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Oh Maine, how I love you so. Maine was one of those places that remained (see what I did there) on my travel list for so long before we finally took the trip. I am not sure why it took us so long- maybe more “adventurous” places always took precedence.  Maine surprised me in all the best ways. It was one of those rare trips where pictures just don’t do it justice. It was a sweet, picturesque, relaxing, and reconnecting kind of trip with way more to offer than I ever imagined. If you are looking for something different for your next summer trip, I can’t recommend Maine more. I am currently researching and planning for our next visit.  

After a lot of research, I settled on staying in Wells (known as the friendliest town in Maine, and we would have to agree). It seemed to be centrally located to all the places we wanted to visit on our first trip. And I was exactly right in doing so, as always. For real, my research is exhausting but man does it payoff to be right (humble winky face). So, we booked a flight from JAX to BOS, per usual, rented a car from Boston and took the 1.5 hour drive up to Wells, Maine. We also stayed in Boston for an extra night/day on both ends of the trip. Because we just love Boston. It’s the best. Go there too.

We arrived late at night and spent our first full day exploring Wells and enjoying the little compound we were staying at, the Elmwood Resort Hotel. We loved it, it was quintessential Maine vibes, and all units are apartment style with multiple bedrooms. Which is how we must travel with kids. We need space. They need theirs. Win-win. The property was adorable with an indoor heated pool (and sauna my husband used every day) and an outdoor pool. We pretty much always had both pools to ourselves. There was also a lovely little fire pit area where we ended every day with a fire, glass of wine and giant Jenga. It was the absolute best. I’ll be staying here again.

There was also a Dunkin right across the street, where we got breakfast daily. I just love how New Englanders love Dunkin so much. Oh, and they love ice cream. Like obsessed. You’ll find delicious soft serve on practically every street. We basically started each day with Dunkin and ended with soft serve. But we walked a ton, so it was fine. Nobody came back squishier than before we left.


Our first day trip was to Kennebunkport. It was about a 15-minute drive from our hotel, and we arrived just as this beautiful town was cracking its eyes open for the day. There are quaint and bountiful shops that we perused thoroughly. We found beautiful streets to walk along, windows to shop, and all the delicious little restaurants and sweets you could ever want.

We were advised to hit up The Clam Shack and to get there early and we’re super glad that we listened to that advice. We got there for a nice early lunch (before the long line formed) and ordered fresh lobster rolls, clam strips and clam cakes. You take your order to a little picnic table with a nice side of warm butter and dig in. The lobster was very tasty, but we all agreed that the clams were the star of our Maine trip. Of course, we are very accustomed to fresh fish & shrimp, being from Jacksonville, Florida so maybe that’s why the lobster didn’t completely knock our britches off. But man, those clam cakes on a fresh roll with butter or dipping sauce was our jam. We quickly started ordering them everywhere and for a fraction of the price of the lobster that everyone was ordering by the masses. You might disagree, and that’s okay. We’re allowed to do that from time to time.

After walking around a bit more, we stumbled upon the Spirit of Massachusetts Restaurant, a gorgeous old sailboat turned restaurant and ordered an appetizer and a few cocktails while the kiddos enjoyed drinking some soda on a restaurant-boat. The staff was so friendly and wonderful, the day was clear, sunny and perfect- we really could have sipped cocktails all day on deck. But eventually (and reluctantly) we moved on and started exploring some other shops, drove out to the beach and walked around, dipped our toes in the freezing water and then made our way back to Wells.

Ogunquit (Pronounced Uh-Gun-Quit)

Our next full day out was to Ogunquit, and we loved it, yet another little town that had way more to offer than I imagined. I researched enough to decide that the Marginal Way hike looked like something we would enjoy, and man did it blow us away with its gorgeous water-kissing cliffs, winding paths, and unreal clear blue water. We parked down in Perkins Cove, where I had booked a sailboat cruise later in the day and walked from Perkins Cove along the Marginal Way up to Ogunquit. Along our hike we stumbled upon Anchorage by the Sea right as they were opening for lunch so decided to stop and relax there. It was a beautiful little spot on a point with astroturf and wide-open spaces for our boys to be maniacs. I tried (and failed) to snap a family pic, so check out their website pictures instead to see how cute it was.  This resort looked potentially like a fabulous place to stay if you’re looking for more out-your-window views.  The food was super yummy too and we opted for more basic fare- sandwiches, fries and salad.

Once we reached Ogunquit, we walked along all the charming streets and popped into practically every art, souvenir, candy & home décor shop. The kids found adorable classic toy shops with old school toys like wooden train whistles and metal spinning tops. After a soft serve and cocktail stop, we walked our way back to Perkins Cove and found more delicious little chocolate shops, grabbed a much-needed coffee and relaxed at the cove, watching boats come and go.

There was an adorable draw bridge that you draw up yourself by pushing a button. Incoming boats honk their horns until someone walks up to the bridge and presses the button. It was a lot of fun, but I forgot to ask what happens when nobody is nearby. Hmmmm. Anyway, we love boats so just checking out some gorgeous old wooden boats and sailboats was cool.

Eventually it was time for our own sailing trip up the coast and we went with Silver Lining Sailing. We loved it, the captain and his mate were very friendly and fun, and we so enjoyed chatting with them while oohing and awing up and down the stony coast. The weather was less than ideal, which worked out for us because the other couple that was supposed to cruise with us canceled so the 4 of us had the boat to ourselves. Our youngest immediately passed out as soon as the sails went up and that fresh air hit his face. For the rest of the time, we sipped our cocktails (soda for the kid) and just enjoyed the scenery and relaxation that comes with not having to drive the boat. I highly recommend booking a sailing trip during your Maine adventure. Sailing was way more fun than I thought it would be. It was definitely a standout.


We took two separate trips up toward Portland, about a 30-minute drive from Wells. On our first day we explored downtown Portland, ate (lobster & clam cakes) at the wharf, shopped, explored and checked out the Portland Observatory, which was surprisingly interesting and wonderful. We were the only ones in our tour group, arriving right when they opened once again, and our guide was fantastic and informative. We climbed all of the steps (with lots of little stops for history lessons along the way) and enjoyed the magnificent views from the tippy top. And since they weren’t super busy, we weren’t ushered back down too quickly so got to really relax and enjoy the panoramic views for a bit.

We then took the Casco Bay Lines ferry to Peaks Island and spent a few hours exploring this charming island. There are many year-round and seasonal residents that live on this boat-accessible only island in gorgeous Maine-esq homes. We also stumbled upon a stunning little beach within a tiny cove (I couldn’t give you directions here to save my life) and waded in the freezing yet crystal-clear water. The town streets were adorable with beautiful homes and cars and trucks with their keys sitting on the dash. We grabbed some soft serve, because of course we did, popped in a few shops, and enjoyed some treats while looking out on the water. There are a few tours and rentals you can sign up for in advance, that are typically full each day. We didn’t do any of those, but it did look like a lot of fun to grab a scooter to explore a bit more, so maybe next time we’ll plan for that.

Our next day trip toward Portland was to go and see the Portland Head Light because you just MUST do this when traveling to Maine. It has to be the most photographed lighthouse in North America. I have no facts, other than my own suspicions, to back that up. I might add, we stopped at numerous little lighthouses during our trip, but the Portland Head Light really is just the most beautiful. We even witnessed a proposal along the rock cliffs (my kids screaming and laughing in the background of this recorded proposal will forever be memorialized for the happy couple- you’re welcome) and it was just oh so sweet! I thought it would be a short, enjoyable visit but really you can spend quite a few hours exploring this cliff, the lighthouse, and the surrounding landscape. It was breathtaking.

On our way home we went to Palace Playland because, why not? This charming all-year carnival is built right along the beach and boardwalk and is exactly what I think of when imagining northeast old school nostalgic carnivals. The kids loved it and I’ve got to say, we did too. We loved going around on the ferris wheel and getting nice views of the coastline, eating carnival food, playing games, and watching our kids have fun and run wild. We spent a few hours being kids, grabbed pizza (from Lisa’s pizza, of course) and ended the day with (drum roll please…) SOFT SERVE as the sun set.

We also spent our time exploring beaches, coastlines, skipping rocks, riding bikes, collecting sticks and shells, popping in shops, swimming in our pool(s) and buying local foods to prepare fresh meals in our kitchen. Our trip to Maine was both adventurous and somehow also re-energizing. I found that my kids never picked up their electronics or played with the toys they packed in their backpacks. Everything was so close to Wells, so we were never in the car long and we spent our days going non-stop and ready to relax each evening. We drove back to Boston and spent another two days there before hopping on our nonstop flight back to Jax. And don’t worry, a Boston blog will be coming soon.

This trip was so much better than I imagined it would be. Every single person that we met was more than kind and welcoming, the natural elements were more beautiful than I imagined, the food was fresh and delicious, my kids were sufficiently exhausted at the end of each day and our time together made more memories than I could have hoped for.

Top 10 things to pack for your summer trip to Maine:

  1. Camera or a good phone with solid recording capabilities (because you will want to take LOTS of picture).
  2. Layers, the days are warm and breezy, and the nights are cool.
  3. Walking shoes, to do Maine right you are going to do lots and lots of walking and exploring.
  4. Bathing suit (if you’re brave enough to swim in the cold waters) or if you’re lucky enough to find a heated pool and sauna like we did.
  5. Tickets purchased ahead of time, if you want to do a sailing trip like we did or other excursions, these do book up quickly, so you’ll want to plan and book ahead.
  6. Games, for the kids to play on the flight/drive or to enjoy as a family during your down times and relaxing evenings in.
  7. Money for the kids, our kids always want all of the things when traveling, so we give them a set amount of money to spend ahead of time and when they’re broke, they’re broke! There are SO many adorable shops and things to buy, you’ll want to set their expectations ahead of time.
  8. Travel backpack (water bottles, etc.), you’ll need a nice travel bag and water bottles for the hikes and day trips you’ll want to do. If you’re looking for a good one, check out my friend’s awesome backpack perfect for all your travel adventures: CLICK
  9. Hats, bright sunny days, and beach walks will guarantee you’ll want some nice hats on your head. And I mean if you need a new one, check out a sublime rides hat.
  10. Sandals or flip flops, there will be many days you’ll end up walking along the beach and dipping your toes in the water and you’ll want to be able to throw on some sandals to do so. I always kept ours in our rental car so that at the end of the day we could throw these on instead of getting your kids wet sandy feet back into their sneakers! Every day we needed both sneakers and sandals.

I hope you enjoy your trip to Maine as much as we did, and maybe I’ll see you on the trail one of these summers. Next time, we might try to sneak a fall trip up that way to see the changing of the leaves. To be determined and you know I’ll blog about it…eventually when we do. Keep on adventuring my sublime riders!

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