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Wander the white-sand beaches of St. Johns on your Virgin Islands cruise

Sailboat Cruises in Lesser Antilles

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Experience the Caribbean's rich tapestry of vibrant cultures and stunning landscapes with Adventure Life's array of 25 small ship sailing tours. Sail away to lesser-known ports and hidden gems on the sea, from the historic Bridgetown in Barbados to the lush island of St. Lucia and the charming Martinique. Swim and snorkel amidst the pristine waters, discover the Dutch colonial charm of Curacao, and witness the breathtaking beauty of the Pitons in St. Lucia. Whether you're exploring sophisticated Martinique or relaxing on the famous beaches of St. Barts, each moment offers a unique opportunity to immerse yourself in the wonders of the Caribbean. Engage in snorkeling, wildlife viewing, and island-hopping cruises that will fill your days with adventure and relaxation. With prices starting at $1,960 to $62,480, begin your Caribbean adventure today and contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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    • Lesser Antilles
Tropical waterfall and turquoise pool in lush forest of Dominica
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
Cruise Details
0
Relax on the sunny beaches of the Caribbean
from $9,990
2for1
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Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Azzurra
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.
  • Soak in Soufriere’s volcanic spring
  • Explore Les Saintes’ French charm
  • Visit Antigua’s Nelson’s Dockyard
  • Stroll Nevis’ Georgian towns
Cruise Details
0
St Barts harbor view
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
0
Relax on the beaches of St. Maarten
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
0
Enjoy the beautiful blue Caribbean
from $21,340
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
Cruise Details
0
Gustavia Harbor in St. Barths
from $9,990
2for1
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Cruising the Leeward Islands

Roundtrip Marigot - 8 Day Itinerary aboard Emerald Azzurra
Starts / Ends
Marigot / Marigot
Activities
Wildlife Viewing
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
0
Gustavia Harbor in St. Barths
from $9,990
2for1
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Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Azzurra
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.
  • Explore Prickly Pear Cays waters
  • Admire Nevis’ Georgian buildings
  • Visit Soufriere’s volcanic springs
  • Wander Bridgetown’s streets
Cruise Details
0
Relax on the sunny beaches of the Caribbean
from $7,990
2for1
EXPLORE

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
Cruise Details
0
Explore colorful Gustavia
from $7,990
2for1
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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
Cruise Details
0
Play on the famously beautiful beaches of St. Barth's
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
0
Caribbean landscapes and harbors
from $11,990
2for1
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Caribbean Sojourn

Bridgetown - Marigot - 7 Day Itinerary aboard Emerald Azzurra
Starts / Ends
Bridgetown / Marigot
Activities
Archaeological Site Visits
Activity Level
Variable
Embark on a 7-day Caribbean adventure aboard the Emerald Azzurra. Set sail from Barbados and explore diverse islands including Soufriere’s mud baths, Falmouth Harbor’s historic dockyard, Iles des Saintes’ picturesque beaches, Gustavia’s vibrant streets, and Marigot’s charming French town.
  • Visit UNESCO-listed Nelson's dock
  • Discover Iles des Saintes town
  • Stroll Gustavia’s colorful street
  • Dip into a therapeutic mud bath
Cruise Details
0
Relax on the shores of the Caribbean
from $15,180
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
Cruise Details
0
Explore the famous rock formations of the baths
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
0
St. George's, Grenada's charming capital city known for having the most beautiful harbor in the Caribbean.
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
Cruise Details
0
Enjoy the beautiful blue Caribbean
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
Cruise Details
0
Explore beautiful Jost van Dyke
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
Cruise Details
0
Beautiful beach in Dominica
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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Boats Moored to the Quay at Bridgetown Harbour
from $4,350
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Barbados to Panama

15 Day Itinerary aboard Royal Clipper
Starts / Ends
Bridgetown / Balboa
Activity Level
Variable
Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to the Panama Canal, visiting Grenada, Bonaire, Curacao, Aruba, and Colombia along the way. Explore the tropical jungles, snorkel in vibrant reefs, immerse yourself in tribal culture, and marvel at the Panama Canal.
  • Explore Bridgetown, Barbados
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Transit the historic Panama Canal
Cruise Details
0
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