Looking for the perfect winter vacation? 4 reasons why Windstar Cruises should be on your short list
Quick summary
I get it. Life is a constant whirlwind with a billion things to do at home, at work and in our communities. If it feels like there's never enough time to get it all done, you're not alone. But let me share some words of wisdom: Pick something else on your to-do list to skimp on. Instead, make time — right now — to plan a winter getaway.
Don't wait until the leaves start falling and you're spending every weekend raking. If you don't yet have any travel planned for this fall and winter, there's still time to redeem yourself and play the hero for your spouse, friends or family. Here's the secret: Windstar Cruises.
I've sailed with Windstar four times, aboard both classes of ships in its fleet, which are:
- Wind Class masted sailing ships (Wind Surf, Wind Spirit and Wind Star)
- Star Class motor yachts (the forthcoming Star Seeker and Star Explorer will join Star Breeze, Star Legend and Star Pride)
The two smallest ships in the fleet each accommodate 148 guests in 74 cabins. The brand's largest ship, 342-passenger Wind Surf, is closely followed by a trio of 312-passenger yachts (Star Breeze, Star Legend and Star Pride).
I adored each sailing and look forward to Windstar's future because there are a lot of cool things on the horizon, including the completion of a multimillion-dollar revamp of its sailing ships and the forthcoming launch of two new motor yachts to join its fleet (Star Seeker in late December and Star Explorer in late 2026). And, most importantly, Windstar has some very compelling sailings available, from the Caribbean and the Panama Canal to Europe year-round and beyond.
I'm tempted to say that this indeed may even be the best time to book a well-deserved fall or winter Windstar Cruise. Let's talk about why.
Greatest hits, plus new and expanded itineraries
For my money, Windstar itineraries are some of the most interesting in the cruise world.
If you're a first-timer who wants to see a region's "greatest hits" cities, you'll find that. You'll also find longer "grand voyages" and year-round cruises through the Mediterranean and Europe, as well as the South Pacific.
Are you a longtime cruiser looking for something a bit different? Windstar also offers itineraries calling on an array of off-the-beaten-path destinations that larger ships can't access. When you post your selfies to Instagram, your friends are going to tag you to ask, "Where in the world are you? It looks fab!"
Mediterranean and Canary Island sailings
I think one of the most interesting itineraries of 2026 is the seven-night Winter in Italy and the Adriatic. You'll depart from the Eternal City, Rome, and call on Naples, Italy (home to the best pizza in the world); enjoy overnights in Catania, Sicily, and Corfu, Greece; visit Delphi, Greece; and cruise Greece's Corinth Canal before disembarking in Athens.
Frankly, though, I think the highlight of this voyage is Crotone. On the sole of Italy's boot, Calabria is the least-visited region of the country, and it's fabulous. (I'm an Italian citizen with roots near Crotone, and it's one of the most beautiful places on the planet. Don't miss it!)
Star Legend makes this trip from March 31 to April 8, 2026, starting around $425 per person, per day.
If you like the idea of a wintertime Mediterranean sailing but have your heart set on an island vibe, check out the Canary Island Idyll round-trip cruise out of Santa Cruz de Tenerife on Wind Star. Starting around $273 per person, per night, the ship calls on San Sebastian, Santa Cruz de Palma, Lanzarote and includes overnights in both Funchal and Las Palmas.
Shorter Med cruises
Also in the Med, in spring 2026, don't miss out on new three- to five-night "bite-size cruises" that are a perfect match for people with limited vacation time or anyone who wishes to tack a shorter cruise onto another trip.
These quick getaways are optimized for those departing from the East Coast. Jump on a plane, get your z's on board the aircraft and arrive fresh in Europe to begin your cruise.
There is a trio of three-night sailings: Depart from London aboard Star Pride to visit Bruges and Antwerp, Belgium, or St. Malo, France. Set out on a Rome round-trip sailing as Wind Surf calls on Portovenere, Italy, and Bonifacio, France. Or, check out southern France and Spain on a route from Barcelona to Tarragona, Spain, with calls on Sete and Collioure, France. There's also a five-night cruise from Rome to Barcelona, calling on Portofino, Italy; Monte Carlo, Monaco; Sanary-sur-Mer, France; and Palamos, Spain. Cruise-only fares start around $1,299 per person.
More short itineraries will be announced soon for 2027.
Caribbean and the Panama Canal
Windstar's Caribbean and Costa Rica/Panama Canal voyages are the ticket if you want to reserve some time in the sunshine this winter. Some top itineraries include:
- San Juan & the Virgin Islands: San Juan, Puerto Rico, round-trip, with calls on St. John (U.S. Virgin Islands), Basseterre (St. Kitts), Gustavia (St. Barts), Philipsburg (St. Maarten) and Jost Van Dyke and Virgin Gorda (British Virgin Islands) (starting around $331 per person, per night)
- Windward Islands Surf & Sunsets: Calling on Bequia and Mayreau (the Grenadines), Les Saintes (Guadeloupe), Soufriere (St. Lucia) and Philipsburg (St. Maarten), round-trip out of San Juan (starting around $642 per person, per night)
- Costa Rica & Panama Canal: Colon, Panama, to Puerto Caldera, Costa Rica, including transiting through the Panama Canal (starting around $428 per person, per night)
- Jewels of the Windward Islands: Barbados round-trip to visit St. Lucia, Bequia, Mayreau and Tobago Cays (starting around $385 per night, per person)
South Pacific
I've sailed the South Pacific with Windstar, too, and it's a special experience. There's still availability for these exotic voyages throughout the end of the year and early in 2026. Consider the Dreams of Tahiti seven-night round-trip cruise on Star Breeze out of Papeete, Tahiti. It calls on Moorea, Tahaa, Huahine and offers overnights in both Raiatea and Bora Bora. The price? The Dec. 4–11, 2025 cruise starts around $366 per day per person.
Or, check out the 10-night Tahiti & the Tuamotu Islands voyage sailing out of Papeete for Fakarava, Rangiroa, Tahaa, Huahine, Moorea and an overnight in Bora Bora. The Nov. 10–20 cruise starts around $331 per day per person.
An offer that delivers more for your dollar
Did any of those itineraries above make you check your calendar? There's still time to book! Windstar Cruises has the right mix of inclusions for the price. That's especially true right now with the line's Travel Is Better When You're All-In promotion, which is available on all voyages departing through March 31, 2026.
Passengers booking this deal receive free Wi-Fi; included gratuities; and unlimited select wine, beer and cocktails. These inclusions are worth up to $1,350 per couple on a seven-night cruise. This offer is valid on new bookings only and is subject to availability.
New ships
It's also important to know that Windstar is on the cusp of taking delivery of a brand-new ship. There's a lot of buzz about Windstar's forthcoming Star Seeker. It's a small yacht with 112 cabins to accommodate up to 224 passengers. The same will hold true for the line's second forthcoming ship, Star Explorer, which will launch in time to see out 2026 and ring in 2027.
Most accommodations on both yachts feature either a private veranda or a floor-to-ceiling infinity window that opens to let in sea breezes.
Star Seeker's maiden voyage begins in Malaga, Spain, on Dec. 28, 2025. It will join sister ship Wind Star in the Canary Islands to celebrate the new year with fireworks and an all-night party.
Then, its inaugural season continues in the Caribbean. That will probably be the last time the ship sails there (according to the line), which may be enough of a reason to book a Caribbean wintertime escape on Star Seeker.
The ship will then transit the Panama Canal and move on from the region to spend time in Alaska before crossing the Pacific in September 2026 to explore Japan.
In fact, the Japan itineraries proved so popular when the inaugural season went on sale that Windstar decided to open bookings early for its 2027 "Land of the Rising Sun" voyages.
While these new yachts are intimate, they don't skimp on amenities. Star Seeker and Star Explorer both offer a spa, a fitness center and an aft water sports platform that, according to the line, "turns the ocean into an infinity pool by letting guests access the sea directly from the ship." I'm not the world's best swimmer, but I felt completely comfortable enjoying Windstar's water sports platform. It makes you feel as if you're traveling aboard a friend's private yacht!
Star Seeker will feature Basil + Bamboo on board, a complimentary specialty restaurant. (It will replace Cuadro 44 fleetwide.) The menu blends Mediterranean and Asian flavors. High-end provisions, such as black cod, iberico de bellota ham, pickled wood ear mushrooms and free-range chicken, will be served. Basil + Bamboo joins Amphora (the main dining room), The Yacht Club (for casual breakfast and lunch), Star Grill (for lunch and dinner) and free 24-hour room service aboard Star Seeker.
Don't forget that Windstar is the official cruise line of the James Beard Foundation, so you know you'll be in for a culinary treat on your next cruise.
Revamped ships
Windstar is also renovating its Wind Class ships. Wind Surf, Windstar's 342-passenger sailing yacht, holds a special place in my heart. It was the first Windstar ship I sailed (a Caribbean itinerary), and it was such a fantastic experience that I sailed again in the Mediterranean.
Earlier this year, the ship emerged from a massive "transformation project" with improvements to the yacht's public areas, including the lobby and reception area, Yacht Club Cafe, Compass Rose Bar and Lounge, and Amphora Restaurant and Wine Room, as well as the pool bar and deck. The Owner's Suite was also revamped, while all cabins were outfitted with new TVs.
Finally, the ship added two new accommodation options — the Broadmoor and Sea Island suites — inspired by the high-end sister resorts in Colorado and Sea Island, Georgia, respectively.
A second revamp phase will update all of Wind Surf's cabins with new furniture and decor. Stella Bistro, Veranda and the onboard gym are also part of that refresh.
Windstar's other two Wind Class sailing ships — Wind Star and Wind Spirit — are also going through their own metamorphoses. All sailing ships have completed phase 1 of the refurbishment project. Wind Star will emerge from the final phase in April 2026 and Wind Spirit in March 2027.
Bottom line
Now is the time to take advantage of Windstar Cruises' Travel Is Better When You're All-In deal. You'll find excellent values for sailings this autumn and winter.
Don't wait until the leaves start to fall! Scroll the itinerary list now, and make some plans. Then, when others are stuck in the middle of winter's doldrums, you'll be out exploring the globe with Windstar.