NEW ITINERARIES!

Windstar's 2025-2026 Itineraries

Windstar Cruises / Specials / Windstar's 2025-2026 Itineraries
Cruise Line Windstar Cruises
Prices From $1,999
Expires 6/30/24

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 (877) 734-6858 to get the best staterooms first and huge savings and extra perks!

Connect With A CruiseInsider Expert About This Special Offer!

Submit the form below or call us at 1 (877) 734-6858

Includes free extras and bonus savings available only from CruiseInsider.

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
$3,399
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
$1,999
7-night Dreams of Tahiti Cruise

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
12/4/25
From
$3,199
7-night Costa Rica & Panama Canal

Puerto Caldera to Colon

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
12/6/25
From
$2,599
7-night Classic Caribbean

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
12/7/25
From
$2,299
14-night Star Collector: Caribbean Explorations

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
12/7/25
From
$3,699
7-night Dreams of Tahiti Cruise

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
12/11/25
From
$3,199
14-night Star Collector: Caribbean Explorations

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
12/14/25
From
$3,999
14-night Star Collector: Caribbean Explorations

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
12/21/25
From
$4,299
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
$6,099
7-night Beach Fun & Sun: A Remote Caribbean Getaway

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
12/14/25
From
$2,399
11-night Tahiti and the Tuamotu Islands Cruise

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
12/18/25
From
$4,499
10-night Canary Island Idyll

Roundtrip Santa Cruz de Tenerife

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
12/20/25
From
$3,799
7-night Classic Caribbean

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
12/21/25
From
$2,699
10-night Canary Island Idyll

Roundtrip Santa Cruz de Tenerife

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
12/30/25
From
$3,799
7-night Dreams of Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
1/8/26
From
$2,699
10-night Canary Island Idyll

Roundtrip Santa Cruz de Tenerife

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
1/9/26
From
$3,899
7-night Dreams of Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
1/15/26
 
Call For Pricing
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
$2,499
7-night Beach Fun & Sun: A Remote Caribbean Getaway

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
12/28/25
From
$2,699
10-night Tahiti and the Tuamotu Islands Cruise

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
12/29/25
From
$4,699
7-night Beach Fun & Sun: A Remote Caribbean Getaway

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
1/4/26
From
$2,499
7-night Lush & Lovely Island of the Lesser Antilles

Barbados to St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
1/7/26
 
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
$4,799
10-night Canary Island Idyll

Roundtrip Santa Cruz de Tenerife

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
1/19/26
From
$3,499
7-night Dreams of Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
1/22/26
 
Call For Pricing
7-night Dreams of Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
1/29/26
From
$2,799
10-night Canary Island Idyll

Roundtrip Santa Cruz de Tenerife

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
1/29/26
From
$3,499
7-night Dreams of Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
2/5/26
From
$2,799
7-night Beach Fun & Sun: A Remote Caribbean Getway

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
1/31/26
From
$2,499
14-night Star Collector: Caribbean Exploration

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
1/31/26
From
$4,099
18-night Star Collector: Twice the Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
2/5/26
From
$5,899
7-night Classic Caribbean

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
2/7/26
From
$2,599
14-night Star Collector: Caribbean Explorations

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
2/7/26
From
$4,099
10-night Canary Island Idyll

Roundtrip Santa Cruz de Tenerife

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
2/8/26
From
$3,499
7-night Costa Rica and Panama Canal

Colon to Puerto Caldera

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
2/9/26
From
$2,999
11-night Tahiti & the Tuamotu Islands

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
2/12/26
From
$4,599
7-night Beach Fun & Sun: A Remote Caribbean Getway

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
2/14/26
From
$2,599
7-night Costa Rica and Panama Canal

Puerto Caldera to Colon

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
2/16/26
From
$2,999
10-night Canary Island Idyll

Roundtrip Santa Cruz de Tenerife

Cruise Line
Windstar Cruises
Cruise Ship
Wind Star
Departs
2/18/26
From
$3,499
7-night Beach Fun & Sun: A Remote Caribbean Getway

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
2/21/26
From
$2,599
17-night Star Collector: Twice the Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
2/23/26
 
Call For Pricing
10-night Tahiti & the Tuamotu Islands

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
2/23/26
From
$4,499
14-night Star Collector: Leeward & Windward Caribbean Havens

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
2/21/26
From
$3,999
21-night Star Collector: A Lesser Antilles Odyssey

St. Maarten to Barbados

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
2/21/26
From
$6,099
7-night Costa Rica and Panama Canal

Colon to Puerto Caldera

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
2/23/26
From
$2,599
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
$2,399
14-night Star Collector: Caribbean Explorations

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
2/28/26
From
$3,699
14-night Star Collector: Antilles Adventure

St. Maarten to Barbados

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
2/28/26
From
$3,999
7-night Classic Caribbean

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
2/28/26
From
$2,299
7-night Costa Rica and Panama Canal

Puerto Caldera to Colon

Cruise Line
Windstar Cruises
Cruise Ship
Star Pride
Departs
3/2/26
From
$2,999
14-night Star Collector: Captivating Caribbean

Roundtrip Barbados

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
3/7/26
From
$4,099
7-night Dreams of Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
3/5/26
 
Call For Pricing
7-night Jewels of the Windward Islands

Roundtrip Barbados

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
3/7/26
From
$2,599
7-night Beach Fun & Sun: A Remote Caribbean Getaway

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
3/7/26
From
$2,399
7-night Windward Island Delights

Roundtrip Barbados

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
3/14/26
From
$2,599
14-night Star Collector: Captivating Caribbean

Roundtrip Barbados

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
3/14/26
From
$4,099
7-night Dreams of Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
3/12/26
From
$2,699
14-night Star Collector: Caribbean Explorations

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
3/14/26
From
$3,699
7-night Jewels of the Windward Islands

Roundtrip Barbados

Cruise Line
Windstar Cruises
Cruise Ship
Wind Spirit
Departs
3/21/26
From
$2,599
7-night Classic Caribbean

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
3/21/26
From
$2,299
7-night Dreams of Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
3/19/26
From
$3,099
21-night Star Collector: Comprehensive Tahiti & Marquesas Adventure

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
3/19/26
From
$8,399
14-night Star Collector: Caribbean Explorations

Roundtrip St. Maarten

Cruise Line
Windstar Cruises
Cruise Ship
Wind Surf
Departs
3/21/26
From
$3,699
14-night Tahitian Treasures & Magnificent Marquesas

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
3/26/26
From
$6,899
7-night Dreams of Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
4/9/26
From
$2,899
7-night Dreams of Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
4/16/26
From
$2,899
21-night Star Collector: Comprehensive Tahiti & Marquesas Adventure

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
3/26/26
From
$7,899
7-night Dreams of Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
4/23/26
From
$2,899
18-night Star Collector: Twice the Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
4/23/26
From
$5,999
10-night Tahiti & the Tuamotu Islands

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
5/11/26
From
$4,499
7-night Dreams of Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
5/21/26
From
$3,099
11-night Tahiti & the Tuamotu Islands

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
4/30/26
From
$4,599
17-night Star Collector: Twice the Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
5/11/26
From
$5,999
7-night Dreams of Tahiti

Roundtrip Papeete

Cruise Line
Windstar Cruises
Cruise Ship
Star Breeze
Departs
5/28/26
 
Call For Pricing

Terms and 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.