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Windstar Cruises Cruises

971 upcoming sailings across 8 ships, from $1,100 per person. Rates refreshed daily.

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Next Windstar Cruises departures — page 2 of 8

DepartureShipItineraryLengthFrom portFrom*
Nov 15, 2026 Star Pride San Juan to San Juan 7 nights San Juan $3,038
Nov 15, 2026 Star Seeker Halong Bay (Hanoi) to Phuket, Thailand 21 nights Halong Bay (Hanoi) on request
Nov 15, 2026 Star Seeker Halong Bay (Hanoi) to Klong Toei (Bangkok), Thailand 10 nights Halong Bay (Hanoi) $4,463
Nov 17, 2026 Wind Spirit Hidden Gems of The Canary Islands & Madeira 10 nights Santa Cruz De Tenerife, Spain $4,120
Nov 22, 2026 Star Pride San Juan to San Juan 14 nights San Juan $5,344
Nov 22, 2026 Star Pride San Juan to San Juan 7 nights San Juan $2,411
Nov 23, 2026 Star Breeze Star Collector: Twice the Tahiti 17 nights Papeete, Tahiti $7,087
Nov 23, 2026 Star Breeze Tahiti & the Tuamotu Islands 10 nights Papeete, Tahiti $4,316
Nov 24, 2026 Wind Star Colombian & Southern Caribbean Coastlines - Bridgetown to Colón 11 nights Bridgetown, Barbados $4,761
Nov 24, 2026 Wind Star Bridgetown to Puerto Caldera 18 nights Bridgetown, Barbados $8,051
Nov 25, 2026 Star Seeker Klong Toei (Bangkok), Thailand to Phuket, Thailand 11 nights Bangkok $6,337
Nov 27, 2026 Star Legend Jewels of The Windward Islands - Bridgetown to Bridgetown 7 nights Bridgetown, Barbados $2,699
Nov 27, 2026 Wind Spirit Hidden Gems of The Canary Islands & Madeira 10 nights Santa Cruz De Tenerife, Spain $3,320
Nov 27, 2026 Star Legend Captivating Caribbean - Bridgetown to Oranjestad 15 nights Bridgetown, Barbados $5,459
Nov 29, 2026 Star Pride San Juan to San Juan 14 nights San Juan $9,124
Nov 29, 2026 Star Pride San Juan to San Juan 7 nights San Juan $3,283
Dec 3, 2026 Star Breeze Papeete to Papeete 7 nights Papeete, Tahiti $3,376
Dec 4, 2026 Star Legend Windward Ways & Tobago Cays - Bridgetown to Oranjestad 8 nights Bridgetown, Barbados $3,060
Dec 4, 2026 Star Legend Emeralds Of The Southern Caribbean - Bridgetown to Balboa 16 nights Bridgetown, Barbados $5,742
Dec 5, 2026 Wind Star Colón to Puerto Caldera 7 nights Colon, Panama $3,695
Dec 6, 2026 Star Pride San Juan to San Juan 14 nights San Juan $7,514
Dec 6, 2026 Star Pride San Juan to San Juan 7 nights San Juan $3,881
Dec 7, 2026 Wind Spirit Santa Cruz de Tenerife to Santa Cruz de Tenerife 10 nights Santa Cruz De Tenerife, Spain $3,370
Dec 10, 2026 Star Breeze Papeete to Papeete 7 nights Papeete, Tahiti $2,851
Dec 10, 2026 Star Breeze Star Collector: Twice the Tahiti 18 nights Papeete, Tahiti $7,683
Dec 12, 2026 Wind Star Costa Rica & Panama Canal -Puerto Caldera to Colón 7 nights Puerto Caldera, Costa Rica $4,115
Dec 12, 2026 Star Legend Panama Canal, Cartagena, San Blas Islands 8 nights Oranjestad, Aruba $3,246
Dec 12, 2026 Star Legend Oranjestad to Puerto Caldera 16 nights Oranjestad, Aruba $6,188
Dec 13, 2026 Star Pride San Juan to San Juan 14 nights San Juan $7,444
Dec 13, 2026 Star Pride San Juan to San Juan 7 nights San Juan $3,668
Dec 17, 2026 Wind Spirit Santa Cruz de Tenerife to Santa Cruz de Tenerife 10 nights Santa Cruz De Tenerife, Spain $3,670
Dec 17, 2026 Star Breeze Far Flung French Polynesia and Marquesas Magic 11 nights Papeete, Tahiti $5,462
Dec 17, 2026 Star Seeker Klong Toei (Bangkok), Thailand to Halong Bay (Hanoi) 10 nights Bangkok $5,613
Dec 17, 2026 Star Breeze Star Collector: Marquesas, Tuamotus & Society Islands 21 nights Papeete, Tahiti $9,273
Dec 19, 2026 Wind Surf Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten 14 nights Philipsburg, St. Martin $8,030
Dec 19, 2026 Wind Star Colón to Puerto Caldera 7 nights Colon, Panama $3,660
Dec 19, 2026 Wind Surf Beach Fun & Sun: A Remote Caribbean Getaway - Philipsburg, St. Maarten to Philipsburg, St. Maarten 7 nights Philipsburg, St. Martin $3,708
Dec 20, 2026 Star Legend Naturally Costa Rica - Balboa to Puerto Caldera 8 nights Fuerte Amador, Panama $2,942
Dec 20, 2026 Star Pride San Juan to San Juan 14 nights San Juan $10,104
Dec 20, 2026 Star Pride San Juan to San Juan 7 nights San Juan $4,161
Dec 26, 2026 Wind Surf Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten 14 nights Philipsburg, St. Martin $7,960
Dec 26, 2026 Wind Star Costa Rica & Panama Canal -Puerto Caldera to Colón 7 nights Puerto Caldera, Costa Rica $5,410
Dec 26, 2026 Wind Surf Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten 7 nights Philipsburg, St. Martin $4,742
Dec 27, 2026 Wind Spirit Santa Cruz de Tenerife to Santa Cruz de Tenerife 10 nights Santa Cruz De Tenerife, Spain $4,120
Dec 27, 2026 Star Seeker Halong Bay (Hanoi) to Phuket, Thailand 21 nights Halong Bay (Hanoi) $16,405
Dec 27, 2026 Star Seeker Halong Bay (Hanoi) to Klong Toei (Bangkok), Thailand 10 nights Halong Bay (Hanoi) $6,913
Dec 27, 2026 Star Pride San Juan to San Juan 14 nights San Juan $8,074
Dec 27, 2026 Star Pride San Juan to San Juan 7 nights San Juan $3,143
Dec 28, 2026 Star Breeze Tahiti & the Tuamotu Islands 10 nights Papeete, Tahiti $4,666
Dec 28, 2026 Star Explorer Star Explorer Inaugural Voyage 9 nights Barcelona, Spain $3,994
Dec 28, 2026 Star Breeze Star Collector: Twice the Tahiti 17 nights Papeete, Tahiti $7,682
Dec 28, 2026 Star Legend Puerto Caldera to Colón 8 nights Puerto Caldera, Costa Rica $3,438
Jan 2, 2027 Wind Star Colón to Puerto Caldera 7 nights Colon, Panama $3,450
Jan 2, 2027 Wind Surf Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten 14 nights Philipsburg, St. Martin $6,420
Jan 2, 2027 Wind Surf Philipsburg, St.Marteen to Philipsburg, St.Marteen 7 nights Philipsburg, St. Martin $3,568
Jan 3, 2027 Star Pride San Juan to San Juan 14 nights San Juan $12,764
Jan 3, 2027 Star Pride San Juan to San Juan 7 nights San Juan $3,881
Jan 5, 2027 Star Legend Colón to Puerto Caldera 7 nights Colon, Panama $3,928
Jan 6, 2027 Wind Spirit Hidden Gems of The Canary Islands & Madeira 10 nights Santa Cruz De Tenerife, Spain $4,120
Jan 6, 2027 Star Seeker Klong Toei (Bangkok), Thailand to Phuket, Thailand 11 nights Bangkok $8,207

*Per person, double occupancy, cruise fare from. Taxes and fees may apply. Rates refresh daily — email us for today's exact price.