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Family Road Trip Itinerary around Maine: Portland to Boothbay

  • 5 min read

I’m convinced everyone talks about visiting Maine during fall foliage because they want to keep summertime in Maine to themselves. You could feel it everywhere you went – this unspoken, unforgettable energy and joy for just being in Maine. 

And, then there were the spoken moments, as if Yelp and Trip Advisor were coming to life and giving us rave reviews in person. From the resorts to restaurants, we’d strike up conversations with families who have long been visitors to the Pine Tree State. For generations, they had come to Maine every summer for a week or longer to slow down, reconnect, and have their “only in Maine” adventures. Their enthusiasm made you feel like you’ve been missing out your whole life and now it’s time to catch up. 

Even before we visited I noted that one of the top Google Searches about Maine was “Is there anything bad about Maine,” I’’d later find out that the answer is… not much.

With more miles of coastline than California, you’re never too far from a body of water. The bays were filled with kayakers and canoers, out for an early paddle to see harbor seals or porpoises. The lakes were warm, buzzing with kids jumping off the platforms, teenagers on a sunfish, or adults riding the waves on water skis. 

From spending every second of daylight out on the emerald lake water, paddling a canoe, kayak or sunfish around, to trying each bite of lobster, crab and fish we could sink our teeth into, the days were filled with sun-kissed shoulders and smiles wide from all the adventures. 

This was our family’s first visit to Maine and before we even left, I was already dreaming of how to make this trip a yearly tradition. 

While you could spend all your time in one area, a road trip really lets you experience what Maine is all about: boating on the lakes, rolling hills, small fishing towns, camp wood, lobster picnics, kayaking in the bays, seafood bbqs, and of course, lighthouses. Plus, you get to meet all the local Maine residents, “Down Easters”, and hear and see why they love Maine so much.

Our Trip at a Glance:

Trip Length:  minimum 4 nights, 5 days

Want to extend the trip? Easily add on an overnight in Portland or a drive further north to Acadia National Park or south to the small seaside town of Kennebunkport. 

Points of Interest:

  • Portland
  • Portland Head Light
  • Sebago Lake State Park
  • Migis Lodge at Sebago Lake
  • Railway Village Museum
  • Coastal Maine Botanical Gardens
  • Boothbay Craft Brewery
  • Boothbay Harbor
  • Ocean Gate Resort
  • Cap’n Fish’s Cruises
  • Robinson’s Wharf

Where to Stay:

Migis Lodge at Sebago Lake: 

Migis Lodge is a lake-side, all-inclusive resort straight out of The Parent Trap or Dirty Dancing. The cabins are charming, with built-in fireplaces for those cool summer nights and porches with rocking chairs perfect for reading a book while the afternoon sun dips below the horizon. With the included kid’s club, parents can sneak away for cocktail hour and dinner, mingling with other guests and getting a relaxing meal, while the kids are having a blast with the onsite crew. You’ll want to book a full week here, but if you can’t get away that long, two to three nights is perfect. They have everything you could want, from massages and saunas to kayaks and pontoon boats. This is one of those places where you don’t lock your cabin door and you won’t need to get in the car the entire time.

Ocean Gate Resort, Southport:

Ocean Gate Resort, with a putt putt golf course, swimming pool, and access to kayaks and canoes, is a great family-friendly resort. And while all of the amenities are amazing, the bayfront location, with gorgeous ocean views, makes this place unforgettable. Use Ocean Gate as your homebase as you explore all of Boothbay and Southport, from the Botanical Gardens to the puffin and whale watching cruises. 

Itinerary:

Day 1 & 2:

We spent our first two nights at Migis Lodge and the surrounding Sebago Lake area. Just 45-minutes from Portland International Jetport, you are driving under thick pine trees to your lakeside retreat. We spent the whole day on the lake, paddling, canoeing, and swimming. After we showered, we dropped our daughter off at the kid’s club so we could enjoy cocktail hour and dinner. Everyone dresses up for dinners, and you can enjoy a cocktail or glass of wine looking out over the lake. 

The next morning, we went for a hike at Sebago Lake State Park. If hiking isn’t your thing, bring your bathing suit or enjoy the large playground. We loved exploring the lakeshore, watching the baby ducks and swinging on the swings. 

Back at Migis Lodge, we had a lobster cook-out before taking the sailboat out on the lake. The best part about the lodge is the availability to try new things and go at your own pace. We sailed around several of the small lake islands before heading back and getting ready for dinner. That night was a bit cooler, so we lit a fire in our cabin and enjoyed reading by the flickering light until bedtime. 

Day 3:

From Migis Lodge, we drove over to Boothbay Harbor. On the way there we stopped by the Railway Village Museum for a quick train ride and walked around the outdoor museum. If you have a train lover in your crew, this is a must-stop. Next, we drove a little bit further to Coastal Maine Botanical Gardens, where there is an incredible giant troll exhibit right now. Our entire family loved it – we kept saying how this was the best botanical garden we’d ever been to. The scavenger hunt to find all the trolls kept our 5- year-old entertained and excited for three hours – that is a huge feat! Once we found all the trolls, we stopped by Boothbay Craft Brewery for a pint and a slice of pizza before a full dinner. The sun sets so late that you can enjoy a later dinner and not miss one second of daytime adventures.

Day 4 & 5: 

With Ocean Gate Resort as our homebase, we popped around Boothbay Harbor and Southport all day long. We started the morning with a puffin and whale watching tour with Cap’n Fish’s and spent the rest strolling around Boothbay Harbor, shopping, looking through the art galleries and eating ice cream. We ended the day back at the resort for a late afternoon paddle. Our final dinner at Robinson’s Wharf was one of the best of the trip, with drinks and apps flowing plus the staff was incredibly friendly and even showed our daughter the live lobsters and crabs. On our final morning drive back to Portland, we stopped off at the local lighthouses before boarding our flight home. 

  • 5 min read

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