Note: All travel is subject to frequently changing governmental restrictions—please check federal, state and local advisories before scheduling trips. This article was updated on August 20, 2020.

Here’s a fact that will blow your mind: Maine has a longer coastline than California! When you count all of the bays and coves, Maine has 3,478 miles of tidal shoreline, besting California by about 50 miles. With 65 historic lighthouses and, arguably, some of the country’s most scenic fishing harbors, there’s a lot to explore. Whether you’re out for a romantic escape, a solo adventure or a family vacation, we’ve got the ultimate coastal Maine road trip planned for you. You’ll find the best places to stay, eat and play as we take you along much of the famed Lobster Trail — so you’d better pack that bib!

Day 1

Fly into Boston, rent a car and make the two-hour drive to Kennebunkport, where your trip officially begins. Plan plenty of time to mosey along the coast, stopping at key spots for selfies and picnics, and just taking in the slow life of coastal Maine.

Photo courtesy of Nonantum Resort

Stay: Check into the Nonantum Resort, a New England-style hotel perched on a quiet fishing cove. The resort is divided into sections: the historic Carriage House Inn and the more modern Portside Lodge, featuring balcony rooms looking out over the harbor.

Eat: A short walk from the resort, you’ll find Mabel’s Lobster Claw, a cozy restaurant that will make you feel like you’ve stepped into your grandmother’s dining room. Start your trip right by ordering Mabel’s traditional Maine feast featuring New England clam chowder, native steamed clams and a whole Maine lobster.

Day 2

Rise, shine and take the Rugosa Lobster Tour just off the docks of Nonantum Resort. Captain Bob and his mate, Phil, host an incredibly educational two-hour excursion out to the lobster pots. You’ll learn about the history, sustainability and fascinating business of lobster fishing.

Portland Head Light

Jump back on the road for the short drive north to Portland. Stop at Cape Elizabeth to see Maine’s oldest lighthouse, Portland Head Light. Take advantage of the amazing vistas—perfect for selfies or a nice family portrait.

Eat: Housed in an old car ferry, DiMillo’s On the Water serves great local seafood with a view out over the harbor and makes for an ideal lunch spot. Continue on to Freeport, home of L.L. Bean!

Stay: Cozy and comfortable, the Harraseeket Inn is located right on Freeport’s main shopping street. The rooms are spacious (great for families) and many have in-room fireplaces to take the edge off that New England chill. The Inn offers an award-winning brunch and afternoon tea by the fireplace. You won’t need to walk far to reach the Broad Arrow Tavern; it’s located within the inn. Be sure to order their award-winning lobster stew. After dinner, head out to the patio’s fire pit and enjoy an after-dinner cocktail.

Day 3

There’s so much to do in Freeport that you’ll feel pressed for time. Just a short walk from the inn is Freeport Village Station, home to dozens of outlet stores including top outdoor brands. This is also the home of L.L. Bean, and trust us, you could spend a week just exploring all of the different stores. If the true outdoors are calling, take a hike nearby in Wolfe’s Neck Woods State Park featuring some great waterfront trails.

Rockland

Pack up those shopping bags and continue onward to Rockland. Along the way, stop in Boothbay Harbor, one of the state’s most popular destinations for whale watching.

In Rockland, experience coastal Maine by water. Board the Stephen Taber, a 150-year-old schooner for a 3- or 4-day trip (yup, you’ll need to budget enough time for this detour) to discover secret coves and beaches that make up the 4,600 islands off Maine’s coast. The sailing is amazing … but the gourmet food and wine (often a theme of the cruises) is spectacular!

Photo courtesy of Berry Manor Inn

Stay: In Rockland, spend the night at the historic Berry Manor Inn, a Victorian home built in 1898 that has been restored to all its grandeur. It’s centrally located for exploring the town’s historic seaport.

Eat: Cafe Miranda has an extensive menu and the portions are huge; we recommend sharing a few of the more eclectic dishes.

Day 4

Visitors are often surprised to find that sleepy little Rockland boasts two renowned cultural institutions: the Farnsworth Art Museum, specializing in American art, and the Center for Maine Contemporary Art. There’s also the interactive Coastal Children’s Museum that’s perfect for families. Continue your road trip north to scenic Bar Harbor, about two hours away.

Bar Harbor

Stay: The 4-star Bar Harbor Inn has so much to offer, you may never want to leave the resort to venture into the village. You can sit by the outdoor pool, enjoy a relaxing spa treatment, or while away the afternoon with cocktails at the waterfront restaurant.

Eat: Located just a short walk from the inn in the heart of town, you’ll find the ultra-casual Side Street Cafe. Sit outdoors on the deck and if you’re not sick of lobster, order the restaurant’s famous lobster mac ‘n’ cheese.

Day 5

Photo courtesy of Beth Graham

Learn about Maine’s Native American culture at the Abbe Museum or visit the Mount Desert Oceanarium, both great venues for families. Be sure to set aside a few hours to visit Acadia National Park, considered the crown jewel of the North Atlantic Coast. Drive to the top of Cadillac Mountain for some of the state’s (and arguably the country’s) most picturesque views.

From here, drive one more hour and fly out of Bangor or retrace your steps to Boston. If time permits, most travelers choose to retrace their steps as there’s just so much to see along the Maine coast. Many of the businesses in coastal Maine close for the winter months, so plan accordingly.

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Beth Graham

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• Lobsta and Lighthouses: The Ultimate Coastal Maine Road Trip - July 2, 2018

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