PENINSULA Boothbay

riving feels effortless with 360 degrees of classic scenery. We turn off Route 27 toward Boothbay Harbor, passing Wildcat Creek, patches of woods, and the Boothbay Playhouse, keeping an eye out for glints of water. It’s a busier stretch than anything we’ve seen so far, but a fun contrast. Our room at the Spruce Point Inn overlooks Boothbay’s bluerthan-blue harbor—and it’s Windjammer Days, a full-on celebration of wind, sails, and water, in a town that needs no excuse to celebrate any of the above.

The inn’s motorboat, helmed by Captain Richard Baines, runs guests into Boothbay Harbor from 10:00 to 6:00. As we skim the water, he points out Ram Island Light, a bald eagle on Mouse Island, and Cuckold’s Lighthouse, a B&B. Among his recommendations? Lobster Dock for lobster rolls, Down East Ice Cream Factory for the cold stuff, and Blue Moon Café for breakfast. It’s morning, so we saunter into Blue Moon. Smells like fresh blueberry muffins. “Fred just made ’em,” the woman behind the counter tells us. She points to a photo on the wall from SKI magazine that reads Fred Munro . “And now you know everything I do,” she adds.

Well, the man of mystery makes a mean breakfast. “This is the best French toast I’ve ever had in my life!” exclaims a customer, polishing off his “Texas Toast,” a delirious mash-up of pecan crisp and French toast. Peoplewatching is in a dead heat with Fred’s food: The café’s deck overlooks Pier 8, hub central for Balmy Days Cruises, Burnt Island Lighthouse Tours, whale watches, and puffin cruises.

You can cross the harbor via the longest wooden footbridge in the U.S. A charming, wood-shingled house dangles off the bridge, perched on pillars: the 1902 Bridgehouse. A sign on the door says it’s for sale. At that moment, a man sets up a precarious ladder and begins touching up the red window trim. We shout hello, and in short order we’re inside Allan Miller’s shipshape shack, admiring the gleaming wood interior and the Adirondack chairs on the back deck, facing a long view out across the boat-strewn harbor. There’s no quirkier or more inviting waterfront property.

But when we learn that Allan also owns Pepe’s Café, the “oldest eating house” in Key West, it clicks. All the best coastal vacation towns feel like a cross between Provincetown and Key West—a mix of liveliness and looks— and Boothbay Harbor fits the bill. With no shortage of cafés, restaurants, and shops, there’s also enough beauty to stop you cold.