My high school besties and I have been talking about a Maine girls’ trip for years. This year we all turned 50, and decided to make it happen. My friend Caryn lives in Maine, and she was the best hostess and tour guide we could have asked for. She LOVES Maine and was able to provide us with an experience that only a local could provide, and Maine now has a special place in my heart after this trip! We were able to see exactly why she loves her home state for the last 20+ years. It is my hope that anyone who reads this will want to add Maine to your bucket list of places you must visit. If the words don’t convey the value, the pictures definitely will!

Caryn lives in Falmouth which is just 10-15 minutes north of Portland, and about a two hour drive from Boston which is where we flew in. You can fly in to either Portland or Boston, so it is worth your time to compare costs. We were able to save money and my friend Lori was able to use points by flying into Boston. If you would like to read about our Girls’ Trip to Boston and how to spend 24 hours in Boston with your girlfriends, you can find that post here.

To get to Maine from Boston, we had to pass through New Hampshire. I was expecting to check off two states on this trip, but New Hampshire was an added bonus! I’ve noticed that state lines almost everywhere that I travel are on bridges.

Our first stop was one of my favorite parts of our entire trip. We visited The Cliff House, a luxury hotel located in Cape Neddick, near Ogunquit. The hotel is oceanfront on the cliffs in southern Maine, and such an exquisite hotel with an even more exquisite view! I did not want to leave. You will want to make your way through the courtyard where the firepit is located and back toward the pool area. Be sure to walk along the back side of the hotel for a different and equally captivating view with every turn. There were lots of “oohs” and “ahhs” and so many pictures taken!

If you stop by to walk the grounds at The Cliff House please ask the employee at the gate. We explored with permission and our friend is a repeat customer of the spa there. This is a high end resort and you would want to carry yourself as such while you are there. This belongs on your Maine bucket list!

Our next stop was Kennebunkport. I was so excited to drive through this beach town! I follow an influencer on Instagram, @thenashvillemom. She posts about Kennebunkport, particularly at Christmas, and her posts are so inspiring that you want to go there! To see it firsthand, I understand now why it’s so special to her.

We stopped for lunch in Kennebunkport at The Boathouse, what would end up being one of my favorite meals of the trip. It was a pretty hot day for Maine, but outside the breeze coming off the water was so nice! We decided to eat outside. I always love eating outdoors, and the atmosphere here was part of what made the experience so special. I loved watching the boats and activity in the water and the yellow striped umbrellas added to the charm and overall aesthetic.

The star of the show was the food! The menu was amazing and made it challenging to decide. I find that is almost always a good sign that wonderful food is to come. I got the Maine Coast Monkfish Stew. Sound strange? If you’ve never tried monkfish you are truly missing out; it’s known as “poor man’s lobster” because it has such a similar flavor to lobster, but more affordable. In this soup I really couldn’t distinguish it from it’s fancier counterpart. I also got the lobster fried rice which was such a generous serving and a table favorite. We had lobster rolls in our future later in the evening and the girls teased me about getting lobster items for lunch too, but my love for lobster runs DEEP. It is not possible to get tired of it. Why wouldn’t you get as much lobster as possible while in “lobster land?” We live in landlocked Tennessee and I am convinced now that the flavor and the freshness factor is nowhere near back home compared to what we got here. My friends got a burger and Korean lettuce wraps which they also loved! 100% recommend The Boathouse in Kennebunkport!

After lunch, we headed to the beach! One of the things we had requested to do while in Maine was go to a “real beach.” Goose Rocks Beach fit the bill. Powder soft sand and gentle waves. We didn’t spend a lot of time here, but it was enough for me to get my dose of “vitamin sea.” In the pictures of Goose Rocks Beach below, you will notice a design of concentric circles in the sand. I have always been fascinated with crop circles and how they get them so perfect? I can’t make one circle that isn’t lumpy!

As if this had not already been special enough, our next stop was one of my favorite memories we made on the entire trip. We got to see the Portland Head Light, a real lighthouse! It is Maine’s oldest and most beautiful. I’m pretty sure I’ve seen it in paintings and other pieces of art. It looked so iconic. Again, I did not want to leave. Just like at the Cliff House, every twist and turn down the path revealed even a more beautiful view than the previous one. Portland Head Light is must on your Maine bucket list!

Finally, the cherry on top of this whole trip, we were treated to lobster rolls! You should know that you can get lobster rolls just about anywhere in Maine, even some gas stations had them. And you can pay big money for them too. Caryn had a friend who has access to lobster right off the boat, and all the best ingredients. Rolls buttered and toasted properly with lettuce and mayo. He came to her house and made them for us! This was definitely the best thing I put in my mouth on the entire trip and in my top ten for best bites of my life. Another friend and neighbor is a talented singer and guitar player and entertained us by the fire pit afterward. I will not forget this night or the hospitality!

We flew out the next day, but before our flight we had time to enjoy breakfast together and spend a couple of hours at LL Bean and the other outlets in Freeport. I could not have been prepared for how big LL Bean was. It’s multiple buildings that cover several blocks, with other outlet stores nestled all around. And each LL Bean store held categories of items. There was an LL Bean store that was primarily clothing (huge), another for camping, and another for boating. You get the idea. In front of the LL Bean clothing outlet is a photobooth experience where you can take a pic with the giant LL Bean boot or where the ginormous LL Bean backpack. It was fun to watch little kids put on this big backpack! Part of the charm of the area is that the Starbucks, McDonalds, and some other restaurants and stores were formally houses. The whole area is very walkable and there were also some amazing souvenir shops that allowed us to grab some gifts from our families.

This trip to Maine was one that I will never forget and I look forward to bringing my family here (hopefully one day soon) and sharing it with them. When people think of Maine, they may think of snow and cold weather, but we had such nice temps during this July visit! If you have been planning to visit Maine, consider going in the summertime. However, I think for my next visit I would like to see the beautiful fall leaves when they change color.