STAR COLLECTOR: GRAND CARIBBEAN ADVENTURE on 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
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 exper
Jan 04, 2026 through
Feb 28, 2026
Dec 29, 2025
7:00 PM
Category b
Inside
Outside
Balcony
Suite
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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 | 9:00 PM |
13 | Pigeon Island | 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 | 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, British Virgin Islands | 8:00 AM | 5:00 PM |
56 | Philipsburg, St. Maarten | 6:00 AM |