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St. Martin Sailboat Cruises

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Experience the enchanting world of small ship sailing in the Caribbean with Adventure Life's array of 5 captivating cruises for 2025. Join us on a sailing journey through the mesmerizing Treasure Islands and the French Riviera of the Caribbean, from the chic St Barths to historic Antigua and beyond. From exploring the famous “Baths” in Virgin Gorda to snorkeling at Iles des Saintes, each moment offers a unique opportunity to immerse yourself in the wonders of this region. Enjoy the laid-back lifestyle of Soper's Hole, walk the charming streets of Basseterre, and relax on the famous beaches of St. Barts. With activities like snorkeling and small ship sailing, this adventure offers a relaxed pace suitable for all travelers. Don't miss this opportunity to discover the beauty and culture of the Caribbean. Contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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    • St. Martin
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
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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
Activities
Snorkeling
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
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Relax on the sunny beaches of the Caribbean
from $7,990
2for1
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Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Sakara
Starts / Ends
Marigot / Bridgetown
Activities
Wildlife Viewing
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
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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
Small Ship Sailing, Village Visits, Local Market Visits, 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
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Explore the beautiful Canary Islands
from $4,820
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Westbound Atlantic Ocean Crossing

25 Day Itinerary aboard Star Flyer
Starts / Ends
Malaga / Philipsburg
Activity Level
Variable
Embark on a 25-day cruise aboard the Star Flyer, visiting Malaga, Gibraltar, Tangier, Cadiz, Safi, Arrecife, Puerto del Rosario, Las Palmas, San Sebastian, and Philipsburg. Explore historic sites, natural beauty, charming towns, golden beaches, and unique shopping experiences.
  • Discover the Rock of Gibraltar
  • Experience Tangier
  • Visit Cadiz
  • Explore Safi
Cruise Details
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