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STAR COLLECTOR: THE BEST OF THE WINDWARD & LEEWARD ISLES 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
Explore the Caribbean’s most picturesque destinations and little-known treasures while indulging in a longer cruise vacation along the most scenic stops throughout the Windward and Leeward Islands and relaxing afternoon in the warm Caribbean off the Watersports Platform. Swim amid sea turtles, colorful coral, eagle rays, and parrot fish during a snorkel safari off the coast of St. Kitts. Buzz about with a beekeeping guide and sample the delicious sweetness of rare and exotic Black Mangrove honey during an agricultural collective tour outside of Castries. Kayak to a beachside village for beverages and souvenirs during an overnight stay in Jost Van Dyke. Dine on conch fritters paired with tropical refreshments. Walk in the childhood footsteps of the future Empress Josephine among flowers and rustic gardens at the Pagerie Habitation, a former sugar plantation on Martinique. Seek out brown pelicans, blue herons, and iconic pink flamingos while gliding silently along lattice-like mangrove roots in Lac Bay National Park on Bonaire.
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 04, 2026 through
Feb 01, 2026
Dec 29, 2025 7:00 PM
28 Nights from
$9,099.00 (USD)
Per Person
+ $96.00 taxes/fees
Category bx

Itinerary

Day Port Arrive Depart
1 Philipsburg, St. Maarten 7:00 PM
2 Falmouth Harbour 8:00 AM 6:00 PM
3 Road Bay 8:00 AM 6:00 PM
4 Jost Van Dyke, Great Harbour 7:00 PM
4 Soper's Hole 8:00 AM 6:00 PM
5 Jost Van Dyke, Great Harbour 10:00 PM
6 Virgin Gorda / Prickly Pear, British Virgin Islands 8:00 AM 5:00 PM
7 Gustavia 8:00 AM 10:00 PM
8 Philipsburg, St. Maarten 6:00 AM 7:00 PM
9 Basseterre 8:00 AM 9:00 PM
10 Gustavia 8:00 AM 10:00 PM
11 St. John's 8:00 AM 10:00 PM
12 Les Saintes 8:00 AM 1:00 PM
13 Mayreau 8:00 AM 5:00 PM
14 Kingstown 7:00 AM 2:00 PM
15 Bridgetown 5:00 AM 6:00 PM
16 Anse Mitan 9:00 AM 11:00 PM
17 Pigeon Island 6:00 PM
17 Castries 8:00 AM 4:00 PM
18 Pigeon Island 6:00 PM
19 Bequia 8:00 AM 10:00 PM
20 Mayreau 8:00 AM 6:00 PM
21 St. George's 7:00 AM 2:00 PM
22 Bridgetown 6:00 AM 6:00 PM
23 Bequia 8:00 AM 5:00 PM
24 Mayreau 8:00 AM 6:00 PM
25 Soufriere 8:00 AM 4:00 PM
26 At Sea
27 Kralendijk 1:00 PM 10:00 PM
28 Willemstad 8:00 AM 6:00 PM
29 Oranjestad 6:00 AM
Prices are per-person based on double occupancy, unless otherwise noted.