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Windstar's 2025-2026 Itineraries

Start planning for your future cruise with Windstar's 2025-2026 itineraries!

EXPIRESJun 30, 2025

Details & Inclusions

Start planning for your future cruise with Windstar's brand new 2025-2026 itineraries!

 

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 1-800-439-7963 to get the best staterooms first and huge savings and extra perks!

Itineraries

  1. 12-night Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Dec 2, 2025

    Prices From

    $3,502
  2. 5-night Barefoot Break in the British Virgin Islands Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Dec 2, 2025

    Prices From

    $2,150
  3. Extra Amenities Included
    7-night Dreams of Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Dec 4, 2025

    Prices From

    $2,915
  4. 7-night Costa Rica & Panama Canal Cruise
    Puerto Caldera (Puntarenas) -> Colon (Panama)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Dec 6, 2025

    Prices From

    $3,569
  5. 7-night Classic Caribbean Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Dec 7, 2025

    Prices From

    $2,351
  6. Extra Amenities Included
    14-night Star Collector: Caribbean Explorations Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Dec 7, 2025

    Prices From

    $4,119
  7. 10-night Canary Island Idyll Cruise
    Santa Cruz de Tenerife -> Santa Cruz de Tenerife

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Star

    Departs

    Dec 10, 2025
  8. Extra Amenities Included
    18-night Star Collector – Twice the Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Dec 11, 2025

    Prices From

    $6,633
  9. Extra Amenities Included
    7-night Dreams of Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Dec 11, 2025

    Prices From

    $3,215
  10. Extra Amenities Included
    6-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Dec 14, 2025

    Prices From

    $2,667
  11. Extra Amenities Included
    14-night Star Collector: Caribbean Explorations Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Dec 14, 2025

    Prices From

    $4,919
  12. Extra Amenities Included
    11-night Tahiti & the Tuamotu Islands Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Dec 18, 2025

    Prices From

    $4,517
  13. Extra Amenities Included
    10-night Canary Island Idyll Cruise
    Santa Cruz de Tenerife -> Santa Cruz de Tenerife

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Star

    Departs

    Dec 20, 2025

    Prices From

    $3,619
  14. 7-night Classic Caribbean Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Dec 21, 2025

    Prices From

    $2,951
  15. 14-night Star Collector: Caribbean Explorations Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Dec 21, 2025

    Prices From

    $5,119
  16. Extra Amenities Included
    10-night Canary Island Idyll Cruise
    Santa Cruz de Tenerife -> Santa Cruz de Tenerife

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Star

    Departs

    Dec 30, 2025

    Prices From

    $3,819
  17. Extra Amenities Included
    7-night Dreams of Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Jan 8, 2026

    Prices From

    $3,315
  18. Extra Amenities Included
    10-night Canary Island Idyll Cruise
    Santa Cruz de Tenerife -> Santa Cruz de Tenerife

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Star

    Departs

    Jan 9, 2026

    Prices From

    $3,919
  19. 7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Jan 24, 2026

    Prices From

    $2,760
  20. Extra Amenities Included
    6-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Dec 28, 2025

    Prices From

    $3,067
  21. Extra Amenities Included
    10-night Tahiti & The Tuamotu Islands Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Dec 29, 2025

    Prices From

    $4,715
  22. 6-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Jan 4, 2026

    Prices From

    $2,610
  23. 17-night Star Collector: Hidden Gems of the Caribbean Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Jan 14, 2026

    Prices From

    $6,394
  24. Extra Amenities Included
    10-night Canary Island Idyll Cruise
    Santa Cruz de Tenerife -> Santa Cruz de Tenerife

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Star

    Departs

    Jan 19, 2026

    Prices From

    $3,519
  25. Extra Amenities Included
    7-night Dreams of Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Jan 29, 2026

    Prices From

    $3,615
  26. Extra Amenities Included
    10-night Canary Island Idyll Cruise
    Santa Cruz de Tenerife -> Santa Cruz de Tenerife

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Star

    Departs

    Jan 29, 2026

    Prices From

    $3,519
  27. Extra Amenities Included
    7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Jan 31, 2026

    Prices From

    $2,560
  28. 14-night Star Collector: Caribbean Explorations Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Jan 31, 2026

    Prices From

    $5,078
  29. Extra Amenities Included
    7-night Dreams of Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Feb 5, 2026

    Prices From

    $3,715
  30. 18-night Star Collector – Twice the Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Feb 5, 2026

    Prices From

    $7,333
  31. Extra Amenities Included
    7-night Classic Caribbean Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Feb 7, 2026

    Prices From

    $3,017
  32. Extra Amenities Included
    14-night Star Collector: Caribbean Explorations Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Feb 7, 2026

    Prices From

    $5,178
  33. Extra Amenities Included
    10-night Canary Island Idyll Cruise
    Santa Cruz de Tenerife -> Santa Cruz de Tenerife

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Star

    Departs

    Feb 8, 2026

    Prices From

    $3,519
  34. Extra Amenities Included
    7-night Costa Rica & Panama Canal Cruise
    Colon (Panama) -> Puerto Caldera (Puntarenas)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Pride

    Departs

    Feb 9, 2026

    Prices From

    $3,557
  35. Extra Amenities Included
    11-night Tahiti & The Tuamotu Islands Cruise/Land Package
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Feb 12, 2026
  36. Extra Amenities Included
    6-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Feb 14, 2026

    Prices From

    $2,660
  37. Extra Amenities Included
    7-night Costa Rica & Panama Canal Cruise
    Puntarenas -> Colon (Panama)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Pride

    Departs

    Feb 16, 2026

    Prices From

    $3,357
  38. Extra Amenities Included
    10-night Canary Island Idyll Cruise
    Santa Cruz de Tenerife -> Santa Cruz de Tenerife

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Star

    Departs

    Feb 18, 2026

    Prices From

    $3,519
  39. 14-night Star Collector: Leeward & Windward Caribbean Havens Cruise
    St. Maarten (Philipsburg) -> Bridgetown (Barbados)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Feb 21, 2026

    Prices From

    $4,181
  40. 17-night Star Collector – Twice the Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Feb 23, 2026
  41. 10-night Tahiti & the Tuamotu Islands Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Feb 23, 2026

    Prices From

    $5,415
  42. Extra Amenities Included
    7-night Costa Rica & Panama Canal Cruise
    Colon (Panama) -> Puerto Caldera (Puntarenas)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Pride

    Departs

    Feb 23, 2026

    Prices From

    $3,357
  43. Extra Amenities Included
    7-night Lush & Lovely Islands of the Lesser Antilles Cruise
    St. Maarten (Philipsburg) -> Bridgetown (Barbados)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Feb 28, 2026

    Prices From

    $2,620
  44. 14-night Star Collector: Caribbean Explorations Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Feb 28, 2026

    Prices From

    $4,619
  45. Extra Amenities Included
    15-night Star Collector: Antilles Adventure Cruise
    St. Maarten (Philipsburg) -> Bridgetown (Barbados)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Feb 28, 2026

    Prices From

    $4,237
  46. 7-night Classic Caribbean Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Feb 28, 2026

    Prices From

    $2,651
  47. 7-night Costa Rica & Panama Canal Cruise
    Puntarenas -> Colon (Panama)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Pride

    Departs

    Mar 2, 2026

    Prices From

    $3,357
  48. 7-night Dreams of Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Mar 5, 2026

    Prices From

    $4,615
  49. 7-night Jewels of the Windward Islands Cruise
    Bridgetown (Barbados) -> Bridgetown (Barbados)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Mar 7, 2026
  50. 14-night Star Collector: Captivating Caribbean Cruise
    Bridgetown (Barbados) -> Bridgetown (Barbados)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Mar 7, 2026

    Prices From

    $4,133
  51. Extra Amenities Included
    7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Mar 7, 2026
  52. Extra Amenities Included
    7-night Windward Island Delights Cruise
    Bridgetown (Barbados) -> Bridgetown (Barbados)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Mar 14, 2026
  53. Extra Amenities Included
    14-night Star Collector: Captivating Caribbean Cruise
    Bridgetown (Barbados) -> Bridgetown (Barbados)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Mar 14, 2026
  54. 7-night Dreams of Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Mar 12, 2026

    Prices From

    $3,815
  55. 14-night Star Collector: Caribbean Explorations Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Mar 14, 2026

    Prices From

    $4,119
  56. 7-night Dreams of Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Mar 19, 2026

    Prices From

    $3,715
  57. 21-night Star Collector: Comprehensive Tahiti & Marquesas Adventure Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Mar 19, 2026

    Prices From

    $10,534
  58. Extra Amenities Included
    7-night Jewels of the Windward Islands Cruise
    Bridgetown (Barbados) -> Bridgetown (Barbados)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Spirit

    Departs

    Mar 21, 2026

    Prices From

    $2,616
  59. Extra Amenities Included
    7-night Classic Caribbean Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Mar 21, 2026

    Prices From

    $2,451
  60. Extra Amenities Included
    14-night Star Collector: Caribbean Explorations Cruise
    St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Wind Surf

    Departs

    Mar 21, 2026

    Prices From

    $3,819
  61. 14-night Tahitian Treasures & Magnificent Marquesas Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Mar 26, 2026

    Prices From

    $7,918
  62. Extra Amenities Included
    7-night Dreams of Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Apr 23, 2026

    Prices From

    $3,815
  63. 18-night Star Collector – Twice the Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Apr 23, 2026

    Prices From

    $7,633
  64. Extra Amenities Included
    11-night Tahiti & the Tuamotu Islands Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    Apr 30, 2026

    Prices From

    $5,217
  65. 17-night Star Collector – Twice the Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    May 11, 2026

    Prices From

    $8,231
  66. Extra Amenities Included
    10-night Tahiti & The Tuamotu Islands Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    May 11, 2026

    Prices From

    $5,015
  67. 7-night Dreams of Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    May 21, 2026

    Prices From

    $4,115
  68. 7-night Dreams of Tahiti Cruise
    Papeete -> Papeete

    Cruise Line

    Windstar Cruises

    Cruise Ship

    Star Breeze

    Departs

    May 28, 2026

    Prices From

    $4,115

Terms & Conditions

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. Other restrictions may apply. Contact Bon Voyage Travel for complete terms and conditions.