Windstar Cruises Wind Surf Cruise Itineraries

Select an upcoming Wind Surf cruise itinerary list below to find a Wind Surf sailing itinerary by cruise area or departure port.

Group Cruises by:   Destination  |  Date  |  Cruise
Caribbean
03/13/2027
6 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$1,812
-
$2,532
03/13/2027
6 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$1,812
-
$2,532
03/13/2027
6 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$1,812
-
$2,532
03/13/2027
6 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$1,812
-
$2,532
12/19/2026
7 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$2,345
-
$3,185
01/02/2027
7 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$2,131
-
$2,971
01/09/2027
7 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$2,121
-
$2,961
01/09/2027
7 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$2,121
-
$2,961
01/09/2027
7 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$2,121
-
$2,961
01/09/2027
7 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$2,121
-
$2,961
01/16/2027
7 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$2,121
-
$2,961
01/16/2027
7 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$2,121
-
$2,961
01/23/2027
7 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$2,121
-
$2,961
03/06/2027
7 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$2,121
-
$2,961
03/20/2027
7 Night Caribbean Cruise
on the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St Maarten
Interior
Oceanview
Balcony
Suite
-
$2,191
-
$3,031
Mediterranean
06/11/2026
3 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Barcelona, Spain
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
10/25/2026
5 Night Mediterranean Cruise
Quick Getaways: Yachtsman's Harbors of the Rivieras
on the Windstar Cruises Wind Surf departing from Civitavecchia, Italy
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
10/25/2026
5 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Civitavecchia, Italy
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
05/04/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$4,359
-
$5,304
05/11/2027
7 Night Mediterranean Cruise
Athens Pre Cruise Tour Itinerary
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
05/11/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$3,964
-
$4,909
05/18/2027
7 Night Mediterranean Cruise
Athens Pre Cruise Tour Itinerary
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
05/18/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$4,359
-
$5,304
05/25/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$3,964
-
$4,909
05/25/2027
7 Night Mediterranean Cruise
Athens Pre Cruise Tour Itinerary
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
06/08/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$3,964
-
$4,909
06/08/2027
7 Night Mediterranean Cruise
Athens Pre Cruise Tour Itinerary
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
06/15/2027
7 Night Mediterranean Cruise
Athens Pre Cruise Tour Itinerary
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
06/15/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$4,149
-
$5,094
06/22/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$3,964
-
$4,909
06/22/2027
7 Night Mediterranean Cruise
Athens Pre Cruise Tour Itinerary
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
07/06/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$3,964
-
$4,909
06/14/2026
8 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Tarragona, Spain
Interior
Oceanview
Balcony
Suite
-
$2,269
-
$4,532
06/22/2026
8 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Lisbon, Portugal
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
07/07/2026
8 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Civitavecchia, Italy
Interior
Oceanview
Balcony
Suite
-
$4,722
-
$5,802
07/24/2026
8 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
-
$2,802
-
$3,922
08/18/2026
8 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
-
$2,802
-
$3,922
09/02/2026
8 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Civitavecchia, Italy
Interior
Oceanview
Balcony
Suite
-
$4,722
-
$5,802
09/19/2026
8 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
-
$2,802
-
$3,922
10/07/2026
8 Night Mediterranean Cruise
James Beard Foundation & Wine Cruise: Classic Italy & Dalmatian Coast
on the Windstar Cruises Wind Surf departing from Civitavecchia, Italy
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
10/07/2026
8 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Civitavecchia, Italy
Interior
Oceanview
Balcony
Suite
-
$4,722
-
$5,802
10/07/2026
8 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Civitavecchia, Italy
Interior
Oceanview
Balcony
Suite
-
$4,722
-
$5,802
10/07/2026
8 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Civitavecchia, Italy
Interior
Oceanview
Balcony
Suite
-
$4,722
-
$5,802
07/15/2026
9 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
-
$2,839
-
$4,859
08/09/2026
9 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
-
$2,839
-
$4,859
09/10/2026
9 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
-
$2,839
-
$4,859
09/10/2026
9 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
-
$2,839
-
$4,859
09/10/2026
9 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
-
$2,839
-
$4,859
09/10/2026
9 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
-
$2,839
-
$4,859
08/18/2026
10 Night Mediterranean Cruise
Classic Italy & Dalmatian Coast
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
09/19/2026
10 Night Mediterranean Cruise
Classic Italy & Dalmatian Coast
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
10/15/2026
10 Night Mediterranean Cruise
Classic Italy & Dalmatian Coast
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
10/15/2026
10 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
-
$5,524
-
$6,924
06/11/2026
11 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Barcelona, Spain
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
07/06/2027
14 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
10/15/2026
15 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
OCG Class
Luxury
Wind Surf
Year Built1990
Year Last Refurbished2019
Capacity342 passengers
Decks7
Tonnage14,745
RegistryBahamas
Contact
www.windstarcruises.com