2019 Monterey 295 Sport YachtSold

Step aboard and the first thing you notice is how much Monterey squeezed into 29 feet without it ever feeling cramped. The aft bench converts quickly from a social lounge to a sunpad, so you can face the conversation or the wake. The walkthrough windshield and molded steps make foredeck access simple and safe, even with a drink in hand. Below, the mid-cabin isn’t an afterthought—it’s a genuinely usable sleeping space with good headroom at the entry and clever storage tucked everywhere. The cockpit wet bar keeps snacks and drinks in easy reach, and the LED lighting throughout sets a relaxed mood for those evenings when you don’t feel like heading back to the dock.

This 29-foot sport yacht is ideal for local waters where conditions can change from calm, narrow creeks to open, choppy stretches in a single outing. The single inboard/outboard package keeps operating costs manageable while still offering the punch to run between harbors or out to a lunch spot quickly. With its compact length and wide beam, docking in tight slips and busy marinas is far less stressful than with a larger cruiser. Overnight capability in a boat this size means you can comfortably stretch weekend cruises without committing to a big-boat footprint, making it a sweet spot for exploring nearby shorelines, anchorages, and waterfront towns.