1995 Boston Whaler 21 Outrage

Step aboard and you’ll notice how the deep, secure cockpit feels bigger than 21 feet, with high gunnels that keep crew confident when the chop kicks up. The classic Whaler hull wears its age well—solid underfoot, no flex, and that reassuring “thud” when you knock the glass. The helm is simple and uncluttered, with good sightlines whether you’re standing or leaning on the bolster. Wide walkaround space makes it easy to work a fish from bow to stern, and the forward seating area doubles as a comfortable spot for cruising or sandbar days. It’s a straightforward, no-nonsense layout that’s easy to clean, easy to service, and built to keep running season after season.

For these waters—where a day can swing from glassy mornings to afternoon wind chop—the 21 Outrage’s classic deep-V entry and unsinkable construction shine. It’s compact enough to trailer easily to different ramps and sandbars, yet heavy and capable enough to cross open bays and nearshore stretches with confidence. The twin 4-strokes offer the redundancy offshore anglers appreciate, while still sipping fuel on long runs to distant flats or reef lines. With its open, self-bailing deck and simple systems, it shrugs off sudden showers, tidal changes, and frequent use in a salt-heavy environment, making it an ideal “use it hard and hose it off” workhorse for local conditions.