STAR COLLECTOR: GRAND CARIBBEAN ADVENTURE on Wind Surf
Cruise, Ocean cruise, Small Ship/Yacht
Photo Credit: Roger Paperno
Explore the depth and breadth of the Caribbean on this 35-day odyssey, from tiny yachtsmen’s favorites to glitzy celebrity getaways, historic colonial towns to the incredible jungles of wildlife. Go cave tubing in Belize and diving in Bonaire. Snorkel with friendly sea turtles and rays in waters as clear as glass. Climb the battlements of colonial forts and the arrowhead peak of Gros Piton in St. Lucia. It’s the ultimate cruise, circling the Caribbean discovering the brilliant colors, textures and fascinating history found here.
About Wind Surf
About Windstar Cruises
THE WORLD'S BEST SMALL SHIP CRUISE LINE
NO ONE ELSE GOES SO FAR TO GET TRAVELERS SO CLOSE …
You’re closer to secluded coves, tiny villages, misty fjords. To ancient ruins, medieval alleyways, quaint marinas. To unspoiled beaches, unfamiliar cultures, undiscovered atolls. To enlivening your curiosity and awakening your sense of wonder. You’re closer than ever to the kind of authentic and unforgettable experiences that you travel to find in the first place. You’re about to board Windstar. And you’re closer to all the places that larger ships can’t reach.
SEE A WORLD FEW WILL EVER SEE …
Welcome to a world of understated elegance and uncommon beauty. A world that leaves crowds and commonplace behind to find unique ports of call, and local, exotic cultures that are at once fascinating and wondrous. A world that’s equal parts intimate, indulgent and inspiring. Where the allure and beauty and magic of the places you sail to is equaled only by the ship that takes you there.
NO ONE ELSE GOES SO FAR TO GET TRAVELERS SO CLOSE …
You’re closer to secluded coves, tiny villages, misty fjords. To ancient ruins, medieval alleyways, quaint marinas. To unspoiled beaches, unfamiliar cultures, undiscovered atolls. To enlivening your curiosity and awakening your sense of wonder. You’re closer than ever to the kind of authentic and unforgettable experiences that you travel to find in the first place. You’re about to board Windstar. And you’re closer to all the places that larger ships can’t reach.
SEE A WORLD FEW WILL EVER SEE …
Welcome to a world of understated elegance and uncommon beauty. A world that leaves crowds and commonplace behind to find unique ports of call, and local, exotic cultures that are at once fascinating and wondrous. A world that’s equal parts intimate, indulgent and inspiring. Where the allure and beauty and magic of the places you sail to is equaled only by the ship that takes you there.
Jan 04, 2026 through
Feb 28, 2026
Dec 29, 2025
7:00 PM
Category b
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Itinerary
Day | Port | Arrive | Depart |
---|---|---|---|
1 | 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 | 8:00 AM | 5:00 PM |
7 | Gustavia | 8:00 AM | 10:00 PM |
8 | St. Maarten | 6:00 AM | 7:00 PM |
9 | Basseterre | 7:00 AM | 10:00 PM |
10 | Little Bay | 8:00 AM | 6:00 PM |
11 | Gustavia | 8:00 AM | 11:00 PM |
12 | Deshaies | 12:30 AM | 10:00 PM |
13 | Roseau | 8:00 AM | 5:00 PM |
14 | Pigeon Island | 7:00 AM | 4:00 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 | Man-O-War Bay | 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 | 6:00 PM |
30 | At Sea | ||
31 | Santa Marta | 7:00 AM | 6:00 PM |
32 | Cartagena | 8:00 AM | 3:30 PM |
33 | At Sea | ||
34 | Bocas del Toro | 5:30 PM | |
35 | At Sea | ||
36 | Colón | 7:00 AM | |
37 | Colón | 4:00 PM | |
38 | Bocas del Toro | 10:00 AM | 4:00 PM |
39 | Isla San Andres | 1:00 PM | 7:00 PM |
40 | At Sea | ||
41 | At Sea | ||
42 | Roatan | 9:00 AM | 5:00 PM |
43 | Belize City | 9:00 AM | 7:00 PM |
44 | Costa Maya | 8:00 AM | 5:00 PM |
45 | Cozumel | 8:00 AM | 6:00 PM |
46 | At Sea | ||
47 | Grand Cayman | 8:00 AM | 6:00 PM |
48 | Cayman Brac | 7:00 AM | 1:00 PM |
49 | Port Antonio | 6:00 PM | |
50 | At Sea | ||
51 | Santo Domingo | 1:00 PM | 10:00 PM |
52 | La Romana | 7:00 AM | 5:00 PM |
53 | At Sea | ||
54 | Jost Van Dyke, Great Harbour | 8:00 AM | |
55 | Virgin Gorda / Prickly Pear | 8:00 AM | 5:00 PM |
56 | St. Maarten | 6:00 AM |