Windstar's Most Beloved Sailing Yacht Is Completely Unrecognizable After Its 40-Year Makeover

Forty years is a long time to sail. It’s long enough to build a loyal following, develop a distinct identity, and accumulate the kind of wear that even the most carefully maintained ship can’t fully hide. So when Windstar Cruises announced it was putting the Wind Star through a comprehensive two-phase overhaul, the question wasn’t whether the ship needed it — it was whether they could do justice to a vessel that helped pioneer the modern small-ship cruising experience.

As of April 2026, the answer appears to be yes. According to a press release from Windstar Cruises, the Wind Star has become the first vessel in Windstar’s Wind Class fleet to complete both phases of the company’s Setting Sails refurbishment program — and the transformation is significant.

What Is Setting Sails?

Setting Sails is Windstar’s multi-year, fleet-wide initiative to bring its three Wind Class sailing yachts — Wind Star, Wind Surf, and Wind Spirit — into a new era. The program runs in two phases, and the scope goes well beyond a fresh coat of paint.

Phase 1 addressed technology and connectivity: Starlink internet, new TVs with on-demand content, upgraded stateroom technology, and a fully redesigned Owner’s Suite. Phase 2 — the one just completed on Wind Star — tackled the ship’s personality: the spaces where guests actually live, eat, and gather.

What Actually Changed

The most visible changes are in the dining venues. The Amphora restaurant received new flooring, wall finishes, ceiling treatments, custom banquette seating, and updated furnishings throughout. The Veranda — the ship’s casual dining spot — got a refreshed interior and a completely reimagined buffet layout.

Public spaces were equally overhauled. The lobby, Compass Rose Lounge, Yacht Club Café, and pool deck were all renovated. The World Spa by Windstar was refreshed, and the fitness center was upgraded. New teak decking runs throughout the vessel, alongside commissioned artwork created in partnership with Miami-based Fountainhead Art, enhanced lighting, and updated audio systems.

None of these are cosmetic-only fixes. Windstar’s COO Stijn Creupelandt put it plainly: “This transformation honors where we started while sailing confidently into what’s next.”

Why This Matters for Boutique Cruise Travelers

The Wind Star is a 148-guest sailing yacht — a category that exists almost nowhere else in cruising. It’s not a river boat, not a small expedition ship, and not a scaled-down version of a big-ship experience. It’s a genuine sailing yacht, with five masts and 21,000 square feet of sails, that happens to carry guests in a way that feels closer to a private charter than a cruise.

That intimacy has always been the core of the Windstar appeal. But intimacy alone doesn’t compensate for dated staterooms or tired dining rooms. Guests choosing a boutique luxury experience have high expectations for the quality of the spaces around them, and the Setting Sails program is Windstar’s acknowledgment that the hardware needed to match the philosophy.

Completing both phases on a single ship is also a milestone for the program. It gives Windstar — and prospective guests — a finished template to evaluate. The Wind Surf is scheduled to complete its Phase 2 in December 2026, followed by Wind Spirit in March 2027. By early 2027, the entire Wind Class fleet should be sailing in fully refreshed form.

Where the Wind Star Is Sailing Now

The timing works out well for travelers planning ahead. The Wind Star’s first sailing after its refit was a 10-night Lisbon to Barcelona voyage from April 7-17, 2026. From June through October, the ship operates seven-night roundtrip sailings from Athens (Piraeus), exploring the Greek Isles — one of the most popular itineraries in small-ship cruising and a near-perfect fit for a vessel this size.

Looking further out, Wind Star is also expanding into Tahiti with year-round sailings planned for 2027. That’s a meaningful itinerary addition for a sailing yacht — French Polynesia is one of the regions where a smaller, more maneuverable ship can reach anchorages that larger vessels simply cannot.

The Bigger Picture

Windstar occupies a specific and somewhat rare niche. It’s not competing with river cruise lines, and it’s not trying to be Silversea or Regent. It’s building a case for a particular kind of traveler: someone who wants the experience of being on a real sailing ship, in smaller ports, with a guest count that keeps crowding off the table entirely.

The Setting Sails investment — applied now to the Wind Star in full — sends a clear message that Windstar isn’t resting on the nostalgia of a 40-year legacy. The ship that helped define boutique cruising in the 1980s is being repositioned for a new generation of travelers who want that same intimacy, but with the comforts and finishes that modern expectations demand.

If you’ve been curious about small-ship sailing and have been waiting for the right moment to try Windstar, the Wind Star’s post-refit Mediterranean season is about as good a reason as any to stop waiting.

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Source: Windstar Completes Full Transformation of Wind Star, the Yacht That Pioneered Modern Sailing Cruises — Business Wire via Yahoo Finance, April 2026