Wind Surf sailing on January 4th, 2026

55-Night Caribbean (Caribbean - Extended) Windstar Cruises
Windstar Cruises Wind Surf 55-Night Caribbean (Caribbean - Extended)
Departure Port:
Philipsburg
Sailing Date: 
Sunday, 01/04/26
Return Date: 
Saturday, 02/28/26
Nights: 
55
Ship: 
Wind Surf
Cruise Line: 
Windstar Cruises
 
Special Sale: Ways to Winter Sales Event (view details) Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details) Special Sale: Travel Is Better When You're All-In (view details)
About The Cruise

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea.

 
Day # Date Port Arrive Depart
1 Sunday, 1/4/26 Philipsburg, St. Maarten --   7:00pm 
2 Monday, 1/5/26 Falmouth, Antigua and Barbuda 8:00am  6:00pm 
3 Tuesday, 1/6/26 Road Bay, Anguilla 8:00am  6:00pm 
4 Wednesday, 1/7/26 Tortola, British Virgin Islands 8:00am  6:00pm 
4 Wednesday, 1/7/26 Great Harbour, Jost Van Dyke BVI 7:00pm  --  
5 Thursday, 1/8/26 Great Harbour, Jost Van Dyke BVI --   10:00pm 
6 Friday, 1/9/26 Leverick Bay, Virgin Gorda, British Virgin Islands 8:00am  5:00pm 
7 Saturday, 1/10/26 Gustavia 8:00am  10:00pm 
8 Sunday, 1/11/26 Philipsburg, St. Maarten 6:00am  --  
9 Monday, 1/12/26 Basseterre, Saint Kitts and Nevis 8:00am  9:00pm 
10 Tuesday, 1/13/26 Little Bay, Montserrat 8:00am  6:00pm 
11 Wednesday, 1/14/26 Gustavia 8:00am  11:00pm 
12 Thursday, 1/15/26 Pointe a Pitre, Guadeloupe 8:00am  5:00pm 
13 Friday, 1/16/26 Roseau, Dominica 8:00am  5:00pm 
14 Saturday, 1/17/26 Pigeon Island, Saint Lucia 7:00am  4:00pm 
15 Sunday, 1/18/26 Bridgetown, Barbados 5:00am  6:00pm 
16 Monday, 1/19/26 Grande Anse, Martinique 9:00am  11:00pm 
17 Tuesday, 1/20/26 Castries, Saint Lucia 8:00am  4:00pm 
17 Tuesday, 1/20/26 Pigeon Island, Saint Lucia 6:00pm  --  
18 Wednesday, 1/21/26 Pigeon Island, Saint Lucia --   6:00pm 
19 Thursday, 1/22/26 Admiralty Bay, Bequia 8:00am  10:00pm 
20 Friday, 1/23/26 Mayreau, Saint Vincent and the Grenadines 8:00am  6:00pm 
21 Saturday, 1/24/26 St. George's, Grenada 7:00am  2:00pm 
22 Sunday, 1/25/26 Bridgetown, Barbados 6:00am  6:00pm 
23 Monday, 1/26/26 Man-O-War, Tobago 8:00am  5:00pm 
24 Tuesday, 1/27/26 Mayreau, Saint Vincent and the Grenadines 8:00am  6:00pm 
25 Wednesday, 1/28/26 Soufriere Bay 8:00am  4:00pm 
26 Thursday, 1/29/26 At Sea --   --  
27 Friday, 1/30/26 Kralendijk, Bonaire, Netherlands Antilles 1:00pm  10:00pm 
28 Saturday, 1/31/26 Willemstad, Curacao 8:00am  6:00pm 
29 Sunday, 2/1/26 Oranjestad, Aruba 6:00am  6:00pm 
30 Monday, 2/2/26 At Sea --   --  
31 Tuesday, 2/3/26 Santa Marta, Colombia 7:00am  6:00pm 
32 Wednesday, 2/4/26 Cartagena, Colombia 8:00am  3:30pm 
33 Thursday, 2/5/26 At Sea --   --  
34 Friday, 2/6/26 Bocas Del Toro, Panama 12:01pm  5:30pm 
35 Saturday, 2/7/26 At Sea --   --  
36 Sunday, 2/8/26 Colon, Panama 7:00am  --  
37 Monday, 2/9/26 Colon, Panama --   4:00pm 
38 Tuesday, 2/10/26 Bocas Del Toro, Panama 10:00am  4:00pm 
39 Wednesday, 2/11/26 San Andres Island, Colombia 1:00pm  7:00pm 
40 Thursday, 2/12/26 At Sea --   --  
41 Friday, 2/13/26 At Sea --   --  
42 Saturday, 2/14/26 Roatan, Honduras 9:00am  5:00pm 
43 Sunday, 2/15/26 Belize City, Belize 9:00am  7:00pm 
44 Monday, 2/16/26 Costa Maya, Mexico 8:00am  5:00pm 
45 Tuesday, 2/17/26 Cozumel, Mexico 8:00am  6:00pm 
46 Wednesday, 2/18/26 At Sea --   --  
47 Thursday, 2/19/26 Grand Cayman, Cayman Islands 8:00am  6:00pm 
48 Friday, 2/20/26 Cayman Brac, Cayman Islands 7:00am  1:00pm 
49 Saturday, 2/21/26 Port Antonio, Jamaica 12:01pm  6:00pm 
50 Sunday, 2/22/26 At Sea --   --  
51 Monday, 2/23/26 Santo Domingo, Dominican Republic 1:00pm  10:00pm 
52 Tuesday, 2/24/26 La Romana, Dominican Republic 7:00am  5:00pm 
53 Wednesday, 2/25/26 At Sea --   --  
54 Thursday, 2/26/26 Great Harbour, Jost Van Dyke BVI 8:00am  11:59pm 
55 Friday, 2/27/26 Leverick Bay, Virgin Gorda, British Virgin Islands 8:00am  5:00pm 
56 Saturday, 2/28/26 Philipsburg, St. Maarten 6:00am  --  
Number of Nights: 55
Prices are per person, double occupancy, cruise only and on select sailings. Prices shown are for stateroom categories as noted and are shown in US Dollars. Government taxes and fees are additional. Airfare is not included. Prices and itineraries are based on availability and are subject to change without notice.