1966 Columbia 31

What stands out on this Columbia 31 is how honest and straightforward she is as a sailor’s boat. The long fin keel and skeg-hung rudder give a predictable, seakindly motion that makes longer weekends aboard much less tiring. Side decks are wide enough to move forward securely, and the low coachroof keeps windage down while still giving decent headroom below. The cockpit is deep and protected, with coamings that actually keep you in place when she’s heeling. Underway, these boats track beautifully, so you spend more time trimming and less time fighting the helm. For a classic glass boat, access to systems is unusually generous, making upgrades and routine maintenance far less of a contortion act.

The Columbia 31 shines in this region’s mix of light-air afternoons and surprise squalls. Her moderate displacement and generous sail plan help her ghost along when the breeze goes soft, yet she has the ballast and hull form to stay composed when the wind pipes up. The draft is well suited to exploring shallower anchorages without sacrificing upwind ability, and the roomy cockpit is ideal for days spent daysailing with friends or evenings at anchor. With her robust fiberglass layup and forgiving manners, she’s a reassuring platform for extending your cruising grounds, whether you’re hopping between nearby harbors or stretching into longer summer cruises.