LUSH & LOVELY ISLANDS OF THE LESSER ANTILLES on Wind Surf

Cruise, Ocean cruise, Small Ship/Yacht
Wind Surf at Sea
Exterior view of Wind Surf
Photo Credit: Roger Paperno
  • Exterior view of Wind Surf - Photo Credit: Roger Paperno
  • Captain's Bridge
  • Deck
  • Pool Bar
  • Lounge
  • PoolArea
Enjoy the perfect mix of must-see Caribbean towns and harbors off the beaten path as you cruise and sail the royal beauties of the Lesser Antilles islands. Explore colonial history in pastel waterfronts, weathered forts and former sugar plantations. See the Caribbean at its most wild and beautiful on Dominica, St. Lucia and St. Kitts. Join the jetsetters on St. Barts, and everywhere you go, find delicious white beaches that turn rose and orange under Caribbean sunsets.
About Wind Surf
About Windstar Cruises
Windstar Cruises logo

THE WORLD'S BEST SMALL SHIP CRUISE LINE

All cruise ships let you see the world. Only Windstar’s private yacht style cruises brings you close enough so you can truly experience it. Each of our Windstar Cruises yachts serves between 148 and 342 guests. This intimacy provides you with the luxuries of time, space, and freedom to immerse yourself in both the journey and the destination — in ways you may never have imagined possible.

Jan 11, 2026 through
Jan 18, 2026
Jan 5, 2026 7:00 PM
7 Nights from
$2,899.00 (USD)
Per Person
+ $37.00 taxes/fees
Category b

Itinerary

Day Port Arrive Depart
1 Philipsburg, St. Maarten 7:00 PM
2 Basseterre 8:00 AM 9:00 PM
3 Gustavia 8:00 AM 10:00 PM
4 St. John's 8:00 AM 10:00 PM
5 Les Saintes 8:00 AM 1:00 PM
6 Mayreau 8:00 AM 5:00 PM
7 Kingstown 7:00 AM 2:00 PM
8 Bridgetown 5:00 AM
Prices are per-person based on double occupancy, unless otherwise noted.