DealNews - Best Windstar Cruises Deals & Sales for September 2026

Windstar 8-Night Bermuda Wellness Cruise for From $5,814 for 2

Fri, 18 Sep 2026 07:00:00 -0400

Sail aboard the Star Pride from Boston to San Juan on this 8-night wellness cruise departing October 20, 2026. The voyage spends two days in Hamilton and two days in St. George's, Bermuda, with wellness programming led by yoga teacher and life coach Debbie Dixon. 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

Features

Complimentary all-in package
Reduced deposit
Meditation, breathwork, and yoga
Wellness-focused talks and healthy food options

Windstar 8-Night Aruba to Panama Cruise for From $6,492 for 2

Fri, 18 Sep 2026 06:00:00 -0400

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

Features

Complimentary all-in package
Reduced deposit
8 nights aboard Star Legend
December 12 to 20, 2026 sailing

Windstar 11-Night Leeward Islands Cruise for From $15,076 for 2

Thu, 17 Sep 2026 11:00:00 -0400

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

Features

11 nights aboard Star Pride
Roundtrip cruise from San Juan
Visits to the U.S. and British Virgin Islands, St. Barts, St. Kitts, Antigua, Guadeloupe, St. Lucia, and Grenada
Complimentary all-in package
Reduced deposit
312-guest yacht

Windstar 11-Night Thailand, Singapore & Malaysia Cruise for From $11,446 for 2

Thu, 17 Sep 2026 10:00:00 -0400

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

Features

11 nights aboard Star Seeker
Bangkok-to-Phuket itinerary
Visits to Thailand, Singapore, and Malaysia
Overnight stay in Singapore
Complimentary all-in package
Reduced deposit

Windstar 10-Night Canary Islands & Madeira Cruise for From $6,740 for 2

Thu, 17 Sep 2026 09:00:00 -0400

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

Features

Roundtrip Santa Cruz de Tenerife cruise
10 nights aboard Wind Spirit
Visits to La Palma, El Hierro, La Gomera, Porto Santo, Madeira, and Lanzarote
Overnight stay in Funchal
Complimentary all-in package
Reduced deposit

Windstar 8-Night Spanish Mystery Cruise for From $5,862 for 2

Thu, 17 Sep 2026 08:00:00 -0400

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

Features

8 nights aboard Star Legend
Barcelona-to-Málaga itinerary
7 mystery ports revealed 36 hours before arrival
Shore excursions available at mystery ports
Windstar Destination Discovery Event
Travel November 4 to 12, 2026

Windstar 10-Night Tahiti Cruise with Flights for From $11,974 for 2

Thu, 17 Sep 2026 07:00:00 -0400

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.

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

Features

Roundtrip Los Angeles-Papeete airfare
Pre-cruise Tahiti hotel stay
Airport, hotel, and ship transfers
Complimentary all-in package
Windstar Destination Discovery Event in Bora Bora
Reduced deposit

Windstar 11-Night French Polynesia & Marquesas Cruise for From $11,804 for 2

Thu, 17 Sep 2026 06:00:00 -0400

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

Features

Complimentary all-in package
Reduced deposit
Windstar Destination Discovery Event in Bora Bora
Signature beach experiences
11 nights aboard Star Breeze

Windstar 13-Night Tahiti & Tuamotu Islands Cruise for From $16,294 for 2

Thu, 17 Sep 2026 05:00:00 -0400

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

Features

Roundtrip airfare from Los Angeles
1-night pre-cruise hotel stay
Post-cruise day room
Airport, hotel, and ship transfers
Pre-cruise breakfast and Wi-Fi
Complimentary all-in package
Windstar Destination Discovery Event in Bora Bora