Sail the eastern Caribbean aboard the elegant Sea Cloud II, exploring a broad sweep of islands shaped by volcanic landscapes, colonial history and vibrant local cultures. From the intimate harbors of the Grenadines to French-influenced Guadeloupe, historic St. Kitts, wild Dominica and the dramatic coastline of St. Lucia, each destination reveals a distinct facet of the region. Unhurried days at sea beneath billowing sail allow the timeless rhythm of tall-ship life to unfold, while each island visit blends cultural discovery with the Caribbean’s extraordinary natural beauty. Together, these experiences create a richly varied journey through the eastern Caribbean.
Highlights
Experience life aboard the tall ship Sea Cloud II, where classic sailing traditions meet modern comforts
Witness the crew hand-set towering sails, bringing centuries-old maritime practice vividly to life
Explore a broad spectrum of Caribbean cultures, landscapes and histories across multiple island nations
Visit historic fortresses, colonial towns and UNESCO World Heritage sites that shaped the region’s past
Discover diverse natural environments—from rainforests and volcanic peaks to coral bays and palm-lined beaches
Immersive shore experiences are balanced with relaxed days under sail, leaving time to savor the passage between islands
From
$13,000
/ per person
Does not include any flights
View our brochure for more details
Explorations
From
$13,000
/ per person
View our brochure for more details
Explorations
From
$13,000
/ 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
Basseterre, Saint Kitts and Nevis
With its mountainous interior and rugged coastline of sheltered bays, St. Kitts is a striking island with a relaxed, local character. Spend the morning exploring Brimstone Hill Fortress, a UNESCO World Heritage site, along with the gardens of Romney Manor and a traditional Caribbean batik workshop. In the afternoon, stroll the historic streets of Basseterre or take a refreshing dip in the warm Caribbean waters.
Meals Included: Breakfast, Lunch, Dinner
Day 6
Basseterre, Saint Kitts and NevisWith its mountainous interior and rugged coastline of sheltered bays, St. Kitts is a striking island with a relaxed, local character. Spend the morning exploring Brimstone Hill Fortress, a UNESCO World Heritage site, along with the gardens of Romney Manor and a traditional Caribbean batik workshop. In the afternoon, stroll the historic streets of Basseterre or take a refreshing dip in the warm Caribbean waters.
Meals Included: Breakfast, Lunch, Dinner
Day 7
Under Sail
While sailing between islands, enjoy impeccable service and cuisine and deepen your understanding of the region with lectures from your expedition team. On the Lido Deck, settle into comfortable steamer chairs with a drink in hand and watch the crew adeptly navigate clear waters as you relax in the warm, balmy breeze.
Meals Included: Breakfast, Lunch, Dinner
Day 7
Under SailWhile sailing between islands, enjoy impeccable service and cuisine and deepen your understanding of the region with lectures from your expedition team. On the Lido Deck, settle into comfortable steamer chairs with a drink in hand and watch the crew adeptly navigate clear waters as you relax in the warm, balmy breeze.
Meals Included: Breakfast, Lunch, Dinner
Day 8
Dominica
Spend the day exploring Dominica, known as “the Nature Island” 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 8
DominicaSpend the day exploring Dominica, known as “the Nature Island” 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 9
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 9
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 10
Bridgetown, Barbados / Disembark Ship
Disembark Sea Cloud II after breakfast for flights home.
Meals Included: Breakfast
Day 10
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
COMBINING OFFERS
10% OFF BACK-TO-BACK VOYAGES
View our brochure for more details
Explorations