Windstar Wind Surf

Wind Surf (launched 1989 as Club Med 1, sailing for Windstar since 1998) is one of the largest sailing cruise ships afloat: five masts, 342 guests, and computer-controlled sails. Most cabins are ocean-view staterooms rather than balcony suites, so you are paying for the ship and the ports, not the room. A 2024 renovation redesigned many public spaces and suites. She splits her year between Mediterranean sailings from Athens and Caribbean sailings from St. Maarten, and in the fares we track she sits at the cheaper end of Windstar's per-night range.