Virgin Islands Cruises

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

Cruise Details

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from $9,990

2for1

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Vibes of the Virgin Islands

St Thomas Roundtrip - 8 Day Itinerary aboard Emerald Sakara

Starts / Ends

St. Thomas / St. Thomas

Activities

Snorkeling, Small Ship Sailing, Archaeological Site Visits, Local Market Visits

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.

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

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from $7,990

2for1

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Quintessential Caribbean

San Juan - St Thomas - 8 Day Itinerary aboard Emerald Sakara

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 Harbor, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays.

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

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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

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

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 $8,390

2for1

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Caribbean Yachting Discovery

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

Starts / Ends

St. John's / St. Thomas

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.

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

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

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.

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

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 $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

Cruise Details

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from $3,090

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Jamaica to Antigua

12 Day Itinerary aboard Star Clipper

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.

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

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, Village 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

0

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

Cruise Details

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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

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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 $8,370

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Gliding the Waters of the Windward Islands

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

Starts / Ends

Dominica / Anses d'Arlet

Activities

Scuba Diving

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.

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

Cruise Details

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from $4,800

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Bridgetown to Bridgetown

8 Day Itinerary aboard Silver Spirit

Starts / Ends

Bridgetown / Bridgetown

Activities

Wildlife Viewing, 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.

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

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

Starts / Ends

Les Saintes / Bridgetown

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.

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

Cruise Details

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from $4,350

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Panama to Antigua

15 Day Itinerary aboard Royal Clipper

Starts / Ends

Balboa / St. John's

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.

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

Cruise Details

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