Just 10 miles south of Portland (about 15 minutes driving time from downtown), the historic Black Point Inn is a Maine classic. When new ownership took over the property back in 2007, the inn dispensed with one of its pools and all of the cottages, slashing the room count by more than two-thirds and giving the place more of a boutique feel than a resort vibe. The remaining rooms have been updated and upscaled. Situated on 9 acres with views along the coast both north and south, the inn was built as a summer resort in 1873 on the same attractive rocky point memorialized by landscape painter Winslow Homer. What remains is as elegant as ever, perhaps more so, and the expansive porch (with its constant sea breezes) thankfully remains. Dinner at The Point is a stately, white-tablecloth affair, while the pubbier Chart Room offers three squares and a killer outdoor seating area with beach views. Meal plans available.