Have questions? We're here.
Visit beautiful Basseterre

St. Kitts Sailboat Cruises

Travel made your way
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Experience the enchanting allure of small ship sailing in the Caribbean's Treasure Islands and the French Riviera with Adventure Life's array of 3 captivating cruises for 2025. Sail aboard the Star Flyer or the Royal Clipper and set course to explore breathtaking beaches, old forts, and seaside villages starting from Philipsburg or Bridgetown. Walk the charming streets of Basseterre, relax on the famous St. Barts, discover the lush island of St. Lucia, and immerse yourself in the sophisticated ambiance of Martinique. From snorkeling in crystal-clear waters to exploring Falmouth Harbour and enjoying the lifestyle of Soper's Hole, each moment offers a unique opportunity to delve into the wonders of the Caribbean. Engage in a variety of activities suitable for all travelers, including village visits, hiking, and wildlife viewing. Don't miss the chance to embark on this adventure and 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
    • Basseterre
Tropical waterfall and turquoise pool in lush forest of Dominica
from $1,960
Upgrade
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
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
Enjoy the beautiful blue Caribbean
from $8,050
EXPLORE

Grenada to Antigua

St. George - St. John - 11 Day Itinerary aboard Star Clipper
  • Explore St. George’s harbor
  • Experience Charlotteville coast
  • Relax at Englishman’s Bay
  • Wander through Admiralty Bay
Starts / Ends
St. Georges / St. John's
Activity Level
Variable
Take an 11-day cruise on the Star Clipper from St. George's, Grenada to St. John's, Antigua, exploring secluded bays and historic towns in Tobago and the Grenadines. Enjoy highlights like snorkeling in Tobago Cays and relaxing on beautiful beaches, while immersing yourself in vibrant local cultures.
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