Have questions? We're here.
Gustavia Harbor in St. Barths

St. Barth Sailboat Cruises

Travel made your way ™
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Talk with an expert
Experience the Caribbean's ultimate relaxation on Adventure Life's small ship sailing tours for 2026. Set sail to the Treasure Islands and the French Riviera of the Caribbean, from St. Martin to St. Barths, Antigua, and Dominica, discovering breathtaking beaches, old forts, and charming seaside villages along the way. Engage in snorkeling, explore historic streets, and bask in the chic ambiance of St. Barts. Whether you choose the laid-back lifestyle of Sea Cloud II's Caribbean island-hopping cruise or opt for the Leeward Islands tour to visit Dominica Island and snorkel at Iles des Saintes, each journey promises total relaxation and unforgettable experiences. Delve into the unique charm of Gustavia and immerse yourself in the turquoise waters and white sands that define the Caribbean. Don't miss this opportunity to sail through paradise - contact one of Adventure Life's tour specialists for help planning your next seamless trip.
Filter (3 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Gustavia
Relax on the beaches of St. Maarten
from $1,970
EXPLORE

Leeward Islands

8 Day Itinerary aboard Star Flyer
  • Visit Dominica Island
  • Snorkel at Iles des Saintes
  • Sail across Rivière Salée
  • Enjoy Gustavia's unique charm
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.
Cruise Details
0
Tropical waterfall and turquoise pool in lush forest of Dominica
from $1,970
EXPLORE

Treasure Islands

St. Maarten Roundtrip - 8 Day Itinerary aboard Star Flyer
  • Visit Virgin Gorda's famous “Baths”
  • Enjoy the lifestyle of Soper's Hole
  • Walk the streets of Basseterre
  • Relax on famous St. Barts
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!
Cruise Details
0
Gustavia Harbor in St. Barths
from $1,970
EXPLORE

Antigua to Antigua

Roundtrip St John - 8 Day Itinerary aboard Star Clipper
  • Explore St. John's dockyards
  • Sail Sir Francis Drake Channel
  • Stroll Norman Island's beach
  • Tour Basseterre's old plantations
Starts / Ends
St. John's / St. John's
Activities
Small Ship Sailing, Snorkeling, Local Market Visits, Village Visits
Activity Level
Variable
Embark on an 8-day cruise in the Caribbean aboard the Star Clipper, starting and ending in Antigua. Discover the beaches and boutiques of St. Barts, explore Norman Island, and enjoy the charm of Jost van Dyke, while swimming at Virgin Gorda and experiencing St. Kitts’ history and nature.
Cruise Details
0
1-3 of 3 Results
  • 1

Caribbean Travel Guide

Favorite Caribbean Caribbean All Trips

Top Caribbean Travel Destinations

Caribbean Trips by Departure Date

Top Experiences in Caribbean

Caribbean Trips by Duration

Caribbean Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By

Franny Friesz Adventure Life employee profile
Franny F
Plan My Trip
We love travel, talk with an expert 1.800.344.6118