Boothbay Harbor is arguably where the real Maine coast begins for cruising on your boat. The landscape takes shape with dramatic coastline and glittering granite shoals. Seals and porpoise dance on the water as you tour these waters on your sailboat or power boat in summer.
Boothbay Harbor is a boater’s paradise with inlets, harbors, and passages that are inviting for yachtsmen, plus some very friendly marinas with dock slips and moorings.
Seguin Island, two miles off shore with its 186′ towering lighthouse (Maine’s second oldest Lighthouse 1795 after Portland Head Light), marks the entry to the Kennebec and Sheepscot Rivers to Boothbay Harbor.
Upon approaching Boothbay, Damariscove Island juts out toward the sea. Damariscove is where the Mayflower landed in 1620 with 102 pilgrims prior to settling in Massachusetts. A daunting narrow channel provides limited anchorage (bow and stern) in 20-foot depths.
It’s worthwhile to visit Damariscove Island – but only during the daylight, you can row to shore where the island keepers may be on hand to provide directions to walking paths around the quiet 1.7 mile island. It’s quite spectacular with views out toward Monhegan Island, and back toward Boothbay.
Damariscove Island is apparently haunted by a Sea Captain, who was beheaded by the Indians in 1689; his headless body and his dog roam the island to this day, so we suggest heading to Boothbay Harbor, to a marina, for staying overnight on your boat!
As you cruise into Boothbay Harbor from Damariscove Island, you are surrounded by pretty granite shores, including Southport Island to the west with the unique octagonal Cuckolds Light on Cape Small. While continuing toward Boothbay Harbor, passing Squirrel Island, you may see the sailing schooners East Wind and Lazy Jack out on their frequent sailing tours from Boothbay.
There are several hotel marinas in Boothbay, including Brown’s Wharf on the east side of the harbor, and Tugboat Inn and Marina to the west. We stayed at Tugboat with nice docks which include power, cable and fresh water, and an easy walk to downtown Boothbay’s shops, great restaurants, even the Boothbay Opera House and the historic wooden footbridge that crosses the upper end of the harbor.
Tugboat Inn has its own restaurant, an actual Tugboat, now grounded, with water views from the Upper Deck dining room and the Lower Deck Lounge outside seating.
Boothbay is a great walking town, a treat to get off your boat and browse the Maine craft shops. The village of Boothbay Harbor is brimming with shops, jewelry and art stores, and many good restaurants serving fresh Maine seafood – several offer views of the harbor.
Stroll the waterfront Piers 8-1 on your way back to Tugboat (let us know if you find Piers 5-2?). Boothbay even offers a little nightlife in what they call the Bar-muda Triangle, a cluster of three bars on the Pier including Mine Oyster, The Pier Pub, and McSeagulls which has live bands in summer. Also the Boat Bar is a cool place for a cocktail.
Departing from Boothbay Harbor by boat, you pass Spruce Point to port, then Ocean Point. Ocean Point Inn, by the way, is another possible mooring spot. This classic inn and cottage resort has a few moorings available and dining in their restaurant with outstanding ocean views (try the Maine crab cakes and lobster stew).
Keep in mind, this is not as well-protected an anchorage as Boothbay or Linekin Bay, you may bob through the night on your boat, and you’ll need a dinghy to row in to the Ocean Point Town Pier. The sunsets from Ocean Point, however, are some of the best we have ever encountered sailing the Maine coast.
Cruising out of Boothbay, you will pass Ram Island Light and you can venture up the Sheepscot Bay to the Sheepscot River and a beautiful marina at Robinhood Cove that offers docks slips, moorings and a great restaurant, The Osprey.
If you want to head just a bit further Down East, cruise around the eastern Ocean Point from Boothbay and enter the Damariscotta River to visit Christmas Cove in South Bristol, one of the prettiest coves in Maine.
These boating tips are not meant for navigational purposes, just for your boating pleasure as you plan where to sail or boat in Boothbay Harbor and the mid coast of Maine.