier age of travel, when crossing the world's oceans was as adventurous as it was challenging.

It's an experience that's all about the feeling of the wind in your hair, the lean of the vessel (known as the heel) as it's pushed by the wind and the sway from the waves (which is actually smoother than what you get on a motor ship).

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In contrast to what you'll find on so many motor-powered ships, cruising on a masted ship is about the simple thrill of traveling across the sea and not about all the many attractions you'll find on board.

Only a handful of small cruise brands — so small that you might never have heard of them — offer trips on sailing ships. Here, we look at the three biggest players in this niche subset of the cruise industry.

Sea Cloud Cruises

If it's an authentic, old-style sailing experience you want, then Sea Cloud Cruises is the line for you. The Germany-based company operates three large sailing ships where the sails are unfurled by hand, just as they were on sailing ships centuries ago.

On the biggest of these three vessels, the 136-passenger Sea Cloud Spirit , 18 deckhands scurry high into the rigging on sea days to manually untie and prepare the sails, an amazing sight. Unveiled in 2021 , it's a full-rigged, three-masted sailing ship of the sort that hasn't been common on the world's oceans for more than a century.

Related: Why Sea Cloud Spirit is a sailing vessel you'll want to try

Sea Cloud Cruises' two other vessels — Sea Cloud 2 and Sea Cloud — are smaller but offer a similar show as the sails are set by hand the old-fashioned way. The former is a 23-year-old, three-masted barque propelled by 23 sails (five fewer than Sea Cloud Spirit); the latter is a 93-year-old, four-masted barque with 30 sails and a storied past.

Now configured to carry 64 paying passengers, Sea Cloud was originally the private yacht of Postum Cereals heiress Marjorie Merriweather Post and her husband, the famed financier E. F. Hutton. At the time, the vessel was the largest private yacht in the world. It later served the U.S. Navy as a weather ship during World War II, after which it became the presidential yacht for the Dominican Republic. It only began sailing as a cruise vessel in the 1980s.

If you have money to spare, you can still book Post's opulent private quarters on Sea Cloud, now its owner's suite. It'll set you back around $5,000 per day per couple. Her husband's slightly smaller quarters are also available to book at a similar rate.

Post, the wealthiest woman in the U.S. during her lifetime, notably also built Mar-a-Lago, the massive estate in Florida that is now the official residence of Donald Trump.

Sea Cloud Cruises is the most all-inclusive and upscale of the three brands listed in this story, with pricing to match. Expect to pay nearly $1,000 per person per day or more for many sailings.

Sea Cloud Cruises' three vessels offer a diverse array of sailings in the Mediterranean, Northern Europe, the Canary Islands and Morocco, the Caribbean or along the west coast of Central America.

Related: Cruising Costa Rica, Panama with Sea Cloud Cruises

Windstar Cruises

Founded in the 1980s, Windstar Cruises got its start as a sailing ship line. While it now operates traditional motor-powered ships, too, voyages on sailing ships are still a big part of its business.

Three of the Seattle-based brand's six vessels — Wind Spirit, Wind Star and Wind Surf — are sailing vessels, and they all offer a similar yacht-like, small-ship experience.

Two of the three vessels (Wind Spirit and Wind Star) are particularly intimate, measuring 5,407 tons and carrying just 148 passengers with every berth full.

Related: The 2 types of Windstar ships, explained

The line's third sailing vessel, Wind Surf, is nearly three times the size at 14,745 tons. It's one of the biggest sailing ships in the world (only a sister vessel that sails for Club Med is bigger). Wind Surf carries 342 people, an enormous number for a sailing ship.

Unlike on the vessels operated by Sea Cloud, the sails on Windstar's sailing ships aren't unfurled by hand in the old-fashioned way but by the push of a button from the bridge. It's a fully automated system that is much more modern, if less dramatic.

Still, the experience of slicing through the waves by the power of the wind alone on Windstar ships is as glorious and romantic as it is on the Sea Cloud ships.

Windstar Cruises is less all-inclusive and pricey than Sea Cloud but still offers a relatively upscale experience. Its dining program is done in partnership with the food-focused James Beard Foundation, which also brings James Beard Award-winning chefs to the ships regularly for food-themed itineraries.

For an extra $89 per person per day, passengers can also make the experience more all-inclusive with included Wi-Fi, unlimited beer, wine and cocktails, and gratuities (three things that aren't included in regular fares).

The line's three vessels typically spend nearly all of their time sailing in the Mediterranean, the Caribbean or along the west coast of Central America.

Related: Read more about Windstar's itineraries

Star Clippers

Like Sea Cloud and Windstar, Star Clippers operates three sailing vessels that are among the biggest and most elegant sailing vessels in the world.

The belle of the ball at the line is Royal Clipper, a stunning five-masted ship that is billed as the largest square-rigged ship in the world. Its enormous array of 42 sails has a sail area of 56,000 square feet — significantly more than the sails atop any of the Sea Cloud or Windstar vessels. (Only Sea Cloud Spirit comes relatively close with a sail area of 44,100 square feet spread across 28 sails.)

Built to resemble Preussen, a legendary tall ship of the 19th century, the 24-year-old Royal Clipper shares the spotlight at Star Clippers with two smaller sister vessels, Star Flyer and Star Clipper.

Carrying 166 passengers apiece, the smaller vessels were designed to resemble the speedy clipper ships of the 19th century, which were known for their narrow profile and large sail area. Each vessel has a sail area of 36,000 square feet spread across 16 sails, a large amount for the size.

When it comes to the setting of sails, Star Clippers vessels offer a level of old-style authenticity that is in between the ships of Sea Cloud and Windstar. Like on Sea Cloud vessels, the sails are pulled into position by a team of deckhands using hand power and winches to tighten the "sheets," or ropes.

Unlike on Sea Cloud vessels, the deck hands don't climb high into the rigging to untie and prepare the sails for winching. That part is done automatically at the push of a button from the bridge, as it is on Windstar vessels.

In one key difference, though, Star Clippers lets passengers harness up and climb into the crow's nest of its vessels — a thrilling experience. Just be prepared for your knees to go a bit wobbly as you get to the top; it's way up there.

Star Clippers sailings are the most affordable option among the three sailing brands, in part because the onboard experience is less all-inclusive and upscale.

The three Star Clippers vessels mostly operate sailings in the Mediterranean, the Canary Islands, the Caribbean and along the west coast of Central America.

Bottom line

It's still possible to get a taste of what traveling the world's oceans was like in the days before motor power. Three small cruise companies — Sea Cloud Cruises, Windstar Cruises and Star Clippers — offer voyages on large sailing ships that are as majestic as anything that has sailed the seas in centuries past.

Planning a cruise? Start with these stories:

• The 5 most desirable cabin locations on any cruise ship
• A beginners guide to picking a cruise line
• The 8 worst cabin locations on any cruise ship
• The ultimate guide to what to pack for a cruise
• A quick guide to the most popular cruise lines
• 21 tips and tricks that will make your cruise go smoothly
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• The ultimate guide to choosing a cruise ship cabin

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