STAR COLLECTOR: GRAND CARIBBEAN ADVENTURE on Wind Surf
Cruise, Ocean cruise, Small Ship/Yacht

Exterior view of Wind Surf
Photo Credit: Roger Paperno
See all the flavors of the Caribbean as you visit 28 islands and 39 ports from the lush jungles of Dominica to arid Aruba, trendy French enclaves to quiet ports known only to yachtsmen. Then go beyond, to the shores of the conquistadors in Colombia, to the Mayan legacy in Belize, and to Mexico’s golden Yucatán. On Day 36, part-way through your 55-day voyage, explore one of mankind’s greatest achievements as you make a partial transit of the Panama Canal, passing through three sets of locks and sailing into Lake Gatun before returning to the Caribbean. There’s a little bit of everything on this voyage: cultures, cuisine, beaches, nature, history, and shopping. With this epic tour of the Caribbean, you’re sure to come home with unforgettable memories, new friends, and new perspectives.
About Wind Surf
About Windstar Cruises

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 28, 2026
Dec 29, 2025
7:00 PM
Category bx
8905913
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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 | 6:00 PM |
30 | At Sea | ||
31 | Cartagena | 8:00 AM | |
32 | Cartagena | 3:30 PM | |
33 | At Sea | ||
34 | Bocas del Toro | 6:00 PM | |
35 | At Sea | ||
36 | At Sea | 8:00 AM | 1:00 PM |
37 | Colón | 7:00 AM | 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 | Ocho Rios, Jamaica | 8:30 AM | 2:00 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 | 10:00 PM |
55 | Virgin Gorda / Prickly Pear, British Virgin Islands | 8:00 AM | 5:00 PM |
56 | Philipsburg, St. Maarten | 6:00 AM |