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 Caribbean12/02/20255 Night Caribbean Cruise Barefoot Break in the British Virgin Islandson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,099-$2,89903/22/20257 Night Caribbean Cruise Beach Fun & Sun: A Remote Caribbean Getawayon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,399-$4,09912/07/20257 Night Caribbean Cruise Classic Caribbeanon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,299-$3,19912/14/20257 Night Caribbean Cruise Beach Fun & Sun: A Remote Caribbean Getawayon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,399-$3,29912/21/20257 Night Caribbean Cruise Classic Caribbeanon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,699-$3,59912/28/20257 Night Caribbean Cruise Beach Fun & Sun: A Remote Caribbean Getawayon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,699-$3,59901/04/20267 Night Caribbean Cruise Beach Fun & Sun: A Remote Caribbean Getawayon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,599-$3,49901/11/20267 Night Caribbean Cruise Lush & Lovely Islands of the Lesser Antilleson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,599-$3,49901/18/20267 Night Caribbean Cruise Jewels of the Windward Islandson the Windstar Cruises Wind Surf departing from Bridgetown, BarbadosInteriorOceanviewBalconySuite-$2,699-$3,59901/25/20267 Night Caribbean Cruise Windward Ways & Tobago Cayson the Windstar Cruises Wind Surf departing from Bridgetown, BarbadosInteriorOceanviewBalconySuite-$2,799-$3,69902/28/20267 Night Caribbean Cruise Classic Caribbeanon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,499-$3,39903/21/20267 Night Caribbean Cruise Classic Caribbeanon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,299-$3,19903/28/20267 Night Caribbean Cruise Beach Fun & Sun: A Remote Caribbean Getawayon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,399-$3,29902/17/202611 Night Caribbean Cruise Stars of the Greater Antilleson the Windstar Cruises Wind Surf departing from Cozumel, Quintana Roo, MexicoInteriorOceanviewBalconySuite-$3,999-$4,99912/02/202512 Night Caribbean Cruise Star Collector: Ivory Beaches & Sapphire Seas of the Caribbeanon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,399-$4,99912/07/202514 Night Caribbean Cruise Star Collector: Caribbean Explorationson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,699-$5,39912/14/202514 Night Caribbean Cruise Star Collector: Caribbean Explorationson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,999-$5,69912/21/202514 Night Caribbean Cruise Star Collector: Caribbean Explorationson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$4,299-$5,99901/04/202614 Night Caribbean Cruise Star Collector: Leeward & Windward Caribbean Havenson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$4,099-$5,79901/11/202614 Night Caribbean Cruise Star Collector: Antilles Adventureson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$4,199-$5,89901/18/202614 Night Caribbean Cruise Star Collector: Captivating Caribbeanon the Windstar Cruises Wind Surf departing from Bridgetown, BarbadosInteriorOceanviewBalconySuite-$4,599-$6,29902/28/202614 Night Caribbean Cruise Star Collector: Caribbean Explorationson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$4,199-$5,89903/14/202614 Night Caribbean Cruise Star Collector: Caribbean Explorationson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,699-$5,39903/21/202614 Night Caribbean Cruise Star Collector: Caribbean Explorationson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,699-$5,39901/25/202615 Night Caribbean Cruise Star Collector: Windward Islands & Spanish New Worldon the Windstar Cruises Wind Surf departing from Bridgetown, BarbadosInteriorOceanviewBalconySuite-$4,999-$6,69902/17/202618 Night Caribbean Cruise Star Collector: Deep Dive Into the Blue: Underwater Worlds of the Caribbeanon the Windstar Cruises Wind Surf departing from Cozumel, Quintana Roo, MexicoInteriorOceanviewBalconySuite-$5,399-$7,19901/04/202621 Night Caribbean Cruise Star Collector: A Lesser Antilles Odysseyon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$6,299-$8,89903/28/202621 Night Caribbean Cruise Star Collector: Spectacular Transatlantic Journey: Caribbean to the Azoreson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$3,999-$5,39901/04/202628 Night Caribbean Cruise Star Collector: the Best of the Windward & Leeward Isleson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$8,399-$11,89901/04/202655 Night Caribbean Cruise Star Collector: Grand Caribbean Adventureon the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$17,899-$24,199Central America & Panama Canal02/01/20268 Night Central America & Panama Canal Cruise In the Wake of the Spanish Armadason the Windstar Cruises Wind Surf departing from ArubaInteriorOceanviewBalconySuite-$3,199-$4,09902/09/20268 Night Central America & Panama Canal Cruise Mayan Legacieson the Windstar Cruises Wind Surf departing from Colon, PanamaInteriorOceanviewBalconySuite-$3,299-$4,19902/01/202616 Night Central America & Panama Canal Cruise Star Collector: Natural History Meets Ancient Mystery: Latin America & Beyondon the Windstar Cruises Wind Surf departing from ArubaInteriorOceanviewBalconySuite-$5,199-$6,89902/09/202619 Night Central America & Panama Canal Cruise Star Collector: Caribbean Cultures: Latin America & the Greater Antilleson the Windstar Cruises Wind Surf departing from Colon, PanamaInteriorOceanviewBalconySuite-$6,099-$7,899Mediterranean05/13/20257 Night Mediterranean Cruise Yachtsman's Harbors of the Rivierason the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$3,999-$4,62907/20/20257 Night Mediterranean Cruise Yachtsman's Harbors of the Rivierason the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$3,199-$4,10911/03/20257 Night Mediterranean Cruise Wine Cruise: Yachtsman’S Harbors of the Rivierason the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$2,799-$3,42904/27/20258 Night Mediterranean Cruise Classic Italy & Dalmatian Coaston the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$4,699-$5,41905/05/20258 Night Mediterranean Cruise Classic Italy & Dalmatian Coaston the Windstar Cruises Wind Surf departing from Venice, ItalyInteriorOceanviewBalconySuite-$4,699-$5,41906/06/20258 Night Mediterranean Cruise Classic Italy & Dalmatian Coaston the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$6,099-$6,41908/04/20258 Night Mediterranean Cruise Spanish Symphonyon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuite-$3,799-$4,83908/19/20258 Night Mediterranean Cruise Classic Italy & Dalmatian Coaston the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$4,299-$5,33909/14/20258 Night Mediterranean Cruise Classic Italy & Dalmatian Coaston the Windstar Cruises Wind Surf departing from Venice, ItalyInteriorOceanviewBalconySuite-$5,299-$6,39910/10/20258 Night Mediterranean Cruise Classic Italy & Dalmatian Coaston the Windstar Cruises Wind Surf departing from Venice, ItalyInteriorOceanviewBalconySuite-$4,099-$5,13910/18/20258 Night Mediterranean Cruise Classic Italy & Dalmatian Coaston the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$4,099-$4,81910/26/20258 Night Mediterranean Cruise Classic Italy & Dalmatian Coaston the Windstar Cruises Wind Surf departing from Venice, ItalyInteriorOceanviewBalconySuite-$3,999-$4,71904/18/20268 Night Mediterranean Cruise Spanish Symphonyon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuite-$3,999-$5,03904/20/20259 Night Mediterranean Cruise Vatican & Italian Riviera Cruise Touron the Windstar Cruises Wind Surf departing from Barcelona, SpainInteriorOceanviewBalconySuiteContact cruise line for pricing & availability05/11/20259 Night Mediterranean Cruise Vatican & Italian Riviera Cruise Touron the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability06/14/20259 Night Mediterranean Cruise Adriatic Archipelagos & Greek Goddesseson the Windstar Cruises Wind Surf departing from Venice, ItalyInteriorOceanviewBalconySuite-$5,199-$5,99906/23/20259 Night Mediterranean Cruise Adriatic Archipelagos & Greek Goddesseson the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$4,299-$5,46907/18/20259 Night Mediterranean Cruise Vatican & Italian Riviera Cruise Touron the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability08/12/20259 Night Mediterranean Cruise Vatican & Italian Riviera Cruise Touron the Windstar Cruises Wind Surf departing from Barcelona, SpainInteriorOceanviewBalconySuiteContact cruise line for pricing & availability08/27/20259 Night Mediterranean Cruise James Beard Foundation & Wine Cruise: Adriatic Archipelagos & Greek Goddesseson the Windstar Cruises Wind Surf departing from Venice, ItalyInteriorOceanviewBalconySuite-$6,099-$6,59909/05/20259 Night Mediterranean Cruise Adriatic Archipelagos & Greek Goddesseson the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$6,899--11/01/20259 Night Mediterranean Cruise Vatican & Italian Riviera Cruise Touron the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability04/25/202510 Night Mediterranean Cruise Vatican & Croatian Coastlines Cruise Touron the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability05/05/202510 Night Mediterranean Cruise Vatican & Croatian Coastlines Cruise Touron the Windstar Cruises Wind Surf departing from Venice, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability05/27/202510 Night Mediterranean Cruise Sicilian Splendorson the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$7,749-$7,99906/04/202510 Night Mediterranean Cruise Vatican & Croatian Coastlines Cruise Touron the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability07/10/202510 Night Mediterranean Cruise Sicilian Splendorson the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$5,199-$6,19908/17/202510 Night Mediterranean Cruise Vatican & Croatian Coastlines Cruise Touron the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability09/14/202510 Night Mediterranean Cruise Vatican & Croatian Coastlines Cruise Touron the Windstar Cruises Wind Surf departing from Venice, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability10/01/202510 Night Mediterranean Cruise Vatican & Croatian Coastlines Cruise Touron the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability10/10/202510 Night Mediterranean Cruise Vatican & Croatian Coastlines Cruise Touron the Windstar Cruises Wind Surf departing from Venice, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability10/16/202510 Night Mediterranean Cruise Vatican & Croatian Coastlines Cruise Touron the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability10/26/202510 Night Mediterranean Cruise Vatican & Croatian Coastlines Cruise Touron the Windstar Cruises Wind Surf departing from Venice, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability04/27/202511 Night Mediterranean Cruise Lake Como & Adriatic Romance Cruise Touron the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability06/06/202511 Night Mediterranean Cruise Lake Como & Adriatic Romance Cruise Touron the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability08/19/202511 Night Mediterranean Cruise Lake Como & Adriatic Romance Cruise Touron the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability10/03/202511 Night Mediterranean Cruise Lake Como & Adriatic Romance Cruise Touron the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability10/18/202511 Night Mediterranean Cruise Lake Como & Adriatic Romance Cruise Touron the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuiteContact cruise line for pricing & availability04/08/202512 Night Mediterranean Cruise Portuguese Passages & Spanish Shorelines Cruise Touron the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuiteContact cruise line for pricing & availability04/08/202512 Night Mediterranean Cruise Portuguese Passages & Spanish Shorelines Cruise Touron the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuiteContact cruise line for pricing & availability04/16/202512 Night Mediterranean Cruise Yachtsman’S Mediterranean Rivieras & Madrid Cruise Touron the Windstar Cruises Wind Surf departing from Madrid, SpainInteriorOceanviewBalconySuiteContact cruise line for pricing & availability07/23/202512 Night Mediterranean Cruise Spanish Symphony & Madrid Medley Cruise Touron the Windstar Cruises Wind Surf departing from Madrid, SpainInteriorOceanviewBalconySuiteContact cruise line for pricing & availability07/27/202512 Night Mediterranean Cruise Portuguese Passages & Spanish Shorelines Cruise Touron the Windstar Cruises Wind Surf departing from Barcelona, SpainInteriorOceanviewBalconySuiteContact cruise line for pricing & availability07/31/202512 Night Mediterranean Cruise Portuguese Passages & Spanish Shorelines Cruise Touron the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuiteContact cruise line for pricing & availability08/08/202512 Night Mediterranean Cruise Yachtsman’S Mediterranean Rivieras & Madrid Cruise Touron the Windstar Cruises Wind Surf departing from Madrid, SpainInteriorOceanviewBalconySuiteContact cruise line for pricing & availability11/06/202512 Night Mediterranean Cruise Spanish Symphony & Madrid Medley Cruise Touron the Windstar Cruises Wind Surf departing from Madrid, SpainInteriorOceanviewBalconySuiteContact cruise line for pricing & availability11/10/202512 Night Mediterranean Cruise Portuguese Passages & Spanish Shorelines Cruise Touron the Windstar Cruises Wind Surf departing from Barcelona, SpainInteriorOceanviewBalconySuiteContact cruise line for pricing & availability07/20/202513 Night Mediterranean Cruise Star Collector: Enchantment of the Western Medon the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$6,899-$8,74911/03/202513 Night Mediterranean Cruise Star Collector: Enchantment of the Western Medon the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$5,299-$6,54904/12/202515 Night Mediterranean Cruise Star Collector: Enchantment of the Western Medon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuite-$5,599-$7,44904/20/202515 Night Mediterranean Cruise Star Collector: Italian Trioon the Windstar Cruises Wind Surf departing from Barcelona, SpainInteriorOceanviewBalconySuite-$6,999-$8,24905/05/202515 Night Mediterranean Cruise Star Collector: Italian Trioon the Windstar Cruises Wind Surf departing from Venice, ItalyInteriorOceanviewBalconySuite-$8,099-$9,04908/04/202515 Night Mediterranean Cruise Star Collector: Enchantment of the Western Medon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuite-$5,799-$7,64908/12/202515 Night Mediterranean Cruise Star Collector: Italian Trioon the Windstar Cruises Wind Surf departing from Barcelona, SpainInteriorOceanviewBalconySuite-$5,799-$7,64910/26/202515 Night Mediterranean Cruise Star Collector: Italian Trioon the Windstar Cruises Wind Surf departing from Venice, ItalyInteriorOceanviewBalconySuite-$5,399-$6,64904/18/202615 Night Mediterranean Cruise Star Collector: Enchantment of the Western Medon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuite-$5,599-$7,44906/06/202517 Night Mediterranean Cruise Star Collector: Stories of Italy, Croatia & Greeceon the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$10,929--07/10/202517 Night Mediterranean Cruise Star Collector: Cruising on the Rivierason the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$7,399-$9,00908/19/202517 Night Mediterranean Cruise Star Collector: Stories of Italy, Croatia & Greeceon the Windstar Cruises Wind Surf departing from Civitavecchia, ItalyInteriorOceanviewBalconySuite-$10,289-$11,30909/05/202517 Night Mediterranean Cruise Star Collector: Stories of Italy, Croatia & Greeceon the Windstar Cruises Wind Surf departing from Piraeus, GreeceInteriorOceanviewBalconySuite-$11,799--04/12/202525 Night Mediterranean Cruise Star Collector: Riviera Rhapsodyon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuite-$8,799-$11,36904/12/202525 Night Mediterranean Cruise Star Collector: Riviera Rhapsodyon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuite-$8,799-$11,36908/04/202525 Night Mediterranean Cruise Star Collector: Riviera Rhapsodyon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuite-$8,799-$11,68904/18/202625 Night Mediterranean Cruise Star Collector: Riviera Rhapsodyon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuite-$8,799-$11,369Transatlantic03/29/202514 Night Transatlantic Cruise Ocean Crossings + Ponta Delgada, Azoreson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,699-$3,19904/04/202614 Night Transatlantic Cruise Ocean Crossings + Ponta Delgada, Azoreson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$2,599-$3,19911/18/202519 Night Transatlantic Cruise Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossingon the Windstar Cruises Wind Surf departing from Lisbon, PortugalInteriorOceanviewBalconySuite-$3,599-$4,89904/04/202622 Night Transatlantic Cruise Star Collector: Atlantic Interludes & Iberian Indulgenceson the Windstar Cruises Wind Surf departing from Philipsburg, St Maarten, St Martin/St MaartenInteriorOceanviewBalconySuite-$5,299-$6,839 OCG Class Luxury Wind Surf Year Built1990Year Last Refurbished2019Capacity342 passengersDecks7Tonnage14,745RegistryBahamas