Maine Travel Guide

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Hello! I hope you enjoy this post from our Maine trip in 2015! For more up-to-date Maine recommendations, visit my Mini Maine Travel Guide!

Two weeks ago, my boyfriend, Edwin, and I took a little datingmoon (my term for a trip with your significant other when you’re not married, similar to a honeymoon or a babymoon) to Maine! He had to fly across the country from Los Angeles but the traveling was super easy for me. The JetBlue flight from JFK to the Portland airport was just over an hour. We stayed at The Grand Hotel in Kennebunkport but we rented a car so we also explored other parts of Maine. We spent a day in Portland and Cape Elizabeth and another day on Mount Desert Island in Bar Harbor and in Acadia National Park. Neither of us had ever been to Maine before but in four days, we both fell in love with “Vacationland,” as it’s called. If I had a quarter for every time Edwin said he wanted to live in Maine, I’d be rich!

Rhyme & Reason Maine Travel Guide

Day 1:

We landed in Portland at 8:30am so we had the whole day ahead of us! We grabbed our rental car and drove into downtown Portland for some breakfast. In my research for the trip I read about a donut place, The Holy Donut, that it famous for their potato donuts so naturally we had to sample one. I don’t usually love donuts but it was definitely good! We walked around downtown Portland for a little before we got on a sailboat to sail through the little islands around Portland Harbor. We sailed with Portland Schooner Company and enjoyed every minute of being on the water and taking in the views! Our boat was over 100 years old and was a work of art. After spending the morning sailing we had lunch at Duckfat. Just about every article I read and every recommendation I got on Maine included eating at Duckfat as a Portland must. Let me tell you, it was a must! The fries and paninis were amazing! After lunch we window shopped around town (my boyfriend’s favorite activity, not!) and popped into Sea Bags and K Colette. The home decor, coffee table books, cookbooks, and stationary at K Colette are right up my alley and on par with my taste. Next, we drop 20 minutes to Cape Elizabeth to check out the views and the lighthouse, The Portland Head Light (it’s the most photographed lighthouse in America). I wore an easy denim dress for the day around Portland. Wearing denim dresses is one of my favorite summertime looks. Get my denim summer look with one of these four denim dresses: shirt dress, embroidered dress, ombre dress, or drawstring dress. The final stop of the day was the town we stayed in, Kennebunkport. Driving into Kennebunkport, we both knew we were going to love it! It’s right on the water and has restaurants and shops galore, beautiful beaches, and boats everywhere… aka a little slice of Heaven. That night we ate dinner at David’s KTP, which is right on the water so it was fabulous eating yummy food on the outdoor patio. It was slightly chilly our first night so I layered different blue and white patterns… a gingham button-down, a color block sweater, and a stripe scarf.

Rhyme & Reason Maine Travel Guide Rhyme & Reason Maine Travel Guide Rhyme & Reason Maine Travel Guide

Tuesday/Day 2:

We spent the second day entirely in Kennebunkport. We ate lobster rolls and drank fresh squeezed lemonade at The Clam Shack for lunch. The Clam Shack’s lobster roll has been voted the best lobster roll in America. IT IS SO DELICIOUS. We then walked around town and popped into most of the little stores and shops. The afternoon also consisted of ice cream cones at Rococo Ice Cream. They have yummy homemade specialty flavors that you won’t find anywhere else. We spent the evening enjoying the beautiful property at the Hidden Pond Resort. It was so nice to enjoy cocktails around the fire pit outside of Earth, the hotel’s restaurant. We had dinner that night at Earth and we were overjoyed with our meal. Earth is a farm to table restaurant and everything is local or grown onsite in their gardens. We split a couple dishes of veggies, pasta, and fish and loved every bite. I 100% recommend Earth!

Rhyme & Reason Maine Travel GuideRhyme & Reason Maine Travel GuideRhyme & Reason Maine Travel Guide

Wednesday/Day 3:

On our third day we woke up early and grabbed breakfast sandwiches in town at Old Salt’s Delicatessen before hitting the road for Acadia National Park on Mount Desert Island. It is a bit of a drive (just under 4 hours) but we were so happy we made the decision to go because it was absolutely breathtaking. We hiked through the park along one of the many hiking trails and we drove the loop all the way around the park. We stopped at different beaches and different lookouts to take in all of the gloriousness of Maine. We saw rugged cliff beaches, surfing beaches, and perfect beaches to spend the whole day at with family or friends. After exploring the park we went to the small seaside town Bar Harbor. It was packed with summer vacationers but just oozing with All American charm. If you head to Acadia National Park or to Bar Harbor I definitely suggest that you go to the other spot also because they are so close and both located on Mount Desert Island. We then began out trek back to Kennebunkport (Edwin drove the whole way there so I took over on the way home and blasted country music while he fell in and out of sleep!). After waking up early, exploring all day, and driving for hours we were up for a casual, easy dinner. We ended up at Bandaloop Restaurant. They are known for their quesadillas and mac n’ cheese… they did not disappoint.

Rhyme & Reason Maine Travel Guide

Thursday/Day 4:

Neither of us wanted our last day to actually happen! However, we took advantage of the fact that we had a late flight out of Portland by spending the day at the beach and by biking all around Kennebunkport and along the town’s beaches. I wore distressed denim shorts (33% off!), a striped linen shirt (short sleeve version), sunnies, and pearl studded sandals over the gingham swimsuit (ruffle top, triangle top, bottom – all these pieces are on major sale!) I picked up earlier this summer in Nantucket. We had a yummy lunch at Salt & Honey. We liked the haddock sandwich and the french fries. Spending our last day on bikes and on the beach was the perfect way to end our time in Maine! Edwin can see himself spending a lot more time in Maine so we’ll see where the road takes us! My full Maine travel guide of where to eat, drink, stay, and shop is coming soon!

Rhyme & Reason Maine Travel Guide Rhyme & Reason Maine Travel Guide

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  1. My parents spend their summers in Maine, right south of Portland in Scarborough. Isn’t is such a beautiful area. It sounds like you all had a wonderful trip and went to so many great places. You hit up all my favorite spots in Portland + Cape Elizabeth. Duck Fat is my favorite and K.Colette is adorable.
    xo Nan // Simply Elegant Blog

    1. It sounds like I should have talked to you before my trip because you know so much! I’m glad we found some of the good spots! Duck Fat was honestly SOOOO yummy! XO, Jillian

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