Now is the right time to book a perfect winter vacation – Style cruise may be the answer

I get it. Life is a constant whirlwind, with a billion things to do at home, work and in the community. If you don’t feel like you’re not having enough time to do it all, you’re not alone. But let me share some smart words: select something else on your to-do list to signal. Instead, now-plan your winter vacation now.
Don’t wait until the leaves start to fall, and you spend a lot of time every weekend. If you haven’t planned any trips this fall and winter, there’s still time to redeem yourself and play heroes for your spouse, friends, or family. This is the secret: Wind Star Cruise.
I have sailed on Windstar four times, two types of ships in the fleet, here are:
- Wind-class mast sailboat (wind surfing, style and wind star)
- Star Class Motor Yachts (the upcoming Star Seeker and Star Explorer will join Star Breeze, Star Legend and Star Pride)
The two smallest ships in the fleet accommodate 148 guests in 74 cabins. The brand’s largest boat, 342 passenger wind surfing, followed by a trio of 312 passenger yachts (Star Breeze, Star Legend and Star Pride).
I admire every voyage and look forward to the future of Windstar because there are a lot of cool things to do, including completing the multi-million dollar reform of its sailboat and two new motorcycle yachts to join its fleet (star seekers in late December and Star Explorer in late 2026). And, most importantly, Windstar has some very compelling voyages, from the Caribbean Sea and the Panama Canal to Europe throughout the year and beyond.
I would love to say that this is indeed probably the best time to book a well-deserved fall or winter style cruise. Let’s talk about the reasons.
Best hits, as well as new and extended itineraries
For my money, style itinerary is the most interesting in the cruise industry.
If you are a beginner and want to see a region’s “best popular” city, you’ll find this. You will also find longer “big sailings” and year-round cruises in the Mediterranean and Europe as well as the South Pacific.
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Are you a long-term cruiser looking for something different? Windstar also offers itinerary, calling for a range of cubicle path destinations that are not accessible to large ships. When you post a selfie to Instagram, your friend will tag you asking, “Where are you? It looks like Fab!”
Mediterranean and Canary Island Sail
I think one of the most interesting itineraries for 2026 is the seven nights of winter in Italy and the Adriatic. You will leave the eternal city of Rome and call in Naples, Italy (home with the best pizza in the world); enjoy overnight in Catania, Sicily and Corfu in Greece; visit the Greek Delphi; and the Collins Canal in Cruz, Greece, and then disembark in Athens.
Frankly, I think the highlight of this voyage is the crot. On Italian boots, Calabria is the least visited area in the country and it is great. (I am an Italian citizen, close to Crotone, which is one of the most beautiful places on earth. Don’t miss it!)
Star Legend is doing this trip from March 31, 2026 to April 8, 2026 for $425 per person per person.

If you like the idea of a Mediterranean sailing in winter, but keep your heart on the island atmosphere, check out the Canary Island idyllic round trip cruise from the Wind Stars on Santa Cruz de Tenerife. The ship costs $273 per person per night in San Sebastian, Santa Cruz de Palma, Lanzarote and includes overnight in Funchal and Las Palmas.
Shorter medical tours

Also in MED, don’t miss out on the new “bite-size cruise” for three to five nights in spring 2026, which is a perfect match for those with limited vacation time or anyone looking to take a shorter cruise to another trip.
These fast wins are optimized for those starting from the East Coast. Jump onto the plane, send your Z onto the plane, and arrive in Europe freshly to start your cruise.
There are three gala sailing three: set off from London, climb the Stars Pride, visiting Bruges and Antwerp, Belgium or St. Marlo, France. Start during the round trip voyage in Rome while surfing in Portovenere, Italy and Bonifacio, France. Or, check out southern France and Spain on the French route to Tarragona, Spain and call on Sete and Collioure in France. There is still five nights of cruise from Rome to Barcelona, calling on Italy’s Pofino Island. Monte Carlo, Monaco; Sanary-Sur-Mer, France; and Paramos, Spain. The fare for cruises alone is about $1,299 per person.
The shorter schedule will be announced soon for 2027.
The Caribbean Sea and Panama Canal
If you want to keep this winter sun for a while, Windstar’s Caribbean and Costa Rica/Panama Canal sailing is ticket. Some of the top itineraries include:
- San Juan and Virgin Islands: San Juan, Puerto Rico, round trip and round trip and in St. John (US Virgin Islands), Basset Islands (St. Kitts), Gustavia (St. Butters), Philipsburg (St. Maarten) and Jost Van Dyke and Virgin Gorda (UK Virgin Islands) ($331 per night) (about per night)
- Wind toward island surfing and sunset: Calling Bequia and Mayreau (Grenadines), Les Saintes (Guadeloupe), Soufriore (St. Lucia) and Philipsburg (St. Maarten) and round trip from San Juan (about $642 per night)
- Costa Rica and Panama Canal: Panama Bollard, to the Puerto Rico crater in Costa Rica, including transit through the Panama Canal (about $428 per night, about $428 per night)
- Jewelry on the Windward Island: Barbados round-trip visits to the circumference of Saint Lucia, Bequia, Merello and Tobago (about $385 per night)
South Pacific
I also sailed the South Pacific with Windstar, which was a special experience. These exotic voyages remain available throughout the year and early 2026. Consider the dream of a seven-night round trip to Tahiti and set off in Papeete, Tahiti. It called on Moorea, Tahaa, Huahine, and offered overnight at Raiatea and Bora Bora. price? From December 4th to 11th, the 2025 parade is $366 per person per day.
Alternatively, check out the 10-night Tahiti and Tuomotu Islands sailing from Papeete to Fakarava, Rangiroa, Tahaa, Huahine, Moorea, Moorea and overnight stays in Bora Bora. The tour from November 10 to 20 will be approximately $331 per person per day.
More offers to your dollar
Are there any of the above trips that allow you to view the calendar? There is still time to book! Windstar Cruises are priced at inclusions. This is especially true of this route’s trip when you go all out on promotions, which will be set out before March 31, 2026.
Passengers who book this transaction will receive free Wi-Fi; including remuneration; and unlimited wine, beer and cocktails. On the seven-night cruise, these inclusions are worth $1,350 per couple. This offer is only valid on new bookings and is available on a basis of availability.
New ship
It is also important to know that Windstar is the cusp of taking a brand new boat. Windstar’s upcoming star seekers have caused a lot of sensation. This is a small yacht with 112 cabins and can accommodate up to 224 passengers. The same will be true of the second ship of the line, Star Explorer, which will be launched in time for 2026 and will ring in 2027.

Most accommodation on both yachts have a private balcony or unlimited floor-to-ceiling windows that open up the sea breeze.
The Seeker’s Maiden voyage began on December 28, 2025 in Malaga, Spain. It will celebrate the New Year with the Canary Islands sister ship Wind Star, along with fireworks and overnight gatherings.
Then, in the Caribbean, its inauguration season continues. This may be the last voyage of the ship (according to this line), which may be enough reason to book a Caribbean winter escape on Sears Seeker.
The ship will then cross the Panama Canal and continue to spend time from the area to Alaska before exploring Japan across the Pacific Ocean in September 2026.
In fact, when the inauguration season started to be sold, the Japanese itinerary proved so popular that Windstar decided to open bookings for its 2027 “Rise Land of the Sun” voyage as early as possible.
Although these new yachts are intimate, they do not undermine the amenities. Star Seeker and Star Explorer both offer spas, fitness centers and stern water sports platforms, according to the route, “turn the ocean into an infinity pool by allowing guests to enter the ocean directly from the boat.” I’m not the best swimmer in the world, but I feel very comfortable enjoying Windstar’s water sports platform. It makes you feel as if you are traveling on a friend’s private yacht!
Those seeking stars will play Basil + Bamboo at a free specialty restaurant boarding. (It will replace the Cuadro 44 Fleetwide.) The menu combines Mediterranean and Asian flavours. High-end regulations will be provided such as black cod, Iberico de Bellota ham, marinated fungus mushrooms and free range chicken. Basil + Bamboo is free with Amphora (main restaurant), yacht club (casual breakfast and lunch), Star Grill (lunch and dinner) and 24-hour free room service in STAR SEERER.
Don’t forget that Windstar is the official cruise series of James Beard Foundation, so you know you’ll cook on your next cruise.
Modified ship
Windstar is also renovating the Wind Class ship. Windstar’s 342 passenger sailing yachts occupy a special place in my heart. This was my first wind starship sailing (the Caribbean itinerary) and it was a great experience I sailed in the Mediterranean again.

Earlier this year, the ship surfaced from a large-scale “transformation project” and improved the public areas of the yacht, including the lobby and reception area, the 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 has also been modified, while all cabins have new TVs.
Ultimately, the boat added two new accommodation options – Broadmoor and Sea Island Suites – to inspire high-end sister resorts in Colorado and Sea Island in Georgia.
The second remodeling phase will update the Windsurfing cabin with new furniture and decor. Stella Bristro, Veranda and onboard gyms are also part of the refresh.
Windstar’s other two Wind-class sailing ships (Windstar and Style) are also undergoing their own transformations. All sailboats completed the first phase of the renovation project. Wind Star will appear from the final stage of April 2026 and the style spirit of March 2027.
Bottom line
Now it’s time to take advantage of the trip with Windstar Cruises, and it’s better when you go all out. This fall and winter, you will find good value for sailing.
Don’t wait until the leaves start to fall! Scroll the itinerary list now and make some plans. Then, you will explore the earth with Windstar as others get stuck in the winter downturn.