At the height of summer, the body of water that gives Boothbay Harbor its name is so full of boats that it almost looks like you could hop from one to the other without ever getting your feet wet. One of Maine’s most popular stops for cruising sailors, the protected, deep-water harbor is also home to a fishing fleet, tour boats, and the Balmy Days II, which ferries day-trippers and vacationers to Monhegan, 12 miles off the coast. While getting out on the water is the best way to explore the area’s craggy shoreline—and see many of its classic summer homes—there is lots to do on land. For the full Boothbay experience, browse the shops and galleries downtown in the harbor, hike the Boothbay Region Land Trust trails, take in a show at the Opera House at Boothbay Harbor, play a round of mini golf, and be sure to enjoy at least one meal on a waterside deck. Need more ideas (or directions)? Ask a local. The friendly residents of the Boothbay region have been welcoming visitors since the 1880s when steamships brought East Coasters north to spend summers on its rocky and picturesque shores.

While things slow down considerably after Columbus Day, there’s still plenty to enjoy. “My favorite wander is at the Land Trust’s Ovens Mouth Preserve, but for pure sitting and pondering I can’t beat going out to the rocks at Ocean Point,” says Cathy Sherrill, executive director of the Opera House. “I’ve watched whales breach from that location, and there’s always something to see, even in the dead of winter.” For off-season dining, she likes to cozy up with friends at the Thistle in Boothbay Harbor, where “little woodstoves warm the dining rooms,” or stop in for a pizza at the Carriage House, near her long-time home in East Boothbay.

A relatively recent addition to the area is the 295-acre Coastal Maine Botanical Gardens in Boothbay, which now draws 200,000 visitors from spring through the holidays, when it is strung with 650,000 lights for Gardens Aglow—an annual tradition launched in 2015. The celebration has inspired other businesses on the peninsula to join in with their own holiday events and activities, including the Opera House’s Gingerbread Spectacular and Dough Ball.

Just a few miles from the bustling harbor and across a turning draw- bridge, the town of Southport has a much quieter vibe. The island got its name because its first summer residents were from Augusta, which is directly north, and it remains a vibrant summer community with a small yacht club known for its youth sailing program. Southport is home to about 600 year-round residents, and has an elementary school, store, and library. Just over the bridge, Robinson’s Wharf, open from mid-March through December, has served local seafood for 40 years. “On a cold day, I might stop in for one of their generous lobster rolls,” says Sherrill. “It reminds me of summer.”