Places You Go And The People You Meet: Maine

Today I decided to reminisce on my birthday trip to Portland, ME because come tomorrow it’ll be one month since my birthday. This trip, which ended up being more of an adventure through Maine was one for the books.

As one of my birthday gifts from Andrew he booked us a stay up in Portland which I was really excited about because I’ve never been. I’ve grown up going to Ogunquit and Wells so I know those areas quite well. And as good as I am at planning things, I actually loathe planning anything and to my surprise I didn’t have to plan a single part of this trip; Andrew did it all(:

So the morning of, our first stop was to Old Orchard Beach to lay out and soak up the sun.


First we got some lunch at Myst Oceanside Restaurant. Little did we know that this was going to be the start of a Seafood frenzy for the whole weekend.


After laying out all day, up on the pier.


More food on the pier. I had the best view & overseeing the water wasn’t bad either(;


En route to Portland. Which was only about half hour from Old Orchard.

We got to the hotel, checked in, showered, and got ready to explore and more importantly eat! Andrew knew of this awesome restaurant called DiMillio’s and OH MY, this might be my favorite place! It’s a huge boat/restaurant that sits on the water which in itself is really cool but the food, the food is to die for. The ambiance is fancy and high class with fine dining meal options- highly recommend it!

(These 2 pictures of DiMillo’s we’re taken off of google images..thanks google!)


Us in DiMillio’s waiting for our table. We didn’t even mind waiting because you’re surrounded by water and boats everywhere.

The next morning we went to explore downtown Portland, which was one of the cutest/best downtown areas I’ve been to.


A little added perk: Gelato places EVERYWHERE. But what I loved the most was the cobblestone roads and the brick buildings it was old fashioned yet modern and very clean.

We made our way back near DiMillio’s because the water front over there was gorgeous, and of course took 100+ selfies there.


Andrew actually bought me a selfie stick for my birthday but we came to realize that our arms are the best selfie sticks around.

From there, we were 1. thinking about where else we could adventure to and 2. our commute back and the traffic that was to come. Collaboratively we decided that we’d have a little more mettle if we stopped at different spots along the way home.


I was pretty excited because I’ve driven by Kennebunk more times than I can count, yet, I’ve never actually gone to explore the area.

Andrew felt like he needed more of a tan so we ended up here:


Kennebunk Beach; which I can never oppose to laying out and bronzing. The nice thing about this beach was that it was fairly secluded so we had the majority of it to ourselves.

Once we started getting hungry we decided to make our way to Kennebunkport which is the downtown area. I thought I loved Porland’s downtown but Kennebunkport is a close second. Super cute beachy downtown- it almost reminded me of Martha’s Vineyard (nostaglia).

When we got there we found another cute restaurant on a boat in the water called The Spirit and had some of the best seafood tapas. I’m talking about lobster sushi, shrimp spring rolls, and chicken tacos.

We explored, shopped, took some more selfies.


Next stop: Marginal Way in Ogunquit

Andrew’s never been to the Cliff Walk at Marginal Way let alone Ogunquit so it was time to show him my neck of the woods. We made it just in time for the sunset and it was a perfect first time for him to see it.


Last stop of the day: Kittery

It was getting late, however, the traffic was still going strong so we were brainstorming what else we could do to skip over it.

So, we ended up in Kittery for none other than…. PIZZA. Which I did have a picture of it on my snap day of but that’s no longer accessible. Luckily everyone knows what pizza looks like.

And finally made it back home safely. Such a great birthday weekend thanks to the best guy! Feeling blessed and thankful for him.

xo, JJ


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