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Sailing the Caribbean

Caribbean Sailing Cruise

  • Sea Cloud
  • Sailing Vessel
  • 58 Capacity
  • 8 Days
  • 2020 View Departure>
    • 2020
    • Feb 14 Fri Offer
    • Feb 21 Fri Offer
    • Feb 28 Fri Offer
  • Price from
  • $8,990
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Summary : While there are many ways to travel the Caribbean, you’ll find that exploring aboard an authentic square-rigger tall ship offers an unrivaled experience and guarantees you an in-depth encounter with all its wonders. The 58-guest Sea Cloudis an extraordinary, historic yacht that will enable you to experience the power of sailing aboard a four-masted, 30-sail tall ship and sail into smaller, lesser-known ports and anchorages of the “old Caribbean”. Explore the islands’ wildlife, cultures, and the undersea, too, and enjoy the relaxed pace of Caribbean life and traveling by private sailing yacht.

Activities : Birding, Child-Friendly, Culture, Hiking, Snorkeling


Just-Released Offer

  • Free bar tab and crew tips

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Prices from
$8,990 to $17,690

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Day 1
U.S. / Barbados / Embark

Arrive in Barbados and settle into your cabin aboard the elegant Sea Cloud. Cast off this evening, and enjoy dinner and your first Caribbean sunset.

Day 2
Under Sail

Begin the morning on deck, where sailors climb aloft to raise the Sea Cloud’s sails by hand. Enjoy a full day under sail across the Caribbean. Relax with a book, photograph the ship’s exquisite details, and attend talks by your experts on the natural history and culture of the islands you will soon explore.

Day 3

Spend the day exploring Dominica, known as “the nature island” for its spectacular beauty and many protected reserves. Hike through enchanting rain forest. Join our historian in exploring the ruins of Fort Shirley, an 18th-century British garrison, and learn about Dominica’s turbulent colonial history. Go for a refreshing swim before casting off for a sunset seen from the sea.

Day 4
Îles des Saintes / Under Sail

Distinctly French in character and culture, the shops, homes and people of Les Saintes are colorful, tasteful and delightful. Enjoy picture-postcard views from Fort Napoléon, with its cactus garden, iguanas and maritime museum. Then stroll through French colonial Terre-de-Haut and swim and snorkel from a nearby sandy beach. In the afternoon, set sail south on a beam reach, as the winds fill the square sails in a glorious spectacle.

Day 5
Under Sail / Bequia, the Grenadines

Sail aboard your magnificent ship in the morning and anchor at tiny Bequia by afternoon. Explore the charming waterfront and immerse yourself in this unique maritime culture. Go snorkeling at a nearby reef, swim along palm-backed beaches, or join your staff to visit a traditional model boat museum. In Port Elizabeth, you’ll find local crafts, markets, and one of the best bookstores in the West Indies.

Day 6
Under Sail / Exploring the Grenadines

Spend the morning aboard Sea Cloud under sail, exploring the idyllic Grenadine Islands, with their quintessential tropical cays. You’ll have options to snorkel among myriad colorful fish, or enjoy the sheltered white-sand beaches of the area.

Day 7
Les Pitons, St. Lucia / Under Sail

Arrive at St. Lucia and anchor under the island’s iconic twin peaks, Les Pitons, which rise dramatically above the sea. After exploring the fishing port of Soufrière, drive into St. Lucia’s active volcanic crater and discover the otherworldly landscape of mud pools and sulfur springs. Take a tropical walk through botanical gardens alive with birds and the backdrop rush of Diamond Falls. Spend the afternoon sailing as you return to Barbados.

Day 8
Barbados / Disembark / Home

Disembark, tour the island, and transfer to the airport for your return flight.


This itinerary is subject to change. ExpeditionTrips is not responsible for itinerary changes.

Accommodations aboard ship; meals and non-alcoholic beverages aboard ship; shore excursions as per itinerary; transfers to and from group flights; use of snorkeling equipment and wetsuits; port charges and service taxes; services of expedition staff. Subject to change without notice.

Not Included:
Air transportation; extensions; passport, visa, and immigration fees; travel protection plan; items of a personal nature, such as alcoholic beverages, Internet access, and laundry; gratuities to ship's crew are at your discretion.

Photos ©: Lindblad Expeditions

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