I’m so excited to finally be sitting down to write this blog post. I mean it when I saw that our most recent trip to Maine over Labor Day weekend was probably one of my top 5 favorite trips I’ve ever taken! I went back and forth on how to structure this blog post, but I think the best way is to summarize everything that we did, covering our favorites and how we structured our time there. And then you can let me know if you have any questions.

How’d You Decide To Go?

Since we knew Duncan’s first day of his new job in Denver was the day after Labor Day, we wanted to go on one last trip before his official move to Denver. And we were pretty set on going somewhere up north since we’d been struggling through the Texas heat all summer. August can get pretty brutal and if you’re in the south, then you know what I mean.

I’d actually been to Kennebunkport before because one of my good friends actually worked as an aid for the Bush Family. She spent 6 months out of the year up there and so I’d gone to visit her one summer and absolutely LOVED it! So when we were brainstorming places to go, I was like I know just the place! I showed him a few photos of how cute the little town was and he was immediately in!

Where’d You Fly Into?

We flew into Boston and rented a car. The drive is only about an hour and fifteen minutes, so it really wasn’t bad! You could also fly into Portland, Maine and do the same thing if that works better with where you’re coming from. I think these are the two closest airports though!

Above: Kennebunkport Inn

Where’d You Stay?

I had remembered visiting Kennebunkport Inn for drinks while visiting my friend and so I thought that’d be a great place for us to stay since it’s right in town with everything, so that’s where we stayed. Plus, it’s just so dang cute and classic! And although I’d recommend it, there are so many other places to stay as well that we discovered while exploring.

What Are Some Other Places To Say?

Here are some of the other places we visited and thought would be fun to consider next time:

Cape Arundel Inn

We got drinks here one night before dinner and watched the sunset. The Inn is along Ocean Ave and has the most beautiful view! It’s right by Walker Point, which is the bush compound in Kennebunkport.  It’s not too far from town either so you’re close to everything but have a little bit more privacy than if you’re staying somewhere in town. There’s also a nice restaurant at the Inn – we didn’t visit it though.

Above: The Colony Hotel

Above: Pool at the colony hotel

The Colony Hotel

We visited this spot twice during our trip and loved hanging out here. We went one night to watch the sunset before heading to dinner and then another afternoon to hang out and have drinks by the pool. This place is a little older, but the location is great as well.

It’s a little (like down the street) closer to town than Cape Arundel Inn (along the same road), so obviously walkable to everything too. The pool area is GREAT.

I think my only hesitation with staying here is that it’s REALLY BIG and I personally feel like the hotel might need an update; you can tell it’s older which gives it a lot of character but I’m not sure about the rooms? Don’t take my word for it, though, because I never saw the rooms. I’m just going off of what I saw in the common areas and lobby.

The Yachtsman

I didn’t actually didn’t get to check this one out in person (there wasn’t really much of a lobby and I didn’t ask to see the rooms), but a few locals recommended this place. Apparently, it used to be a motel and was recently redone by a popular designer in the area and turned out really neat! So maybe look into this one too – it’s a great location. It’s also along Ocean Ave with all the other spots to stay.

What Did You Do in Kennebunkport?

Even though there are plenty of things to do, we mostly just did a lot of walking and eating! Which, quite frankly, is all I really want to do when on vacation.

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We did plenty of walks down Ocean Ave – all the way to Walkers Point and back (which is about 2 miles from the center of Kennebunkport – Dock Square). Definitely got my 30+ minutes of walking in each day!

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It’s really fun to just walk around town, wandering in all the shops and just taking in everything. It’s such a lovely little town!

The one thing I wish we could have been able to do was go sailing or get on a boat. But since it was Labor Day weekend, ALL the trips were already sold out. So I would suggest booking that ahead of time! There are only a few companies that offer boat trips and I think that for the most part, assuming it’s busy season, the trips book up quickly!

Dinner sitting at the bar at Earth restaurant. We love getting a bar spot when traveling because you feel more immersed in the city/feel, ya know?

Sunday morning brunch at Kennebunkport Inn! Honestly, the food wasn’t that great but the atmosphere is so so lovely that it’s worth fitting it in! Either brunch or even just grabbing drinks outside on their patio one day.

We ended up going to this place (The Spirit Resturaunt) twice because we loved it so much. If you saw my stories (which I saved to highlights), this was the restaurant that was literally on a boat. And the weather was so nice, that it was lovely sitting outside and we made some friends at the bar too.

We took this photo the night that that we had dinner at Earth (early) and then headed to the colony (where this photo was taken) to have drinks and watch the sunset! It was so so beautiful!

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We had dinner here (at Hurricane restaurant) one night and loved it so much! Then we were walking home from dinner one night and heard a party going on with a live band so we stopped to see what it was all about. And we ended up having a BLAST and making so many friends! The band snapped this photo of us while dancing! It was so so fun!!

I’m not sure which nights they do it, but they have life music on the patio at Kennebunkport Inn and it’s really fun to sit and get a drink before  dinner or grab an appetizer!

Where To Eat in Kennebunkport

Oh boy! There are so many great spots to eat here – you truly can’t go wrong!! I’ll list a few them out for y’all, but honestly it’s all really yummy!

Hurricane

It’s a little more on the fancy side, but SO delish and so fun! This is OUR KIND OF SPOT! We loved it so much we almost went there twice! Well actually, we did end up going there one night after dinner because they had a live band and we ended up making so many friends! It was a blast!

Earth at Hidden Pond

It’s a little hard to get into, but TOTALLY worth trying! They open up at 5:30, so I recommend getting there at like 5:15 and snagging a spot at the bar. You won’t be disappointed! We loved the bartender and the other couples sitting at the bar too – made some more friends there too lol.

Ports of Italy

You can’t miss this place because it’s right in the middle of town. We had the BEST Italian food here one night and heard from some locals that it’s one of their go-to spots. It’s a fun atmosphere and apparently the Sunday brunch is amazing too if you have time to catch that!

Pilot House

One of the locals told us this place is amazing. It’s super casual and great for lunch. We didn’t get a chance to go because ended up going to the Spirit House twice, but next time.

Old Salts

Cuttle little shack with amazingly yummy breakfast sandwiches!

Mabels

So many of y’all recommended we eat here for the lobster rolls (it was my first ever)! So we had to give it a try and you guys were right, they did NOT disappoint! We ended up going for lunch but it looked packed at dinner time too. It’s a casual atmosphere and a relatively small spot, but I’d say it’s definitely one you can’t miss.

Visiting Ogunqit, Maine

After spending a few days in Kennebunkport, we heard we HAD to go visit Ogunqit if we had time to drive down the coast a little. So we actually changed our plans and decided to spend a night at the Cliff House over there.

And after getting there, I wish we could have spent more time there. You guys, it was INCREDIBLE! We loved it so much that we didn’t even venture out of the hotel. But there’s a whole other cute town (Ogunqit) that we didn’t even get to explore. So I for sure want to go back there on my next trip!

Outfit Details

Lululemon align leggings (LOVE FOREVER) // Z Supply Leopard Sweater (wearing size XS – love the oversized fit and the side slits) // Gucci loafers (linked similar) // Celine Bag (linked similar)

 

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Madewell skinny jeans (size down one size) // Booties (got at the NSALE!) // Topshop printed tank (wearing size US2)

Outfit Details:

Ribbed Knit high-waisted pants (SO COMFORTABLE! Wearing size XS) // Rails leopard top (wearing size XS) // Sam Edelman Pumps