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"Travel changes people, and people change the world!"

STARS OF THE GREATER ANTILLES on Wind Surf

Cruise, Ocean cruise, Small Ship/Yacht
Wind Surf Capri
Exterior view of Wind Surf sailing near Capri, Italy
Photo Credit: Roger Paperno
  • Exterior view of Wind Surf sailing near Capri, Italy - Photo Credit: Roger Paperno
  • Exterior view of Wind Surf
  • Exterior view of Wind Surf - Photo Credit: Jeff Zaruba
  • Close-up exterior view of Wind Surf bow - Photo Credit: Roger Paperno
  • Exterior view of Wind Surf - Photo Credit: Roger Paperno
Cruise through the Greater Antilles discovering magical places that fell off the map and tiny gems that were never on it in the first place. Skip the crowds of Montego Bay and Ocho Rios and head instead for the silver screen beauty of Port Antonio, "discovered" by Errol Flynn and then long forgotten. Enjoy the retro-Caribbean vibe of Grand Cayman and the undersea wonderland of La Romana. Sink into the sand on perfect white beaches, dive to pirate shipwrecks, swim beneath waterfalls wrapped in jungle and fall in love with a Caribbean you didn’t know still existed.
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.

Feb 17, 2026 through
Feb 28, 2026
Feb 11, 2026 7:00 PM
11 Nights from
$3,999.00 (USD)
Per Person
+ $64.00 taxes/fees
Category b

Itinerary

Day Port Arrive Depart
1 Cozumel 6:00 PM
2 At Sea
3 Grand Cayman 8:00 AM 6:00 PM
4 Cayman Brac 7:00 AM 1:00 PM
5 Ocho Rios, Jamaica 8:30 AM 2:00 PM
6 At Sea
7 Santo Domingo 1:00 PM 10:00 PM
8 La Romana 7:00 AM 5:00 PM
9 At Sea
10 Jost Van Dyke, Great Harbour 8:00 AM 10:00 PM
11 Virgin Gorda / Prickly Pear, British Virgin Islands 8:00 AM 5:00 PM
12 Philipsburg, St. Maarten 6:00 AM
Prices are per-person based on double occupancy, unless otherwise noted.