1999 Four Winns 258 Vista

Step aboard and you’ll notice how Four Winns squeezed big-boat thinking into a trailerable package. The molded swim platform and transom walkthrough make it easy to hop in after a swim or manage lines at the dock. The helm has that classic late‑90s sport-cruiser vibe, with an ergonomic dash and sightlines that make close‑quarters maneuvering less stressful. In the cockpit, the convertible seating lets you shift from cruising to lounging without juggling loose cushions. Below, there’s surprising headroom, warm cabinetry, and enough storage to keep weekend clutter out of sight. It’s the kind of layout that feels intuitive the first time you use it, whether you’re sneaking out for a sunset cruise or stretching the weekend into an overnighter.

A 25‑foot express cruiser like the 258 Vista is tailor‑made for the mix of open water and protected channels you find here. It’s compact enough for easy trailering between ramps and marinas, yet has the freeboard and hull design to handle afternoon chop with confidence. The cabin gives you shelter when weather turns or when you want to extend the day into an impromptu overnight at anchor. With its moderate draft, exploring quieter coves and smaller harbors is straightforward, and docking in tighter slips is far less intimidating than with larger cruisers. It’s a practical, comfortable platform for enjoying local waters all season long.