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Sailing the Caribbean

Caribbean Sailing Cruise

Summary : Stand on deck as Sea Cloud’s 30 white sails fill with wind, and measure the passage of time by a distant island’s approach on the horizon. The reliability of the trade winds in the Caribbean makes this an ideal place to explore under sail. While there are many ways to experience the Caribbean, you’ll find that exploring aboard an authentic square-rigged tall ship offers an unrivaled experience and guarantees you an in-depth encounter with all its wonders.

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


Just-Released Offer Receive complimentary bar tab and crew gratuities.

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Prices from
$8,640 to $17,000

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Day 1

Embark the Sea Cloud in the late afternoon and begin your voyage in the Caribbean. (D)

Day 2
Under Sail

Discover one of the great pleasures of travel anywhere: sailing aboard the barque, seeing the crew go aloft unfurling the sails the traditional way — by hand — as you sail the trade winds. This is a wonderful opportunity to enjoy the many amenities of this unique sailing vessel.

Day 3

Dominica is called the "Nature Island" because of its beauty and many reserves. Dock at historic Prince Rupert Bay, where sailing ships of all flags put in for water, citrus fruits, and solid timber after a long Atlantic crossing. In the morning, drive through a succession of tropical ecosystems and fruit plantations into the Morne Diablotin National Park and rain forest. See spectacular canopy trees with buttress roots and liana vines, home to Dominica's two endemic parrots. After lunch, join an historian for a walk up to beautifully restored Fort Shirley, where English cannons protected the strategic bay below. Then, snorkel in the warm, clear Caribbean waters.

Day 4
Under Sail / Exploring the Grenadines

In the morning, enjoy a rousing sail through the idyllic Grenadines, pass Mustique, Canouan, Tobago Cay, Mayreau, and Union Islands. Anchor in one of the lovely white-sand arcing beaches that are the quintessential image of a Caribbean bay, with protected waters for easy swimming and snorkeling. A few local beach bars with colorful Caribbean names and friendly characters complete the scene.

Day 5
Bequia, The Grenadines / Under Sail

With a historical mix of Scottish indentured servants, buccaneers, whalers, and mariners, Bequia has a maritime culture unlike any other. Scrimshaw and model-boat building endure in this long-time sailors' watering hole. Get to know the local Bequians on a short drive around the island in covered pick-up trucks, stop at a view with gorgeous overlooks and at a very interesting local hawksbill turtle revival initiative. In Port Elizabeth find local crafts, the Rastafarian fruit and vegetable market, elegant Belmont Walk and one of the best bookstores in the West Indies. A good swim, snorkel, and tropical beach are a short walk or Zodiac ride away, near the local beach bar. In the afternoon, set sail across St. Vincent Channel.

Day 6
Soufriere and Les Pitons, St. Lucia / Under Sail

Anchor under the iconic twin peaks of St. Lucia, called "Les Pitons." There is no more iconic image of the Windward Island than these famed mountains. Beneath Petit Piton at the port of Soufriere, explore the active crater and the geologic origins of the region. Take a delightful walk through the local botanical gardens that are fed by mineral-rich hot spring runoff. The gardens are a gallery of tropical blooms and color, alive with hummingbirds, bullfinches, and the backdrop rush of Diamond Falls. Return to Sea Cloud to weigh anchor and spend the afternoon sailing. Conditions permitting, lower into a Zodiac and get great photographs of Sea Cloud.

Day 7
Iles des Saintes / Under Sail

Distinctly French in character and culture, the shops, homes, and people of Les Saintes are full of taste and flavor. Enjoy picture-postcard views from Fort Napoleon, 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 for Guadeloupe Channel for a short but powerful downwind sail, as the winds fill the square sails in a glorious spectacle.

Day 8

Disembark Sea Cloud this morning in Antigua. For those with afternoon departure flights, there will be a morning tour of the island, visiting historic Shirley Heights and Nelson's Dockyard. Enjoy an included light lunch before transferring to the airport for flights home. (B,L)


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

Special Photo Expedition: 3/22/2018
Join National Geographic photographer Susan Seubert on board for this special photo expedition. Her work has been recognized by the department of journalism at Columbia University with an Alfred Eisenstadt Award and most recently by the North American Travel Journalists Association for excellence in photography. In addition to being widely published and exhibited, she also lectures regularly about her work at such institutions as Harvard University and the Portland Art Museum. 

Certified Photo Instructor:
On all departures, a certified photo instructor will be at your side and at your service to inspire and assist you. Take advantage of talks, presentations, slideshows and “laptop gallery” sharing events. All skill and interest levels are welcome; the instructors can meet you wherever you are on your journey. All you need to participate is a camera— point-and-shoot, smartphone, DSLR, whatever—and a sense of adventure. And you’re sure to return home with amazing photos.

Accommodations aboard ship; meals and non-alcoholic beverages aboard ship; shore excursions; sightseeing and entrance fees; special access permits; transfers to and from group flights; use of snorkeling equipment and wet suits; gratuities (except to ship’s crew); taxes and service charges; services of a ship physician on most voyages; services of expedition staff. Subject to change without notice.

Not Included:
Air transportation; extensions; passport, visa, and immigration fees; scuba diving (where available); meals not indicated; 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.

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