Best Windstar Cruises Deals & Sales for May 2026

Sail roundtrip from Papeete aboard Windstar Cruises’ Star Breeze on this 11-night French Polynesia and Marquesas cruise. This package includes a complimentary all-in package and visits remote islands across the Tuamotus, Marquesas, and Society Islands. Ports and stops include Fakarava, Omoa on Fatu Hiva, Atuona on Hiva Oa, Taiohae on Nuku Hiva, Rangiroa, Bora Bora, and Papeete. Book this travel deal by May 31, 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 Cruises’ Star Breeze on this 13-night Tahiti and Tuamotu Islands cruise package from LAX. This package includes round-trip airfare from Los Angeles, one night of pre-cruise hotel accommodations, post-cruise day-room access, transfers between the airport, hotel, and yacht, airline taxes and fuel surcharge, and a complimentary all-in package. Ports and stops include Papeete, Fakarava, Rangiroa, Motu Mahaea, Bora Bora, Huahine, Moorea, and more. Book this travel deal by May 31, 2026.

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

Sail from Barcelona to Málaga aboard Windstar Cruises’ Star Legend on this 8-night Spanish Mystery cruise. This itinerary includes seven mystery ports along Spain’s storied coast, plus a memorable Destination Discovery Event designed to immerse travelers in Spanish culture. Book this travel deal by May 31, 2026.

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

Sail from Bordeaux to Lisbon aboard Windstar Cruises’ Star Legend on this 8-night wine cruise through Northern Spain and Portugal. This all-inclusive cruise visits Bordeaux, Bilbao, Santander, Gijón, Vigo, Leixões for Porto, and Lisbon, with time to sample wines, explore seafood markets, see the Guggenheim in Bilbao, and experience Portugal’s Douro River region. Book this travel deal by May 31, 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 Santa Cruz de Tenerife aboard Windstar Cruises’ Wind Spirit on this 10-night Canary Islands and Madeira cruise. This luxe cruise visits Santa Cruz de Palma, El Hierro, San Sebastian, Porto Santo, Funchal, and Lanzarote, with time to explore natural rock pools, golden beaches, wineries, historic levadas, and volcanic landscapes. Book this travel deal by May 31, 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 Civitavecchia, Rome aboard Windstar Cruises’ Wind Surf on this 7-night Italian and French Rivieras cruise. This summer sailing visits Bastia, Cannes, Monte Carlo, Genoa, Portofino, and Porto Ercole, with late nights in Cannes and Genoa. The cruise includes a complimentary all-in package and opportunities to explore Corsica, the French Riviera, Monaco, the Italian Riviera, and Tuscany. Book this travel deal by May 31, 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 Piraeus, Athens aboard Windstar Cruises’ Wind Star on this 7-night Greek Isles cruise. This all-inclusive yacht cruise visits Mykonos, Kusadasi, Patmos, Santorini, Monemvasia, and Nafplio, with chances to explore seaside villages, ancient sites, whitewashed island scenery, and UNESCO World Heritage Sites. Book this travel deal by May 31, 2026.

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