Virgin Islands Cruises

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 $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 $7,590

2for1

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Vibes of the Virgin Islands

St Thomas Roundtrip - 8 Day Itinerary aboard Emerald Sakara

• Explore Saint John's pristine beach
• Stroll Philipsburg's lively markets
• Snorkel Norman Island's caves
• Visit 'The Baths' in Virgin Gorda

Starts / Ends

St. Thomas / St. Thomas

Activity Level

Variable

Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning beaches of Virgin Gorda, snorkel in Norman Island’s clear waters, and experience Anguilla’s vibrant beauty. Philipsburg’s lively port, Gustavia’s charming streets, and tranquil Saint John Island round out this cruise.

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from $7,990

2for1

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Quintessential Caribbean

8 Day Itinerary aboard Emerald Sakara

• Relax on Prickly Pear Cays' beaches
• Visit Guadeloupe’s fishing village
• Visit port of Falmouth Harbour
• Wander through lively Cruz Bay

Starts / Ends

San Juan / St. Thomas

Activity Level

Variable

Embark on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore the vibrant culture of San Juan, the charm of Saint John, the tranquil beaches of Nevis, the picturesque village of Deshaies, the historic allure of Falmouth Harbour, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays. Enjoy unique experiences and stunning landscapes throughout your cruise.

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

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 $2,020

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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 $7,990

2for1

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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.

Cruise Details

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from $8,390

2for1

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Caribbean Yachting Discovery

St John - St Thomas - 8 Day Itinerary aboard Emerald Azzurra

• Visit Barbuda's pink-sand beaches
• Explore Norman Island hidden caves
• Sail luxury yacht through Caribbean
• Relax on Virgin Gorda beaches
• Snorkel in crystal-clear water

Starts / Ends

St. John's / St. Thomas

Activities

Snorkeling, Urban Exploration, Local Market Visits

Activity Level

Variable

Embark on an 8-day Caribbean cruise aboard Emerald Azzurra from Antigua to St. Thomas. Explore vibrant ports like Barbuda, Illes des Saintes, and Virgin Gorda. Discover unique sites such as Norman Island’s caves and the markets of Guadeloupe. Travel aboard a luxury yacht, exploring beaches, history, and local culture at each stop.

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

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

Starts / Ends

Marigot / Marigot

Activities

Wildlife Viewing

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.

Cruise Details

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from $7,740

2for1

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Caribbean Yachting Hideaways

St Thomas - St John's - 8 Day Itinerary aboard Emerald Azzurra

• Visit The Baths’ granite formation
• Explore Culebra's white-sand beach
• Experience swimming off the yacht
• Discover the history of St. John

Starts / Ends

St. Thomas / Antigua

Activities

Kayaking, Adventure Options

Activity Level

Variable

Embark on an 8-day Caribbean adventure aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches, Vieques’ lovely waterfront, Cruz Bay’s scenic hikes, and Virgin Gorda’s famous Baths. Discover Philipsburg’s vibrant culture, Gustavia’s idyllic beaches, and Montserrat’s volcanic history.

Cruise Details

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from $7,590

2for1

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Cruising the Leeward Islands

Marigot Roundtrip - 8 Day Itinerary aboard Emerald Azzurra

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

Starts / Ends

Marigot / Marigot

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.

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 $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

Activities

Spa Relaxation

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.

Cruise Details

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from $1,960

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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 $1,960

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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 $8,370

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Gliding the Waters of the Windward Islands

Pointe-a-Pitre Roundtrip - 8 Day Itinerary aboard Le Ponant

• Enjoy iconic pitons of Saint Lucia
• Learn about Kalinago culture
• Explore Tobago Cays' coral reefs
• Relax on Marie-Galante's beaches

Starts / Ends

Dominica / Anses d'Arlet

Activities

Scuba Diving, Small Ship Sailing

Activity Level

Variable

Explore the Caribbean on an 8-day cruise aboard Le Ponant. Visit Dominica to explore mangroves and meet the Kalinago people. Cruise through Saint Vincent and the Grenadines, snorkeling in Tobago Cays' clear waters. Experience sunsets, local culture, and beaches in Marie-Galante. This cruise combines relaxation and adventure in the Caribbean.

Cruise Details

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from $6,800

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Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Roundtrip Vieux Fort - 9 Day Itinerary aboard Le Bellot

• Visit UNESCO World Heritage sites
• Visit Portsmouth, Dominica
• Explore Les Saintes, Guadeloupe
• See Mayreau's fishes and corals

Starts / Ends

Les Saintes / Bridgetown

Activities

Hiking, Village Visits

Activity Level

Variable

From Vieux Fort, St. Lucia set sail aboard Le Bellot for a 9-day Caribbean Windward cruise to visit the heart of the most enchanting islands in the Caribbean Sea. Before disembarking in Vieux Fort, explore long stretches of white-sand beaches, idyllic turquoise waters, and the laid-back island way of life.

Cruise Details

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from $4,350

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Panama to Antigua

15 Day Itinerary aboard Royal Clipper

• Explore Balboa’s colonial charm
• Transit Panama’s iconic canal
• Discover San Blas culture
• Enjoy Aruba’s clear waters

Starts / Ends

Balboa / St. John's

Activities

Archaeological Site Visits

Activity Level

Variable

Set sail on a 15-day Royal Clipper cruise from Balboa, Panama, featuring a full Panama Canal transit and visits to the San Blas Islands, Cartagena, and the Caribbean gems of Aruba, Curacao, and Bonaire. Experience lush Grenada and volcanic St. Lucia, and finish your journey in Antigua, all while enjoying elegant sailing and stunning island views.

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