Windstar Cruises: The Anti-Cruise Cruise Line That Actually Gets It Right

Windstar Cruises took one look at the cruise industry’s obsession with cramming thousands of people onto floating shopping malls and said, “Absolutely not.” Since the mid-1980s, they’ve been sailing with the tagline “180° from Ordinary,” and honestly? It’s not marketing fluff – it’s a manifesto.

This is the cruise line that decided intimate beats massive, sails trump smoke stacks, and knowing your bartender’s name matters more than having seventeen different burger joints onboard. If you’ve ever felt claustrophobic watching 5,000 passengers disembark like a locust swarm onto some poor unsuspecting Caribbean island, Windstar is your antidote.

While other cruise lines chase bigger and brasher, Windstar perfected the art of sophisticated intimacy long before small ship cruising became trendy.

What Makes Windstar Cruises Different

Windstar operates six yachts (soon to be eight) that carry between 148 and 342 passengers – numbers so refreshingly small you’ll actually remember people’s faces by the end of the cruise. Half their fleet consists of genuine sailing ships with computer-controlled masts that unfurl billowing white sails at the touch of a button. It’s pure maritime theater, and it never gets old.

Here’s something that’ll blow your mind: Windstar has an open bridge policy. You can literally walk up to the captain’s bridge, chat with the officers, and watch them navigate these technological marvels. Try pulling that stunt on a mega-ship with 6,000 passengers and see how quickly security escorts you away.

The dining philosophy alone proves they’re playing a different game. Instead of herding masses through buffet lines or forcing assigned dinner times, Windstar offers multiple intimate venues with open seating. You eat when you want, where you want, with cuisine crafted by James Beard Foundation-affiliated chefs. This isn’t cruise food – it’s destination dining that happens to float.

But here’s the real kicker: the crew-to-guest ratio of 1.5 to 1 means your suite steward knows whether you prefer your towels folded or hung, your bartender has your cocktail ready before you order it, and the captain probably knows your name. This level of personalized service died on mainstream cruise lines decades ago.

The Fleet: Small Ships with Big Personalities

Windstar’s current six-ship armada falls into two distinct tribes, with two game-changing additions arriving soon.

Wind Class: The Real Deal Sailing Ships

Wind Star and Wind Spirit These sleek four-masted sailing yachts from the late ’80s carry just 148 passengers each. Don’t expect balconies – these ships predate the industry’s balcony obsession – but you do get the genuine romance of sail-powered travel. The computerized mast system is legitimately impressive; watching those sails deploy while classical music swells is guaranteed goosebumps territory.

Wind Surf
The fleet flagship and officially the world’s largest sailing yacht, Wind Surf accommodates 342 guests across five magnificent masts. Originally built for Club Med and rescued by Windstar in 1998, she underwent a complete transformation that turned her into the most sophisticated vessel in the fleet. The extra size allows for additional dining venues without sacrificing that intimate Windstar magic.

Star Plus Class: All-Suite Sophistication

Star Pride, Star Legend, and Star Breeze This trio of 312-passenger all-suite yachts joined Windstar between 2014 and 2015 after the line acquired them from Seabourn. Windstar invested over $21 million transforming these vessels into floating boutique hotels. Every accommodation is a suite – even the smallest clocks in at 277 square feet with marble bathrooms. It’s the kind of thoughtful luxury that makes you wonder why other cruise lines think coffin-sized interior cabins are acceptable.

The New Arrivals: Star Class Revolution

The fleet expansion that has cruise aficionados buzzing centers on two vessels that will redefine what small-ship luxury looks like.

Star Seeker (December 2025) Windstar’s first-ever newbuild represents everything they’ve learned about intimate cruising distilled into 224-passenger perfection. Currently taking shape at WestSEA Shipyard in Portugal, Star Seeker will feature 112 all-suite accommodations, including two jaw-dropping Owner’s Suites with wrap-around balconies perfect for private sunset cocktails. The enhanced watersports platform gets new staircase access, and there’s a two-story spa that’ll make you forget you’re at sea.

Star Explorer (December 2026) Technically an existing ship currently operating for Quark Expeditions, Star Explorer will undergo a complete Windstar makeover before joining the fleet. The refurbishment will make her virtually identical to Star Seeker, ensuring the new Star Class maintains consistency across both vessels.

After sailing on dozens of ships with every type of luggage imaginable, the only cases I pack anymore are from Level8 – they’re built to handle everything from formal nights to beach adventures, and they look sophisticated enough for Windstar’s elegant atmosphere.

Dining: Where James Beard Meets the High Seas

As the official cruise line of the James Beard Foundation, Windstar doesn’t mess around with their culinary credentials. The main dining room, AmphorA, serves menus developed by James Beard-affiliated chefs using ingredients sourced from each port. This isn’t cruise food masquerading as fine dining – it’s actual fine dining that happens to be served at sea.

The genius lies in the variety without overwhelming choice. Veranda serves as the casual daytime venue, then transforms into the romantic Candles restaurant each evening for alfresco dining under the stars. On the Star Plus ships, Cuadro 44 by Anthony Sasso delivers Spanish-inspired tapas that rival anything you’ll find in Barcelona, while Star Grill by Steven Raichlen satisfies barbecue cravings with proper technique and premium ingredients.

The crown jewel experience? Windstar’s legendary deck barbecues – outdoor feasts featuring grilled specialties, live music, and spontaneous dancing under the stars. These aren’t your typical cruise buffets; they’re actual celebrations that capture the joy of being at sea with sophisticated people who know how to have fun.

For travelers seeking culinary cruises that transcend the ordinary, Windstar’s James Beard partnership ensures every meal feels like a destination in itself.

Entertainment: Sophistication Over Spectacle

Forget Vegas-style production shows and casinos the size of aircraft hangars. Windstar’s entertainment philosophy centers on quality experiences that complement rather than compete with the destinations. You’ll find intimate piano bars where conversations flow as smoothly as the cocktails, local performers showcasing authentic regional culture, and enrichment programs featuring genuinely interesting experts.

The real magic happens during sail-away celebrations when the ships unfurl their magnificent canvas, accompanied by classical music and champagne toasts. Or during those spontaneous deck gatherings where passengers and crew create their own entertainment. It’s the kind of authentic social experience that disappeared from larger ships when they became floating theme parks.

The Windstar Passenger: Sophisticated Adventurers

The typical Windstar guest averages around 55, skews affluent, and values experiences over amenities. These are travelers who’d rather sip wine in a hidden Italian port than stand in line for a waterslide. You’ll encounter couples celebrating milestone anniversaries, groups of friends seeking sophisticated adventure, and savvy singles cruise enthusiasts who appreciate the welcoming social atmosphere.

The dress code reflects this sophisticated casualness – think elegant resort wear rather than formal nights. Your designer jeans and stylish tops work perfectly; save the tuxedos for ships that still believe formality equals elegance. Unlike traditional cruise formal night outfits, Windstar embraces refined relaxation.

Serious Diving Operations (Just Not Onboard)

Don’t let Windstar’s focus on water sports fool you – their diving program is surprisingly sophisticated. They’ve cracked the code on coordinating with French Polynesia’s professional dive operators to create seamless underwater experiences that rival purpose-built dive operations.

How Windstar’s Diving Actually Works: The genius lies in the variety of approaches. In Moorea, you’ll tender ashore and transfer to established dive shops – traditional but effective. In Bora Bora, dive boats come directly to the ship to collect you, eliminating coordination headaches while delivering guaranteed giant ray encounters.

Each island offers a completely different diving experience, from Raiatea’s excellent reefs teeming with fish and sharks to Moorea’s protected lagoon sites.

The French Diving Advantage: Here’s something most people don’t realize – French Polynesia follows French diving regulations, which are notably more rigorous than many international standards. All dive guides are French-trained professionals who run tight, safety-focused operations both in and out of the water. If you’re used to variable standards elsewhere, the consistency here will impress you.

The Windstar Water Sports Advantage:

• Direct ocean access when anchored – literally swim off the back of the ship
• Professional-grade snorkeling gear included (no rental fees or questionable equipment)
• Complimentary kayaking and paddleboarding whenever conditions allow
• Perfect for testing the waters before committing to serious diving

What to Expect Diving-Wise:

• Moorea: Traditional shore-based operations with excellent lagoon diving
• Bora Bora: Dive boats pick up directly from the ship, featuring giant manta ray encounters
• Raiatea: Diverse reef systems with abundant fish life and shark encounters
• All sites suitable for Open Water certification – no Advanced cert required

Costs: Diving costs more than US rates but isn’t outrageous, especially compared to places like the Maldives where boat dives can hit $500 per person. The French operational standards and pristine locations justify the premium pricing.

The Reality Check: What Windstar Isn’t

Transparency matters, so let’s address the elephants in the stateroom. Windstar’s smaller vessels mean limited medical facilities compared to floating hospitals disguised as cruise ships. Weather affects these ships more dramatically than their massive cousins – if you’re prone to seasickness, consider the motor yachts over the sailing ships.

The intimate size also means fewer onboard distractions, which might disappoint travelers who need constant stimulation. WiFi exists but performs like it’s still apologizing for interrupting your digital detox. Many passengers consider this a feature rather than a flaw.

The adult-focused atmosphere makes this inappropriate for families with children. It’s not that kids aren’t welcome – it’s that nothing onboard caters to anyone under 18, and frankly, that’s exactly the point. Families seeking kid-friendly options should explore our guides to family cruises and large family cruises instead.

Windstar vs. The Competition

When comparing Windstar to other options, consider what you’re actually seeking. If you want cruise ships with water slides and round-the-clock entertainment, look elsewhere. But if you’re drawn to sophisticated exploration without the crowds, Windstar delivers experiences that larger ships simply cannot match.

Windstar’s smaller ships unlock destinations that exist only in travel fantasies for mega-ship passengers. They regularly slip into ports like Portofino, Italy, where larger vessels can only dream of docking. In the Caribbean, they access intimate harbors throughout the British Virgin Islands where you might be the only ship in sight.

Their Mediterranean cruises emphasize hidden gems over tourist-trampled ports, while their Caribbean cruise port selections focus on authentic experiences rather than shopping mall masquerading as culture.

The Watersports Platform: Your Floating Beach Club

Most Windstar ships feature retractable watersports platforms that transform the stern into your personal marina. When anchored in suitable locations, this isn’t just a convenience – it’s a game-changer. Complimentary kayaks, paddleboards, snorkel gear, and water toys turn every anchorage into an adventure opportunity.

This isn’t marketing fluff. After exploring a port, returning for an afternoon swim directly from the ship, using it as your private base camp, fundamentally changes how you experience each destination.

Planning Your Windstar Adventure

For cruise newcomers, our new to cruising guide provides essential background, though remember that Windstar operates by completely different rules than mainstream lines. Traditional cruise ship tips and tricks often don’t apply here.

Value-conscious travelers should check our how to save money on your cruise guide, though with Windstar, the focus shifts from finding bargains to ensuring you’re booking the right ship for your dream destinations. Understanding cruise cabins becomes crucial since Windstar’s accommodations differ significantly from mainstream options.

UK travelers occasionally find no fly cruises and cruises from Southampton options, though most Windstar itineraries require international flights to reach embarkation ports – a small price for access to extraordinary destinations. Those exploring cruises from UK ports should check seasonal availability.

The Fine Print

Windstar automatically adds $13.50 per person per day for gratuities, covering all service staff. Unlike the envelope-stuffing rituals on other lines, this streamlined approach reflects the more personal crew relationships you’ll develop.

Understanding tipping on your cruise holiday becomes more nuanced here – the intimate atmosphere often leads to more personal recognition of exceptional service beyond standard gratuities.

Common Questions

Can I actually visit the bridge whenever I want? Absolutely, and it’s not a gimmick. Windstar’s open bridge policy welcomes passengers during most operational hours – just not when entering or leaving port. The officers genuinely enjoy sharing their expertise and demonstrating the ship’s technology. It’s one of the last authentically nautical experiences in cruising.

How do sailing ships handle rough weather without traditional stabilizers? The sailing ships use active fin stabilizers plus their deep keels for stability, but they definitely move more than mega-ships in rough seas. The computer-controlled sails can actually help stabilize the vessel in certain conditions. Motion-sensitive passengers should seriously consider the Star Plus motor yachts instead.

What’s actually included beyond the cruise fare? All dining venues, basic beverages during meals, water sports equipment, and that legendary personalized service. However, alcoholic beverages outside meals, spa treatments, shore excursions, and WiFi packages cost extra. It’s transparent pricing without the nickel-and-diming disguised as “value.”

What if I need serious medical attention in remote locations? Each ship carries qualified medical professionals and equipment for routine issues, but serious emergencies may require evacuation to shore facilities. Windstar maintains relationships with medical assistance companies, though comprehensive travel insurance is essential for remote itineraries.

How quickly do specialty restaurants fill up? Unlike mega-ships where dining reservations become competitive sports, Windstar’s intimate venues rarely require advance booking beyond the first few days. The smaller passenger count means most restaurants accommodate walk-ins, though sunset dinners at Candles disappear quickly.

Do the sailing ships actually use wind power, or is it just for show? They absolutely sail! Captains deploy sails whenever conditions permit, which happens on most cruises. The computer-controlled system makes wind-powered cruising both safe and efficient. Many passengers report that sail-powered segments become the highlight of their entire cruise experience.

Windstar Cruises represents everything the cruise industry abandoned in its race toward bigger, flashier, more crowded experiences. These aren’t ships trying to be floating resorts – they’re sophisticated vessels designed for travelers who understand that the best journeys happen when you can actually escape the crowds rather than join them.

In an industry obsessed with scale and spectacle, Windstar proves that sometimes the most extraordinary experiences come in the smallest packages. You won’t find rock-climbing walls or go-kart tracks, but you will discover something far more valuable: the simple pleasure of sailing into harbors that exist in travel dreams rather than tourist brochures.