Caribbean Tours in 2026

from $7,990

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Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Sakara

• Discover Anguilla’s coral coast
• Explore Gustavia’s boutiques
• Wander Nevis seaside buildings
• Visit Antigua’s English Harbor

Starts / Ends

Marigot / Bridgetown

Activity Level

Variable

Embark on an 8-day Caribbean cruise aboard Emerald Sakara. Discover Anguilla’s pristine beaches, Gustavia’s vibrant streets, Nevis' historic charm, Saint Kitts’ stunning nature, Falmouth Harbor’s historical docks, Îles des Saintes’ picturesque islands, and Barbados’ lively culture. Experience crystal-clear waters, vibrant local culture, and luxurious amenities throughout your cruise

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from $2,030

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Windward Islands

Roundtrip Barbados - 8 Day Itinerary aboard Royal Clipper

• Explore beaches in Barbados
• See lush island of St. Lucia
• Discover Falmouth Harbour, Antigua
• Visit sophisticated Martinique

Starts / Ends

Bridgetown / Bridgetown

Activity Level

Variable

Sail aboard the Royal Clipper on an 8-day journey through vibrant Caribbean islands, pristine beaches, and rich history. Highlights include Dominica’s lush Cabrits National Park, Antigua’s Falmouth Harbor, and Martinique’s stunning shores.

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from $7,990

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Grenadines & Windwards Yachting

Roundtrip Bridgetown - 8 Day Itinerary aboard Emerald Sakara

• Discover Bequia’s secluded beaches
• Savor Caribbean dining experiences
• Snorkel Tobago Cays' waters
• Admire panoramic views from Mayreau

Starts / Ends

Bridgetown / Bridgetown

Activity Level

Variable

Embark on an 8-day cruise aboard the Emerald Sakara, starting and ending in Bridgetown, Barbados. Explore historic towns, relax on stunning beaches, and enjoy snorkeling and water activities in the picturesque Saint Vincent and the Grenadines.

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from $9,990

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Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra

• Soak in Soufriere’s volcanic spring
• Explore Les Saintes’ French charm
• Visit Antigua’s Nelson’s Dockyard
• Stroll Nevis’ Georgian towns

Starts / Ends

Bridgetown / Marigot

Activity Level

Variable

Set sail on an 8-day cruise aboard the Emerald Azzurra, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.

Cruise Details

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from $7,990

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Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Sakara

• Explore Soufriere coral reefs
• Visit Iles des Saintes towns
• Discover Falmouth Harbor dockyard
• Experience Charlestown’s Nevis

Starts / Ends

Bridgetown / Marigot

Activity Level

Variable

Set sail on an 8-day cruise aboard the Emerald Sakara, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.

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from $11,070

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Cruising the Leeward Islands

Marigot Roundtrip - 8 Day Itinerary aboard Emerald Sakara

• Explore Virgin Gorda’s iconic Baths
• Swim Norman Island coves
• Unwind Jost van Dyke beach
• Stroll Anegada’s quiet beaches

Starts / Ends

Marigot / Marigot

Activity Level

Variable

Set sail on an 8-day cruise from Marigot, Saint Martin, aboard the Emerald Sakara, visiting stunning destinations like Anguilla and Virgin Gorda. Enjoy snorkeling, exploring grottoes, and embracing the relaxed island lifestyle amidst breathtaking coastal views.

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from $8,390

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Caribbean Yachting Hideaways

San Juan - St John's - 8 Day Itinerary aboard Emerald Azzurra

• Discover Culebra Island’s shores
• Explore Vieques Island waterfront
• Tour St. John’s Annaberg ruins
• Relax on Jost Van Dyke’s White Bay

Starts / Ends

San Juan / St. John's

Activities

Hiking

Activity Level

Variable

Set sail on an 8-day cruise from San Juan to St. John aboard the Emerald Azzurra, exploring stunning beaches and vibrant island towns. Visit highlights like Culebra, Vieques, and Saint Barthelemy while enjoying premium comfort and seamless access to diverse ports.

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from $8,390

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Caribbean Yachting Discovery

St John's - San Juan - 8 Day Itinerary aboard Emerald Azzurra

• Explore Barbuda's pink beaches
• Discover Deshaies’ architecture
• Visit Gustavia’s charming boutiques
• Experience Virgin Gorda’s baths

Starts / Ends

St. John's / San Juan

Activity Level

Variable

Set sail on an 8-day cruise aboard the Emerald Azzurra, uncovering pristine beaches and vibrant coral reefs while island-hopping through a tapestry of diverse cultures. Let the genuine warmth of the locals add a personal touch to your luxurious yacht adventure.

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from $6,995

No SS

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Across a sea of idyllic Islands

Philipsburg, St. Maarten Round - 8 Day Itinerary aboard Sea Cloud Spirit

• Explore chic St. Barths
• Relax at Great Bay
• Visit Virgin Gorda
• Cruise Sir Francis Channel

Starts / Ends

Philipsburg / Philipsburg

Activities

Small Ship Sailing, Snorkeling, Stand Up Paddle Boarding

Activity Level

Variable

Set sail on an unforgettable 8-day Caribbean cruise aboard the Sea Cloud Spirit. Experience the charm of St. Maarten, Antigua, St. Barths, and the Virgin Islands as you explore paradise by sea. Discover rich culture, pristine beaches, and lively island towns filled with color and charm.

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from $6,830

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Pearls of the Caribbean

Roundtrip Fort-de-France - 9 Day Itinerary aboard Le Bellot

• See UNESCO World Heritage Sites
• Visit the Grenadine Islands
• Observe marine animals
• Enjoy the beach on Mayreau Island

Starts / Ends

Fort de France / Fort de France

Activities

Scuba Diving

Activity Level

Variable

Join Le Bellot on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, St. George's, Saint Lucia, Soufrière and many more!

Cruise Details

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from $2,030

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Grenadine Islands

8 Day Itinerary aboard Royal Clipper

• Visit one island in Grenadines
• Smell the aroma of Grenada
• Walk and swim at Marigot Bay
• Taste the spicy Creole cooking

Starts / Ends

Bridgetown / Bridgetown

Activity Level

Variable

On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of nature on this Caribbean adventure.

Cruise Details

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from $2,080

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Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper

• Explore Antigua’s vibrant dockyards
• Discover Les Saintes’ beaches
• Relax on Martinique’s white sands
• Stroll Grenada’s aromatic markets

Starts / Ends

St. John's / Bridgetown

Activity Level

Variable

Set sail on an 8-day cruise aboard the Royal Clipper, starting in Antigua. Highlights include snorkeling in Les Saintes, Dominica’s lush rainforests, Grenada’s spice markets, and Barbados’ rich heritage.

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from $1,970

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Leeward Islands

8 Day Itinerary aboard Star Flyer

• Visit Dominica Island
• Snorkel at Iles des Saintes
• Sail across Rivière Salée
• Enjoy Gustavia's unique charm

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Dominica, Iles des Saintes, Guadeloupe, Antigua, and St. Barts. As the wind blows your ship across turquoise waters through thousands of cays, snorkel in the clear water, relax on sunny beaches, or hike to the tropical mountaintops.

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from $1,970

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Treasure Islands

St. Maarten Roundtrip - 8 Day Itinerary aboard Star Flyer

• Visit Virgin Gorda's famous “Baths”
• Enjoy the lifestyle of Soper's Hole
• Walk the streets of Basseterre
• Relax on famous St. Barts

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

Don't miss the opportunity to relax on one of the beaches and enjoy the tropical sun's warmth. Soak up the sun in one of the world's most gorgeous locations, the Caribbean. Visit St. Maarten, Anguilla, Jost Van Dyke, St. Kitts, and St. Barts on this 8-day small ship trip!

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from $1,970

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Antigua to Antigua

Roundtrip St John - 8 Day Itinerary aboard Star Clipper

• Explore St. John's dockyards
• Sail Sir Francis Drake Channel
• Stroll Norman Island's beach
• Tour Basseterre's old plantations

Starts / Ends

St. John's / St. John's

Activity Level

Variable

Embark on an 8-day cruise in the Caribbean aboard the Star Clipper, starting and ending in Antigua. Discover the beaches and boutiques of St. Barts, explore Norman Island, and enjoy the charm of Jost van Dyke, while swimming at Virgin Gorda and experiencing St. Kitts’ history and nature.

Cruise Details

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from $21,980

2for1

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Discover the Yachting Islands of the Caribbean

Roundtrip Saint John’s - 15 Day Itinerary aboard Emerald Azzurra

• Explore Barbuda’s iconic pink sands
• Visit Les Saintes’ quaint towns
• Discover Deshaies’ lush hills
• Swim off Norman Island’s shores

Starts / Ends

St. John's / St. John's

Activity Level

Variable

Embark on a 15-day cruise with Emerald Azzurra, exploring the Caribbean from St. John’s, Antigua, with stops at stunning destinations like Barbuda, Guadeloupe, and the British Virgin Islands. Enjoy snorkeling in Culebra and the relaxed vibe of Esperanza on Vieques, all amidst beautiful beaches and vibrant island culture.

Cruise Details

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from $21,980

2for1

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Discover the Yachting Islands of the Caribbean

Roundtrip San Juan - 15 Day Itinerary aboard Emerald Azzurra

• Snorkel Culebra’s coral reefs
• Wander Vieques’ Esperanza
• Explore St. John’s plantation ruins
• Stroll Philipsburg’s streets

Starts / Ends

San Juan / San Juan

Activity Level

Variable

Embark on a 15-day Caribbean cruise from San Juan aboard Emerald Azzurra, exploring serene spots like Culebra, Vieques, and St. Barts. Experience stunning beaches, rich culture, and scenic ports, all in a relaxed yacht-style setting.

Cruise Details

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from $21,780

2for1

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Discover the Pearls of the Caribbean

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Azzurra

• Explore Soufriere’s volcanic peaks
• Tour Falmouth’s colonial forts
• Snorkel Anguilla’s coral reefs
• Wander Marigot’s French markets

Starts / Ends

Bridgetown / Marigot

Activities

Village Visits, Wildlife Viewing, Local Market Visits, Archaeological Site Visits, Kayaking

Activity Level

Variable

Embark on a 15-day cruise aboard Emerald Azzurra from Barbados to Marigot, visiting highlights like Nelson’s Dockyard and the beaches of Iles des Saintes. Discover serene islands, snorkel vibrant reefs, and enjoy cultural experiences across the enchanting Caribbean.

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