Windstar Cruises Review: What Sailing Yacht Cruising Actually Feels Like

What Windstar Is

Windstar Cruises is a small-ship cruise line founded in 1984 that operates seven yachts carrying 148 to 342 guests: three motor-sail yachts with computer-controlled sails and four all-suite motor yachts. It sits in the premium band below ultra-luxury lines like Seabourn and Silversea, with drinks, gratuities, and Wi-Fi available as an all-inclusive upgrade rather than bundled into every fare.

Windstar fits neither the expedition mold nor the conventional luxury mold. Its fleet of sailing yachts and near-luxury motor yachts combines the physical romance of sail-powered travel with the port-selection advantage of small ship scale and the comfort standard of a premium, though not ultra-luxury, cruise product.

Founded in 1984 around sail-powered cruising in the Mediterranean and Caribbean, Windstar has expanded and evolved while keeping the sailing identity that sets it apart. No other cruise operator deploys computer-controlled sail systems on vessels carrying paying passengers at this scale. Whether that experience is the right one for a specific traveler is the question this review is designed to answer.

SST Perspective: We have worked with Windstar Cruises for many years and have sent hundreds of clients on sailings across the sailing yacht and motor yacht fleets. First-time guests are most often surprised by the intimacy, by how quickly the 148-guest Wind Star starts to feel like a private sailing club rather than a cruise ship. Returning guests tend to tell us they planned to try something different next time and booked Windstar again.

The Windstar Fleet: Sails and Motors

Windstar's fleet numbers seven ships in 2026: sailing yachts Wind Star and Wind Spirit (148 guests each) and Wind Surf (342 guests), plus motor yachts Star Pride, Star Breeze, and Star Legend (312 guests each) and the new-build Star Seeker (224 guests). An eighth, Star Explorer, joins in December 2026.

The Sailing Yachts: Wind Star, Wind Spirit, Wind Surf

Windstar's three sailing yachts are Wind Star and Wind Spirit, four-masted staysail schooners carrying 148 guests each, and the five-masted flagship Wind Surf, carrying 342 guests, the largest in the fleet.

The sailing yachts are the heart of the Windstar product and the reason the brand exists. Wind Star and Wind Spirit, each carrying 148 guests, are four-masted staysail schooners with computer-controlled sail systems that deploy or retract their full canvas at the touch of a button on the bridge. The sail system is fully operational. The ships sail when wind conditions are favorable, typically achieving 6 to 8 knots under canvas when the Aegean or Caribbean delivers the steady winds that the sail configuration requires.

Wind Surf, at 342 guests and five masts, is among the largest sailing-rigged passenger vessels in the world. The additional size supports more amenity space, with a second dining venue, a larger spa, and a small casino, while maintaining the sailing character that makes Windstar distinctive. Wind Surf is Windstar at its most resort-like without surrendering the sailing identity, and it attracts guests who want both the sailing experience and a slightly fuller amenity base than Wind Star and Wind Spirit provide.

The Motor Yachts: Star Seeker, Star Breeze, Star Legend, Star Pride

The motor yachts do not sail, and the distinction matters for travelers whose primary interest in Windstar is the sailing experience. Star Pride, Star Breeze, and Star Legend, originally Seabourn vessels acquired in 2013–2015, have carried 312 guests each since their 2020–2021 lengthenings. The new-build Star Seeker (224 guests) made its maiden voyage on December 28, 2025. All four share the Windstar port-selection philosophy and the same intimate scale, delivered through engine power rather than wind.

Star Seeker, Windstar's first new-build vessel in more than three decades, is a meaningful step up for the motor yacht side of the fleet. The 224-guest ship is all-suite, with 112 suites, most offering private verandas or floor-to-ceiling infinity windows, and its Alaska inaugural season in summer 2026 makes it a compelling option for travelers who want Windstar's port selection advantage in a near-luxury motor vessel. A sister ship, Star Explorer, is scheduled to join the fleet in late 2026 after a similar conversion.

The Sailing Experience: How Much Is Under Sail?

It varies. The itinerary, the season, and the weather during each individual departure determine how many hours the ships actually spend under canvas.

In the Greek Islands between May and October, the Etesian winds (locally known as the Meltemi) blow reliably from the north and northeast throughout the summer sailing season, and Wind Star and Wind Spirit typically sail under canvas for a meaningful portion of the passage hours in the Aegean. A 7-night Greek Islands itinerary with seven overnight or long-passage legs can deliver several hours of genuine sailing per leg in favorable conditions, which adds up to a substantial fraction of the at-sea hours over the week.

In the Caribbean, the Trade Winds are consistent enough in the winter season that sailing hours are comparable to the Greek Islands, though the typical Caribbean itinerary involves shorter passages between islands, reducing the total sailing time per leg. In Alaska, where Star Seeker operates under engine power, the sailing element is absent entirely. Guests choose Windstar Alaska for the port selection and the scale, not for the canvas.

The moments when the sails are deployed and the engines quiet are, by consistent report from clients we have sent on Windstar sailings, among the most memorable of any cruise voyage. The physical sensation of a ship moving by wind power, with its different motion, different sound environment, and different quality of air on the deck, is unlike anything a motor vessel delivers.

Port Selection: The Other Windstar Advantage

Windstar's port selection philosophy emphasizes smaller harbors, less-visited destinations, and the access that small ship scale enables. It is the brand's second major differentiator after the sailing experience, and for some travelers the primary reason to choose Windstar over alternatives.

In the Greek Islands, where the mainstream cruise port circuit visits Santorini, Mykonos, and Rhodes in a predictable rotation, Windstar regularly calls at Patmos (the island of the Apocalypse, whose medieval Chora preserves a quality of Byzantine religious architecture available nowhere else in the Aegean), Symi (a harbor town of 19th-century neoclassical mansions arranged in a natural amphitheater above the sea), and Folegandros (a small western Cyclades island that receives no large cruise traffic and whose village has changed little in a century). These ports are accessible because Windstar's ships can anchor in harbors too small for any ship carrying more than 400 guests, and together they produce a very different Greek island experience from the standard circuit.

Windstar returned to Alaska in summer 2026 with the 224-guest Star Seeker, sailing 7- to 12-day Inside Passage itineraries built around small harbors most large ships skip: Wrangell (a gold-rush-era town that receives a fraction of Juneau's tourist traffic), Petersburg (the "Little Norway" of Southeast Alaska, where Norwegian fishing heritage is maintained in both community culture and architecture), and the Misty Fjords (a wilderness monument of glacially carved granite accessible only to vessels small enough to navigate its narrow channels).

Dining: Candles, Amphora, and the James Beard Partnership

Candles Dining: The Signature Experience

Candles is dinner on the open deck of Wind Star or Wind Spirit, served under the stars with candles on every table and the ship's rigging forming the architecture above. It is one of the most consistently cited reasons Windstar guests return. The menu is not the most sophisticated in the small ship luxury market, but the setting makes any meal more memorable than the food alone would be. A grilled local fish eaten at anchor in a Cyclades harbor, on a deck lit by candles with no visible land between the table and the horizon, is an experience with no indoor equivalent.

Day-to-Day Dining and the James Beard Foundation

Windstar's day-to-day dining runs above the standard of most similarly priced cruise lines, a culinary investment the brand has maintained through its various ownership changes and through its ongoing partnership with the James Beard Foundation, the American culinary nonprofit whose recipes and guest-chef collaborations shape Windstar's menus across the fleet. The menus rotate daily and incorporate local ingredients from port-market visits when possible. The standard is premium rather than ultra-luxury: excellent ingredients, solid technique, and real variety without the tasting-menu ambition of the ultra-luxury ocean lines.

Onboard Atmosphere and Social Life

The social atmosphere aboard a Windstar sailing yacht is, in our experience and in our clients' reporting, among the most enjoyable of any small ship product. The absence of formal dress codes, fixed dining schedules, and structured entertainment programming means the social life of a Wind Star sailing is organic. It emerges from shared experience: watching the Santorini caldera at sunset from the bow, gathering at the open bar on the stern deck as the sails catch the Meltemi, and comparing notes over dinner about the morning's port with fellow guests who were equally surprised by the harbor's beauty.

At 148 guests, the social community forms quickly and completely. Most guests know most other guests by name by the end of the second day. When guests describe the voyage afterward, the people and the connections come up more often than the ports or the sailing, though both get their share of praise.

Windstar's Scorecard

Sailing experience: Unique in the cruise market. The hours under canvas are the ones guests remember.

Port selection: A consistent emphasis on lesser-visited harbors that larger ships cannot enter.

Dining quality: Excellent for the price point. The James Beard partnership and the Candles experience are signature strengths.

Accommodation quality: Comfortable and well-designed rather than ultra-luxury. Star Seeker is a meaningful step up.

Service culture: Warm and attentive. Less systematized than Seabourn, more relaxed and personable.

Value for money: Strong in its price tier, below the ultra-luxury pricing of Seabourn and Silversea.

First-timer appeal: An excellent introduction to small ship sailing cruising.

Star Seeker (new): The strongest motor yacht in the fleet. The Alaska inaugural season is outstanding.

Who Windstar Is Right For

Windstar is the right choice for travelers who want the sailing experience as a physical and sensory reality rather than as marketing language, and who understand that the experience varies with conditions rather than operating to a fixed schedule. It also suits the Mediterranean and Caribbean traveler who wants hidden harbors over famous ports, and the Alaska traveler aboard Star Seeker who wants the Inside Passage's small-harbor destinations rather than the standard large-ship circuit.

Windstar is also excellent value relative to the ultra-luxury lines (Seabourn, Silversea) for travelers who want the intimacy and port selection of small ship cruising without the ultra-luxury price point. A Wind Star Greek Islands sailing delivers two things the substantially more expensive ultra-luxury sailings cannot: the time under sail and the port access that Windstar's scale allows.

Our Overall Verdict

Windstar is unlike anything else in the small ship market, and for the traveler who responds to it, that counts for a lot. The sailing experience stands alone, the port lists reach harbors most of the industry skips, the value against the ultra-luxury tier is real, and the onboard atmosphere keeps guests rebooking. Book Windstar for the Greek Islands, the Caribbean, the Mediterranean, and, with Star Seeker, for Alaska.

Booking with Small Ship Travel

Small Ship Travel works with Windstar across its sailing yacht and motor yacht fleets. Our team can advise on which ship and which itinerary best fit your priorities, whether the genuine sailing experience aboard Wind Star or Wind Spirit, the resort-scale sailing of Wind Surf, or the new-build Alaska program aboard Star Seeker. Schedule a free consultation or Browse our full inventory of itineraries.

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1. Mediterranean Small Ship Cruises: Hidden Ports the Big Ships Skip
2. Alaska Small Ship Cruises: The Complete Insider Guide
3. The Best Small Ship Cruises for First-Timers: Where to Start Your Journey
4. Best Small Ship Cruises for Wine Lovers