Windstar's 2025-2026 itineraries are here! Immerse yourself in the Caribbean, Latin America, Tahiti, the Middle East and more. Windstar's private yacht style cruises get you closer to the world's most beautiful destinations and allows you the space and freedom to enjoy your vacation the way you want.
The 2025-2026 winter itineraries will explore Costa Rica & the Panama Canal, the Caribbean, the Canary Islands, Tahiti, and the Middle East. Reserve first with us to get the best staterooms and suites and the most value!
Call our Windstar experts at 1 (877) 734-6858 to get the best staterooms first and huge savings and extra perks!
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| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
| 12-night Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 12/2/25 | From $3,502 |
| 5-night Barefoot Break in the British Virgin Islands Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 12/2/25 | From $2,150 |
| 7-night Dreams of Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 12/4/25 | From $2,915 |
| 7-night Costa Rica & Panama Canal Puerto Caldera to Colon | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 12/6/25 | From $3,369 |
| 7-night Classic Caribbean Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 12/7/25 | From $2,351 |
| 14-night Star Collector: Caribbean Explorations Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 12/7/25 | From $3,819 |
| 10-night Canary Island Idyll Roundtrip Santa Cruz de Tenerife | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 12/10/25 | Call For Pricing |
| 18-night Star Collector – Twice the Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 12/11/25 | From $5,933 |
| 7-night Dreams of Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 12/11/25 | From $2,915 |
| 7-night Beach Fun & Sun: A Remote Caribbean Getaway Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 12/14/25 | Call For Pricing |
| 14-night Star Collector: Caribbean Explorations Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 12/14/25 | From $4,619 |
| 11-night Tahiti & the Tuamotu Islands Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 12/18/25 | From $4,517 |
| 10-night Canary Island Idyll Roundtrip Santa Cruz de Tenerife | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 12/20/25 | From $3,619 |
| 7-night Classic Caribbean Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 12/21/25 | From $2,951 |
| 14-night Star Collector: Caribbean Explorations Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 12/21/25 | From $5,019 |
| 10-night Canary Island Idyll Roundtrip Santa Cruz de Tenerife | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 12/30/25 | From $3,819 |
| 7-night Dreams of Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 1/8/26 | From $3,315 |
| 10-night Canary Island Idyll Roundtrip Santa Cruz de Tenerife | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 1/9/26 | From $3,919 |
| 7-night Beach Fun & Sun: A Remote Caribbean Getway Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 1/24/26 | From $2,760 |
| 7-night Beach Fun & Sun: A Remote Caribbean Getaway Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 12/28/25 | Call For Pricing |
| 10-night Tahiti & The Tuamotu Islands Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 12/29/25 | From $4,715 |
| 7-night Beach Fun & Sun: A Remote Caribbean Getaway Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 1/4/26 | Call For Pricing |
| 17-night Star Collector: Hidden Gems of the Caribbean Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 1/14/26 | From $5,994 |
| 10-night Canary Island Idyll Roundtrip Santa Cruz de Tenerife | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 1/19/26 | From $3,519 |
| 7-night Dreams of Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 1/29/26 | From $3,615 |
| 10-night Canary Island Idyll Roundtrip Santa Cruz de Tenerife | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 1/29/26 | From $3,519 |
| 6-night Beach Fun & Sun: A Remote Caribbean Getway Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 1/31/26 | From $2,560 |
| 14-night Star Collector: Caribbean Exploration Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 1/31/26 | From $4,778 |
| 7-night Dreams of Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 2/5/26 | From $3,715 |
| 18-night Star Collector – Twice the Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 2/5/26 | From $7,333 |
| 7-night Classic Caribbean Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 2/7/26 | From $2,917 |
| 14-night Star Collector: Caribbean Explorations Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 2/7/26 | From $4,878 |
| 10-night Canary Island Idyll Roundtrip Santa Cruz de Tenerife | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 2/8/26 | From $3,519 |
| 7-night Costa Rica and Panama Canal Colon to Puerto Caldera | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 2/9/26 | From $3,557 |
| 11-night Tahiti & The Tuamotu Islands Cruise/Land Package Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 2/12/26 | Call For Pricing |
| 6-night Beach Fun & Sun: A Remote Caribbean Getway Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 2/14/26 | From $2,660 |
| 7-night Costa Rica and Panama Canal Puerto Caldera to Colon | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 2/16/26 | From $3,357 |
| 10-night Canary Island Idyll Roundtrip Santa Cruz de Tenerife | Cruise Line Windstar Cruises | Cruise Ship Wind Star | Departs 2/18/26 | From $3,519 |
| 14-night Star Collector: Leeward & Windward Caribbean Havens Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 2/21/26 | From $4,181 |
| 17-night Star Collector – Twice the Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 2/23/26 | From $8,931 |
| 10-night Tahiti & the Tuamotu Islands Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 2/23/26 | From $5,215 |
| 7-night Costa Rica and Panama Canal Colon to Puerto Caldera | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 2/23/26 | From $3,357 |
| 7-night Lush & Lovely Islands of the Lesser Antilles St. Maarten to Barbados | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 2/28/26 | From $2,520 |
| 14-night Star Collector: Caribbean Explorations Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 2/28/26 | From $4,619 |
| 15-night Star Collector: Antilles Adventure St. Maarten to Barbados | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 2/28/26 | From $4,037 |
| 7-night Classic Caribbean Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 2/28/26 | From $2,651 |
| 7-night Costa Rica and Panama Canal Puerto Caldera to Colon | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 3/2/26 | From $3,357 |
| 7-night Dreams of Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 3/5/26 | From $4,015 |
| 7-night Jewels of the Windward Islands Roundtrip Barbados | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 3/7/26 | Call For Pricing |
| 14-night Star Collector: Captivating Caribbean Roundtrip Barbados | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 3/7/26 | From $4,133 |
| 7-night Beach Fun & Sun: A Remote Caribbean Getaway Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 3/7/26 | Call For Pricing |
| 7-night Windward Island Delights Roundtrip Barbados | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 3/14/26 | Call For Pricing |
| 14-night Star Collector: Captivating Caribbean Roundtrip Barbados | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 3/14/26 | Call For Pricing |
| 7-night Dreams of Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 3/12/26 | From $3,615 |
| 14-night Star Collector: Caribbean Explorations Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 3/14/26 | From $4,119 |
| 7-night Dreams of Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 3/19/26 | From $3,715 |
| 21-night Star Collector: Comprehensive Tahiti & Marquesas Adventure Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 3/19/26 | From $10,889 |
| 7-night Jewels of the Windward Islands Roundtrip Barbados | Cruise Line Windstar Cruises | Cruise Ship Wind Spirit | Departs 3/21/26 | From $2,616 |
| 7-night Classic Caribbean Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 3/21/26 | From $2,451 |
| 14-night Star Collector: Caribbean Explorations Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 3/21/26 | From $3,819 |
| 14-night Tahitian Treasures & Magnificent Marquesas Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 3/26/26 | From $7,718 |
| 7-night Dreams of Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 4/23/26 | From $3,615 |
| 18-night Star Collector – Twice the Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 4/23/26 | From $6,933 |
| 11-night Tahiti & the Tuamotu Islands Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 4/30/26 | From $5,017 |
| 17-night Star Collector – Twice the Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 5/11/26 | From $8,231 |
| 10-night Tahiti & The Tuamotu Islands Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 5/11/26 | From $5,015 |
| 7-night Dreams of Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 5/21/26 | From $4,115 |
| 7-night Dreams of Tahiti Cruise Roundtrip Papeete | Cruise Line Windstar Cruises | Cruise Ship Star Breeze | Departs 5/28/26 | From $4,015 |
Fares/rates are per person, based on double occupancy for select sail and travel dates; are capacity controlled and subject to availability at time booking and may be pulled without notice. We reserve the right to correct errors. Information and pricing is subject to change without notice. While we do our very best to ensure that information and pricing appearing in this website is complete and accurate, we cannot be responsible for incomplete and inaccurate representations, which may or may not be under our control. In the event of a pricing error, misrepresentation or omission, we reserve the right to adjust the pricing or make any other corrections.