Windstar occupies a sweet spot between the barefoot adventure of Star Clippers and the formality of a Silversea. The sailing yachts are stunningly beautiful under canvas, and the all-suite motor vessels punch well above their size in dining and service. The 180 Under the Stars deck barbecue is one of cruising's great evenings. I recommend the Wind Surf for the most space and the best watersports platform, though clients should know she's getting a cabin refresh in 2026 and the new Star Seeker will debut later that year.
Windstar Cruises operates a fleet of seven boutique vessels — three sailing yachts and four all-suite motor ships — carrying between 148 and 342 guests each. The sailing yachts are the emotional heart of the brand: Wind Surf, at 613 feet, is billed as the world’s largest motor sailing yacht, with five towering masts and computerised sails that reach 221 feet above the waterline. Her sisters Wind Star and Wind Spirit are smaller and more intimate still. The four Star-class all-suite motor vessels complement the fleet with more conventional accommodation and a wider range of itineraries spanning the Mediterranean, Caribbean, Alaska and French Polynesia.
The sailing experience is genuinely romantic. Standing on deck as the sails unfurl against a Caribbean sunset or a Mediterranean dawn is one of cruising’s iconic moments, and Windstar’s shallow draft allows the ships to slip into harbours, bays and anchorages that no mega-ship could ever approach. The signature 180 Degrees Under the Stars barbecue — a white-tablecloth dinner served on the open aft deck under a canopy of stars — is an evening that guests talk about for years. A fold-down watersports marina provides complimentary kayaking, paddleboarding, waterskiing and snorkelling directly from the ship.
Service is Windstar’s other great strength. A nearly one-to-one crew-to-guest ratio ensures the kind of personalised attention that larger ships cannot replicate, and veteran crew members often recognise returning guests by name. The dress code is resort casual throughout — no formal nights, no tuxedos, no pretension. Dining in the main AmphorA restaurant and the specialty Cuadro 44 by Anthony Sasso draws on regional ingredients and changes nightly, with all meals and 24-hour room service included in the fare.
The fleet is not without its imperfections. Wind Surf launched in 1989 and, despite ongoing refurbishment, shows her age in places — a comprehensive cabin refresh is scheduled for 2026, and the brand-new Star Seeker will join the fleet later that year. For travellers who want the intimacy and romance of a private yacht with the professional crew, culinary ambition and global itineraries of a proper cruise line, Windstar remains one of the most appealing options afloat.
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