Best Windstar Cruises Deals & Sales for September 2026

Explore French Polynesia aboard Windstar's Star Breeze with roundtrip airfare from Los Angeles and a pre-cruise stay at the InterContinental Tahiti Resort & Spa or similar. The voyage sails roundtrip from Papeete and visits Moorea, Raiatea, Motu Mahaea, Bora Bora, and Huahine, with an overnight stay in Bora Bora. A complimentary all-in package is included. Book this travel deal by September 30, 2026.

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Sail from Bangkok to Phuket aboard Windstar's Star Seeker on an 11-night cruise through Thailand, Singapore, and Malaysia. The itinerary visits Ko Kut, Ko Samui, Singapore, Kuala Lumpur, Penang, Krabi, and Ko Yao Noi, with an overnight stay in Singapore. A complimentary all-in package and reduced deposit are included. Book this travel deal by September 30, 2026.

Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Windstar Cruises

Sail aboard the Star Legend from Oranjestad, Aruba, to Fuerte Amador near Panama City on this 8-night Windstar cruise departing December 12, 2026. The itinerary includes two days in Cartagena, plus Bocas del Toro, the San Blas Islands, and a daylight transit through the Panama Canal. Book this travel deal by September 30, 2026.

Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Windstar Cruises

Sail roundtrip from Papeete aboard Windstar's Star Breeze on an 11-night French Polynesia cruise departing December 17, 2026. The itinerary explores the Tuamotu and Marquesas Islands with stops including Fakarava, Fatu Hiva, Hiva Oa, Nuku Hiva, Rangiroa, and an overnight visit to Bora Bora. A complimentary all-in package is included. Book this travel deal by September 30, 2026.

Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Windstar Cruises

Set sail from Barcelona aboard Windstar's Star Legend on an 8-night Spanish Mystery Cruise ending in Málaga. Seven mystery ports along Spain's coast are revealed just 36 hours before arrival, with excursions available at each destination. The voyage also includes a Windstar Destination Discovery Event celebrating Spanish culture. Book this travel deal by September 30, 2026.

Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Windstar Cruises

Sail the Canary Islands and Madeira aboard Windstar's Wind Spirit on a 10-night roundtrip cruise from Santa Cruz de Tenerife. The itinerary visits La Palma, El Hierro, La Gomera, Porto Santo, Madeira, and Lanzarote, with an overnight stay in Funchal. A complimentary all-in package and reduced deposit are included. Book this travel deal by September 30, 2026.

Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Windstar Cruises

Sail roundtrip from San Juan aboard Windstar's Star Pride on an 11-night Caribbean cruise through the Leeward Islands. The itinerary visits St. John, St. Barts, St. Kitts, Antigua, Guadeloupe, St. Lucia, Grenada, Jost Van Dyke, and Virgin Gorda. A complimentary all-in package and reduced deposit are included. Book this travel deal by September 30, 2026.

Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Windstar Cruises

Sail roundtrip from Papeete aboard Windstar's Star Breeze on a 13-night Tahiti and Tuamotu Islands package, departing December 26, 2026. The package includes roundtrip airfare from Los Angeles, a pre-cruise hotel stay at the InterContinental Tahiti Resort or similar, transfers, and a post-cruise day room. Cruise stops include Fakarava, Rangiroa, Taha'a, Bora Bora, Huahine, and Moorea. Book this travel deal by September 30, 2026.

Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Windstar Cruises