All Caribbean Tours

from $2,020

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Windward Islands

Roundtrip Barbados - 8 Day Itinerary aboard Royal Clipper

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.

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

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from $2,020

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Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper

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.

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

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from $2,020

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Grenadine Islands

8 Day Itinerary aboard Royal Clipper

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.

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

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from $1,960

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Treasure Islands

8 Day Itinerary aboard Star Flyer

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!

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

Cruise Details

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from $9,990

2for1

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Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra

Starts / Ends

Bridgetown / Marigot

Activities

Snorkeling, Village Visits

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.

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

Cruise Details

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from $10,990

2for1

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Cruising the Leeward Islands

Marigot Roundtrip - 8 Day Itinerary aboard Emerald Sakara

Starts / Ends

Marigot / Marigot

Activity Level

Variable

Embark on an 8-day Cruising the Leeward Islands aboard Emerald Sakara from Marigot roundtrip. Explore Anguilla, Virgin Gorda, and other stunning destinations, immersing yourself in picturesque landscapes, vibrant cities, and unique natural wonders.

• Dive in Anguilla
• Explore Virgin Gorda
• Discover Anegada
• Experience Jost van Dyke

Cruise Details

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from $7,990

2for1

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Caribbean Yachting Discovery

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

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.

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

Cruise Details

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from $5,520

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Pearls of the Caribbean

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

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!

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

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from $5,245

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A Colorful Caribbean Time-Out

San Juan Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit

Starts / Ends

San Juan / San Juan

Activity Level

Variable

Embark on an 8-day cruise aboard Sea Cloud Spirit sailing to explore Old San Juan's historic charm. Wander streets lined with colorful facades and salsa-filled cafes. Discover UNESCO-listed sites like La Fortaleza and Fort San Felipe del Morro, resonating with centuries of history and cultural vibrancy.

• Explore Old San Juan's forts
• Enjoy salsa music
• Sail in the British Virgin Islands
• Explore unique rock formations

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from $1,960

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Leeward Islands

8 Day Itinerary aboard Star Flyer

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.

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

Cruise Details

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from $21,340

2for1

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Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara

Starts / Ends

Marigot / Bridgetown

Activity Level

Variable

Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the locals as you hop between tropical paradises, creating unforgettable memories aboard the Emerald Sakara.

• Experience Falmouth's historic port
• Discover Soufriere's Sulfur Spring
• Visit Falmouth Harbour in Antigua
• Explore Nelson’s Dockyard

Cruise Details

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from $15,980

2for1

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Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Azzurra

Starts / Ends

Marigot / Bridgetown

Activities

Archaeological Site Visits

Activity Level

Variable

Set sail on a 15-day Caribbean journey, where pristine beaches, vibrant coral reefs, and island-hopping adventures immerse you in diverse cultures. Experience the genuine warmth of local hospitality as you explore tropical paradises aboard the Emerald Azzurra.

• Explore Anguilla, serene landscapes
• Savor Barbados’s cultural delights
• Visit Antigua’s historic dockyard
• Stroll Nevis’s serene beaches

Cruise Details

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from $9,990

2for1

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Cruising the Leeward Islands

Roundtrip Marigot - 8 Day Itinerary aboard Emerald Azzurra

Starts / Ends

Marigot / Marigot

Activities

Wildlife Viewing

Activity Level

Variable

Set sail on an 8-day Caribbean cruise with Emerald Azzurra. Start in Marigot, then visit Anguilla’s coral beaches, Virgin Gorda’s Baths, Jost Van Dyke’s Bubbly Pool, and Anegada’s sandy shores. Explore Saba’s trails and Bonaire’s marine life before ending in Gustavia. Enjoy a luxury cruise with varied landscapes and activities.

• Explore Anguilla’s coral coastlines
• Visit Virgin Gorda granite boulders
• Discover Norman Island's coves
• Relax on Anegada’s remote sands

Cruise Details

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from $9,990

2for1

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Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Azzurra

Starts / Ends

Marigot / Bridgetown

Activities

Small Ship Sailing

Activity Level

Variable

Set sail on an 8-day cruise aboard the Emerald Azzura, island-hopping through vibrant cultures and breathtaking landscapes. Discover pristine beaches, vivid coral reefs, and the genuine warmth of locals while enjoying the elegance of a luxury yacht experience.

• Explore Prickly Pear Cays waters
• Admire Nevis’ Georgian buildings
• Visit Soufriere’s volcanic springs
• Wander Bridgetown’s streets

Cruise Details

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from $7,990

2for1

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Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Sakara

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 Harbour’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

• Experience Falmouth's historic port
• Discover Soufriere's Sulphur Spring
• Visit Falmouth Harbour in Antigua
• Explore Nelson’s Dockyard

Cruise Details

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from $7,990

2for1

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Grenadines & Windwards Yachting

8 Day Itinerary aboard Emerald Sakara

Starts / Ends

Bridgetown / Bridgetown

Activity Level

Variable

Set sail on an 8-day extraordinary Caribbean cruise, discovering pristine beaches and vibrant coral reefs while hopping between culturally rich islands aboard Emerald Sakara. Enjoy pristine beaches, vibrant local cultures, and water activities like swimming and snorkeling.

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

Cruise Details

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from $7,990

2for1

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Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Sakara

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.

• Explore Bridgetown's culture
• Stroll Gustavia's colorful streets
• Admire Marigot’s scenic coastline
• Savor Soufriere's delicious cuisine

Cruise Details

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from $8,390

2for1

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Caribbean Yachting Hideaways

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

Starts / Ends

San Juan / St. John's

Activities

Hiking, Local Market Visits

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.

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

Cruise Details

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