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Pelicans hanging out in the ocean

Sailing the Caribbean

Example 8 Day Cruise aboard Sea Cloud
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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. Join this extraordinary and historic yacht for an 8-day voyage that brings you into lesser-known ports of the "Old Caribbean" and offers the relaxed pace of Caribbean life.
Snorkelling the warm watersRelax on the beach or take a boat outDock going out into the crystal blue oceanA small island sits out in the crystal clear waters of the sea.Pelicans hanging out in the ocean
Highlights
  • Experience the power of sailing aboard a four-masted, 30-sail tall ship
  • Sail into smaller, lesser-known ports and anchorages of the “old Caribbean”
  • Explore the islands’ wildlife, cultures, and the undersea, too
  • Enjoy the relaxed pace of Caribbean life by private sailing yacht
Activity Level: Relaxed
Involves minimal physical effort and is typically associated with leisurely activities. Activities are low-intensity or last less than a few hours each day.
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Full Itinerary

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Day 1: Barbados | Embark

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

Day 2: Under Sail

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
You have the day to enjoy one of the great pleasures of travel anywhere: sailing aboard our authentic barque, seeing the crew go aloft unfurling the sails the traditional way—by hand—as you ride the trade winds. Watch as the crew climbs the rigging and trims the Sea Cloud's 32,000 square feet of canvas, and follow the action with sail plan in hand. This is surely one of the best ways possible to learn about the art and science of sailing, and a wonderful opportunity to enjoy the many amenities of this historic tall ship. 

Day 3: Dominica

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
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 rainforest. The spectacular canopy trees with their buttress roots and liana vines are home to Dominica’s two endemic parrots, which we hope to see or hear on your rainforest hike. After lunch, join our historian for a walk up to beautifully restored Fort Shirley, where English cannons protected the strategic bay below. You’ll also have your first opportunity to snorkel in the warm, clear Caribbean waters. 

Day 4: Îles des Saintes | Under Sail

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
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 sails in the Guadeloupe Channel for a short but powerful downwind reach, as the winds fill the square sails in a glorious spectacle. 

Day 5: Under Sail | Bequia, the Grenadines

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
In the morning, sail aboard our magnificent ship, and in the afternoon, visit Bequia. 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. You’ll get to know the local Bequians on a short drive around the island in covered pick-up trucks, stopping at a view with gorgeous overlooks and at a very interesting local hawksbill turtle revival initiative. In Port Elizabeth, you’ll 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. 

Day 6: Under Sail | Exploring the Grenadines

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
In the morning, enjoy a rousing sail through the idyllic Grenadines, passing Mustique, Canouan, Tobago Cay, Mayreau and Union Islands. You’ll then 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, and a few local beach bars with colorful Caribbean names and characters completing the scene. 

Day 7: Les Pitons, St. Lucia | Under Sail

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
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 the ship returns to Barbados. 

Day 8: Barbados | Disembark

  • 1 Breakfast, 1 Lunch
Disembark, tour the island, and transfer to the airport for your return flight

Ship/Hotel

Sea Cloud

Relax on the sun deck of the Sea Cloud.
Sea Cloud's beautiful interior.
Sea Cloud's beautiful ship exterior.

Dates & Prices

My Preferred Start Date

Per person starting at
$11,830
Rates are subject to change without notice. Book early to get the best rate.
Relax in the Sea Cloud's comfortable cabins.
Select a Date
Category 1
Cabins 28-29 on Promenade Deck. Cabins have two single beds, a window and private bath facilities.
Sea Cloud's Category 1S Cabin.
Select a Date
Category 1S
Cabins 16-17, Promenade Deck. Upper and lower single beds, window. These cabins once housed the ship's officers.
Relax in the Sea Cloud's comfortable cabins.
Select a Date
Category 2
Cabins 18-25 on the Promenade Deck. Cabins have two single beds, a window and private bath facilities.
Relax in the Sea Cloud's comfortable cabins.
Select a Date
Category 3
Cabins 32-37 on Captain's Deck. Cabins have two single beds, a window and private bath facilities.
Sea Cloud's Category 1-4 Cabins.
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Category 4
Cabins 30-31, Captain's Deck. Cabins have a queen bed, forward-facing window and private bath facilities.
Sea Cloud's Category B Cabin.
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Category B
Deluxe Cabins 3-10, Main Deck. Large original cabins have a mix of bed types and decor motifs. All have portholes.
Sea Cloud's Category A Cabin.
Select a Date
Category A
Deluxe Cabins 3-10, Main Deck. Large original cabins have a mix of bed types and decor motifs. All have portholes.
Sea Cloud's Owner's Suite.
Select a Date
Category OS
Original owners suites 1-2, Main Deck. King sized beds, grand marble bathrooms with bathtubs.

Notes

Rates are capacity-controlled and are subject to change without notice.
Included
  • 7 Breakfasts, 7 Lunches, 7 Dinners
  • 7 Nights Accommodations
  • Accommodations as listed
  • Ground transportation as listed
  • Activities as listed
  • Meals as listed
  • Access to a 24-7 Emergency line while traveling
  • All airport transfers mentioned in the itinerary.
  • Use of snorkeling equipment, wet suits, and kayaks (where available)
  • Services of the expert expedition team and guest speakers
  • Shore excursions, sightseeing, entrance fees, and special access permits
  • Taxes, service charges, and tips (except for ship’s crew, at guests’ discretion)
Excluded
  • Gratuities
  • Travel Insurance
  • Personal Expenses
  • Flight costs (please request a quote)
  • Additional excursions during free time
  • Fuel and transportation surcharges (when applicable)
  • Additional Hotel Nights 
  • Private Transfers
  • Expedition Extensions 
  • Laundry 
  • Air transportation (except when indicated in the itinerary, as included)
  • Passport, visa, and immigration fees
  • Special and unique excursions such as scuba diving, flightseeing, etc. (where offered)
  • Alcoholic beverages (alcohol is included on select ships)
  • Items of personal nature
  • Phone and Internet Service
  • Gratuity for ship’s crew, at guests’ discretion (crew tips are included on select ships
  • We strongly recommend our guests to take Travel Protection Plan. A Plan with comprehensive coverage to protect you from cancellation fees, costs incurred due to trip delays/interruption, damaged or lost baggage, medical assistance, and evacuation during your travels

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The trip was terrific with great planning on your part. Most of the adventures were not mainstream and somewhat off the beaten path which made it especially enjoyable!! We felt taken care of and you all were readily available to respond to questions and issues. I would highly recommend your company and friends have already expressed interest based on our pictures and excitement.
Gale Cantor

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