Top Lesser Antilles Trips & Tours in February 2026

from $2,020

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Grenadine Islands

8 Day Itinerary aboard Royal Clipper

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.

• Visit one island in Grenadines
• Smell the aroma of Grenada
• Walk and swim at Marigot Bay
• Taste the spicy Creole cooking

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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

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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 $11,070

2for1

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Cruising the Leeward Islands

Marigot Roundtrip - 8 Day Itinerary aboard Emerald Sakara

Starts / Ends

Marigot / Marigot

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.

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

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from $8,390

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

Activities

Wildlife Viewing

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

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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

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from $22,140

2for1

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Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara

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.

• Experience Falmouth's historic port
• Discover Soufriere's Sulfur Spring
• Visit Falmouth Harbour in Antigua
• Explore Nelson’s Dockyard

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from $7,990

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Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Sakara

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 Harbour’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

• Experience Falmouth's historic port
• Discover Soufriere's Sulphur Spring
• Visit Falmouth Harbour in Antigua
• Explore Nelson’s Dockyard

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from $8,790

2for1

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Grenadines & Windwards Yachting

8 Day Itinerary aboard Emerald Sakara

Starts / Ends

Bridgetown / Bridgetown

Activity Level

Variable

Set sail on an 8-day extraordinary Caribbean cruise, discovering pristine beaches and vibrant coral reefs while hopping between culturally rich islands aboard Emerald Sakara. Enjoy pristine beaches, vibrant local cultures, and water activities like swimming and snorkeling.

• Discover Bequia’s secluded beaches
• Savor Caribbean dining experiences
• Snorkel Tobago Cays' waters
• Admire panoramic views from Mayreau

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from $7,990

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Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Sakara

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.

• Explore Bridgetown's culture
• Stroll Gustavia's colorful streets
• Admire Marigot’s scenic coastline
• Savor Soufriere's delicious cuisine

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from $15,980

2for1

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Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara

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.

• Experience Falmouth's historic port
• Discover Soufriere's Sulfur Spring
• Visit Falmouth Harbour in Antigua
• Explore Nelson’s Dockyard

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from $3,090

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Grenada to Grenada

Roundtrip St George - 12 Day Itinerary aboard Star Clipper

Starts / Ends

St. Georges / St. Georges

Activity Level

Variable

Set sail on a 12-day cruise aboard the Star Clipper, exploring stunning islands like Tobago and Martinique, with highlights including the Tobago Cays and St. Lucia's waterfalls. Experience the Caribbean's serene beauty and rich culture while enjoying activities like snorkeling and history.

• Explore St. George’s Fort George
• Discover Charlotteville’s Tobago
• Unwind on Carriacou beach
• Visit Martinique ruins

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from $8,050

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Grenada to Grenada

Roundtrip St George - 11 Day Itinerary aboard Star Clipper

Starts / Ends

St. Georges / St. Georges

Activities

Snorkeling, Small Ship Sailing, Village Visits, Local Market Visits

Activity Level

Variable

Set sail on an 11-day cruise from St. George aboard the Star Clipper, featuring Grenada, Tobago, the Grenadines, Martinique, and St. Lucia while exploring picturesque villages and stunning beaches. Enjoy swimming, snorkeling, and local culture, concluding with a visit to Mayreau's serene Saline Bay.

• Explore St. George’s panoramic view
• Discover Charlotteville coastline
• Unwind at Englishman’s Bay
• Visit Martinique ruins

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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

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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

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

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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

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