There is no better way to say goodbye to summer, than a romantic weekend in Kennebunkport, Maine. A two night’s stay is all you need to see the sights, soak in some Vitamin sea, and eat seafood to your hearts content.

Below is our low-key, romantic itinerary for our stay. It includes where we stayed, exercised, shopped, ate gluten free and took amazing Instagram photos!

(Disclosure: Some of the product links in this post are affiliate links. This means if you click on the link and book a vacation, I will receive a small affiliate commission. This helps keep my blog running!)

Day 1: Kennebunkport, ME

Morning: Shopping

Outside of downtown, Kennebunkport, has the cutest shops! Après Sea Maine is nestled between mini coastal cottages. Each decorated with shiplap walls and filled with all things New England. Après Sea sells jewelry, handbags, ocean inspired artwork, clothing and more.

Around the corner is a pop-up shop. At the time, Jill Home, was selling her home decor. I picked up a set of bookends simply decorated with white sand dollars. Tip: If you like these oyster trinket dishes, check out my How To Decoupage Oyster Shells blog post.

Lunch and coffee

It was lunch time and we were ready for food! Parking is extremely hard to come by in Kennebunkport, Maine. My suggestion is to go directly to the parking lot. Address is 30 North Street, Kennebunkport, ME.

We ate lunch at Allisson’s Restaurant. Located directly on Dock Square, it is easy to find. While they don’t have a gluten free menu, there are items denoted on the menu. We had the gluten free pizzas.

It was a hot day and after pizza, we had a hankering for iced coffee and a sweet treat. We took a walk over the Mathew J. Lanigan Bridge (Photo Op) and up the hill to Mornings in Paris. There we tasted the best macarons we’ve ever had coupled with a smooth coffee. No other gluten free options here!

Afternoon: Shopping & Check-in

Walking back over the Lanigan Bridge is the Dock Square Emporium gift shop. I found the most delightful travel bag! If you are looking for a gift, this is the place to visit.

3:00pm is check-in at the Yachtsman Hotel and Marina. A touch-less process from start to finish. Certainly, this hotel is a dream! Forgive me as I gush for a bit.

Yachtsman Hotel and Marina Customer Review

  1. Designated parking spots in front of your room!
  2. Keyless entry through OpenKey app that works from 3:00pm check-in to 11:00am check-out.
  3. Single level hotel. No one above you walking on your head!
  4. Every room is on the waterfront with landscaping ideally placed for privacy. Watch the boats come and go all day if you like! Also a perfect spot to watch the sunset.
  5. Walking distance to everywhere you want to be in Kennebunkport, Maine.
  6. Breakfast delivered in a little brown-bag to your room each morning by 8:00am. (Sadly, no gluten free pastries despite requesting them in advance.)
  7. Free bikes to ride around town.
  8. 2 hour complimentary use of kayaks and paddle boards.
  9. Beautifully decorated room that you’ll never want to leave!

After check-in, we made the short walk back to Dock Square for more shopping. My last shop to note is Sea Love Candles and Company. If your romantic getaway gets rained out, stop in here and make candles together! Too busy for a class, pick out your favorite scent and purchase one to go. We did!

Yachtsman Hotel and Marina Guest Room Door Keyless Entry

Evening: Dinner & Sunset

Finding gluten free restaurants in downtown Kennebunkport without a reservation is a bare. Our dinner reservation was cancelled by the restaurant.

Consequently, we opted for a meal in Wells, Maine at Las Olas Taqueria. A fast casual Mexican restaurant. I let the server know of my gluten allergy. As a result, she changed her gloves, cleaned the surfaces and brought out fresh ingredients from the back kitchen.

After dinner, we let our food digest while watching the boats from our patio. I set my camera and tripod up and captured a few sunset photos.

Day 2: Kennebunkport, Me

Sunrise, exercise & breakfast

As a photographer, capturing the sunrise and sunset brings me creative energy. Waking up before the sun stinks, but it’s worth it!

We drove up the street to Colony Beach. There is limited parking on the side of the road. However, at that hour plenty remained. The jetty and beach are a perfect spot to capture the sunrise!

Afterward, walk the Parson’s Way trail along the road next to the ocean. It takes you from Colony Beach to the President Bush Compound on Walkers Point.

We worked up quite the appetite! Next stop, Mike’s All Day Breakfast. They are sensitive to allergies and offered gluten free toast and home fries. We both agreed that the toast was amazing!

MidDay Site Seeing

We parked back at the Yachtsman Hotel and Marina, freshened up and walked toward the ocean. Taking photos along the way, resting on a bench to watch the boats and enjoying the sea air.

We walked past Colony Beach and found our way to St. Ann’s by-the-Sea Episcopal Church. What a beautiful setting with views of the ocean. You can tour the church or sit on the lawn and read a book.

late Lunch

On our walk back to the hotel, we popped into The Colony Hotel. This dog-friendly, chic beach resort with saltwater pool has photo ops everywhere. It’s also a great place for lunch!

We ate at the Poolside Ocean Terrace. A corner table with views of the pool and Atlantic Ocean. It was perfect. Not the most gluten friendly restaurant, but they were accommodating.

I ordered a lobster sandwich with coleslaw. The lobster came out in a small dish with toast on the side. While it wasn’t how I imagined it, the lighter fare coupled with my berry margarita was perfect.

Rest and relaxation

The rest of the afternoon was enjoyed in our Adirondack chairs, napping and deciding on where to eat for dinner!  We decided on take-out from Bandaloop in Arundel, Maine.

This bistro and bar offer organic global fare with vegetarian options. I had the Pan Seared Haddock with lemon-horseradish aioli, saffron basmati rice and a summer vegetable medley. We ate on our private patio. The Yachtsman Hotel and Marina decorate each spot with Safavieh woven french bistro sets positioned by the Kennebunk River. It was a wonderful beginning to our last night on the Maine seacoast.

Following dinner, we walked over to the bar, picked a spot by the firepit and ordered a couple drinks. We stayed until closing time, walked back to our room and slept like babies.

Day 3: Kennebunkport, ME

We rose with the local early risers and walked to the ocean and back. A brisk, somewhat damp morning that prepared us to say goodbye to this seaside hideaway.

Yachtsman Hotel and Marina starts serving coffee at 8:00am so we stopped by for our first cup of caffeination! We enjoyed the yogurt, fruit and fresh orange juice supplied by the hotel for breakfast.

We took one last walk along the marinas, popped into a few stores that had been closed and finished with packing for the road trip home.

Romantic Getaway to Kennebunkport Summary

In conclusion, you can be as busy or as relaxed as you like in this seacoast town. Ride bikes, take the kayaks down the river, walk the local trails and have an adventure seekers getaway. Sleep in late, drink your coffee in complete privacy overlooking the water, take a stroll through tourist-free back roads and sun yourself on the one-of-a-kind floating barge pool for the complete romance getaway. There is something for everyone here.

Let me know if you have any questions in the comments section below. I am a New Englander and love to talk about my home!



Diagnosed with Celiac Disease eleven years ago, I've been on a journey discovering what it means to be truly healthy. Join me as I share my personal fitness goals, gluten free recipes I've tried, travel tips, curly hair product reviews and all things creative.

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