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Windstar's 2025-2026 Itineraries
Start planning for your future cruise with Windstar's 2025-2026 itineraries!
EXPIRESMar 31, 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
12-night Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
5-night Barefoot Break in the British Virgin Islands
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
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
$3,215
7-night Costa Rica & Panama Canal
Puerto Caldera (Puntarenas) -> Colon (Panama)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Dec 6, 2025
Prices From
$2,969
7-night Classic Caribbean
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Extra Amenities Included
14-night Star Collector: Caribbean Explorations
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
10-night Canary Island Idyll
Santa Cruz de Tenerife -> Santa Cruz de Tenerife
Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
Dec 10, 2025
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
$6,133
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
Extra Amenities Included
7-night Beach Fun & Sun: A Remote Caribbean Getaway
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
Dec 14, 2025
Prices From
$2,467
Extra Amenities Included
14-night Star Collector: Caribbean Explorations
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
Dec 14, 2025
Prices From
$4,119
Extra Amenities Included
11-night Tahiti and the Tuamotu Islands Cruise
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Dec 18, 2025
Prices From
$4,517
Extra Amenities Included
10-night Canary Island Idyll
Santa Cruz de Tenerife -> Santa Cruz de Tenerife
Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
Dec 20, 2025
Prices From
$3,819
7-night Classic Caribbean
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
Dec 21, 2025
Prices From
$2,751
14-night Star Collector: Caribbean Explorations
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
Dec 21, 2025
Prices From
$4,419
Extra Amenities Included
10-night Canary Island Idyll
Santa Cruz de Tenerife -> Santa Cruz de Tenerife
Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
Dec 30, 2025
Prices From
$3,819
Extra Amenities Included
7-night Dreams of Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Jan 8, 2026
Prices From
$3,315
Extra Amenities Included
10-night Canary Island Idyll
Santa Cruz de Tenerife -> Santa Cruz de Tenerife
7-night Dreams of Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Jan 15, 2026
7-night Beach Fun & Sun: A Remote Caribbean Getway
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Jan 24, 2026
Prices From
$2,660
Extra Amenities Included
7-night Beach Fun & Sun: A Remote Caribbean Getaway
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
Dec 28, 2025
Prices From
$2,767
Extra Amenities Included
10-night Tahiti and the Tuamotu Islands Cruise
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Dec 29, 2025
Prices From
$4,715
7-night Beach Fun & Sun: A Remote Caribbean Getaway
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
7-night Lush & Lovely Island of the Lesser Antilles
Bridgetown (Barbados) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Jan 7, 2026
17-night Star Collector: Hidden Gems of the Caribbean
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Jan 14, 2026
Prices From
$5,194
Extra Amenities Included
10-night Canary Island Idyll
Santa Cruz de Tenerife -> Santa Cruz de Tenerife
Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
Jan 19, 2026
Prices From
$3,519
7-night Dreams of Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Jan 22, 2026
7-night Dreams of Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Jan 29, 2026
Prices From
$3,615
Extra Amenities Included
10-night Canary Island Idyll
Santa Cruz de Tenerife -> Santa Cruz de Tenerife
Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
Jan 29, 2026
Prices From
$3,519
7-night Beach Fun & Sun: A Remote Caribbean Getway
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Jan 31, 2026
14-night Star Collector: Caribbean Exploration
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Jan 31, 2026
Prices From
$4,178
Extra Amenities Included
7-night Dreams of Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Feb 5, 2026
Prices From
$3,615
18-night Star Collector: Twice the Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Feb 5, 2026
Prices From
$6,833
Extra Amenities Included
7-night Classic Caribbean
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Feb 7, 2026
Prices From
$2,617
Extra Amenities Included
14-night Star Collector: Caribbean Explorations
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Feb 7, 2026
Prices From
$4,178
Extra Amenities Included
10-night Canary Island Idyll
Santa Cruz de Tenerife -> Santa Cruz de Tenerife
Extra Amenities Included
7-night Costa Rica and Panama Canal
Colon (Panama) -> Puerto Caldera (Puntarenas)
Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
Feb 9, 2026
Prices From
$3,557
Extra Amenities Included
11-night Tahiti & the Tuamotu Islands
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Feb 12, 2026
Prices From
$4,917
Extra Amenities Included
7-night Beach Fun & Sun: A Remote Caribbean Getway
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Feb 14, 2026
Prices From
$2,660
7-night Costa Rica and Panama Canal
Puntarenas -> Colon (Panama)
Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
Feb 16, 2026
Prices From
$3,357
Extra Amenities Included
10-night Canary Island Idyll
Santa Cruz de Tenerife -> Santa Cruz de Tenerife
Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
Feb 18, 2026
Prices From
$3,519
7-night Beach Fun & Sun: A Remote Caribbean Getway
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Feb 21, 2026
Prices From
$2,660
14-night Star Collector: Leeward & Windward Caribbean Havens
St. Maarten (Philipsburg) -> Bridgetown (Barbados)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Feb 21, 2026
Prices From
$4,181
21-night Star Collector: A Lesser Antilles Odyssey
St. Maarten (Philipsburg) -> Bridgetown (Barbados)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Feb 21, 2026
17-night Star Collector: Twice the Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Feb 23, 2026
Prices From
$7,536
10-night Tahiti & the Tuamotu Islands
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Feb 23, 2026
Prices From
$5,215
Extra Amenities Included
7-night Costa Rica and Panama Canal
Colon (Panama) -> Puerto Caldera (Puntarenas)
Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
Feb 23, 2026
Prices From
$3,357
Extra Amenities Included
7-night Lush & Lovely Islands of the Lesser Antilles
St. Maarten (Philipsburg) -> Bridgetown (Barbados)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Feb 28, 2026
Prices From
$2,520
14-night Star Collector: Caribbean Explorations
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
Feb 28, 2026
Prices From
$4,319
Extra Amenities Included
14-night Star Collector: Antilles Adventure
St. Maarten (Philipsburg) -> Bridgetown (Barbados)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Feb 28, 2026
7-night Classic Caribbean
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
Feb 28, 2026
Prices From
$2,551
7-night Costa Rica and Panama Canal
Puntarenas -> Colon (Panama)
Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
Mar 2, 2026
Prices From
$3,357
7-night Dreams of Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Mar 5, 2026
Prices From
$3,370
7-night Jewels of the Windward Islands
Bridgetown (Barbados) -> Bridgetown (Barbados)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Mar 7, 2026
14-night Star Collector: Captivating Caribbean
Bridgetown (Barbados) -> Bridgetown (Barbados)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Mar 7, 2026
Prices From
$4,133
Extra Amenities Included
7-night Beach Fun & Sun: A Remote Caribbean Getaway
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
Mar 7, 2026
Extra Amenities Included
7-night Windward Island Delights
Bridgetown (Barbados) -> Bridgetown (Barbados)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Mar 14, 2026
Extra Amenities Included
14-night Star Collector: Captivating Caribbean
Bridgetown (Barbados) -> Bridgetown (Barbados)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Mar 14, 2026
7-night Dreams of Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Mar 12, 2026
Prices From
$3,515
14-night Star Collector: Caribbean Explorations
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
Mar 14, 2026
Prices From
$3,819
7-night Dreams of Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Mar 19, 2026
Prices From
$3,715
21-night Star Collector: Comprehensive Tahiti & Marquesas Adventure
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Mar 19, 2026
Extra Amenities Included
7-night Jewels of the Windward Islands
Bridgetown (Barbados) -> Bridgetown (Barbados)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
Mar 21, 2026
Prices From
$2,616
Extra Amenities Included
7-night Classic Caribbean
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
Mar 21, 2026
Prices From
$2,351
Extra Amenities Included
14-night Star Collector: Caribbean Explorations
St. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
Mar 21, 2026
Prices From
$3,819
14-night Tahitian Treasures & Magnificent Marquesas
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Mar 26, 2026
Prices From
$7,718
7-night Dreams of Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Apr 9, 2026
Extra Amenities Included
7-night Dreams of Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Apr 16, 2026
Prices From
$3,212
21-night Star Collector: Comprehensive Tahiti & Marquesas Adventure
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Mar 26, 2026
Extra Amenities Included
7-night Dreams of Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Apr 23, 2026
Prices From
$3,615
18-night Star Collector: Twice the Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Apr 23, 2026
Prices From
$6,933
11-night Tahiti & the Tuamotu Islands
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
Apr 30, 2026
Prices From
$5,017
17-night Star Collector: Twice the Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
May 11, 2026
Prices From
$8,231
Extra Amenities Included
10-night Tahiti & the Tuamotu Islands
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
May 11, 2026
Prices From
$5,015
7-night Dreams of Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
May 21, 2026
Prices From
$4,115
7-night Dreams of Tahiti
Papeete -> Papeete
Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
May 28, 2026
Prices From
$4,270
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.