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STAR COLLECTOR: GRAND CARIBBEAN ADVENTURE 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
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
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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
55 Nights from
$17,899.00 (USD)
Per Person
+ $247.00 taxes/fees
Category b
Inside
N/A
Outside
$17,899.00
Cat:B
$325.44 per night
Balcony
N/A
Suite
N/A
8569852

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
Prices are per-person based on double occupancy, unless otherwise noted.