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Caribbean Small Ship Cruises

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A Caribbean cruise on a small ship or sailboat (Windjammer) is the best way to explore the turquoise waters, beaches, rich marine life and cultures of the Caribbean. The vessel you choose for your Caribbean cruise has a dramatic impact on the experience. On a small sailboat or small luxury ship with only 24-250 passengers aboard, you can access small coves, reefs and ports that are impossible on a huge cruise ship carrying hundreds or even thousands of passengers. Enjoy the serenity of sailing on a small sailboat like the Mandalay, Panorama, or the Liberty Clipper. Up the ante on a luxury small ship like the Variety Voyager, or new Le Champlain and Le Dumont-d'Urville by Ponant. Contact our Caribbean cruise experts today and escape the average Caribbean experience.
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10 Best Caribbean Small Ship Cruises for 2025-2026

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Top 3 Luxury Caribbean Small Ship Cruises for 2025-2026

Trip Name From Days Next Departure Summary
Pearls of the Caribbean $5,520 9 Dec 12, 2025 Join Le Bellot on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, St. George's, Saint Lucia, Soufrière and many more!
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Discover Eastern Caribbean & Grenadines $15,180 15 Nov 15, 2025 Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the locals as you hop between tropical paradises, creating unforgettable memories aboard the Emerald Sakara.
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Westbound Atlantic Ocean Crossing $4,820 25 Oct 29, 2025 Embark on a 25-day cruise aboard the Star Flyer, visiting Malaga, Gibraltar, Tangier, Cadiz, Safi, Arrecife, Puerto del Rosario, Las Palmas, San Sebastian, and Philipsburg. Explore historic sites, natural beauty, charming towns, golden beaches, and unique shopping experiences.
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8 Best Small Caribbean Cruise Ships & Sailboats for 2025-2026

Ship Name Max Passengers From Summary
Royal Clipper 227 $1,260 The Royal Clipper is the largest full-rigged sailing ship in the world, carrying just 227 privileged guests aboard. She offers the ultimate tall ship sailing experience, balancing the grandeur, adventure, and tradition of sailing with the superb service, amenities, and accommodations of the finest modern yacht. .
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Sea Cloud II 94 $7,990 The Sea Cloud II is a legendary windjammer comparable to her sister ship, the Sea Cloud. Featuring her own unique character, the Sea Cloud II combines the high standards expected of a 5-star cruise ship with the unique atmosphere of a romantic tall ship.
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Liberty Clipper 24 $0 The Liberty Clipper is a 125-foot beautifully renovated gaff-rigged schooner, a replica of the renowned Baltimore Clippers, made famous over a century ago for their speedy and safe rounding of Cape Horn on expeditions to the California Gold Rush. Her authentic design is exceeded only by a state-of-the-art galley, modern accommodations for up to 24 guests, and a beautifully adorned grand salon.
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Le Dumont-d'Urville 184 $5,520 Discover a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with environmentally-friendly equipment. Le Dumont-d'Urville features elegantly designed cabins, spacious suites with windows, and lounge areas opening to the outside, offering a unique cruising experience.
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Sea Cloud 64 $3,980 With occupancy for just 64 guests, the Sea Cloud is a modern and elegant windjammer outfitted with modern amenities and uniquely decorated cabins. Multiple decks allow you to enjoy the ambiance of the Mediterranean & Caribbean Seas in tranquility as the wind guides the journey.
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Mandalay 58 $0 On the s/v Mandalay, experience a Caribbean few others ever see or even dream of. Partake in raising the sails, take a turn at the helm or just enjoy the winds of the Caribbean sea filling the sails with new friends aboard. The choice is yours!
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Sea Cloud Spirit 136 $4,850 Sea Cloud Spirit is a modern and elegant windjammer with occupancy for 136 guests and a crew of 85. It gives you an amazing opportunity of traveling with a high comfort level and enjoying the best panorama views.
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Vela 26 $0 Her name means ?sail.? One look, and you?ll be taken back to a time when tall ships ruled the waves. Everything about Vela will light your imagination and inspire a sense of wanderlust. Newly refitted, Vela?s snug cabins all feature portholes and private bathrooms. Her teak decks are spacious and inviting with plenty of room to spread out.
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Variety Voyager 72 $3,490 The sleek & modern Variety Voyager is a state of the art mega-yacht which accommodates just 72 passengers in 36 cabins. Enjoy unobstructed views of the ocean & Cuba's charming ports, and onboard amenities including a spa, reception, bar, library, and lounge & dining areas with ample deck space. With five cabin options, the yacht guarantees comfort.
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Top Caribbean Cruise Deals for 2025 and 2026

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Caribbean Small Ship Cruising Guide & Travel Tips

Highlights of the Caribbean

The Lesser Antilles 
 are home to some of the most popular destinations in  the Caribbean, like the Virgin Islands, St. Lucia & St. Martin, where delightful cafes, tranquil towns, and serene beaches highlight the sea side scenery.

The Grenadines: 
Sail to Grenada, Bequia, Union Island, Mayreau, Tobago Cays, Carriacou, Sandy Island, Canouan and Happy Island; try some of the famous local Caribbean rum; relax on the beach; or participate in various land excursions.

The Bahamas: As you cruise through the Bahamas on a small sailboat, get into the groove of the laid back lifestyle of the islands, the culinary delights of the local cuisine, and perhaps even have a chance to try hoisting the sails or taking over the helm of your sailboat.

The Virgin Islands: Offer you some of the best snorkeling opportunities in the whole Caribbean, featuring crystal clear waters and diverse marine life, in addition to stops in charming port towns along the way, where you can get a taste of the local island culture.

The Panama Canal: In the far south of the Caribbean, see the breathtaking marvel that is the Panama Canal, when the greatest minds and thousands of dedicated workers labored internationally to connect the Atlantic & Pacific trade routes.
 

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.
What to Expect on a Luxury Caribbean Cruise
When you book a luxury Caribbean cruise aboard one of our hand-selected small ships, you are signing up for an unforgettable combination of comfort and service. 

We feature only small ships, yachts, and windjammers for our luxury Caribbean cruises, because we believe that this should be an intimate experience that you share with your loved ones, and that's exactly the ambiance the small ships offer. 

While each ship has a unique design, we guarantee elegance and style, in addition to comfortable and spacious suites - often with their own private balconies - and the best onboard amenities of any small Caribbean ships.

Luxury cruises offer all kinds of included activities to fill your days, but there are also add-on packages that can bring even more adventure and exploration to your itinerary. Plus there's plenty of free time built in to these cruises at each port so that you can simply relax on the beach and meander around the small towns if you prefer.
 

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.

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