The Ultimate Maine Road Trip: A Week of Driving and Sailing on the Maine Coast

There’s a reason that a Maine Coast road trip is one of the most revered in American travel. Quaint towns, rugged coasts, fantastic food, and outdoor adventure aplenty. Diana Ballon spent a week there recently, and offers her advice on the perfect trip along the Maine Coast, with a nice mixture of time on scenic roads and on stunning water.

Sunsets in Maine don’t disappoint. Photo Credit: Diana Ballon

I first heard about idyllic summers on Maine’s Penobscot Bay when reading Robert McCloskey’s Time of Wonder to my children — of racing sailboats and cruising schooners and porpoises “puffing and playing around your boat” at sunset, and islands that you could call home.

So I was excited when I discovered I could enjoy three glorious days on these waters on an “all-inclusive” windjammer excursion, while fitting in some road tripping.

Although this was the impetus for my husband’s and my trip to Maine this summer, we added on a couple of nights in the bustling port city of Portland, followed by time several pretty towns further north in Maine’s midcoast.

Maine’s coastline is deceptively large for such a small state. It runs for about 5,600 kilometres, with thousands of craggy coves and peninsulas and inlets, and myriad islands beckoning to be discovered.

Don’t trust me when I describe its beauty. Turn to the works of the many famous artists who paid tribute to this area – Winslow Homer who captured its rugged beauty, Edward Hopper its majestic solitude, and Andrew Wyeth its wind-blown meadows and shadows dancing in the trees.

While you can drive to Maine’s coast from many Canadian provinces, we chose to fly to Boston and were amazed that, within 3.5 hours driving (which we did by a combination of bus and rental car), we could cover all the towns and coast I describe in this week-long itinerary.

You can too. Here’s what we did.

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Your Maine Coast Itinerary

This is a beautiful state, and you can built out a Maine itinerary that suits however you want to explore.

Some travellers may want to drive from day to night, stopping and taking pictures wherever they can, while others may like to find an easier rhythm, staying put in places that they connect with, and even fitting in a boat trip in the middle of a road trip!

Day 1: Boston to Portland

The 19th century Portland Company Complex in Portland, Maine. Photo Credit: Blue Motel Room Photography

Rather than driving, we actually flew from Toronto to Boston Logan Airport (about 1.5 hours), and then simply walked one floor down to catch the Concord Coach Lines bus to Portland. The bus runs about every hour (check their schedule), costs 33 USD at the time of publication, and takes about two hours. That meant we were able to leave Toronto in the afternoon and be eating a late dinner in Portland.

Portland may be small, but it has a huge food scene with a wide range of cuisine from high end to family friendly to innovative and award winning. We ate inexpensive vegetarian Thai at the Green Elephant before checking into the Holiday Inn Portland-By The Bay.

A word of warning - hotels in Portland can be expensive in the summer months. This Holiday Inn wasn’t cheap, but it was central and included complimentary e-bikes.

Day 2: Discover Portland and Peak Island

E-bikes were a great way to see the city. We visited Munjoy Hill, a trendy, up-and-coming neighbourhood in the east end known for its many restaurants, galleries and distilleries. We cycled along Commercial Street on the waterfront and the city’s bustling main thoroughfare, Congress Street. We took photos of the narrow-gauge railway car near the waterfront. (You can also board one of these svelte railway cars at the Maine Narrow Gauge Railroad & Museum, for a leisurely 40-minute ride.)

And — for one of our “peak” Maine experiences — we took our bikes on the 20-minute ferry to Peaks Island on Casco Bay. For just $7.70 per adult at the time of publication, and another $6.50 to board a bike (or you can rent one there), you can while away a pretty magical afternoon on the island.

Peaks Island equals peak happiness. Photo Credit: Diana Ballon

Sharing the road with cars and golf carts, we did the 6.3 km loop around the perimeter of the island, stopping to walk along the rocky coast, and taking detours to explore quaint residential streets.

There are several restaurant options within about five minutes of the harbour. We chose Il Leone for its delicious thin-crusted Neapolitan pizza that we ate at a picnic table under the shade of some trees. Their wood-burning Forza Forni oven on wheels was brought over from Italy, yet their prep is done, rather perfectly, out of the side of a food truck. And the setting in a wooded grove with a wee glimpse of the bay feels decadently remote.

DAY 3: Portland to Rockland

In the morning, we visited The Portland Museum of Art, which has an impressive collection of works, ranging from Winslow Homer to Andy Warhol and Claude Monet. Their exhibit “Drawn to the Light” showcased 100 photographs, spanning more than five decades, from the Rockport-based Maine Media Workshops & College. I loved how their landscape photos could evoke a sense of wonder: like good travel writing, the artist uses a keen eye to evoke the emotional essence of place.

The exhibit was only running until September 10th, but that gives you an idea of what you can expect when you visit.

We then took Concord Coachline’s once daily bus from Portland to Rockland (just over two hours, and only around 25 USD per person). Rockland is a small, pretty coastal town, with fewer tourists than neighbouring towns like Camden, but with many boutiques, galleries, restaurants and cafés that are all easily walkable. (However, note that much is closed Sundays to Tuesdays, so book accordingly).

The exterior of the Granite Inn. Photo Credit: Diana Ballon

We checked in for the night at the Granite Inn, a pretty stone building, originally constructed in 1840, that overlooks the harbour. We had booked the smallest and least expensive of their eight guest rooms — only around one hundred dollars, that included a delicious home-cooked breakfast and use of their living room with its mid-century modern furniture, original terrazzo floors, and a wide front porch, providing perfect options for lounging with a glass of wine in the evening.

Rockland has many restaurants to choose from: Primo, with two-time James Beard Award-winner Melissa Kelly, is one of the best in New England, while other more casual but noteworthy options include Ada’s Kitchen, for homemade pasta and other Italian classics; Claws lobster shack for “dining in the rough,” with fresh local catch; Suzuki’s Sushi Bar for seafood; and Rockland Café, a favourite local haunt for classics like fish and chips and their popular sea chowder.

Day 4: Boarding a windjammer in Rockland

Our delicious Granite Inn breakfast included freshly baked scones, and both a savoury (eggs with hollandaise) and sweet (pancake) option.

We then visited the Farnsworth Art Museum. Celebrating its 75th anniversary, the museum showcases a two-part exhibition of American art (on until December 31) and a fabulous exhibit of Edward Hopper and Andrew Wyeth, each artist depicting Rockland’s hardworking history, three decades apart. That exhibit was only on until late August, but again it gives you an idea of what you may see there when you visit.

Although we were limited on time, Rockland also has a Sail Power and Steam Museum, a Maine Lighthouse Museum, the small but compact Center for Maine Contemporary Art, the Project Puffin Visitor Center and other galleries. As well the Rockland Breakwater Lighthouse is just about a five-minute drive from Main Street.

The Stephen Taber from the Maine Windjammer Association. Photo Credit: Blue Motel Room Photography

At 4pm, we boarded the Stephen Taber, one of nine schooners that the Maine Windjammer Association operates, ”offering three- to seven-day all-inclusive sailing experiences for the adventurous traveller.” Although each schooner has its own distinct character, the 152-year-old Taber distinguishes itself as being the longest continually operating sailing ship in the country. It also has the added allure of serving wine nightly, along with its gourmet dining, much of it produced in a tiny below-deck kitchen using a 1910 wood-burning stove.

I am exciting to get going. On this first evening, we each climb down ladders, backwards of course, to plant our duffel bags in our tiny “state rooms.” We then go back on deck for the official meet and greet from the Captain, who has gathered with his five-member able-bodied crew to introduce my husband and me, plus 20 other passengers, to life aboard a schooner.

“This is a beautiful, secret unexplored area,” he says, of the protected waterway that we are about to set sail on. In Penobscot Bay, you are more likely to see porpoises, great blue heron, working lobster boats and other schooners than the standard marine traffic congesting other parts of the coast. And while I am keen to hear the itinerary, I learn that there is none.

“We go where the wind takes us,” says the Captain. With dozens of beautiful anchorages within 20 kilometres, we could be mooring close to many different islands, including North Haven, Vinalhaven and Deer Isle, he tells us.

After the introduction, we are then free to dine in town, return to the ship to sleep, to be ready to leave the next morning. I am both excited and a little apprehensive at the close quarters, a 33.5-metre sailing ship to accommodate 28?

But as I am to learn, size really doesn’t matter.. An easy congeniality develops quickly.

(By the way, If you want to get out on the water in Penobscot Bay, consider this Historic Schooner Day Sailing Trip).

Day 5: On the water / Penobscot Bay

After a collective effort to hoist the sails (participation is option, but not required), and we are off.

The woods of Wreck Island. Photo Credit: Diana Ballon

As we sail, the sun glistens like sparkling diamonds off the undulating surface of the water. After several hours, we arrive at Wreck Island: it is small, uninhabited, and a magical destination to swim to (rather than going in the yawl boat with most of the other guests.) The water is about a refreshing 15 degrees Celsius.

Once arriving, we have time to take a stroll along the shore and relax in the sun with a glass of wine as dinner is prepared! There’s a lobster boil - 50 pounds of lobster, and corn on the cob slathered in butter. Then dessert is a rich, creamy decadent mixture of melted chocolate, marshmallow and peanut butter cooked over the open fire on a pizzelle.

After returning to our windjammer that night, I sleep soundly. It may be “ship camping,” but I love being anchored out at sea, with a cool breeze blowing into our cabin from the opening above our heads. (We have elected to keep the hatch board open.)

Day 6: Stonington (on Deer Isle)

The town of Stonington on Deer Isle, Maine. Photo Credit: Blue Motel Room Photography

Today we break up a day of sailing with a stop at the picturesque town of Stonington on Deer Isle, so named because of the abundance of deer that once roamed the island. Landing here is like stepping back in time.

Following its narrow main street that overlooks the harbour, we wander into a bookstore and then an antique shop before grabbing a delicious fresh-brewed cup of organic coffee at 44 North. Stonington is like a little village that has been untouched by the sped-up living I have grown accustomed to in Toronto.

That evening back on board, we start with an elaborate selection of cheeses and wine, and then enjoy our final dinner on board, a delicious variety of vegan and meat curries.

Day 7: From Water to Rockland to Camden

After another gourmet breakfast — this time a lobster and dill frittata, freshly baked scones and granola, we say good-bye to our fellow passenger and crew mates, feeling nostalgic already for the intimate experience we have had on these open waters.

We get a lift to pick up our rental car at nearby Knox County Regional Airport. Then we are off to Camden, only about 10 minutes more by car.

Camden Harbour at sunset. Photo Credit: Diana Ballon

Also in Knox County, Camden is another charming seaside town along Maine’s midcoast, “self-dubbed the Jewel of the Coast,” a village where mountains extend down to the sea. Entering it is like stepping into a Norman Rockwell painting. There is a harbour that dominates its shoreline, the quintessential church steeple interrupting the skyline, and upscale boutiques, vintage clothing stores, quaint cafés and eateries all in close proximity.

We begin by checking into our pretty waterside hotel, the four-diamond Grand Harbor Inn. This boutique inn has 10 luxury guest rooms and suites, each with a private balcony and a gas fireplace, with a contemporary vibe and homey feel. I loved our large bathroom with Jacuzzi tub and marble- and glass-enclosed rain shower, as well as the Turkish towels (a nice touch). It was the perfect dose of comfort after life on a ship. You can look at availability for an upcoming stay here.

For dinner, we walked a few minutes down the road to The Waterfront, a laid-back restaurant with a wide patio overlooking the harbour, and fresh reasonably priced fish and seafood. It was a good choice, but I would have also liked to try the Asian fare at Long Grain Restaurant. (Note that reservations, by phone, are recommended, and it was full by the time we got there.)

Day 8: Camden

Included with our stay at the Grand Harbor Inn was a delicious breakfast, delivered to our suite each morning. As someone who suffers terribly from FOMO (fear of missing out), I was delighted to discover that rather than having to choose which option you want from the meal card you fill in the night before, you can choose everything (!), so I did – quiche, granola, fruit, muffins and coffee!

Properly fortified, we headed to Maine Sport Outfitters to rent bikes for the day — my favourite way to sightsee. Our route (suggested at the Outfitters) had us cycling through the beautiful village of Rockport and then around Beauchamp Point, past a children’s chapel and a golf course, and past a field populated by Belted Galloway cattle, where we stopped to take photos. We went for a swim at Laite Memorial Beach, which overlooks Penobscot Bay and Camden Harbour, and then ended up back in Camden, where we grabbed sandwiches at Ferreira Delicatessen to eat at a nearby park.

In the afternoon we cycled uphill to Barrett’s Cove, a freshwater beach on Megunticook Lake, for another swim. There the water was warm and shallow, clearly a local landing pad for many families in the area.

Later that evening, back in Camden, we ate at Peter Ott’s on the Water, which is right next to our hotel and — you guessed it — it’s right on the water! The burgers there were great, and reasonably priced.

It was a relaxed way to end our vacation before driving back the 3.5 hours to the Boston airport the next morning.

By Boat or By Car - Beautiful Maine Awaits

A yawl boat on the shore. Photo Credit: Blue Motel Room Photography

Maine is a place where you could spend one week a million different ways, but the key thing is to be near or on the water, taking in the wonder of the landscape and local scenery, and soaking up the sights, sounds and tastes of the communities that are intimately connected to the water, and will be forevermore.