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 Search All Cruises Caribbean03/13/20276 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,286-$4,12612/19/20267 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,310-$3,15012/26/20267 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,841--01/02/20277 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,306-$3,14601/09/20277 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,576-$3,13601/16/20277 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,971-$3,49601/23/20277 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,136-$5,72601/30/20277 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,936-$3,77602/06/20277 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,506-$3,34602/13/20277 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,496-$4,16102/20/20277 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,381-$4,22102/27/20277 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,286-$4,12603/06/20277 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,681-$3,31103/20/20277 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,296-$3,13611/20/20278 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,676-$3,63612/19/20278 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,956-$3,91611/20/202715 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$4,222-$5,72212/12/202715 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$4,222-$5,64712/19/202715 Night Caribbean Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,997-$5,497Mediterranean04/27/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$2,526-$2,94604/27/20277 Night Mediterranean Cruise Wine Cruise: Enchanting Greece & the Amalfi Coaston the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability05/04/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,484-$4,11405/11/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,169-$4,11405/18/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,169-$4,11405/25/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,484-$4,11405/25/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability06/01/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,169-$4,11406/08/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239-$4,18406/08/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability06/15/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability06/15/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239-$4,18406/22/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239-$4,18406/22/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability06/29/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239-$4,18406/29/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability07/06/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,159-$4,10407/13/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239-$4,18407/13/20277 Night Mediterranean Cruise James Beard Foundation: Treasures of the Greek Isleson the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability07/20/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239-$4,18407/20/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability08/05/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability08/05/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239-$4,18408/12/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability08/12/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239-$4,18408/19/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,229-$4,17408/26/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239-$4,18408/26/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability09/02/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability09/02/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239-$4,18409/09/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239-$4,18409/09/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability09/16/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability09/16/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,589-$4,56909/23/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239-$4,18409/30/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability09/30/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239-$4,18410/07/20277 Night Mediterranean Cruise Athens Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability10/07/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,239--10/14/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$2,071-$3,01610/14/20277 Night Mediterranean Cruise James Beard Foundation: Enchanting Greece & the Amalfi Coaston the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuiteContact cruise line for pricing & availability10/21/20277 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$2,396-$3,34110/21/20277 Night Mediterranean Cruise Yachtsman's Harbors of the Rivierason the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability04/11/20278 Night Mediterranean Cruise Lisbon Pre Cruise Tour Itineraryon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuiteContact cruise line for pricing & availability04/11/20278 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuite-$2,729-$3,80904/19/20278 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Tarragona, SpainInteriorOceanviewBalconySuite-$2,519-$3,59904/19/20278 Night Mediterranean Cruise Yachtsman's Harbors of the Rivierason the Windstar Cruises Wind Surf departing from Tarragona, SpainInteriorOceanviewBalconySuiteContact cruise line for pricing & availability10/28/20278 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Barcelona, SpainInteriorOceanviewBalconySuite-$4,049-$5,12910/28/20278 Night Mediterranean Cruise Spanish Symphonyon the Windstar Cruises Wind Surf departing from Barcelona, SpainInteriorOceanviewBalconySuiteContact cruise line for pricing & availability07/27/20279 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$12,104-$15,16407/06/202714 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$5,418-$7,02808/12/202714 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$5,488-$7,09808/19/202714 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$5,488-$7,09810/14/202714 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$3,802-$5,41204/19/202715 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Tarragona, SpainInteriorOceanviewBalconySuite-$5,040-$5,86510/21/202715 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$5,500-$7,22504/11/202716 Night Mediterranean Cruiseon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuite-$4,728-$6,648Transatlantic03/27/202715 Night Transatlantic Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,544-$4,34411/05/202715 Night Transatlantic Cruiseon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuite-$2,319-$4,11903/27/202723 Night Transatlantic Cruiseon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$4,778-$7,308 OCG Class Luxury Wind Surf Year Built1990Year Last Refurbished2019Capacity342 passengersDecks7Tonnage14,745RegistryBahamasContact888-393-6070www.windstarcruises.com