Unique Cruise Specialist
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STAR COLLECTOR: CARIBBEAN EXPLORATIONS on Wind Surf

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
Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.
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.

Mar 21, 2026 through
Apr 04, 2026
Mar 15, 2026 7:00 PM
14 Nights from
$3,699.00 (USD)
Per Person
+ $120.00 taxes/fees
Category b
Inside
N/A
Outside
$3,699.00
Cat:B
$264.21 per night
Balcony
N/A
Suite
$9,799.00
Cat:OS
$699.93 per night
Signature Collection
8860579

Itinerary

Day Port Arrive Depart
1 Philipsburg, St. Maarten 7:00 PM
2 Charlestown 8:00 AM 5:00 PM
3 Roseau 8:00 AM 4:00 PM
4 Mayreau 8:00 AM 5:00 PM
5 Les Saintes 6:00 PM
6 Basseterre 8:00 AM 10:00 PM
7 Gustavia 8:00 AM 10:00 PM
8 Philipsburg, St. Maarten 6:00 AM 7:00 PM
9 St. John's 8:00 AM 5:00 PM
10 Road Bay 8:00 AM 6:00 PM
11 Jost Van Dyke, Great Harbour 7:00 PM
11 Soper's Hole 8:00 AM 6:00 PM
12 Jost Van Dyke, Great Harbour 10:00 PM
13 Virgin Gorda / Prickly Pear, British Virgin Islands 8:00 AM 5:00 PM
14 Gustavia 8:00 AM 10:00 PM
15 Philipsburg, St. Maarten 6:00 AM
Prices are per-person based on double occupancy, unless otherwise noted.