Coastal Maine
Nothing beats an East Coast summer—nine days from Boston to Bar Harbor and back.
There’s one thing you should know about our family: we’re not much of a sit on the beach and order strawberry daiquiris bunch. As much as my children would probably prefer that, we have a lot of space at home. So when we go on vacation, we like to see as much as we can. Fair warning: this itinerary may have stretched that threshold, even for the most ambitious travelers.
Maine has been on our radar since I made a winter visit in 2024. January in Maine? I know, not a trip most people would be taking, but I was writing a book and needed somewhere to cozy up without distraction. The Norumbega turned out to be the perfect destination. Though the roadside lobster shacks had disappeared for the season and the trails were covered with ice, Camden delivered an abundance of fireplaces, locally-run restaurants, and boutiques.
When it was time to return with my family, I knew we’d pass up beloved Kennebunkport to return to Midcoast Maine and even further north.
Our July trip was planned around a direct flight in and out of Boston. My kids knew that I lived and worked there earlier in my career, but had never experienced this city I love. So we hopped in the Wrangler we booked (thinking it would be so much fun to drive up the coast—spoiler alert, it was not) and immediately hightailed it out of the city for our first planned stop in Portsmouth, NH.
The year prior, I’d spent my fortieth birthday in New Hampshire, enjoyed a meal at Cure, and shopped at Sault, and knew it would be a perfect lunch stop before our first night in Portland. After a flight delay, traffic, and a morning of junk food, we ate a hearty meal at The Kitchen and braved a downpour to explore the downtown square. Fun fact: I do almost all of my wardrobe shopping while traveling and highly recommend Summer Sessions if you’re in town.
Portland was our first planned stop. With only one night there, we quickly found we could have stayed longer. What a cool little city. Lots of local designers and a walkable downtown area. For some reason (high season or otherwise), hotels were pushing $1200 a night, even for the Canopy we stayed in. So the next morning, after some coffee and a stroll around town, we left the cruise ship tourists for I-295 north.
I was craving a lobster roll—what I would give for one now—which made our first planned stop Wiscasset. My online research told me the line for Reds Eats was worth it, so we scooted into place right before noon, holding up the end up the line, which was wrapped around the block. Thirty minutes later with nearly zero movement, we ditched the line for Sprague’s. So worth it! My roll, while expensive, was packed with meat. They pick your lobster from a cooler and prepare everything fresh and we were back to our car before the people standing in line with us had placed an order back at Reds.
We’ve established that I can be slightly irrational with the amount of land I want to cover in a day, so while I had two planned stops that afternoon, I had to contend with the fact that 1) my kids, even though they’re great travelers, have limits, and 2) the World Cup was on in two hours and my soccer-loving son would not miss it. That made Boothbay Harbor our next stop.
Boothbay feels like quintessential New England to me. It’s got Sherman’s, the beloved Maine indie bookshop, waterfront restaurants and bars, shops, and lots and lots of buoys and boats. It was the perfect place to spend an afternoon, just a turn to the right and fifteen minutes down the road.
We were zonked, ready to land at our hotel for the night, but I was adamant about stopping at Owl’s Head Lighthouse. I’d visited in winter—snow and ice covering the beach—but I never got over the views. My son got a kick of out the rope installed from the grassy parking lot area to the beach below. He, as any nine-year-old boy would, grabbed on and acted like he was on American Ninja Warrior. The beautiful thing about this area is how uncrowded it was. Granted, it was right before sunset and the water could not be much about sixty degrees, there was only one other family down on the beach, which meant the kids could be kids—something they craved after much time in the car.
For the next two nights we stayed at Camp DeForest in Lincolnville, Maine. To be honest, I stumbled across this recently renovated motel. The branding called me in and the bend towards families locked in our choice. I wanted to stay in Camden, but even the top rated hotels appeared in desperate need of an interior facelift. As it turned out, Camp was one of the highlights of the trip. Had we booked early enough, we could have rented a cabin to fit the whole family. Luckily there were two rooms still available and I requested them close to each other and was lucky to get that wish granted.
A few things I loved about Camp: they send you text confirmations leading up to your trip, including a guide with recommendations of things to do, restaurants, and places to see. They also had fire pits out front, which truly made it feel like summer camp. My son and husband played frisbee golf and we even swam in the frigid water at the small beach across the street.
On our first morning we wandered through town, grabbing a late breakfast at Buttermilk Kitchen, followed up with a visit to one of my all-time favorite boutiques that I’d wandered into on my last visit—Jessie Tobias Design—and picked up snacks and water at the cutest corner store, French & Brawn. We finished the afternoon with a hike up Mt. Battie. You can drive to the top—many did—but it’s a manageable hike and was so rewarding to see the views overlooking Camden and the entire wharf.
The one reservation we had while in town was at Salt Wharf, harborside. I gotta say, this was the big letdown of our stop. Most expensive meal of the trip and the food and service was underwhelming. I would have much preferred to return to Long Grain or Cafe Louis.
On our way out of town, we walked the shipyard in Belfast. It was pretty amazing to see ships being built and repaired. If you find yourself here, do yourself a favor and stop into Dos Gatos—another place I visited on my winter solo trip with hearty Mexican dishes.
And then it was time for the straight shot to Bar Harbor. Because of our itinerary, we knew we wanted to be planted and a pool was a must. It was down to Bar Harbor Inn and Harborside. If I had my way, we would have stayed at Salt Cottages, but there weren’t any family rooms remaining. Bar Harbor Inn won out, honestly because of the customer service. I wasn’t aware of the Asticou at the time (nor was it in our budget) but it sure did look nice.
So we made it to Bar Harbor! Now what? Over the next two days we walked the town, ate some ice cream, and wandered the path looping in front of our hotel and out towards the ragged coastline. Honestly, just having the space waterfront allowed the kids to be kids. They threw rocks, alternated between the pool and the hot tub, and searched for the best Bar Harbor sweats (a necessity due to the drop in temps).
The next morning, weather gloomy, we took our time with breakfast and headed to Bar Island. During low tide, a land bridge appears to walk from the mainland to Bar Island. There’s only a three-hour window to get across and back, so it was us and hundreds of our best friends waiting to cross. Many (myself included) got impatient and walked in ankle-deep water across parts to get to the short hike on the other side. Make sure you plan accordingly! If you stay past low tide you’ll get stuck and have to call a water taxi for $100 to get you back across.
We left the hotel for Acadia on our last day in town, gaining entrance before 8:30 a.m. Fun thing to note, if you have a fourth grader, you can get into national parks for free when you sign up with Every Kid Outdoors. My son was very proud that he “paid” to get us in. We chose to do the Gorham Mountain hike, leaving the rest of our visit open to what we saw. I was shocked at how much the views resembled Big Sur. Rocky coast, clear water, evergreens. Pretty much my favorite setting in the world.
That evening was the highlight of the trip for me: a sunset lobster boat tour with Sail Acadia. I learned about this company because of another travel guide where the visitor recommended them over the more crowded boats departing from Bar Harbor. I put in an order at Beal’s Lobster in Southwest Harbor and drove the three minutes to the boat. For the next two hours we geeked out learning about lobstering, the life of a fisherman, and what families own the massive homes along Northeast Harbor. My son got to drive the boat and we all held a live lobster. It’s easy to glamorize living in the latest “it” spot, which Maine happens to be, but it’s a whole ‘nother thing to learn what’s required to make vacationland just that.
Friday was the big drive. The final destination. Nearly five hours back to Boston. We weren’t going to rush our way through it, so we allowed the kids some pool time in the morning and planned a stop in Freeport for Maine Beer Company (for my husband) and the obligatory L.L.Bean visit. Lemme say it: Maine Beer Company has good beer, but I did not expect the food to be so on point. After a few misses in Bar Harbor (except for Rosalie’s—that was delish!), we needed a solid meal.
We landed by 6:00 at our Boston on day seven of the trip. With just over twenty-four hours, we hit up my old stomping grounds: Boston University, where I worked in admissions at twenty-two, and my first solo apartment. We visited Boston Public Library, checked off the North End and its cannolis, and even made it to Fenway before the game. We rode the T and walked Back Bay. Of course, there was more to see, but given the week prior we gave ourselves a pat on the back and tucked in early with a promise to return.
Updated September 2026
My Top Five Tips
Portland
Take some time to land in Portland. The art and small business scene is booming here and I was shocked at how manageable and walkable this city is. Allagash Brewing is located here as are six lighthouses within a twenty-minute drive. One of the most interesting parts of our visit was stepping into Harbor Fish Market at the Portland Harbor to see fresh seafood displayed, packed up, and shipped. It gave us a whole new appreciation for the hard work that goes into fishing and distributing fresh food.
Midcoast Maine
I am in love with Midcoast Maine. Could have spent my whole trip between Wicasset and Belfast. The rocky coast is gorgeous, towns are quaint, and architecture is dreamy. This is how I think of New England and because we were covering so much ground, there were plenty of towns we missed. A few places we missed or just brushed over that I could have lingered longer: Bath, Wicasset, Damariscotta, Pemaquid Point, Rockland.
Acadia National Park
Get in early and plan your hikes! Acadia is a relatively small national park and finding parking after 9:00 a.m. can be challenging. While most of the beaches in and around Bar Harbor are rocky, Sand Beach in Acadia offers a more traditional beach experience. You do need reservations for Cadillac Mountain Road, so make those in advance if that route is part of your plan!
Bar Harbor
Pack some sweats—even though it's summer you'll need them! The temps dropped into the fifties in early August and since you're spending all of your time outdoors here, you need to prepare to layer. Bar Harbor is a quaint town, but you don't have to stay in town to enjoy it. I'll be honest, the food scene is mediocre, but you should still be prepared to shell out anyway. Hannaford, the regional grocery chain, is right in town and perfect for stocking up on snacks and drinks.
Boston
Boston really is a trip of its own. Flying in and out of a major airport is convenient, but tacks on a half day of travel on either end of the trip. If you're trekking all the way up to Bar Harbor, resist the temptation to add Boston unless you have at least ten nights total.
