Windward Islands Small Ship Cruises

from $9,990

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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

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.

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from $4,330

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Barbados to Panama

Bridgetown - Balboa - 15 Day Itinerary aboard Star Clipper

• Explore Bridgetown’s heritage
• Discover St. George’s coastal views
• Admire Kralendijk’s marine life
• Wander Willemstad’s streets

Starts / Ends

Bridgetown / Balboa

Activities

Small Ship Sailing

Activity Level

Variable

Set sail on a 15-day cruise with Star Clipper from Bridgetown, Barbados, exploring the Caribbean’s rich culture and history, ending in Balboa, Panama. Visit stunning destinations like Tobago Cays, Grenada, and the San Blas Islands, and experience the Panama Canal.

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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.

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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 $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

Snorkeling, 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 $9,990

2for1

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Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Azzurra

• Explore Prickly Pear Cays waters
• Admire Nevis’ Georgian buildings
• Visit Soufriere’s volcanic springs
• Wander Bridgetown’s streets

Starts / Ends

Marigot / Bridgetown

Activity Level

Variable

Set sail on an 8-day cruise aboard the Emerald Azzura, island-hopping through vibrant cultures and breathtaking landscapes. Discover pristine beaches, vivid coral reefs, and the genuine warmth of locals while enjoying the elegance of a luxury yacht experience.

Cruise Details

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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 $4,450

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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

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.

Cruise Details

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from $19,990

2for1

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Island Odyssey: Bahamas to the Grenadine

Nassau - Bridgetown - 11 Day Itinerary aboard Scenic Eclipse

• Explore Nassau’s vibrant capital
• Visit Staniel Cay’s beaches
• Discover San Salvador’s coral reefs
• Stroll St. Barts iconic Shell Beach

Starts / Ends

Nassau / Bridgetown

Activities

Stand Up Paddle Boarding, Helicopter Tours

Activity Level

Variable

Set sail on an 11-day Caribbean cruise from Nassau to Bridgetown on the Scenic Eclipse, visiting remote gems like Staniel Cay, Turks and Caicos, and St. Barts. Enjoy ultra-luxury amenities and guided excursions for a refined and relaxing experience.

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from $4,800

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San Juan to Bridgetown

San Juan - Bridgetown - 8 Day Itinerary aboard Silver Spirit

• Explore Historic San Juan
• Snorkel Trunk Bay Reefs
• Stroll Willemstad Waterfront
• Explore Bridgetown

Starts / Ends

San Juan / Bridgetown

Activities

Archaeological Site Visits, Local Market Visits, Wildlife Viewing, Spa Relaxation, Whale Watching

Activity Level

Variable

Set sail on an 8-day Silver Spirit voyage from San Juan to Bridgetown. Discover Caribbean charm in St. John’s national park, Nevis’s golden beaches, Bonaire’s vibrant reefs, and Curaçao’s colorful Dutch heritage. Enjoy time at sea before disembarking in Bridgetown, where rich culture meets island beauty.

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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

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 $2,940

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Westbound Atlantic Ocean Crossing

Lisbon - Barbados - 16 Day Itinerary aboard Royal Clipper

• Explore Lisbon’s vibrant streets
• Discover Portimão’s historic charm
• Wander Funchal’s lush landscapes
• Cruise Barbados’ stunning shores

Starts / Ends

Lisbon / Bridgetown

Activity Level

Variable

Sail across the Atlantic on this 16-day cruise aboard the Royal Clipper, blending culture and adventure. Discover Lisbon’s charm, Portimao’s historical treasures, Madeira’s vibrant nightlife, and Barbados’ stunning shores, with serene days at sea in between.

Cruise Details

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from $2,970

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Westbound Atlantic Ocean Crossing

Las Palmas to Barbados - 16 Day Itinerary aboard Star Flyer

• Visit Las Palmas, Gran Canaria
• Take in the fresh ocean breeze
• Explore San Sebastian, La Gomera
• Relax on paradise beaches

Activity Level

Variable

Sit back and take in the smell of the fresh ocean breeze up on deck on this extraordinary 16-day cruise that takes you across the Northern Atlantic Ocean. Start at the famous and charming city of Las Palmas, Gran Canaria, and voyage all the way to the stunningly beautiful Caribbean Islands.

Cruise Details

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from $8,490

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Panama, Colombia & Caribbean Islands

Colon to Fort-de-France - 13 Day Itinerary aboard Le Champlain

• Sail through the Central America.
• See San Blas, Bonaire & Grenadines
• Experience swim and snorkel.
• Learn traditions of the Kuna people
• Dive with an experienced instructor

Starts / Ends

Colon / Fort de France

Activities

Land & Sea Exploration

Activity Level

Variable

Join Le Bellot for an exceptional 13-day cruise sailing from Colón to Fort-de-France. This itinerary gives you the opportunity to appreciate the richness and diversity of Afro-Caribbean cultures, an azure blue sky, and white-sand beaches. Visit stunning ports, including Portobelo, Cartagena, Santa Marta, Mayreau Island, and Soufriére.

Cruise Details

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from $2,820

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Westbound Atlantic Ocean Crossing

16 Day Itinerary aboard Star Clipper

• Visit Las Palmas, Gran Canaria
• Take in the fresh ocean breeze
• Explore San Sebastian, La Gomera
• Relax on paradise beaches

Starts / Ends

Las Palmas / Bridgetown

Activity Level

Variable

Sit back and take in the smell of the fresh ocean breeze up on deck on this extraordinary 16-day cruise that takes you across the Northern Atlantic Ocean. Start at the famous and charming city of Las Palmas, Gran Canaria, and voyage to the stunningly beautiful Caribbean Islands.

Cruise Details

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from $3,199

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Southern Caribbean Yacht Harbors

Halifax - Bridgetown - 9 Day Itinerary aboard Seabourn Venture

• Tour Citadel Hill
• Visit Brimstone Hill Fortress
• Snorkel at Pigeon Island
• Visit Saint Lucia’s famous Pitons

Starts / Ends

Halifax / Bridgetown

Activities

Photography Seminars

Activity Level

Variable

Cruise from Halifax, Nova Scotia to Bridgetown, Barbados aboard the Seabourn Venture on a 9-day Southern Caribbean Yacht Harbors cruise. Enjoy relaxing days at sea and explore scenic Caribbean islands like Saint Kitts, Montserrat, and Saint Lucia. Visit UNESCO World Heritage Sites, snorkel in clear waters, and experience rich history and culture.

Cruise Details

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