Why Cruise with Windstar? Discover the Difference
- Kathie
- May 16
- 6 min read
Updated: May 28
If you’re looking for the elevated dining of a luxury cruise line without the pretentious vibe, then Windstar may be the just cruise line for you. Windstar’s motto is “180 degrees from ordinary," and that’s exactly what I discovered on my recent cruise: exceptional cuisine in a relaxed, welcoming setting, with a crew that is delightful and fun.
When was the last time someone asked you "How was your vacation?" And you could surprisingly reply, "It was fun!"
This isn’t a cruise where you’re expected to dress to the nines, sip champaign, and quietly watch the string quartet perform. This is a cruise where you return from an excursion, slip into your swimsuit, head out on deck, order a cocktail, hop in the hot tub, and chat with your fellow cruisers while watching the sun sink lower on the horizon.
Of course, you can still enjoy a nightcap while listening to a performer sing enchanting music and strum their guitar. But on Windstar, the experience is much more personal — they make eye contact and even ask if you have any requests. This is the kind of cruise where participation is encouraged, and every guest is part of the fun.
One night, for example, there was line dancing on the deck. As my cabin steward saw me filming the festivities, he asked, "You're going to dance the next one, right? It's the Macarena!" Well, who can resist the Macarena?! So, of course, I had to join the fun. That’s the spirit that makes Windstar 180 degrees from ordinary.
Another night, they had a Crew Talent Show and even then they engaged the guests by giving out a lei during one song, a rose during another, and asking questions to encourage audience participation. And the crew was having so much fun, and it was so entertaining that we were enjoying it and laughing along with them.
Regarding the crew, it is common on luxury cruise lines for the crew to pride themselves on remembering your preferences and making you feel at home from the moment you board. But I have to tell you, the crew on Windstar was the best that I have experienced.
I think it starts from the top. Our well loved hotel manager, Andreas, must really enjoy his job because he was always on deck, smiling and chatting with the guests and encouraging everyone to have a good time.
He even helped us with our dining issue. My roommate and I were discussing having room service for dinner because we had eaten at the main dining room twice and didn't want to spend 3 hours at dinner. We mentioned it to Andreas and when we went to dinner the next night, the server asked us, "Do you want a quick dinner, or a slow dinner?" We were like, "Wait, what?! ... Oh, Andreas talked to you!"
We were at Candles that night, which is one of their fine dining venues. So we wanted to enjoy our meal (I had Fillet Mignon. Cooked to perfection!) but not spend all night eating bread and making small talk. We had a very enjoyable meal at the perfect pace - neither too rushed nor too slow.
Note: I mentioned that the server asked how we wanted our dinner served. So it is up to you to determine how much time you want to spend at dinner. If you choose a Windstar cruise to celebrate your honeymoon (like a couple we met in the hot tub), and you want to spend quality time together over a lovely dinner, then you have the opportunity to do that.
More fun is to be found at the water sports platform on the back of the ship. The platform opens up to allow you to enjoy water sports like kayaking, paddle boarding, sailing or jumping on a trampoline. [1]
If this sounds like your type of cruise, then check out this cruise from Rome to Venice with special incentives on Oct 7, 2026. Contact me for more details!
Why Cruise with Windstar?
When it comes to luxury cruising, Windstar stands apart as a boutique cruise line that delivers an experience “180 degrees from ordinary.” From its iconic sailing ships to its exclusive access to the heart of Venice, Windstar offers a rare blend of intimacy, adventure, and authenticity that is hard to find any where else. Here’s why you should consider Windstar for your next cruise.
Unmatched Access: Docking in Venice’s Old Town
One of Windstar’s most remarkable distinctions is its ability to dock in the heart of Venice’s Old Town (a privilege denied to larger cruise ships due to local restrictions). While other vessels are forced to anchor far from the city, requiring lengthy transfers, Windstar’s small ships glide right up Venice’s main waterway, offering guests an unrivaled arrival and departure experience. Step off the ship and you’re instantly immersed in the city’s labyrinth of ancient streets, canals, and Venice at your doorstep.
The Romance of Sailing: Windstar’s Iconic Sailing Ships
Windstar’s fleet includes two smaller sailing ships: Wind Star and Wind Spirit, as well as the majestic Wind Surf, the largest sailing yacht in the world. These vessels combine the timeless romance of traditional sailing with all the comforts and amenities of a modern luxury yacht.
Wind Star: A four-masted sailing yacht, Wind Star accommodates just 148 guests in 74 staterooms, offering an intimate and authentic sailing experience. Its compact size allows it to visit secluded harbors and hidden gems that larger ships simply can’t reach.
Wind Spirit: Sister ship to Wind Star, Wind Spirit also hosts 148 guests and is designed for those who crave the thrill of the open sea under billowing sails, all while enjoying gourmet dining, a spa, and personalized service.
Wind Surf: The flagship of the Windstar fleet, Wind Surf carries up to 342 guests and is renowned for its impressive five-masted profile. It’s the largest sailing yacht in the world, blending grandeur with the same intimate atmosphere that defines the Windstar experience.
Sailing on these ships is not just about transportation-it’s about the journey itself. Feel the wind fill the sails, and enjoy the unique sensation of gliding quietly from port to port, often under starry skies.
Intimate Yet Fun, Yacht-Like Atmosphere
Windstar’s ships are intentionally small, carrying between 148 and 342 guests. This boutique size fosters a sense of camaraderie and exclusivity, more akin to a friend's private yacht than a mass-market cruise ship. You’ll quickly get to know fellow travelers and the wonderful crew.
With a nearly 1:1 crew-to-guest ratio, service is highly personalized. Expect to be greeted by name, have your favorite drink remembered, and enjoy thoughtful touches throughout your voyage.
Access to Hidden Ports and Authentic Experiences
Because of their size, Windstar’s ships can slip into smaller ports and off-the-beaten-path destinations that are inaccessible to larger vessels. This means you’ll discover places most travelers never see, from secluded Mediterranean harbors to remote South Pacific islands.
Windstar’s shore excursions are designed for immersion and authenticity. Whether it’s a private dinner with a local family in Croatia, a hands-on cooking class with regional chefs, or a guided stroll through ancient ruins, these experiences go beyond the typical tourist trail. Each itinerary is carefully crafted to maximize cultural engagement and genuine exploration.
Casual Elegance and Culinary Excellence
Forget the formality and crowds of traditional cruising. Windstar’s atmosphere is relaxed yet refined-no need for tuxedos or ball gowns, just comfortable elegance.
Dining is a highlight, with flexible seating, no assigned tables, and menus inspired by the regions you visit. Windstar partners with the James Beard Foundation to deliver world-class cuisine, ensuring every meal is a memorable event.
Modern Comforts with Classic Charm
Despite their classic sailing profiles, Windstar’s ships are equipped with modern amenities: dining rooms with a nice touch, seating areas looking out to the sea, fitness centers, and spas.
AND they take care of their crew: Enhancing and upgrading living spaces for the crew is part of an ongoing initiative with all Windstar renovations. The new Star Seeker will include a crew gym, along with the addition of a crew day room.[2]
The Windstar Difference: For Discerning Travelers
Windstar Cruises is for those who value authenticity, intimacy, and adventure. It’s for travelers who want to explore the world’s most enchanting destinations, and who appreciate the romance of sailing, the luxury of personalized service and a nice boutique shop onboard.
Why Cruise with Windstar?
If you’re seeking a cruise experience that’s truly different, where the journey is as memorable as the destinations, Windstar is the clear choice. Step aboard, enjoy watching the hoisting of the sails, and discover the world from a new perspective - one that includes good food and good times!
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