Best sail escapes of the season: Popular destinations, cooler weather + seasonal savings

For travelers seeking spontaneity and adventure this fall, Windstar Cruises, leader in small ship luxury cruising, is sharing its top sailing destinations and savings to take advantage of for the new season. Whether it’s a vacation to chase the warmth of the summer sun, celebrate a special autumn occasion or holiday, or to explore some of the world’s most beautiful destinations, travelers can take advantage of Windstar’s exclusive savings on select sailings in Tahiti, the Caribbean and the Mediterranean for this upcoming autumn season. Think: booking a last-minute trip to the Mediterranean and enjoying the beauty of autumn’s warm days, cool nights, and European fall harvest — all from the luxury of an intimate small cruise ship.

Here are some of Windstar’s best sail escapes and savings of the season:

A Last-Minute Upgrade Ending Soon: Complimentary All-Inclusive Upgrade is Available Through September 30. One of Windstar’s most popular deals, travelers can still take advantage of this complimentary all-inclusive upgrade until September 30 for select voyages departing through March 31, 2025. The upgrade (valued at $89/day per person) includes free Wi-Fi, unlimited beer, wine and cocktails and all gratuities, plus reduced deposits on 2024 voyages. Travelers can still receive this special upgrade on autumn and winter sailings to Europe, French Polynesia, Latin America and the Caribbean.

Savings for Solo Travel

Windstar Cruises is known for offering an exceptional solo travel experience with its intimate small ship setting, small group excursions, and on-board programming. but also its single supplement savings. In addition to lower seasonal airfare in the fall, solo travelers can take advantage of even more savings. Windstar Cruises is offering a single supplement of 120% on select sailings this autumn and early winter.

“Our small ships attract friendly, well-traveled people who enjoy meeting new people, and with fewer people on board, it’s simply easier to make new friends and find people you want to socialize with throughout the cruise.” says Janet Bava, Windstar’s chief commercial officer.

The special single supplement is also available for travelers chasing the summer sun to warm weather destinations like Windstar’s Balboa/Fuerte Amador to Oranjestad itinerary. Guests have the unique opportunity to explore the Panama Canal, San Blas Islands of Panama, Cartagena, and Aruba all in one trip.

Explore Europe’s Hottest Destinations in Cooler Weather

Windstar’s complimentary all-inclusive upgrade offer is available on select trips to the Mediterranean where travelers can enjoy some of the world’s most iconic destinations and attractions with less crowds and beautiful mild weather. A season of harvest, cruising in the fall means enjoying golden vineyards and carefully curated itineraries and opportunities to enjoy the fall flavors and traditions of some of Europe’s top destinations. Travelers can explore extraordinary itineraries which include discovering Croatia’s coast, picturesque Greek islands, and the historic cities of Barcelona and Rome. Travelers can indulge in local autumn delicacies, visit ancient ruins, and enjoy the benefits of a quieter season when it’s easier to get entry into top museums, historical sites and restaurants. Windstar’s autumn and winter sailings also highlight ports that Windstar doesn’t normally visit during the summer like Valencia, Spain; Crotone, Italy; and Catania in Sicily.

“Autumn in the Mediterranean is fabulous,” says Bava. “It’s normally mild weather in the 60s with sunny, cool days, perfect for exploring and enjoying the coastal scenery, and wandering around plazas and historical sites. In fall and winter, locals are more prevalent than tourists so it’s definitely a more leisurely vibe. I also love Autumn for dining on fresh, local specialties, and you can enjoy fall harvest festivals such as the olive harvest in Greece, grape harvest in Croatia and chestnut festivals in Sardinia.”

Bava notes that travelers will usually be able find significantly lower airfares from the United States to Europe in the fall.

Take the Time to Travel to Tahiti

Still have Olympic fever? Those who miss tuning in to the summer Olympics to watch athletes catch a wave can actually sail their own wave with Windstar’s cruises in French Polynesia. With more than 36 years’ experience operating cruises in French Polynesia, Windstar Cruises is the small ship expert of the region. Fall offers the perfect climate for exploring Tahiti’s islands. With temperatures averaging in the mid-70s to low 80s Fahrenheit and lower humidity levels, travelers can enjoy French Polynesia’s iconic sites, beaches, and Windstar’s Polynesian shore excursions in comfortable weather. Earlier this year, Windstar moved its all-suite, 312-passenger Star Breeze to sail in Tahiti year-round, replacing 148- passenger classic sailing yacht Wind Spirit. The move doubled guest capacity due to interest in travel to the region and fall is the perfect time to enjoy Windstar’s itineraries which explore popular destinations such as Bora Bora but also lesser-known islands and beaches like Motu Mahaea (Tahaa).

A Caribbean Cruise

Not a fan of fall’s cooler weather? The Caribbean offers an inviting endless summer escape. Cruising allows one of the best ways to explore several islands and beaches in one trip with the opportunity to unpack just once. As a small cruise ship, Windstar can also access beaches and cities that many of the larger cruise ships cannot. Windstar Cruises not only offers trips aboard its Wind Class sail ships, but also Windstar’s all-suite, 312-guest Star Pride is sailing the Caribbean Sea with stops in San Juan, St. Maarten, St. Lucia, St. Barts, Bequia, Guadelope and more. Two main itineraries sail roundtrip from San Juan, Puerto Rico – San Juan & the Virgin Islands and Windward Island Surf & Sunsets – both with plenty of beach time, swimming, snorkeling and small islands to explore.