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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 2024-2025

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Top 10 Luxury Caribbean Small Ship Cruises for 2024-2025

Trip NameFromDaysNext DepartureSummary
Sailing the Caribbean$118308Jun 19, 2025Experience the Caribbean in the most authentic way under the 30 white sails of Sea Cloud on this 8-day round trip cruise of Barbados. As you delight …
Windward Islands$17008Dec 14, 2024Board the luxurious Royal Clipper sailing ship for this 8-day roundtrip cruise of the Caribbean, departing from Bridgetown, Barbados to St. Lucia, …
Pearls of the Caribbean$54309Nov 4, 2024Join the Le Champlain on its 9-day sailing expedition to explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, Bequia Island …
Barbados to Panama$444015Nov 2, 2024Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to …
Classic Yachtsman Caribbean$17008Nov 30, 2024Royal Clipper offers the ultimate sea-going experience as you travel to the beautiful beaches and landscapes of the Caribbean. This 8-day sailing …
Panama to Antigua$444015Nov 16, 2024Starting in Balboa, Panama, sail through warm Caribbean waters as you make your way to the Antigua aboard the Royal Clipper. Over the course of 15 …
Cruising the Leeward Islands$102708Nov 30, 2024Embark on an 8-day Cruising the Leeward Islands aboard Emerald Sakara from Marigot roundtrip. Explore Anguilla, Virgin Gorda, and other stunning …
Enjoy Caribbean Rhythms at the Turn of the Year$1159515Dec 20, 2024Explore the best of the Caribbean on this cruise aboard the Sea Cloud. From the Dutch Colonial port town of Philipsburg, sail to the British Virgin …
The Essential of the Caribbean$815013Dec 17, 2024Sail the lovely seas of the Caribbean roundtrip from Fort-de-France to discover the stunning islands of Antigua, Jost van Dyke, Gustavia, and …
A Colorful Caribbean Time-Out$75008Jan 10, 2025Embark on an 8-day cruise aboard Sea Cloud Spirit sailing to explore Old San Juan's historic charm. Wander streets lined with colorful facades and …

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8 Best Small Caribbean Cruise Ships & Sailboats for 2024-2025

Ship NameMax PassengersFromSummary
Royal Clipper227$1700The Royal Clipper is the largest full-rigged sailing ship in the world, carrying just 227 privileged guests aboard. She offers the ultimate tall ship …
Sea Cloud II94$10995The Sea Cloud II is a legendary windjammer comparable to her sister ship, the Sea Cloud. Featuring her own unique character, the Sea Cloud II …
Le Dumont-d'Urville184$4840Discover a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with …
Sea Cloud64$6995With occupancy for just 64 guests, the Sea Cloud is a modern and elegant windjammer outfitted with modern amenities and uniquely decorated cabins. …
Sea Cloud Spirit136$7500Sea 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 …
Variety Voyager72$3490The sleek & modern Variety Voyager is a state of the art mega-yacht which accommodates just 72 passengers in 36 cabins. Enjoy unobstructed views of …

Top Caribbean Cruise Deals for 2024 and 2025

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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.

Video: Sailing the Caribbean on a Small Ship Cruise

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