A Review of Windstar Cruises - From a "Non-Cruise-Lover"
*Disclosure: I only recommend products/services that I would use myself & all opinions expressed here are my own. This post may contain affiliate links, meaning that, at no additional cost to you, I may earn a small commission, which in turn helps fund my next adventure! This blog post is in partnership with Windstar Cruises, but I can assure you that all opinions are my own and based on my own experience. Please read the Privacy Policy for more information.
I am not a “cruise-person”. Or so I thought. My first ever cruise was when I was in middle school, and I remember not having much fun on the ship and always counting down the hours until we docked. The second cruise I went on was also with my family, but I was older and had just graduated from college. I thought I would enjoy cruising more, but I again found myself yearning to be on land so I could explore new destinations. Since then, I had sworn off cruising until I saw an ad in Travel + Leisure for a more intimate sailing experience with Windstar Cruises. Fast forward to 2025, when I had the opportunity to experience what a Windstar Cruise is really like, and after seven days on board Windstar’s Star Pride ship, my concept of cruising has completely changed.
In all honesty, I realized after just one day on board Star Pride that it wasn’t cruising that I despised; it was the massive ships and the large number of people. You get neither of these things on a Windstar Cruise, and it is pure bliss!
My dad and I met several other people on our ship, and we were surprised by how many people were repeat customers. Almost everyone we spoke to had been on multiple Windstar Cruises; one couple was even on their 25th Windstar Cruise! Can you imagine?! To me, this held a lot of weight. There’s a reason why people keep booking with Windstar and why I will be doing the same.
In front of the Pitons in St. Lucia on the Star Pride
What Makes Windstar Special
Windstar Cruises offers a truly unique and intimate cruising experience that sets it apart from larger, more traditional cruise lines. With a fleet of small, yacht-like ships carrying fewer than 350 guests, Windstar provides a level of personalized service and access to off-the-beaten-path destinations that is simply unmatched. Their tagline is “180 degrees from ordinary”, and they do everything possible to ensure that it’s true.
One of the key differentiators of Windstar is the size of their ships. Unlike the massive floating cities operated by other cruise lines, Windstar's vessels feel more like a private yacht, allowing them to navigate into smaller, more secluded ports and harbors that larger ships cannot reach. This means you'll have the opportunity to explore hidden gems and experience authentic local cultures in a way that simply isn't possible on a larger cruise.
In addition to their unique itineraries, Windstar prides itself on delivering a highly personalized and attentive level of service. With a nearly 1:1 crew-to-guest ratio, you'll feel like part of a pampered family, with staff members quickly learning your preferences and catering to your every need. From the moment you step aboard, you'll feel the warm, welcoming atmosphere that seems more like a boutique hotel than a cruise ship. Throughout your sailing, you’ll make friends with other guests and members of the crew, including the captain!
Another hallmark of the Windstar experience is the emphasis on authentic, immersive experiences, which is something I really appreciate and loved experiencing on my cruise. Rather than being herded from one tourist trap to another in large groups, you'll have the opportunity to truly engage with the local culture, whether it's through shore excursions led by knowledgeable guides, cooking demonstrations with local chefs, or simply wandering the charming streets and markets of each port of call.
Overall, Windstar Cruises offers a refreshingly different take on cruising, one that prioritizes intimacy, personalized service, and authentic cultural experiences over the mass-market approach of larger lines.
Everything You Need to Know About the Ship
Windstar Cruises operates a fleet of seven boutique ships that offer an intimate and luxurious cruising experience. The fleet consists of three sailing yachts and four all-suite ships (with a fifth debuting in December 2026), each with a capacity ranging from 148 to 342 guests. The sailing yachts, Wind Surf, Wind Star, and Wind Spirit, combine the romance of sailing with modern amenities, providing a unique and memorable experience on the open waters.
The all-suite ships, Star Breeze, Star Legend, Star Pride, and Star Legend offer a more contemporary and sophisticated ambiance, with spacious suites, elegant decor, and top-notch amenities. Star Pride is the ship I was on, and although I loved it, I want to experience one of their sailing yachts on my next cruise.
Room & Amenities
The Star Pride is one of Windstar's intimate, yacht-like ships that can carry up to 312 guests. It is absolutely gorgeous on both the inside and outside, and I was shocked by how spacious my room was!
The all-suite accommodations range from 277 sq. ft. rooms to the luxurious 820 sq. ft. Grand Suite. Yes, you read that right. Every guest room is a suite!
Each stateroom features ocean views, whether that be a porthole, window, or balcony. Amenities include flat-screen TVs, a walk-in closet, and marble bathrooms with luxurious toiletries from L'Occitane and a spacious shower. There’s also a well-stocked mini bar, a fresh fruit basket that is refilled daily, and reusable water bottles that you are encouraged to take with you on your excursions.
One thing that I loved in the room was the ample living space, which includes a plush seating area perfect for unwinding after a day of exploration. The beds are heavenly, with high-quality linens and plush mattresses that promise a restful night's sleep.
The Crew
The crew aboard the Star Pride truly made the Windstar Cruise experience exceptional. From the moment we stepped on board, we were greeted with warm smiles and a genuine eagerness to ensure our voyage was nothing short of remarkable. The attentiveness and personalized service from every staff member, whether it was our stateroom attendant, the dining staff, or the activities coordinators, left a lasting impression.
My dad and I went on this cruise together as a father-daughter trip, and it happened to be his birthday halfway through the cruise. He doesn’t like a lot of attention, but I wanted to do something special for his birthday, so I went to chat to the woman at the reception desk, and to my surprise, they already knew of his birthday and had little surprises in the works! Our stateroom attendant, Alisa, decorated our room while we were listening to the Port Talk and left a sweet handwritten note for him. It was all very sweet, and he really appreciated it.
Overall, the crew aboard the Star Pride was truly the heart and soul of our Windstar Cruise experience. Their professionalism, warmth, and unwavering commitment to excellence left us feeling not just like valued guests but like part of an extended family. They even participate in a Staff Talent Show during the cruise, and it was one of the best nights!
Dining Onboard
Based on my previous cruise experiences with other cruise lines, my expectations around food were pretty low, but again, Windstar Cruises knocked it out of the park, and I was pleasantly surprised by the offerings. Windstar is the only cruise line that partners with the James Beard Foundation and selects nominees and award-winning chefs to create dishes offered on the ship across all restaurants on board.
The main dining room on Star Pride, Amphora, serves up everything from succulent seafood to hearty meat dishes and an impressive selection of vegetarian and vegan options. Unlike larger cruise ships, where you have certain seatings for dinner and most likely end up sharing a table with other guests, again, Windstar does things differently. Guests are welcome to dine in the main dining room at any time they choose, and you are seated at your own private tables, so there’s no need for forced conversations with strangers.
Additionally, there are two other more intimate dining options on board Star Pride, Cuadro 44 and Candles. And on top of that, there’s a more casual option for dinner, Star Grill. Cuadro 44 has a menu filled with Spanish dishes that represent almost every region of Spain. I was a little disappointed that the Basque region wasn’t represented, given that it’s the food mecca in Spain, but overall, the food at Cuadro 44 was very good. Candles is located at the back of the boat, and you have the option to dine inside or out on the deck if the weather permits. Their specialty is steak, which was amazing! Both of these restaurants require reservations, so I recommend making those as soon as you board the ship. Star Grill is open for both lunch and dinner, and there is no special dress code. It’s buffet style, and the menu changes daily. We dined at all four options, and Candles was our favorite!
To make your experience on these luxury small ships even more special, each Windstar cruise has a special night, sometimes two, where all restaurants are shut down and the staff put together something truly spectacular. On our cruise, we had a beach BBQ one day for lunch, and the following night, we had a deck BBQ. Both were over the top and immaculately laid out - everyone enjoyed every minute of it!
Another thing to point out in regards to the food on board is that at every meal, in every restaurant, there were vegetarian and vegan options. They go above and beyond to make sure everyone feels included and has options. And if you have a food allergy or intolerance, fear not! I met a woman who has a gluten allergy, and every night, someone brings her the menus for the next da,y and she selects what she’d like to eat and they make a special batch just for her. If that’s not five-star service, I’m not sure what is, then!
Windstar Routes & Itineraries
Windstar Cruises offers a wide range of itineraries to destinations around the world. From the Caribbean to the ancient wonders of the Mediterranean, the company's routes cover some of the world's most fascinating regions.
In the Caribbean, Windstar Cruises offers several island-hopping itineraries, allowing guests to explore the diverse cultures, vibrant cities, and stunning natural landscapes of destinations like Antigua, St. Barts, St. Lucia, and the British Virgin Islands. The itinerary I did is called Jewels of the Windward Islands, and it departed from Barbados and stopped in St. Lucia, Martinique, Grenada, and St. Vincent and the Grenadines. I especially loved this itinerary because we didn’t have any full days at sea and woke up every morning at a new port, some of which we anchored instead of docking.
The Mediterranean is another popular destination, with itineraries that showcase the rich history, stunning architecture, and culinary delights of countries like Italy, Greece, Spain, and France. Guests can explore iconic cities like Rome, Venice, Barcelona, and Santorini, as well as lesser-known gems.
The most talked-about route is in Tahiti, and guests on board my cruise had nothing but positive things to say about that itinerary. Hopefully, it’s one that I get to experience one day; it sounded magical!
Is a Windstar Cruise Worth It?
After an incredible week aboard the Star Pride sailing through the Caribbean, I can confidently recommend Windstar Cruises for those seeking a luxurious yet laid-back cruising experience. I absolutely loved the small ship size and was impressed with the excursions available at each port of call.
For a luxury cruise line, I was happy to see how welcoming the staff were and how the overall vibe was relaxed and friendly. I was expecting other guests to be dressed to the nines or be judgmental, but none were. Yes, the clientele is a little on the older side, but there were also families with children ranging from 9 to well into their 30s. It’s perfect for couples of any age, and multigenerational family vacations - there were even a few solo travelers on my ship!
The only potential downside is the premium pricing, which reflects Windstar's boutique cruising approach. However, for travelers willing to splurge, a Windstar cruise delivers an unparalleled and memorable luxury experience at an exceptional value compared to similar upscale cruise options.
So, would I go on another Windstar cruise? Yes! Hands down.
Happy travels!
-Tess
Tess Arnold
Hi! I’m Tess, founder of TravelingTessie.com, and not only do I love to travel, but I love immersing myself in new places and finding off the beaten path experiences wherever I go! I’ve lived in 4 different states & traveled to 13 countries and counting. I believe that tourism is meant to benefit both visitors and locals alike—and I want to bring that idea back into the travel industry by highlighting companies run by locals such as tours, hotels, restaurants, and more. On Traveling Tessie you can find hidden gems in top destinations around the world, travel tips, detailed city guides, and tons of inspiration for your next trip! If you love travel as much as I do, then please join me on this journey! I hope you enjoy my content as much as I enjoy providing it for you!
