PICNIC ON AN ISLAND

Depending on which way you’re coming from, stop at a local store—Southport General Store, the East Boothbay General Store, or Pinkham’s Gourmet Market—to pick up supplies for a picnic before making your way to Boothbay Harbor. Stop at Tidal Transit Kayak Company to rent kayaks, and paddle out to the 200-year-old Burnt Island Light, located on a small island just outside the harbor. “If you’re lucky, you’ll meet Elaine Jones and she may unlock the door so you can climb to the top of Maine’s oldest light tower,” says Danielle Betts, a longtime local. If you’re not into kayaking, hop on Balmy Days Cruises’ Novelty on its mail run to Squirrel Island, home to one of the first settlements in the area. Old cottages and boardwalks from the 1880s here transport you to another place in time. Stop for ice cream at the teahouse before heading back to the harbor.

EXPLORE A SALTWATER FARM

Oak Point Farm is a 32-acre saltwater farm with something for everyone. “Here, you can truly experience the diversity of the Boothbay region,” says Betts. There’s a freshwater pond teeming with wildlife, trails that wind through fields, forest and old apple groves, a historic 1800-era farmhouse serving as the headquarters for the Boothbay Region Land Trust, and deep-water access, so it’s reachable by boat. The outdoor oasis overlooks Hodgdon Cove and is open year-round.

GRAB A MEMORABLE BITE TO EAT

For sandwich connoisseurs, stop in at the Carriage House Restaurant for the best fish sandwich in the region. Haddock blackened with chef-owner Kelly Patrick Farrin’s own spice blend is served with pickled red onion and the chef’s special sauce. “Whatever you order, he is a master at unique, balanced, seasonal flavor pairings,” says Betts. Call ahead to make a reservation, and check to see if there are any dining restrictions in place.

TAKE A WALK WITH AN ALPACA

At the southern end of Southport Island, stop at Cape Newagen Alpaca Farm for a quick animal fix. Choose between a farm tour or an alpaca trek, during which you will walk your companion through woodland trails and seaside neighborhoods with local farm owners as your guides. The slow-paced 75-minute walk gives ample time to learn about your new furry friend, and at the end of the day you’ll have multiple photos to take home to commemorate the experience. Private tours are available during the summer.

WATCH THE SUNSET OVER THE WATER

Ocean Point is a three-mile loop, two-thirds of which runs directly along the water. Take a leisurely stroll along the rocky coastline, or find a spot to enjoy the sweeping panoramic views and watch the sunset as boats go by. Head to the pebble beach at Grimes Cove for a quiet place to relax, or take the path off the cove to get to a local hangout spot where you can feel the ocean spray on big surf days. If you’re hungry, grab a seat at a waterfront restaurant (“The food at Coastal Prime is amazing,” says Betts) and watch the sun sink down behind the islands.