1999 Grady-White 268 Islander

Slide into the helm of this 268 Islander and you’ll feel right away why these hulls have such a loyal following. The deep, secure cockpit coamings make it easy to brace in when the chop stands up, and there’s plenty of room to work a fish from bow to stern. Grady’s signature wide walkaround keeps the foredeck safely accessible, even with crew up front handling lines. Down below, the cabin has more headroom and storage than most 26-footers, with smart cubbies for tackle, spare gear, and overnight bags. The heavy hardware, solid latches, and beefy rails all speak to the kind of build that still feels tight and quiet decades on.

This 268 Islander shines in waters where conditions can shift from glassy to snotty in a single tide change. The deep-V hull and substantial weight help it shoulder through wind chop and boat wakes on longer runs to offshore structure or distant sandbars. It’s compact enough to slip into tighter slips and crowded marinas, yet offers a cockpit that feels like something from a larger platform when you’re trolling, bottom fishing, or setting up for drift fishing. The enclosed helm and cabin give welcome shelter during shoulder seasons, while the open cockpit and swim access make it equally at home on hot, calm days spent swimming and cruising with family.