Southern Belle in Training

Fashion, Travel & Lifestyle Blog || Est. 2012 || Virginia Beach, VA

September 26, 2023

TRAVEL GUIDE: 5 Days in Maine - First Timer's Itinerary.

       For Labor Day Weekend this year, my boyfriend Ryan came to visit my home state of Maine with me for the first time. While I always enjoy seeing the beauty of southern Maine in the summer months, it was definitely special to see my hometown and home state through the eyes of a first-time visitor. I feel like my parents and I did a great job planning out a good itinerary for Ryan's first Maine trip, and I'd recommend a similar itinerary for other first-time Maine visitors.

      There were a few points in our trip that we visited with my family and friends, and I'll also add in additional suggestions for other activities you could do as a tourist with that extra time.

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Where to stay: 

     I highly recommend staying in Kennebunkport, ME as a central location to all of the places I'm sharing in this itinerary! My hometown is the neighboring town of Kennebunk, but Kennebunkport is where all of the quaint hotels and inns are. Definitely check out The Kennebunkport Inn or The Nonantum. I also have additional Kennebunkport lodging recommendations in my Kennebunks Travel Guide blog post. I will note that Kennebunkport area hotels can be expensive in peak season. The neighboring town of Wells can often have better deals on lodging, so you can always check places there too.

     I also highly recommend renting a car in Maine if you're flying like we did, and don't have family to drive you around! There are Ubers in Maine, but in the smaller towns it can sometimes be quite expensive or have longer wait times. 

The Kennebunkport Inn

Day 1: 

       We flew into Portland, Maine in the evening. After my parents picked us up, we drove to my grandma's assisted living facility to visit with her for a bit. Our flight was a little delayed getting in, so it cut our visit time a little shorter, but I was still glad to see her and finally have Ryan meet her! (She's 98!) My parents then took us to dinner at a favorite local spot of mine, Pizza by Alex in Biddeford. Biddeford is a large town between Portland and the Kennebunks. I'll share more about Biddeford later on in this post, but I will tell you that Pizza by Alex is such a great spot. The restaurant has looked the exact same for more entire life, which just adds to its charm. Hello wood paneled walls and old tables and chairs! Pizza by Alex literally only sells pizza- they do one thing and do it very well! It was a great later evening meal to enjoy after a long travel day (and working that morning!). 

      If you weren't visiting family like we did right after the airport, I'd consider having dinner at a great restaurant in the Portland area instead closer to the airport before heading south to Kennebunkport! (Although Pizza by Alex is great too. 😊)

Day 2: 

     My best friend Julia, her husband, and their newborn came over to my mom's house so that we could meet the baby and they could finally meet Ryan! It was such a special time together. 

      That afternoon, we had a late lunch at a very popular and beloved local spot in Wells (neighboring town of Kennebunk): The Maine Diner! My parents and I ate here often throughout my childhood, but I don't think I had been back since high school! They have classic diner staples on the menu (including all-day breakfast), but also several unique Maine items like various lobster dishes and blueberry pie. They also have their own gift shop on the property, so it really is a fun spot if you're visiting the area. Ryan loved it and has already requested to go back on future trips! The Maine Diner does get really busy at peak mealtimes, so I recommend doing a late lunch like we did so it won't be as busy.

     We then continued driving a little bit further south into the next coastal town, Ogunquit! Ogunquit is a tiny little town but filled with charm. It has a quaint little downtown with shops and restaurants that is similar to Kennebunkport. It's also a very art-focused town, with several art galleries. (My mom shows some of her work at The Barn Gallery in Ogunquit- look for the name Annie Lemieux on the pieces if you happen to visit that one!) I think the best part of Ogunquit though is a stunning ocean trail that's open to the public called Marginal Way. The sights that you'll see while walking Marginal Way are stunning. It's Maine's rocky coast at its finest, and you also get to walk by some really incredible houses in the cliffs! Take a look at the unique pedestrian bridge and some of the shops in Perkins Cove first before you start walking! After our walk at Marginal Way, we headed back home where we got ready to go to a music performance at Vinegar Hill Music Theater. My dad is a drummer and was playing in a local show that night!

     If you don't have family and friends plans like we did that morning and evening, I'd recommend grabbing an easy breakfast to-go at Boulangerie Bakery in downtown Kennebunk, and then heading out for a morning beach walk on one of the various beaches in Kennebunk. For the evening, I'd recommend sticking around Ogunquit for drinks or dinner! You could even try to see a show at the historic Ogunquit Barn Playhouse, which is southern Maine's premiere theater venue!

Day 3: 

      We spent the morning in the Biddeford/Saco area, which are two larger towns between Kennebunk and Portland. We met my cousin and her family for coffee at a local place in Saco, and then we ran an errand for my mom in downtown Biddeford. Biddeford is a former mill town that has seen a lot of revitalization in the last five years. As recently as when I was in high school, downtown Biddeford was not a nice area or a place you'd really want to hang out (give or take a couple restaurants). Today, it is a lively downtown with so many new shops, cafes, loft apartments, restaurants and other businesses like coworker space and a new boutique hotel called The Lincoln! We enjoyed taking a little stroll over a newer pedestrian bridge to enjoy the river views and some of the old mill buildings. 

      On our way back home, we took a little detour and I drove Ryan through Dock Square, which is Kennebunkport's downtown area! We kept driving and I took him to see the viewing area for Walker's Point, which is the summer home of President Bush(es). We then came back home to eat a nice lunch that my mom made for us, and then headed back into Kennebunkport a couple hours later. Ryan and I had about an hour to explore the shops in Dock Square. I brought him into a couple of my favorite ones, and also showed him the store I worked at during school breaks in college. 

       We were supposed to take a charter sailboat ride in the early evening, but unfortunately the seas had gotten too rough as the day went on, and the captain canceled our boat ride shortly before it was supposed to start. Boo! Hopefully we can do that with Ryan another time. We enjoyed a little bit more time outside exploring Kennebunkport, but then headed back up to Biddeford, where we had been that morning. We got pizza at Otto, another great local spot. They're a Portland restaurant that recently opened a Biddeford location. They have some incredible gourmet pizza flavors and it's just a great spot. Pizza by Alex (also in Biddeford) is your classic pizza spot, whereas Otto is a little more gourmet. We then spent the rest of the night at a get-together with my mom's side of the family that my aunt and uncle hosted. This was Ryan's first-time meeting all of those extended family members!

     If you don't have family and friend plans like we did, I'd still go to Biddeford to walk around and explore in the morning and try to grab coffee or breakfast at a local spot. Then spend the whole rest of the day in Kennebunkport! Hopefully your sailboat cruise would not be cancelled like ours. 😉 Then stay in Kennebunkport for dinner and drinks! A few spots I'd recommend: Batson River, Pedro's, Stripers. See more of my Kennebunkport restaurant recommendations in this blog post

Day 4: 

     I went for a walk in the morning with my childhood friend Katie. We walked the beautiful trails at the nearby Franciscan Monastery (free and open to the public). That afternoon, Ryan and my parents and I did a beach day! While there are many great beaches in Southern Maine, we went to my favorite: Gooches Beach. I even managed to enjoy a swim in the frigid Maine ocean! It's so cold, but always so exhilarating. We then headed home to get ready for dinner. My parents wanted to do a nicer early birthday dinner for me while we were in Maine, and I picked Hurricane in Kennebunkport. This great spot is in my Kennebunkport Travel Guide. I've liked it in the past... but I loved it this time! My cocktail, dinner and dessert were all phenomenal.

     No itinerary changes to suggest for this day- the monastery walk, beach day and dinner at Hurricane are all things I'd recommend for visitors!

Day 5:

      We had an evening flight back to Virginia, which meant that we got to enjoy the full day beforehand in Maine. We headed up to Portland for my favorite Maine day trip adventure: taking the ferry to Peaks Island!! Peaks Island is a charming small island just off the coast of Portland. It's only a couple square miles in size, so it's very easy to explore the island by bike or golf cart (both are available for daily rental). My dad arranged for a golf cart rental, and it was great!! Cars are also allowed onto the island too if you do want to take that route- you can bring them onto the Peaks Island ferry. 

     This was only my sixth time ever visiting Peaks Island, but it truly is one of my favorite places in Maine. The most memorable time that I ever went was definitely for my 16th birthday (all the way back in 2010!). It was cool to end Ryan's first Maine trip by showing him a place I love so much. For full details on why you should visit Peaks Island and things to do there check out this blog post!

     We took the ferry back to Portland in the late afternoon, and spent a couple of hours checking out Portland's Old Port area. There's tons of local shops to explore and enjoy. I grabbed some (Maine whoopie pie flavored!) ice cream at a newer spot called Coastal Creamery in the Old Port that I'd highly recommend. Before we knew it, the day was coming to an end and it was time to head to the airport for our evening flight back to Virginia. And Ryan's first visit to Maine came to an end!


     I haven't written a Travel Guide quite in this style before, but I hope that you enjoyed it! I put a lot of thought into what I thought the best local places were for Ryan to see during his first Maine trip, and I really do think our itinerary would be great for someone else to duplicate. Please don't hesitate to reach out to me if you have any questions!

      Other Maine blog posts:

      God Bless,

      xoxo Annaliese


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