Leeward Islands Tours in 2026

from $8,390

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Caribbean Yachting Hideaways

San Juan - St John's - 8 Day Itinerary aboard Emerald Azzurra

• Discover Culebra Island’s shores
• Explore Vieques Island waterfront
• Tour St. John’s Annaberg ruins
• Relax on Jost Van Dyke’s White Bay

Starts / Ends

San Juan / St. John's

Activities

Hiking

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.

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from $6,830

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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!

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from $11,600

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Bridgetown to Bridgetown

22 Day Itinerary aboard Silver Spirit

• Explore top Caribbean islands
• Visit Bequia and Iles des Saintes
• Explore Gustavia’s historic harbor
• Experience the Caribbean culture

Starts / Ends

Bridgetown / Bridgetown

Activities

Archaeological Site Visits, Local Market Visits

Activity Level

Variable

Sail round-trip from Bridgetown aboard Silver Spirit on a 22-day Caribbean cruise. Explore top islands like St. Lucia, Martinique, and Barbados, plus hidden gems like Bequia and Iles des Saintes. Enjoy beach days, island tours, and cultural stops with long port calls.

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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.

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from $3,420

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Eastbound Atlantic Ocean Crossing

Philipsburg - Malaga - 21 Day Itinerary aboard Star Flyer

• Explore Philipsburg’s Dutch side
• Experience Marigot’s markets
• Unwind while crossing the Atlantic
• Visit Ponta Delgada’s churches

Starts / Ends

Philipsburg / Malaga

Activities

Small Ship Sailing

Activity Level

Variable

Set sail on a 21-day cruise aboard the Star Flyer, starting in Philipsburg and visiting Ponta Delgada in the Azores. End your journey in Malaga, Spain, exploring its Moorish heritage while enjoying 18 days at sea.

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from $22,140

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Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara

• Explore Anguilla’s turquoise waters
• Stroll through Gustavia
• Admire Nevis’ tranquil shores
• Visit Antigua’s Falmouth Bay

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.

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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

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.

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from $15,980

OBC

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Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara

• Explore Bridgetown’s capital
• Wander Speightstown’s streets
• Discover Kingstown’s gardens
• Unwind on Bequia Island

Starts / Ends

Bridgetown / Marigot

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.

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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.

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from $4,800

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Bridgetown to Bridgetown

8 Day Itinerary aboard Silver Spirit

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

Starts / Ends

Bridgetown / Bridgetown

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.

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from $2,820

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Grenada to Antigua

St. George - St. John - 11 Day Itinerary aboard Star Clipper

• Explore St. George’s harbor
• Experience Charlotteville coast
• Relax at Englishman’s Bay
• Wander through Admiralty Bay

Starts / Ends

St. Georges / St. John's

Activities

Snorkeling, Village Visits

Activity Level

Variable

Take an 11-day cruise on the Star Clipper from St. George's, Grenada to St. John's, Antigua, exploring secluded bays and historic towns in Tobago and the Grenadines. Enjoy highlights like snorkeling in Tobago Cays and relaxing on beautiful beaches, while immersing yourself in vibrant local cultures.

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from $9,870

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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

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.

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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

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.

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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.

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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.

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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

Wildlife Viewing, Spa Relaxation, Kayaking, 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.

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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.

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