Sail with the trade winds aboard a graceful tall ship, anchoring in the sheltered bays of the eastern Caribbean’s most captivating islands. Swim in warm, clear waters; wander through waterfront towns shaped by seafaring traditions; and follow rainforest trails into lush interiors. Explore historic forts, relax on palm-fringed beaches and experience the distinctive character of each island—from Dominica’s wild natural beauty to Guadeloupe’s French-inflected culture and the dramatic volcanic landscapes of St. Lucia. Along the way, settle into a relaxed rhythm that invites deeper connection with the region’s rich island heritage.
Highlights
Sail the sparkling Caribbean Sea aboard the romantic tall ship Sea Cloud II
Watch the crew go aloft in the rigging to handset 30 sails in a timeless sailing tradition
Experience a rich variety of landscapes, from rainforests and volcanic terrain to turquoise bays and palm-lined beaches
Explore historic sites, including Fort Shirley in Dominica and the 18th-century Fort Napoléon in Guadeloupe
Take in the beauty of St. Lucia’s iconic twin peaks, the Pitons, rising dramatically above the sea
From
$10,500
/ per person
Does not include any flights
View our brochure for more details
Explorations
From
$10,500
/ per person
View our brochure for more details
Explorations
From
$10,500
/ per person
View our brochure for more details
Explorations
Itinerary
Expedition
Download ItineraryStarts atBridgetown, BarbadosEnds atBridgetown, Barbados
Day 1
Bridgetown, Barbados / Embark Ship
Arrive in Barbados and settle into your cabin aboard the elegant Sea Cloud II. Cast off this evening as you enjoy dinner and your first Caribbean sunset.
Meals Included: Dinner
Day 1
Bridgetown, Barbados / Embark ShipArrive in Barbados and settle into your cabin aboard the elegant Sea Cloud II. Cast off this evening as you enjoy dinner and your first Caribbean sunset.
Meals Included: Dinner
Day 2
Under Sail / Bequia, Saint Vincent and the Grenadines
Begin the morning on deck, where the crew climbs aloft to raise the sails of Sea Cloud II by hand. Anchor at tiny Bequia by afternoon. Explore the charming waterfront and immerse yourself in this unique maritime culture. Swim along palm-fringed beaches or join the expedition team to visit a traditional model boat museum. In Port Elizabeth, browse the local market and stroll the waterfront Belmont Walkway.
Meals Included: Breakfast, Lunch, Dinner
Day 2
Under Sail / Bequia, Saint Vincent and the GrenadinesBegin the morning on deck, where the crew climbs aloft to raise the sails of Sea Cloud II by hand. Anchor at tiny Bequia by afternoon. Explore the charming waterfront and immerse yourself in this unique maritime culture. Swim along palm-fringed beaches or join the expedition team to visit a traditional model boat museum. In Port Elizabeth, browse the local market and stroll the waterfront Belmont Walkway.
Meals Included: Breakfast, Lunch, Dinner
Day 3
Union Island
Just three miles long and one mile wide, Union Island is nicknamed "the Tahiti of the West Indies" due to its dramatic volcanic silhouette. After a day at sea, stretch your legs with a walk along the beach at Chatham Bay, go for a swim in the surrounding turquoise waters and admire Sea Cloud II anchored off the coast. Enjoy a BBQ lunch on the bay and indulge in some local flavors before setting sail this afternoon.
Meals Included: Breakfast, Lunch, Dinner
Day 3
Union IslandJust three miles long and one mile wide, Union Island is nicknamed "the Tahiti of the West Indies" due to its dramatic volcanic silhouette. After a day at sea, stretch your legs with a walk along the beach at Chatham Bay, go for a swim in the surrounding turquoise waters and admire Sea Cloud II anchored off the coast. Enjoy a BBQ lunch on the bay and indulge in some local flavors before setting sail this afternoon.
Meals Included: Breakfast, Lunch, Dinner
Day 4
Under Sail
Enjoy a full day under sail on the Caribbean Sea. Relax with a book, photograph the ship's exquisite details and attend talks by experts on the natural wonders and cultures of the islands that await.
Meals Included: Breakfast, Lunch, Dinner
Day 4
Under SailEnjoy a full day under sail on the Caribbean Sea. Relax with a book, photograph the ship's exquisite details and attend talks by experts on the natural wonders and cultures of the islands that await.
Meals Included: Breakfast, Lunch, Dinner
Day 5
Terre-de-Haut, Îles des Saintes, Guadeloupe
Distinctly French in character and culture, Terre-de-Haut charms with colorful houses and bustling island life. Enjoy postcard views from Fort Napoléon, with its cactus garden, iguanas and maritime museum. Then stroll through the French colonial town center and swim from a nearby sandy beach.
Meals Included: Breakfast, Lunch, Dinner
Day 5
Terre-de-Haut, Îles des Saintes, GuadeloupeDistinctly French in character and culture, Terre-de-Haut charms with colorful houses and bustling island life. Enjoy postcard views from Fort Napoléon, with its cactus garden, iguanas and maritime museum. Then stroll through the French colonial town center and swim from a nearby sandy beach.
Meals Included: Breakfast, Lunch, Dinner
Day 6
Dominica
Spend the day exploring Dominica, known as “the Nature Island” of the Caribbean for its untamed beauty and many protected reserves. Hike through lush rainforest, then join a historian in exploring the ruins of Fort Shirley, an 18th-century British garrison, to learn about Dominica's turbulent colonial history. Enjoy a sunset cocktail at the fort or go for a refreshing swim before casting off.
Meals Included: Breakfast, Lunch, Dinner
Day 6
DominicaSpend the day exploring Dominica, known as “the Nature Island” of the Caribbean for its untamed beauty and many protected reserves. Hike through lush rainforest, then join a historian in exploring the ruins of Fort Shirley, an 18th-century British garrison, to learn about Dominica's turbulent colonial history. Enjoy a sunset cocktail at the fort or go for a refreshing swim before casting off.
Meals Included: Breakfast, Lunch, Dinner
Day 7
Soufrière, Saint Lucia / Under Sail
Arrive at St. Lucia and anchor under the island's iconic twin peaks, the Pitons, which rise dramatically above the sea. After exploring the fishing port of Soufrière, drive into St. Lucia's volcanic caldera and discover the otherworldly landscape of mud pools and sulfur springs. Visit the tropical Mamiku botanical gardens—backed by the gorgeous Diamond Falls—and delve into the grounds’ complex history, which dates back to the reign of Louis XIV. Weather permitting, set sail as the winds fill the sails in a glorious spectacle. Enjoy the captain’s farewell reception and dinner to celebrate the end of a fantastic voyage.
Meals Included: Breakfast, Lunch, Dinner
Day 7
Soufrière, Saint Lucia / Under SailArrive at St. Lucia and anchor under the island's iconic twin peaks, the Pitons, which rise dramatically above the sea. After exploring the fishing port of Soufrière, drive into St. Lucia's volcanic caldera and discover the otherworldly landscape of mud pools and sulfur springs. Visit the tropical Mamiku botanical gardens—backed by the gorgeous Diamond Falls—and delve into the grounds’ complex history, which dates back to the reign of Louis XIV. Weather permitting, set sail as the winds fill the sails in a glorious spectacle. Enjoy the captain’s farewell reception and dinner to celebrate the end of a fantastic voyage.
Meals Included: Breakfast, Lunch, Dinner
Day 8
Bridgetown, Barbados / Disembark Ship
Disembark Sea Cloud II after breakfast for flights home.
Meals Included: Breakfast
Day 8
Bridgetown, Barbados / Disembark ShipDisembark Sea Cloud II after breakfast for flights home.
Meals Included: Breakfast
Minimum Age Requirement: Any children booked on Sea Cloud II voyages must be at least 1 year old at time of embarkation.
Ships
Sea Cloud II
GUESTS 88
CABINS 44
DECKS 4
Sea Cloud II is an alluring sailing vessel perfectly suited to travel the scenic shores of the Mediterranean, exploring little-seen archipelagos and anchoring in small coves.
Expedition Team
Our captains, crew, staff and guides make up the most experienced team in the industry—committed to making every voyage unforgettable. Veteran captains, with decades at sea, are experts at navigating in all conditions, while seasoned naturalists bring advanced knowledge in fields such as geology, wildlife biology and climate science. Many of these professionals have been with us for decades, and their insights bring each destination to life in ways that profoundly enrich your journey. Their expertise is the foundation for the meaningful and transformative experiences we offer in the world’s most extraordinary places.
Special Offers
CELEBRATE LIFE'S MILESTONES
10% OFF BACK-TO-BACK VOYAGES
SAVE 10% WHEN YOU SAIL WITH A GROUP OF SIX OR MORE
COMBINING OFFERS
View our brochure for more details
Explorations