Have questions? We're here.
Sunset over Philipsburg

Philipsburg 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 thrill of small ship sailing through the Caribbean's Treasure Islands and the French Riviera with our 4 unique cruises for 2025. Join us on a sailing adventure aboard small ships to uncover the hidden gems of St. Martin, St. Barths, Antigua, Dominica, and more. From exploring the famous “Baths” in Virgin Gorda to relaxing on the pristine beaches of St. Barts, each day offers a new opportunity for discovery. Snorkel in crystal-clear waters, stroll through historic towns, and soak in the laid-back Caribbean lifestyle. With activities like snorkeling and small ship cruising, this journey offers a relaxed pace suitable for all travelers. Don't miss this chance to set sail on a memorable Caribbean escapade and contact one of Adventure Life's tour specialists for help planning your next seamless trip.
Filter (4 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Philipsburg
Relax on the beaches of St. Maarten
from $1,870
SS 25%
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
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.
Cruise Details
0
Enjoy a Caribbean escape
from $3,980
EXPLORE

Save the Best for Last

Roundtrip St. Maarten - 8 Day Itinerary aboard Sea Cloud
  • Discover The Baths
  • Relax at Bitter End
  • Sail to Jost van Dyke
  • Experience St. Barths
  • Explore Nevis
Starts / Ends
Philipsburg / St. Martin
Activities
Small Ship Sailing
Activity Level
Variable
Sail aboard the Sea Cloud on a 10-day Caribbean adventure through the British Virgin Islands, St. Barths, Nevis, and St. Maarten. Explore Virgin Gorda’s iconic Baths, unwind at the Bitter End Yacht Club, and sail the Sir Francis Drake Channel to Jost van Dyke. Stroll St. Barths’ luxury shops, discover Nevis’ lush rainforests, and end in vibrant Philipsburg.
Cruise Details
0
Tropical waterfall and turquoise pool in lush forest
from $1,960
SS 25%
EXPLORE

Treasure Islands

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
Explore the beautiful Canary Islands
from $4,820
EXPLORE

Westbound Atlantic Ocean Crossing

25 Day Itinerary aboard Star Flyer
  • Discover the Rock of Gibraltar
  • Experience Tangier
  • Visit Cadiz
  • Explore Safi
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.
Cruise Details
0
1-4 of 4 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

Jeff Rottschafer Adventure Life employee profile
Jeff R
Plan My Trip
We love travel, talk with an expert 1.800.344.6118