Hello friends! This post came highly requested after our trip this summer, but if I am honest, I feel ill equipped to give any real “guide to Maine” type post because we stayed in one area the whole time.

Here’s how this trip came to be: in September of 2024 Nate and I were bemoaning the constant Charleston heat. It was “fall” and still 90+ degrees outside. We were hot and ornery. Over the last few years we had left Charleston for a two week span to do a road trip to see friends in NC and family in PA, and had talked about doing a longer trip even further north. I looked at Nate and said, “If we are going to do a trip next summer, we have to book it now, while we are in the heat. Otherwise I fear we will never actually book it.”

And so, we got on the computer and started looking. I knew I would need to work while on our trip and be available for things related to the book releasing in August, so we decided to look for one house we could live in for an extended period of time. For that reason, the house and its location felt most important. We wanted a home base where we could live a fairly normal schedule (Nate and I both taking shifts working in the mornings, cooking a lot at home, finding a local park to go play, etc.) and after looking all up and down the east coast, we landed on Maine. Because of how the Maine coastline is, it’s got a ton of rentals on or close to the water. We also thought, if we are going to do this, let’s DO THIS. Maine felt far north, like a big adventure with the kids. Nate found a house that looked great, and we contacted the owner about renting. Because we wanted it for 3 weeks, we were able to get a small discount (if you are ever looking at booking an airbnb for over two weeks I highly suggest contacting the owner; oftentimes they will provide a discount because you’re staying for a longer time gives them guaranteed income and less turnover/cleaning fees.)

The plan was for the kids and me to fly up via Breeze Air (another reason we chose Kennebunkport – it’s less than an hour from the Portland airport and Charleston has a direct flight to Portland via Breeze airways) and for Nate to bring the car. However, when we booked our flights they were so cheap we opted to get Nate a ticket and rent a car for our time there. This was an added cost but felt worth it to not have Nate do the 20-hour drive solo.

So, from July 7th to August 1st we headed to Maine! And it was absolutely dreamy in every single way. We really had a very low key “vacation” (in quotes because while in a new place, we worked daily). We took day trips within an hour of our house, spent a ton of time playing out on the rocks in front of our rental, and more than anything basked in being OUTSIDE without sweating through our clothes or getting eaten alive by mosquitoes.

KENNEBUNK/KENNEBUNKPORT, MAINE

We technically stayed in Kennebunk, very close to the Kennebunk beaches. It’s a bit confusing because these two towns are right next to each other. We absolutely loved where we stayed and I have tried to find the airbnb but the listing is gone! I actually wonder if the person did it on a whim because the house was veryyyy lived in (a little too lived in, lol). Like it felt like the owner moved out for us to move in and was moving back in right when we left.

We spent a ton of time in this area and really just tried to enjoy being outside without humidity and mosquitos. We spent a few beach days at Mother’s Beach and walked/shopped around downtown Kennebunkport often.

One of the most fun activities we did was kayaking! We left from Kennebunkport Marina and it was the most gorgeous day and I just loved it so much. Beware: make sure you don’t paddle one way too far with the current and then have to paddle against the current back…lol. I am very glad we did this when my parents visited for the extra help with the kids.

Eats: We ate at shockingly few places now that I think about it!

• FiaFia was my absolute favorite place to get a smoothie bowl. (Bonus: this is right next to a Big Daddy’s Ice Cream if half the people want ice cream).
• Bennett’s was hands down the best subs — get the cheesesteak!! You could grab some before heading to a Kennebunk Beach and it would be amazing.
• The Boathouse was a great vibe for eating outdoors and we went there with both my parents and Nate’s stepdad. I wish we had tried Arundel Wharf (also waterfront dining).
• Boulangerie was a great bakery in downtown Kennebunk Scout and I went to early one morning to get cinnamon rolls for everyone.

HERE’S SOME OF OUR FAVORITE DAY TRIPS WE TOOK:

**I use the word day very loosely. Since most of these are within an hour, you could really visit in the morning and be back in Kennebunkport by afternoon.

Fun fact: Maine is known as “Vacationland.” Tons of people travel there in the summer, and for this reason they capitalize on ice cream. I had no idea before going, but there are so many incredible ice cream shops!

Oqunquit

We loved this little town! It was a half hour drive and the actual main street felt a lot like a mountain town. Ice cream shop, chocolate shop, great local restaurants, and little boutiques. This is also the home of The Marginal Way which is a gorgeous walk right along the coast. There’s also a really cool beach that is ocean on one side and inlet on the other. People would put in pool floats on the inlet side and float without fear of drifting out to sea.

Eats: We had a great lunch one day at Crew (we are always looking for a place with a solid salad or burger that also has chicken fingers on the kids menu), and delicious smoothies at Loveshack Juicery. There is also a Big Daddy’s ice cream, and I made a point to eat as much s’mores ice cream as humanly possible while we were in Maine.

Wells

We went to Wells Beach on our very first day in Maine but otherwise didn’t go there often because our rental was closer to the Kennebunk beaches, but it was beautiful! Wells is 15 minutes from Kennebunk, and we drove through it often. Wells also has a fun park called ____ that had minigolf, go karts, and an arcade! We took the kids one afternoon and while they weren’t old enough for the go karts (major bummer) they loved the arcade and mini golf.

Eats: if you go to Wells, you MUST go to Congdon’s Doughnuts. I don’t even really like doughnuts and I loved these. The line is always long but they move you through it super fast. They also have killer breakfast sandwiches and a great coffee menu. That leads me to…Congdons After Dark. In the summer, the Congdons parking lot (which is huge) turns into a food truck hot spot complete with a tiny arcade, bar, live music, and ice cream station where you can get ice cream (you guessed it) on a doughnut! We did this with the kids and had a blast. It’s not every night so check before you go; I think it’s normally Thursday-Sunday.

Cape Elizabeth

This was such a fun day we did when with our friends when they came to visit! Cape Elizabeth is home to Maine’s oldest lighthouse: Portland Head. There’s a ton of parking and a really pretty cliff walk (it’s got a wide path and good railing) you can hike. This was a great activity to do with a gaggle of kids who love to run around.

Eats: Our friends Seth and Cali stumbled upon a place for us to eat and it was honestly one of my favorite things that we did all summer. It is called The Lobster Shack at 2 Lights (there are a ton of lobster shacks so make sure you get the right one). The food here was fine, but the atmosphere was incredible! Bright red picnic tables overlooking the ocean. Tons and tons of flat rocks the kids could crawl and play on while we waited for the food. You could order an entire lobster here if you wanted. Just so beautiful.

Portland

Portland has so much going on! We went in on a few different occasions and the kids really loved the Children’s Museum. We didn’t find the time, but there’s also a Cryptozoology Museum that looked really cool (think a museum for things like Bigfoot, unicorns, etc.) Portland has the most shopping (Madewell, Anthropolie, etc are all here). We walked around a few different times but really found the most beautiful spot on our last day when we had a lot of time to kill before heading to the airport. It was called Fort Allen Park and Eastern Promenade Trail. There was a playground, food trucks, and a walking path along the water. Another thing you could do is ride the ferry to look at all the islands off of Portland!

Eats: we could have done so much better with food in Portland. The first day we waited too long and the kids were so hangry we opted for a random place that wasn’t memorable. Portland is known to have an awesome food scene, but I think our four children made finding delicious food a bit harder. I will say, in both Portland and Freeport we found the same chain pizza restaurant that was awesome. It was called Brickyard Hollow Brewing Company and you could get an incredible pizza, a really good salad (like really good, not iceberg with a few tomatoes like a lot of pizza places) and they even had chicken fingers

Portsmouth, NH

We did a morning in Portsmouth and it was lovely! Fun shopping street and even found the farmer’s market. I don’t remember too much other than we stopped in some art galleries and the nicest women gave the kids a bunch of scrap paper for them to paint on back at the house — so kind!

Eats: We had an early lunch at a Napoletana and YUM. I don’t know if we were hangry or sitting in the booth in the front was just that cozy but this meal was a highlight.

Freeport

This is the home of LL Bean and it did not disappoint!! We spent a morning here and could have stayed longer. The entire main street is outlet shops (everything from Old Navy to Lindt Chocolates to Claire’s to Under Armour) and the kids loved it. We took them to Old Navy and let them each get a new outfit – it was so fun! There’s also a great 3-story toy store called Island Treasure Toys the girls loved.

Eats: there was a Starbucks the girls were very excited about (they got very into the summer berry drink with boba balls), and we had lunch at Brickyard Hollow Brewing Company.

Great Diamond Island

When we booked our trip, Breeze air didn’t fly to Charleston on the 31st (when our rental ended) so we knew we would need to get a hotel for one night. Enter: The Inn at Diamond Cove. This was really fun for a night and even had an old-school manual bowling alley. It felt sort of like summer camp! I will say the hotel doesn’t really have any views (it’s tucked into the trees), the rooms were spacious and it was fun for the night. The lobby also has a fireplace, plenty of board games, and it’s a 3-minute walk to the gameroom with the bowling, arcade style games, etc. There was also a heated pool and hot tub and that was a really big hit!

Eats: there is very little to eat on Great Diamond Island. If we were going for any length of time we would definitely get groceries and bring them on the fairy. However, we did have a lovely dinner at Diamond’s Edge. Had it not been pouring, this would have been an easy walk or bike ride from our hotel, but luckily the front desk will drive you wherever you need to go at a moment’s notice and pick you up again once you are done.

Boston

While Boston isn’t super close, I did want to add it and note that there is a train you can take from Wells! We did a day trip driving (we didn’t know about the train option) and if we could do it again we would 100% take the train! Parking was miserable (many lots could not fit our suburban because it was too tall?!) and took us forever to find. In retrospect, it would have been way easier to park outside the city and take the train in. We didn’t have long in Boston and so I really have very few recs other than to say Boston Commons was so lovely. We walked around and road the swan boats and bought ice cream and with seven kids 10 and under this was the best use of our time in Boston, lol.

Wow, when I type it all out we did a lot of things and saw a lot of places!! I hope you find some of this helpful. If you do nothing else, go to Big Daddy’s or Scoop Deck and get the s’mores ice cream with hot fudge. You won’t regret it!