Boutique Cruise Spotlight: Discovering The Windstar Difference In Small Ship Luxury Cruising
- Cyndi
- 2 days ago
- 9 min read
Small Ships, Big Soul: Why Windstar Cruise is the antidote for the big ship blues.
When it comes to small ship cruising, few experiences rival the intimate yet causal elegance of Windstar Cruises. These are not your typical ocean voyage (I hear you saying “cruising is not my style”) but rather it's a boutique luxury ocean experience that redefines what it means to explore the world by sea.
Building on our Boutique Ocean Cruise Spotlight, We are diving into Windstar first. With their "180° from Ordinary" philosophy, Windstar doesn't just offer a cruise; they offer a private yacht-style experience that connects you to the world’s most intimate harbors.
While the big ships dominate with their 1000’s of passengers (some up to 5000), Windstar offers a more intimate vacation that feels more like a private yacht than a traditional cruise line. And one of my favorite benefits of boutique cruising is that you only unpack once! I will repeat this one over and over as it’s such a time saver and stress reducer on a long journey. It really does make a difference!
Meet the Small Ship Luxury Cruise "Fleet”:
With a fleet designed for just 148 to 342 guests, Windstar offers a private yacht-style experience that can access hidden harbors and ports that mega ships can only dream of.
Operating six yachts in two different styles:
Star Plus Class: All Suite Luxury
The Star Breeze, Star Legend and Star Pride recently completed a sunning $250 million transformation. These all suite yachts accommodate just 312 guests and feature ocean view suits starting at 277 square feet complete with luxury bath amenities and fully stocked mini bars (its like your own luxury apartment!) Two new dining venues, an infinity pool, a world class spa and redesigned Star Suites with new layouts.
Wind Class: The Romance of Sailing
For those that are drawn to sails, Windstar’s classic Wind Class vessels offer an unforgettable experience combining the romance of traditional sailing with modern yacht amenities. The Wind Surf, the world's largest sailing ship, carries only 342 guests into some of the most interesting ports/destinations.
The fleet’s main point of differentiation is its unparalleled access. Because these yachts carry 148-342 guests, they can slip into tiny ports like Le Lavandu, France or navigate narrow waterways like the Corinth Canal in Greece that larger ships can not make.
Why Choose Windstar
Windstar has partnered with the James Beard Foundation as their official cruise line, bringing celebrated chefs onboard for cooking demonstrations and special dinners. Onboard chefs have the freedom to shop local fish markets at each port, creating nightly menus that showcase authentic regional flavors with fresh, seasonal ingredients.
Dining venues range from the elegant Amphora restaurant to Cuadro 44, a Spanish-inspired venue with an open kitchen serving small plates inspired by a Michelin-starred NYC restaurant. The casual Veranda transforms into a steakhouse by evening, while Star Grill features daily fresh fish, international grilling, and rotisserie specialties.
Other guest favorites:
Open Bridge Policy: Ever wanted to ask the captain questions while watching navigation? On Windstar, the bridge welcomes curious guests.
Watersports Platform: Complimentary access to kayaks, stand-up paddleboards, snorkeling gear, and even floating trampolines—all launching directly from your yacht.
Concierge Collection Excursions: Curated shore experiences that go deeper, from home-hosted lunches to exclusive access to UNESCO World Heritage sites.
World-Class Service: With crew outnumbering guests nearly one-to-one, the "friendliest crew at sea" delivers personalized attention that anticipates your every need.
Personality Type: For the Romantic and/or the Adventurer (or both!)
Who is Windstar for? Let’s dive into why Windstar is a perfect fit for a romantic soul or curious adventurer.
The “Vibe Check”: Windstar’s personality is defined by its “unscripted” and authentic in nature. Imagine a casual-elegant atmosphere where the crew, the ship’s greatest asset, is there to genuinely build relationships with you.
The staff to guest ratio is nearly 1:1 so guest relationships and service is taken seriously.
Whether you are onboard the classic Wind Class (ships with sails) or on the recently transformed Star Plus class, an all suite yacht, the feeling remains the same.
The Romantic: Celebrating Life's Milestones
Whether you're planning a honeymoon, anniversary, or milestone celebration, Windstar Cruises creates the intimate atmosphere romance requires. With just 148 to 342 guests aboard, you'll never feel lost in a crowd. Instead, imagine watching the sun set over Santorini's caldera from your private balcony, or raising a glass of champagne as those magnificent white sailing yachts glide into the harbor at Positano.
Intimate Moments, Elevated
The all suite yachts of the Star Plus Class Star Breeze, Star Legend, and Star Pride all recently underwent a $250 million transformation designed with couples in mind. Every suite offers ocean views and over 277 square feet of romantic retreat, complete with luxurious linens, L'Occitane bath amenities, and those thoughtful touches that matter: fresh fruit, waffle weave robes, and a fully stocked mini bar for private celebrations.
The private yacht-style atmosphere extends throughout the ship. Dine under the stars at an intimate table for two. Relax in the infinity pool as your yacht sails toward the next enchanting port. Book a couples' massage at the spa, where regional treatments like Hawaiian Lomi Lomi create unforgettable shared experiences.
The Adventurer: Active Exploration & Immersive Experiences
For the adventurer at heart, Windstar delivers access that larger vessels simply cannot match. These yachts slip into Mediterranean small ports like Monemvasia and Rovinj, navigate narrow waterways like the Corinth Canal in Greece, and dock in the heart of Old Town Dubrovnik while mega-ships can only pass by in the distance.
Your Personal Adventure Platform
Every Windstar yacht features a complimentary Watersports Platform at the stern which is your launching pad for kayaking, stand-up paddleboarding, snorkeling with personalized gear, and even floating on water trampolines in crystal-clear bays. This isn't just cruising; it's active exploration from a vessel that becomes your adventure basecamp.
The Open Bridge Policy invites curious minds to visit the captain, learn about navigation, and watch as your yacht approaches the next incredible destination. This level of access and engagement transforms passive tourism into active discovery.
Dreamy Destinations
Windstar designs itineraries for travelers who want to experience destinations, not just see them from a distance. From the sun-drenched Mediterranean small ports of Italy and Greece to the secret harbors of the Caribbean that big ships pass by, from the Norwegian fjords to emerging destinations in Australia and New Zealand, Windstar's global reach ensures there's always a perfect voyage for your romantic celebration or next adventure.
Europe Year Round Cruising all year in Europe offers the unique advantage of experiencing diverse cultures and destinations across the different season, each offering something new to see and experience.
Check out this itinerary: James Beard Foundation & Wine Cruise: Classic Italy & Dalmation Coast
Tahiti
With 36 years of experience in French Polynesia, Windstar has built deep relationships with local communities allowing for creating immersive cultural experiences that you wont find on other cruise lines.
What’s Included in your Cruise?
One of the most refreshing aspects of the Windstar experience is their pricing philosophy., which is designed to give you control of your vacation budget. Unlike other lines that force a one size fits all / inclusive rate, Windstar offers a “Pick Your Perk” approach with two ways to book:
The All In Package: For those who want a truly seamless, worry free experience, this option bundles wi fi, unlimited wine, beer and cocktails and all gratuities into one upfront price.
The Cruise only Fare: If you prefer to pay as you go, this “a la carte: option offers a lower base price while still including the core essentials into what makes Windstar special.
What is Always Included?
Regardless of which pricing path you choose, every Windstar guest enjoys a wealth of premium amenities as standard:
Gourmet Dining: All onboard meals in all venues, including 24-hour room service and open seating with no reservation fees.
Beautifully appointed ocean view staterooms and suites
Watersports: Unlimited use of the Watersports Platform, including kayaks, paddleboards, and snorkeling gear.
Beverages: All non-alcoholic drinks, including specialty coffees, teas, and sodas.
24 hour room service
Signature Events: Access to the legendary Signature Onboard Barbecue and local destination performances.
Insider Access: The famous Open Bridge policy, allowing you to visit the officers and learn about navigation.
Small Luxuries: Fresh flowers and fruit in your suite, plush L'Occitane bath amenities, and a champagne welcome reception
By offering this choice, Windstar ensures that whether you are a connoisseur of fine wines or a focused explorer who spends every minute in port, you are paying for the vacation that fits your lifestyle.
So…Is Windstar Your Soulmate?
This is for you if...
You crave intimacy: You prefer a guest list of 148 to 342 people over 5,000. You value being welcomed by name by a crew that remembers you and your preferences
You are a foodie at heart: As the official cruise line of the James Beard Foundation, Windstar features menus crafted by renowned chefs and local ingredients sourced directly from port markets
You love "Secret" places: You want to dock in the heart of Old Town Dubrovnik while the big ships stay out at sea, or tuck into tiny harbors like Monemvasia, Greece, and Road Bay, Anguilla.
You value active discovery: You look forward to using the complimentary Watersports Platform to kayak, paddleboard, or snorkel directly off the back of the yacht
On the other hand, Windstar may not be the right fit if…
You want casinos, Broadway-style theater productions, or kids' clubs.
You prefer a "suit and tie" formal environment (Windstar is strictly Casual Elegant).
You need dozens of different dining venues on a single ship
Booking Strategy: Because these ships are small, popular itineraries like Tahiti or Greek Isles fill up fast. Book early to secure your preferred suite layout, especially the new Star Suites.
Frequently Asked Questions (FAQ)
Is Windstar Cruises all-inclusive? Windstar offers flexibility with both "All-In" and "Cruise Only" fares. Their standard fare always includes non-alcoholic beverages, 24-hour room service, and use of the Watersports Platform.
Why are Windstar Cruises expensive? Windstar Cruises are considered upscale premium cruise line, offering great value for a luxury, small-ship experience, not "cheap" but reasonably priced for what you get, with options to pay a bit more for all-inclusive packages (drinks, Wi-Fi, gratuities) or stay a la carte for lower base fares, saving you money on essentials while still covering meals and water sports. Prices vary by destination, season, and deals, but often fall in the $2,500-$6,000+ range per person for shorter European trips, offering personalized, intimate travel.
Are shore excursions included?
On most Windstar cruises, shore excursions are not included in the base fare and must be purchased separately. Windstar follows a "personalized luxury" model where they offer two primary ways to book your cruise, but neither of which automatically includes shore excursions in the standard price. This allows you to explore independently or book a special excursion as you would like. Explore on your own, or with a guided excursion or relax at the pool on the ship. It's your choice!
What is the dress code on Windstar? The vibe is Casual Elegant. Think sundresses and slacks; there are no "Formal Nights," so you can leave the tuxedos and evening gowns at home.
What are the average ages of the passengers on a Windstar Cruise? The average age is around 50 years old, appealing to a mix of adventurous couples, honeymooners, and seasoned travelers, often ranging for 30-60s.
Are children allowed on Windstar? Yes, but children must be 8 years or older. While Windstar welcomes families, the yachts do not have dedicated kids' clubs or childcare facilities, making them best suited for adults and older children who enjoy destination exploration.
Can I visit the Bridge? Yes! Windstar maintains an Open-Bridge Policy, allowing guests to visit the officers and learn about the yacht's navigation while at sea.
Want More Proof? Check Out Windstar in the News.
Your Next Chapter in Small Ship Sailing Awaits!
Whether you're celebrating love's milestones or answering the call of adventure—or both, Windstar Cruises delivers an experience that matters most to you. This is travel for romantics who seek intimate moments and adventurers who crave authentic connections, all wrapped in the comfort and service that travelers deserve.
Ready to plan your romantic adventure? Contact me to discover which Windstar voyage will become your story—because the best journeys are always 180° From Ordinary!
Meet Your Travel Strategist!
Hi, I'm Cyndi Smith, a passionate traveler, certified Windstar Cruise specialist and owner Tailor Made Travel Studio. I craft tailored travel experiences for busy people who want to travel the world ease and a little bit of luxury!
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