Lesser Antilles Cruises

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.

Cruise Details

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from $7,990

2for1

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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.

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

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

Starts / Ends

Bridgetown / Marigot

Activities

Hiking

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.

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

• 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.

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

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

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.

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 $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.

Cruise Details

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from $5,850

Save 10%

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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 $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.

Cruise Details

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from $2,080

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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 $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.

Cruise Details

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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!

Cruise Details

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from $1,970

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Antigua to Antigua

Roundtrip St John - 8 Day Itinerary aboard Star Clipper

• Explore St. John's dockyards
• Sail Sir Francis Drake Channel
• Stroll Norman Island's beach
• Tour Basseterre's old plantations

Starts / Ends

St. John's / St. John's

Activity Level

Variable

Embark on an 8-day cruise in the Caribbean aboard the Star Clipper, starting and ending in Antigua. Discover the beaches and boutiques of St. Barts, explore Norman Island, and enjoy the charm of Jost van Dyke, while swimming at Virgin Gorda and experiencing St. Kitts’ history and nature.

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

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

Starts / Ends

Marigot / Bridgetown

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.

Cruise Details

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from $15,980

2for1

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Discover the Pearls of the Caribbean

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Azzurra

• Explore Soufriere’s volcanic peaks
• Tour Falmouth’s colonial forts
• Snorkel Anguilla’s coral reefs
• Wander Marigot’s French markets

Starts / Ends

Marigot / Bridgetown

Activities

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

Activity Level

Variable

Embark on a 15-day Caribbean cruise aboard Emerald Azzurra, exploring stunning coral reefs, granite pools, and picturesque landscapes across destinations like Anguilla and Virgin Gorda. Enjoy snorkeling, hiking, and vibrant local culture while visiting Saint Barthelemy and the British Virgin Islands.

Cruise Details

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from $21,780

2for1

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Discover the Pearls of the Caribbean

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Azzurra

• Explore Soufriere’s volcanic peaks
• Tour Falmouth’s colonial forts
• Snorkel Anguilla’s coral reefs
• Wander Marigot’s French markets

Starts / Ends

Bridgetown / Marigot

Activities

Kayaking

Activity Level

Variable

Embark on a 15-day cruise aboard Emerald Azzurra from Barbados to Marigot, visiting highlights like Nelson’s Dockyard and the beaches of Iles des Saintes. Discover serene islands, snorkel vibrant reefs, and enjoy cultural experiences across the enchanting Caribbean.

Cruise Details

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from $9,990

2for1

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Grenadines & Windwards Yachting

Bridgetown, Barbados Roundtrip - 8 Day Itinerary aboard Emerald Azzurra

• Explore historic Kingstown
• Swim Tobago Cays reefs
• Discover Mayreau views
• Relax on Bequia Island

Starts / Ends

Bridgetown / Bridgetown

Activity Level

Variable

Embark on an 8-day Caribbean cruise from Bridgetown, Barbados aboard Emerald Azzurra. Visit Kingstown, Bequia, Mayreau, Union Island, and Tobago Cays. Discover small island communities, historical landmarks, coral reefs, and quiet beaches. Enjoy daily opportunities for swimming, snorkeling, and local exploration in Saint Vincent and the Grenadines.

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

• 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.

Cruise Details

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