Boothbay Lobster Wharf (97 Atlantic Ave, Boothbay Harbor, ME 04538) (outdoor deck with harbor view, counter-service seafood, and $1 oysters between 5:30 and 7:30 pm!) Boathouse Bistro (12 By-Way, Boothbay Harbor, ME 04538) (higher-end tapas, seafood, and blueberry sangria; rooftop deck overlooking harbor; veggie, vegan, and gf friendly) Tugboat Restaurant (80 Commercial St, Boothbay Harbor, ME 04538) (old-school maine, indoor table service in a boat, looks over harbor) Brady's (25 Union St, Boothbay Harbor, ME 04538) (low-key american fare and seafood; dog friendly; outdoor deck with harbor view and table service; best at high tide) Pier 1 Pizza & Pub (15 Wharf St, Boothbay Harbor, ME 04538) (only option for late-night food in the harbor)
Robinson's Wharf (20 Hendricks Hill Rd, Southport, ME 04576) (outdoor deck with ocean view; seafood) Spruce Point Inn (88 Grandview Ave, Boothbay Harbor, ME 04538) (higher-end; the end of a peninsula with great ocean views) The Pub at Newagen Seaside Inn (60 Newagen Colony Rd, Southport, ME 04576) (higher-end; the end of a peninsula with great ocean views)
Waves (43 Commercial St, Boothbay Harbor, ME 04538) (indoor booths) Blue Moon Cafe (54 Commercial St, Boothbay Harbor, ME 04538) (outdoor deck overhanging harbor) Mama D's Cafe (50 Union St, Boothbay Harbor, ME 04538) (rustic indoor) Harborside 1901 (12 Bridge St, Boothbay Harbor, ME 04538) (indoor full breakfast and outdoor coffee and pastry bar) Red Cup Coffeehouse (29 Commercial St, Boothbay Harbor, ME 04538) (takeout window) Baker's Way (89 Townsend Ave, Boothbay Harbor, ME 04538) (Vietnamese coffee, baked goods, and lunch; veggie and vegan friendly)
Trevett Country Store (381 W Barters Island Rd, Trevett, ME 04571) (five-minute drive from the harbor)
Downeast Ice Cream Factory (1 By-Way, Boothbay Harbor, ME 04538)
105 Botanical Gardens Drive, Boothbay, ME 04537
Boat pick-up is on the harbor, right below Boothbay Harbor Inn (small green tent). You can buy your tickets on the boat. It gets very windy; bundle up! More information here: https://balmydayscruises.com/
Rentals are available at Maine Kayak Boothbay Harbor Shop, right near the footbridge across from Boothbay Harbor Inn. More information here: https://mainekayak.com/kayak-paddleboard-rentals/
There are trails of varying difficulty. More information here: https://bbrlt.org/trails/