Caribbean Tours & Cruises in 2025

from $2,020

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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.

Cruise Details

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from $2,020

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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 $3,980

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Save the Best for Last

Roundtrip St. Maarten - 8 Day Itinerary aboard Sea Cloud

• Discover The Baths
• Relax at Bitter End
• Sail to Jost van Dyke
• Experience St. Barths
• Explore Nevis

Starts / Ends

Philipsburg / St. Martin

Activities

Small Ship Sailing

Activity Level

Variable

Sail aboard the Sea Cloud on a 10-day Caribbean adventure through the British Virgin Islands, St. Barths, Nevis, and St. Maarten. Explore Virgin Gorda’s iconic Baths, unwind at the Bitter End Yacht Club, and sail the Sir Francis Drake Channel to Jost van Dyke. Stroll St. Barths’ luxury shops, discover Nevis’ lush rainforests, and end in vibrant Philipsburg.

Cruise Details

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from $2,020

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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.

Cruise Details

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from $1,960

SS 25%

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Treasure Islands

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!

Cruise Details

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from $7,990

2-for-1

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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

Activities

Urban Exploration

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.

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

• 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 $5,245

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A Colorful Caribbean Time-Out

San Juan Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit

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

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.

Cruise Details

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from $1,960

SS 25%

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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.

Cruise Details

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from $21,340

2-for-1

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Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara

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

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 $7,590

2-for-1

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Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Sakara

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

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

Cruise Details

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from $8,390

2-for-1

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Grenadines & Windwards Yachting

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

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.

Cruise Details

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from $8,390

2-for-1

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Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Sakara

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

Starts / Ends

Bridgetown / Marigot

Activities

Wildlife Viewing

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.

Cruise Details

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from $15,180

2-for-1

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Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara

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

Starts / Ends

Bridgetown / Marigot

Activities

Snorkeling, Village Visits

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 $3,590

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Cuba Kayaking West Tour

8 Day Itinerary

• See Cuba's great cities
• Visit the Bay of Pigs
• Kayak and snorkel in Cuba
• Enjoy unique architecture & cuisine

Activities

Homestays, Kayaking

Activity Level

Easy Active

Experience Cuba on a unique land and kayaking program. Discover three of Cuba’s greatest resources: its people, colorful culture, and natural wonders. In Havana, meet the artists, musicians, and historians who are preserving tradition. Explore great colonial cities and pristine marine & terrestrial habitats.

Tour Details

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from $3,237

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Dominican Republic: North Coast Expedition

8 Day Itinerary

• Enjoy canyoning in Puerto Plata
• See the landscape using 4x4 buggy
• Visit the Los Pepines murals.
• Learn about tobacco production
• See the lovely bay of Rio San Juan
• Zip line over the Laguna Dudu

Starts / Ends

Puerto Plata / Puerto Plata

Activities

Hiking, Ziplining, Rainforest Exploration, Local Market Visits

Activity Level

Easy Active

Spend your week on the vibrant North Coast of the Dominican Republic. During this 8-day adventure, experience stunning landscapes, beautiful pristine beaches, and rich cultural traditions, and discover the beauty of this magical stretch of coast.

Tour Details

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from $3,125

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Dominican Republic: Culture and Cocktails

8 Day Itinerary

• Visit UNESCO site in Santo Domingo
• Visit coffee factory in Jarabacoa
• Visit Los Pepines murals
• Swim in azure waters of Cayo Arena
• Visit cocoa & chocolate plantation

Starts / Ends

Santo Domingo / Santo Domingo

Activities

Archaeological Site Visits

Activity Level

Easy Active

This 8-day journey will give you a genuine taste of the Dominican Republic. From UNESCO World Heritage Sites to street art and local delicacies, immerse yourself in the diverse landscapes and cultures of this Caribbean gem. With optional beach extensions, savor every moment of your unforgettable journey.

Tour Details

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from $2,612

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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

Volunteering, Hacienda Visits

Activity Level

Relaxed

Discover the best of the Dominican Republic's highlights on this 8-day adventure, from the idyllic beaches of Punta Cana to the historic charm of Santo Domingo, the lush landscapes of Jarabacoa, the cultural richness of Santiago de los Caballeros, the bustling streets of San Francisco de Macoris, and the coastal allure of Las Terrenas.

Tour Details

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