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Virgin Islands Small Ship Sailing

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Discover the enchanting allure of the Virgin Islands with Adventure Life's array of 9 captivating small ship sailing experiences in 2025. Join us on a sailing adventure to explore the mesmerizing beauty and vibrant cultures of the Caribbean islands. From the turquoise waters of Antigua to the lush landscapes of St. Lucia, each moment offers a unique opportunity to immerse yourself in the wonders of the region. Experience the relaxed pace of small ship sailing as you swim and snorkel amidst the pristine waters, enjoy the French flair of Îles des Saintes, and witness breathtaking sunsets over the horizon. Engage in a variety of activities like snorkeling, wildlife viewing, and discovering hidden beaches, all while surrounded by the natural splendor of the Caribbean. Don't miss this chance to sail away from the ordinary and embark on a journey of a lifetime. Contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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Explore the famous rock formations of the baths
from $5,245
EXPLORE

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 Barts harbor view
from $7,990
2for1
EXPLORE

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
Play on the famously beautiful beaches of St. Barth's
from $8,390
2for1
EXPLORE

Caribbean Yachting Discovery

St John - St Thomas - 8 Day Itinerary aboard Emerald Azzurra
Starts / Ends
St. John's / St. Thomas
Activities
Village Visits
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
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
Hiking
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
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
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
Tropical waterfall and turquoise pool in lush forest of Dominica
from $1,960
Upgrade
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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 beaches of St. Maarten
from $1,960
Upgrade
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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
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
Snorkeling, 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
0
Explore colorful Bridgetown, Barbados
from $4,800
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Bridgetown to Bridgetown

8 Day Itinerary aboard Silver Spirit
Starts / Ends
Bridgetown / Bridgetown
Activities
Small Ship Sailing, Local Market Visits, Wildlife Viewing, Archaeological Site Visits, Spa Relaxation
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.
  • Hike to Saint Lucia’s Pitons
  • Snorkel Martinique’s colorful reefs
  • Explore Gustavia’s historic harbor
  • Stroll Bequia’s scenic shores
Cruise Details
0
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