1999 Bayliner 2355 Ciera Sunbridge

Step aboard and you’ll notice how much freeboard and beam you get in a 23-footer, giving a secure, dry ride when the chop kicks up. The helm layout is classic late-90s Bayliner: big, clear gauges and a comfortable captain’s chair with good sightlines whether you’re on plane or easing into a slip. The cockpit seating wraps around for easy conversation, and the transom walkthrough makes it simple to move from swim platform to cabin without climbing over cushions. Down below, the mid-cabin berth tucks neatly under the cockpit sole, creating a surprisingly private sleeping nook for overnight guests or kids. Plenty of opening ports and hatches keep the cabin airy on warm evenings.

This size and style shines on sheltered bays, rivers, and intracoastal stretches where you might mix longer runs with quiet anchorages. The 2355’s moderate draft lets you nose into shallower coves and explore smaller tributaries without anxiety, while still feeling solid when boat traffic kicks up a wake. The integrated swim platform is ideal for sandbar rafting, afternoon swims, or loading up from low docks. With a full windshield and canvas options, you can extend your season well beyond peak summer, staying dry in shoulder-season breezes. For a boater who wants easy trailering, comfortable weekending, and the freedom to roam varied local waters, this model fits the bill nicely.