I get it. Life is a continuing whirlwind with a billion issues to do at dwelling, at work and in our communities. If it seems like there’s by no means sufficient time to get all of it finished, you are not alone. However let me share some phrases of knowledge: Choose one thing else in your to-do listing to stint on. As a substitute, make time — proper now — to plan a winter getaway.
Do not wait till the leaves begin falling and also you’re spending each weekend raking. In the event you do not but have any journey deliberate for this fall and winter, there’s nonetheless time to redeem your self and play the hero to your partner, associates or household. Here is the key: Windstar Cruises.
I’ve sailed with Windstar 4 occasions, aboard each courses of ships in its fleet, that are:
- Wind Class masted crusing ships (Wind Surf, Wind Spirit and Wind Star)
- Star Class motor yachts (the forthcoming Star Seeker and Star Explorer will be a part of Star Breeze, Star Legend and Star Delight)
The 2 smallest ships within the fleet every accommodate 148 company in 74 cabins. The model’s largest ship, 342-passenger Wind Surf, is intently adopted by a trio of 312-passenger yachts (Star Breeze, Star Legend and Star Delight).
I adored every crusing and look ahead to Windstar’s future as a result of there are a whole lot of cool issues on the horizon, together with the completion of a multimillion-dollar revamp of its crusing ships and the forthcoming launch of two new motor yachts to hitch its fleet (Star Seeker in late December and Star Explorer in late 2026). And, most significantly, Windstar has some very compelling sailings out there, from the Caribbean and the Panama Canal to Europe year-round and past.
I am tempted to say that this certainly could even be one of the best time to ebook a well-deserved fall or winter Windstar Cruise. Let’s discuss why.
Best hits, plus new and expanded itineraries
For my cash, Windstar itineraries are a few of the most fascinating within the cruise world.
In the event you’re a first-timer who desires to see a area’s “biggest hits” cities, you will discover that. You may additionally discover longer “grand voyages” and year-round cruises by means of the Mediterranean and Europe, in addition to the South Pacific.
Reward your inbox with the TPG Every day publication
Be a part of over 700,000 readers for breaking information, in-depth guides and unique offers from TPG’s specialists
Are you a longtime cruiser in search of one thing a bit totally different? Windstar additionally provides itineraries calling on an array of off-the-beaten-path locations that bigger ships cannot entry. Whenever you put up your selfies to Instagram, your folks are going to tag you to ask, “The place on the planet are you? It seems to be fab!”
Mediterranean and Canary Island sailings
I believe probably the most fascinating itineraries of 2026 is the seven-night Winter in Italy and the Adriatic. You may depart from the Everlasting Metropolis, Rome, and name on Naples, Italy (dwelling to one of the best pizza on the planet); get pleasure from overnights in Catania, Sicily, and Corfu, Greece; go to Delphi, Greece; and cruise Greece’s Corinth Canal earlier than disembarking in Athens.
Frankly, although, I believe the spotlight of this voyage is Crotone. On the only real of Italy’s boot, Calabria is the least-visited area of the nation, and it is fabulous. (I am an Italian citizen with roots close to Crotone, and it is probably the most lovely locations on the planet. Do not miss it!)
Star Legend makes this journey from March 31 to April 8, 2026, beginning round $425 per individual, per day.

In the event you like the thought of a wintertime Mediterranean crusing however have your coronary heart set on an island vibe, try the Canary Island Idyll round-trip cruise out of Santa Cruz de Tenerife on Wind Star. Beginning round $273 per individual, per evening, the ship calls on San Sebastian, Santa Cruz de Palma, Lanzarote and contains overnights in each Funchal and Las Palmas.
Shorter Med cruises

Additionally within the Med, in spring 2026, do not miss out on new three- to five-night “bite-size cruises” which might be an ideal match for folks with restricted trip time or anybody who needs to tack a shorter cruise onto one other journey.
These fast getaways are optimized for these departing from the East Coast. Soar on a aircraft, get your z’s on board the plane and arrive contemporary in Europe to start your cruise.
There’s a trio of three-night sailings: Depart from London aboard Star Delight to go to Bruges and Antwerp, Belgium, or St. Malo, France. Set out on a Rome round-trip crusing as Wind Surf calls on Portovenere, Italy, and Bonifacio, France. Or, try southern France and Spain on a route from Barcelona to Tarragona, Spain, with calls on Sete and Collioure, France. There’s additionally 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 begin round $1,299 per individual.
Extra brief itineraries shall be introduced quickly for 2027.
Caribbean and the Panama Canal
Windstar’s Caribbean and Costa Rica/Panama Canal voyages are the ticket if you wish to reserve a while within the sunshine this winter. Some high itineraries embrace:
- 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) (beginning round $331 per individual, per evening)
- 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 (beginning round $642 per individual, per evening)
- Costa Rica & Panama Canal: Colon, Panama, to Puerto Caldera, Costa Rica, together with transiting by means of the Panama Canal (beginning round $428 per individual, per evening)
- Jewels of the Windward Islands: Barbados round-trip to go to St. Lucia, Bequia, Mayreau and Tobago Cays (beginning round $385 per evening, per individual)
South Pacific
I’ve sailed the South Pacific with Windstar, too, and it is a particular expertise. There’s nonetheless availability for these unique voyages all through the top of the 12 months and early in 2026. Contemplate the Goals of Tahiti seven-night round-trip cruise on Star Breeze out of Papeete, Tahiti. It calls on Moorea, Tahaa, Huahine and provides overnights in each Raiatea and Bora Bora. The worth? The Dec. 4–11, 2025 cruise begins round $366 per day per individual.
Or, try the 10-night Tahiti & the Tuamotu Islands voyage crusing out of Papeete for Fakarava, Rangiroa, Tahaa, Huahine, Moorea and an in a single day in Bora Bora. The Nov. 10–20 cruise begins round $331 per day per individual.
A suggestion that delivers extra to your greenback
Did any of these itineraries above make you verify your calendar? There’s nonetheless time to ebook! Windstar Cruises has the right combination of inclusions for the value. That is very true proper now with the road’s Journey Is Higher When You are All-In promotion, which is out there on all voyages departing by means of March 31, 2026.
Passengers reserving this deal obtain free Wi-Fi; included gratuities; and limitless choose wine, beer and cocktails. These inclusions are value as much as $1,350 per couple on a seven-night cruise. This provide is legitimate on new bookings solely and is topic to availability.
New ships
It is also necessary to know that Windstar is on the cusp of taking supply of a brand-new ship. There’s a whole lot of buzz about Windstar’s forthcoming Star Seeker. It is a small yacht with 112 cabins to accommodate as much as 224 passengers. The identical will maintain true for the road’s second forthcoming ship, Star Explorer, which can launch in time to see out 2026 and ring in 2027.

Most lodging on each yachts characteristic both a personal 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’ll be a part of sister ship Wind Star within the Canary Islands to rejoice the brand new 12 months with fireworks and an all-night social gathering.
Then, its inaugural season continues within the Caribbean. That may most likely be the final time the ship sails there (based on the road), which can be sufficient of a motive to ebook a Caribbean wintertime escape on Star Seeker.
The ship will then transit the Panama Canal and transfer on from the area to spend time in Alaska earlier than crossing the Pacific in September 2026 to discover Japan.
In reality, the Japan itineraries proved so well-liked when the inaugural season went on sale that Windstar determined to open bookings early for its 2027 “Land of the Rising Solar” voyages.
Whereas these new yachts are intimate, they do not skimp on facilities. Star Seeker and Star Explorer each provide a spa, a health heart and an aft water sports activities platform that, based on the road, “turns the ocean into an infinity pool by letting company entry the ocean instantly from the ship.” I am not the world’s greatest swimmer, however I felt utterly snug having fun with Windstar’s water sports activities platform. It makes you’re feeling as if you happen to’re touring aboard a pal’s non-public yacht!
Star Seeker will characteristic Basil + Bamboo on board, a complimentary specialty restaurant. (It’ll exchange Cuadro 44 fleetwide.) The menu blends Mediterranean and Asian flavors. Excessive-end provisions, comparable to black cod, iberico de bellota ham, pickled wooden ear mushrooms and free-range hen, shall be served. Basil + Bamboo joins Amphora (the principle eating room), The Yacht Membership (for informal breakfast and lunch), Star Grill (for lunch and dinner) and free 24-hour room service aboard Star Seeker.
Do not forget that Windstar is the official cruise line of the James Beard Basis, so you understand you will be in for a culinary deal with in your subsequent cruise.
Revamped ships
Windstar can be renovating its Wind Class ships. Wind Surf, Windstar’s 342-passenger crusing yacht, holds a particular place in my coronary heart. It was the primary Windstar ship I sailed (a Caribbean itinerary), and it was such a incredible expertise that I sailed once more within the Mediterranean.

Earlier this 12 months, the ship emerged from a large “transformation challenge” with enhancements to the yacht’s public areas, together with the foyer and reception space, Yacht Membership Cafe, Compass Rose Bar and Lounge, and Amphora Restaurant and Wine Room, in addition to the pool bar and deck. The Proprietor’s Suite was additionally revamped, whereas all cabins had been outfitted with new TVs.
Lastly, the ship added two new lodging choices — the Broadmoor and Sea Island suites — impressed by the high-end sister resorts in Colorado and Sea Island, Georgia, respectively.
A second revamp part will replace all of Wind Surf’s cabins with new furnishings and decor. Stella Bistro, Veranda and the onboard fitness center are additionally a part of that refresh.
Windstar’s different two Wind Class crusing ships — Wind Star and Wind Spirit — are additionally going by means of their very own metamorphoses. All crusing ships have accomplished part 1 of the refurbishment challenge. Wind Star will emerge from the ultimate part in April 2026 and Wind Spirit in March 2027.
Backside line
Now could be the time to make the most of Windstar Cruises’ Journey Is Higher When You are All-In deal. You may discover glorious values for sailings this autumn and winter.
Do not wait till the leaves begin to fall! Scroll the itinerary listing now, and make some plans. Then, when others are caught in the course of winter’s doldrums, you will be out exploring the globe with Windstar.