Windstar Cruises: Is Small-Ship Luxury Right for You?

October 04, 2026•3 min read

What if luxury cruising wasn't about having the biggest ship, the most entertainment, or the longest list of onboard amenities? What if it was about smaller ships, unique destinations, personalized service, and a more relaxed atmosphere?

That's where Windstar Cruises stands out. In this recent episode of Luxury Cruising, travel advisor Sydney shared her experience sailing the Windstar Windsurf on a seven-night Italian itinerary, offering an inside look at what makes this small-ship cruise line different.

A Different Kind of Luxury

Windstar occupies an interesting space between premium and luxury cruising. Its ships are significantly smaller than those operated by mainstream cruise lines, allowing guests to visit smaller ports and enjoy a more intimate experience.

The Windsurf carries around 342 guests, creating an atmosphere where the crew can get to know passengers personally. For travelers who prefer relaxed luxury rather than a formal or overly structured experience, this can be a major advantage.

The Windstar Marina Is a Standout Feature

One of the most unique features of the Windsurf is its marina platform, which opens at the back of the ship when local conditions and port authorities allow.

Guests can enjoy activities such as kayaking, swimming, and other water activities directly from the ship. The marina isn't available at every port, but when it is open, it provides an experience that's difficult to replicate on larger cruise ships.

Smaller Ships, More Interesting Ports

One of Windstar's biggest strengths is its ability to reach destinations that aren't accessible to larger ships.

During Sydney's Italian sailing, the itinerary included smaller destinations where guests could stay late into the evening, explore independently, and experience local restaurants and attractions after many other cruise passengers had left.

The small-ship experience also allows for memorable moments such as visiting the bridge and sailing close enough to see Stromboli's volcanic activity.

What About the Cabins and Dining?

The Windsurf is an older ship, although its public areas had recently received a major renovation. The cabins were spacious and offered good storage, but they lacked some modern conveniences, and most rooms did not have private balconies.

Dining, however, was a strong part of the experience. Windstar offers multiple dining venues, including Amphora and Candles, along with a culinary partnership with the James Beard Foundation.

Sydney found the food comparable to other premium cruise lines, although travelers accustomed to ultra-luxury brands such as Regent or Silversea may have different expectations.

Who Should Consider Windstar?

Windstar may be a great fit if you:

Prefer small ships over large resorts at sea
Value destinations and port experiences
Enjoy relaxed, casual luxury
Want personalized service
Like exploring independently
Don't consider a private balcony essential
Prefer intimate entertainment over large productions

It may not be the best choice if you want extensive onboard entertainment, numerous amenities, or the all-inclusive experience associated with some ultra-luxury cruise lines.

The Bottom Line

Windstar demonstrates that luxury doesn't have to mean bigger, newer, or more extravagant. Its appeal lies in intimate ships, unique destinations, personalized service, and relaxed experiences.

As Sydney's experience shows, the best cruise isn't necessarily the one with the most amenities, it's the one that matches the way you want to travel.

There's a cruise for everybody, but not every cruise is for everyone.

Join the Conversation

Have you sailed with Windstar Cruises? What matters most to you when choosing a cruise line: small ships, personalized service, food, destinations, entertainment, or onboard amenities?

Email me at: [email protected]

And if you enjoy deep-dive comparisons and luxury travel insights, don’t forget to subscribe to my YouTube Channel and tap the notification bell so you never miss a new post.

If you're trying to decide which cruise line is the right match for your travel style, Sydney of The Poodle Booked It shares her cruise experiences and travel advice on social media.

You can follow her on Instagram at Travel Advisor Sydney and connect with her at [email protected]. She also hosts the River Cruising Masterclass podcast, where she explores river cruise lines and destinations.

Krystal Sodaitis, MD, MPH

Dr. Krystal Sodaitis board-certified pediatrician, who transitioned from academic medicine to health plan leadership in 2013. Krystal has advanced certifications in physician coaching, leadership coaching, and deep dive coaching. Her coaching practice is focused on physicians who have a developmental diagnosis such as ADHD, Autism or dyslexia. Highly intelligent people are often identified as neurodiverse (formally or through self-discovery/diagnosis) well into adulthood. While the diagnosis may come with some understanding and validation, many still have questions. Unsure where to go with their newfound knowledge that’s where she comes in. Krystal helps neurodiverse docs discover their “what now.” She addresses the guilt, shame, and limiting beliefs that come with a diagnosis of attention deficit hyperactivity disorder, learning disorder, autism spectrum disorder or any other disability. Our brains are amazing and Krystal wants us all to embrace the different yet glorious ways our brains work. She helps people harness their gifts, not squelch them.

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