2009 Grady White Chesapeake 290

Step aboard and you’ll notice how the wide walkaround side decks and high bow rails make it easy and secure to move forward, even when the sea is up. The Chesapeake’s deep, protected cockpit is all business, with insulated fishboxes that double as family coolers and a transom door that makes diving or landing a big fish simple. Inside the hardtop enclosure, visibility is excellent and the helm layout keeps everything within easy reach, with stout rocker switches and clear analog gauges. Below, the mid-berth is surprisingly roomy for a 29-footer, and the galley has the storage and counter space to actually cook, not just reheat. Subtle touches—like quality latches, solid hardware, and smart drainage—reveal why these boats age so gracefully.

In this region, conditions can swing from flat calm to tight, choppy seas in a single afternoon, and the Chesapeake 290’s hull really shines in that mix. The sharp entry and solid weight help her slice through short-period waves instead of pounding over them, while the wide beam adds a reassuring, planted feel at drift or troll. Changing weather is less of a concern thanks to the fully enclosed helm and sturdy hardtop, giving you a dry, protected space when squalls roll through. With efficient twin outboards and a comfortable cabin, it’s easy to stretch your range for offshore runs, then tuck into a quiet anchorage for an overnight without sacrificing comfort.