Top Caribbean Trips & Tours in January 2026

from $7,990

2for1

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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 $8,790

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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 $11,390

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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 $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

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 $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.

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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 $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.

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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

Activities

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

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.

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from $4,800

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Bridgetown to Bridgetown

8 Day Itinerary aboard Silver Spirit

• Hike to Saint Lucia’s Pitons
• Snorkel Martinique’s colorful reefs
• Explore Gustavia’s historic harbor
• Stroll Bequia’s scenic shores

Starts / Ends

Bridgetown / Bridgetown

Activities

Spa Relaxation

Activity Level

Variable

Embark on an 8-day Caribbean round-trip cruise from Bridgetown aboard the Silver Spirit. Explore some of the most iconic and lesser-known islands in the region, including Saint Lucia, Martinique, Saint Barthelemy, Dominica, Grenada, and Bequia. Each destination offers unique cultural experiences, breathtaking natural beauty, and vibrant local life.

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from $2,820

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Antigua to Grenada

Antigua to Grenada - 11 Day Itinerary aboard Star Clipper

• Explore Gustavia boutiques
• Swim Norman Island coves
• Visit Jost van Dyke beaches
• Relax in St. Kitts landscapes

Starts / Ends

St. John's / St. Georges

Activities

Hiking

Activity Level

Variable

Set sail on an 11-day Caribbean cruise aboard Star Clipper. Depart from Antigua and explore St. Barts, the British Virgin Islands, St. Kitts, Martinique, Bequia, and Grenada. Discover historic harbors, swim in crystal waters, and relax on world-class beaches.

Cruise Details

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from $22,140

2for1

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Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara

• Explore Anguilla’s turquoise waters
• Stroll through Gustavia
• Admire Nevis’ tranquil shores
• Visit Antigua’s Falmouth Bay

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.

Cruise Details

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from $22,140

2for1

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Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara

• Explore Bridgetown’s capital
• Wander Speightstown’s streets
• Discover Kingstown’s gardens
• Unwind on Bequia Island

Starts / Ends

Bridgetown / Marigot

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.

Cruise Details

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from $2,443

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Best of Dominican Republic

8 Day Itinerary

• Visit UNESCO site in Santo Domingo
• Taste the culture and local food
• Visit coffee factory in Jarabacoa
• Learn about tobacco production
• Visit cocoa & chocolate plantation
• See the beaches of Las Terrenas

Starts / Ends

Punta Cana / Punta Cana

Activities

Hacienda Visits, Volunteering

Activity Level

Relaxed

Visit Dominican Republic and uncover hidden gems, from Jarabacoa coffee farms and cigar factories to coastal escapes in Punta Cana. Our tours include top-rated attractions, immersive cultural visits, and unforgettable nature experiences. Discover the best things to do in the Dominican Republic, from the capital to the coast.

Tour Details

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from $3,090

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Jamaica to Antigua

12 Day Itinerary aboard Star Clipper

• Swim in Montego Bay's waters
• Explore Santo Domingo
• Visit the Treasure Island
• Hike Virgin Gorda trails

Starts / Ends

Port Antonio / St. John's

Activity Level

Variable

Explore a paradise of vibrant coral reefs, powder-soft sand, and warm island hospitality on this 12-day cruise from Jamaica to Antigua aboard Star Clipper. Experience crystal-clear water, bright skies, and gentle breezes. Relish in the beauty of untouched beaches and become enchanted by seductive scents and rhythms.

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