Caribbean Small Ship Cruises
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Small Caribbean cruises or sailboats (Windjammer) are the best way to explore the turquoise waters, beaches, rich marine life and cultures of the Caribbean. The vessel you choose for your small ship 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 the Star Flyer, Royal Clipper, or the Star Clipper. Up the ante on a luxury small ship like the Emerald Sakara or Le Ponant. Contact our experts on small Caribbean cruises today and escape the average Caribbean experience.
| Trip Name | From | Days | Next Departure | Summary |
|---|---|---|---|---|
| Caribbean Yachting Hideaways | $8,390 | 8 | Dec 20, 2025 | Set sail on an 8-day cruise from San Juan to St. John aboard the Emerald Azzurra, exploring stunning beaches and vibrant island towns. Visit highlights like Culebra, Vieques, and Saint Barthelemy while enjoying premium comfort and seamless access to diverse ports. |
| Caribbean Yachting Discovery | $7,990 | 8 | Dec 13, 2025 | Set sail on an 8-day cruise aboard the Emerald Azzurra, uncovering pristine beaches and vibrant coral reefs while island-hopping through a tapestry of diverse cultures. Let the genuine warmth of the locals add a personal touch to your luxurious yacht adventure. |
| Caribbean Yachting Discovery | $8,390 | 8 | Mar 07, 2026 | Embark on an 8-day Caribbean cruise aboard Emerald Azzurra from Antigua to St. Thomas. Explore vibrant ports like Barbuda, Illes des Saintes, and Virgin Gorda. Discover unique sites such as Norman Island’s caves and the markets of Guadeloupe. Travel aboard a luxury yacht, exploring beaches, history, and local culture at each stop. |
| 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! |
| Discover Eastern Caribbean & Grenadines | $21,340 | 15 | Dec 06, 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. |
| 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. |
| Sounds of Discovery: New York to the Bahamas | $24,990 | 13 | Sep 28, 2027 | Experience a 13-day cruise from New York City to Nassau aboard the Scenic Eclipse, featuring stops in Bermuda, Turks and Caicos, San Salvador, Bimini, and Miami. This journey blends culture, history, and relaxation. |
| Pristine Islands of the Bahamas & the Panama Canal | $24,990 | 11 | Oct 16, 2026 | Join an 11-day cruise from Nassau to Panama City on the Scenic Eclipse, exploring the Bahamas' clear waters and vibrant island cultures. Experience highlights like Pig Beach and the Panama Canal, blending leisure with cultural discovery. |
| 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. . |
| 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. |
| 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. |
| Le Dumont-d'Urville | 184 | $6,230 | 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. |
| Sea Cloud | 64 | $9,135 | 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. |
| 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! |
| 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. |
| 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. |
| 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. |
Small ship cruises (Caribbean style, like a Windjammer) is the best way to explore turquoise waters, beaches, marine life, and coastal towns. Unlike large cruise ships, small vessels (typically with 24–250 passengers) can access hidden coves, quiet reefs, and smaller ports that big ships can't reach—giving you a more personal and unique experience.
The best months to be on small cruise ships in the Caribbean are from December to April, when the weather is mostly sunny, dry, and ideal for sailing. These months offer mild temperatures and calm seas, making them the most popular time to travel. Just note that prices and crowds may be higher, especially on large ships. Most Caribbean small ship cruises also run during this season—contact us to learn more about availability and options.
The average cost of many 7-day Caribbean small ship cruises vary based on several factors, depending on the cruise line, cabin type, and amenities included. Our luxury cruises offering premium services, upscale accommodations, and exclusive perks are priced higher than mid-range or 4-star options. Contact our trip specialists for a precise quote based on the vessel and Caribbean small ship cruises you are interested in.
