Planning a weekend in Kennebunkport, Maine? This guide walks you through a 3 day itinerary we loved to celebrate our anniversary getaway slash mini babymoon in the gorgeous coastal town of Maine. This guide includes where to stay, what to do, and where to eat/drink in Kennebunkport!
Kennebunkbort, Maine Weekend Itinerary At a Glance
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- Day 1: Drive to Kennebunkport, Check into Bed & Breakfast Hotel
- Day 2: Shops, The Boathouse, Explore Town, Schooner Boat Ride, White Barn Inn
- Day 3: Bike Ride, Ogunquit Day Trip, Ice Cream, Earth at Hidden Pond
The location was perfect, secluded enough from the hustle & bustle of town, but still walking distance to all the stores and activities. Plenty of free parking available too.
Day 1: Drive to Kennebunkport, Check into Bed & Breakfast Hotel
How to Get to Kennebunkport
Arrivals into Kennebunkport, Maine. We rented a car and drove up from NYC which took most of Friday evening with typical rush hour traffic plus the increase with it being Labor Day weekend. We left after work and didn’t arrive until late at night around 11PM-12AM.
Alternative travel options would be to fly into the closest airport in Portland, ME and then drive into Kennebunkport. We recommend renting a car to make it easier to explore the area. If you don’t want to leave the town of Kennebunkport though, you could get by without your own car.
Where to Stay in Kennebunkport
We adored our stay at the Kennebunkport Captains Collection, and can’t recommend it enough for your weekend in Kennebunkport, Maine. Owned by Lark Hotels, who we also had an amazing stay with them during our 3 days in Newport, Rhode Island. The hotel is a cozy bed and breakfast, with each room having its own charm and decor. Our room came with a fireplace, and they have outdoor seating in the lawn along with free bikes for use. They also have a variety of games and a cute boutique shop downstairs.
The location was perfect, secluded enough from the hustle & bustle of town, but still walking distance to all the stores and activities. Plenty of free parking available too.
For alternative hotel options, you could explore White Barn Inn (luxury), Hidden Pond for a nature escape a bit further out of town, or the Nonantum Resort.
Breakfast at the Hotel
Enjoy a cozy, light breakfast at the hotel and take advantage of their amazing daily buffet spread and hot coffees/teas.
Explore some of the Best Shops in Kennebunkport, Maine
Walk down to town and explore some of the closer shops to the hotel. Some of our favorites nearby included Daytrip Society (also make sure to check out their kids store too if relevant for your), Seacraft Vintage (at Port), and Seas the Day (had adorable lobster sweaters).
Lunch at the Boathouse
Walk over to the Boathouse for lunch on the water with gorgeous views. We got there around 12 to put our name in and just beat the lunch rush. You can hangout at the bar if seating before your table is ready to have a drink and app. The food here was truly phenomenal. I was worried it would be an overhyped spot, but the fish sandwich was one of the best I’ve had, and we enjoyed every minute soaking up the sun outside with water views.
The N/A Heineken also satisfied my pregnancy itch for a beer – highly recommend for all the mommas to be! 🙂
Continue Shopping through Town
Enjoy wandering through all of the remaining shops in town. There are so many to explore with tons of amazing souvenirs treasures to bring home. We loved the Copper Candle to snag an ornament for our Christmas tree, they by far had the best selection in town if you like to collect ornaments on vacation!
Kate Nelligan also had the cutest ‘Go Fish’ shirts and the Knotty Elephant had such a lovely story we recommend hearing from the owner about the elephants. We of course had to snag their book for our future daughter. As you cross the bridge, note that some of the stores started to feel a bit junky, so the ones noted were our favorites and the ones prioritizing checking out.
‘Welcome to Kennebunkport’ Sign + The Clam Shack
Walk across the main town Mathew J Lanigan Bridge for the famous ‘Welcome to Kennbunkport’ sign. This is a great spot to snap some pics! Across the bridge is also where the famous Clam Shack is if you want to try a roll from there. We heard the place was overhyped so did not try during our weekend in Kennbunkport, and the line was insane over LDW! However, definitely still an option if you want to try a lobster roll from there.
Ice Cream Treat!
Stop by Ben and Jerry’s or Rococo’s to cool off with a sweet treat. Since I was exactly 20 weeks pregnant that day aka HALF BAKED – we of course had to get the half baked flavor from Ben & Jerry’s. However, Rococo’s is still high on my list to try and looks so cute and delicious with amazing reviews!
Dress Link – loving this transitional fall dress!
Schooner Eleanor Cruise
Drop off any bags of purchases back at your hotel and then drive to enjoy a boat excursion on the Schooner Eleanor. They had plenty of free parking right in front of the entrance. To make a reservation, call or text them at 207-967-8809.
The boat ride takes you all the way out to sea after first going slower through the town and heavily docked boat area. Note that this may not be the best cruise for you if you get seasick easily. Being pregnant, I was struggling a bit with the choppy waves as we got further out, however they gave some pressure bands to wear which helped. They also have blankets on board if you get chilly + binoculars to enjoy the views.
Dinner at White Barn Inn
Freshen up for a romantic date night at the White Barn Inn. This is definitely a special occasion spot, with a multi course meal. Everything we had was delicious, and the service was 10/10. There was live piano the whole night in a cozy barn setting. They even brought us desserts saying ‘Happy Anniversary’ which was a sweet touch.
Additional Weekend in Kennebunkport Activities to Explore
Breakfast at the Hotel
Bike Ride down Ocean Ave
Day Trip to Ogunquit, ME
Lobster Rolls at Foot Bridge Lobster
Marginal Way Walk
Explore the Town & Shops
Ice Cream at Scoop Deck
Dinner at Hidden Pond
Departures home. If driving back to NYC like we did, we decided to break up the drive home with some pit stongs along the way to explore new town and highly recommend our route:
- Elephantine Bakery in Portsmouth, NH – stop here for brunch. We had a light breakfast at the hotel before leaving to hold us over. There are a ton of cute shops you can explore afterwards in town.
- Newburyport, NH – another cute town with a ton of fun shops to explore. Make sure to stop in the famous Stonewall Kitchen store for some local northeast goodies! We picked up some maple cream for fall baking.
- Stop at either Rein’s Deli in Vernon, CT (where we stopped) or Frank Pepe Pizzeria in New Haven, CT (another favorite), for dinner.
Hope you enjoyed this perfect weekend in Kennbunkport, Maine guide and I’m always a DM or email a way if you have any questions!
xx,
