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
-
$2,971
-
$3,811
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
-
$2,450
-
$3,290
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
-
$2,271
-
$2,936
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
-
$2,086
-
$2,926
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
-
$3,146
-
$3,986
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
-
$3,766
-
$4,431
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
-
$2,086
-
$2,926
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
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
-
$2,200
-
$2,740
05/04/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$3,659
-
$4,604
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
-
$3,274
-
$4,219
05/18/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$3,659
-
$4,604
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
05/25/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$3,764
-
$4,709
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
-
$3,274
-
$4,219
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
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$3,449
-
$4,394
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
06/22/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$3,449
-
$4,394
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
-
$3,274
-
$4,219
07/13/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$3,449
-
$4,394
07/13/2027
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
07/20/2027
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
07/20/2027
7 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$3,274
-
$4,219
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
-
$2,177
-
$3,041
08/18/2026
8 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
08/18/2026
8 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
-
$2,241
-
$3,137
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
-
$5,362
-
$6,442
09/19/2026
8 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
10/07/2026
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
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
10/15/2026
8 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
07/15/2026
9 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
08/09/2026
9 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
Contact cruise line for pricing & availability
09/10/2026
9 Night Mediterranean Cruise
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
-
$4,924
-
-
07/06/2027
14 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Piraeus, Greece
Interior
Oceanview
Balcony
Suite
-
$5,292
-
$6,804
10/15/2026
15 Night Mediterranean Cruise
on the Windstar Cruises Wind Surf departing from Venice, Italy
Interior
Oceanview
Balcony
Suite
-
$5,954
-
-
OCG Class
Luxury
Wind Surf
Year Built1990
Year Last Refurbished2019
Capacity342 passengers
Decks7
Tonnage14,745
RegistryBahamas
Contact888-393-6070
www.windstarcruises.com

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