Portland, Maine

PORTLAND. Such a beautiful, interesting place.

We flew into Portland International Airport at the beginning of this week on Sunday, November 13th. As I’m writing this, I’m sitting at the terminal on the 19th, sad that I have to leave and go home.

Don’t get me wrong, I miss our family, house and our pets, Houdini the hamster and Twix the rabbit. (The latter is a newly acquired pet that I rescued from the wilds. She is so tame and so sweet—I still can’t believe someone just let her go! 😥) I am ready to go home, but hate to leave at the same time. Travel is one of those things that leaves the shimmery dust of magic on you, for at least 72 hours after you get home. Or until you have to go back into work. 🙄 Lucky for me, I am a full time pet sitter and love what I do! I’m actually happy about the Thanksgiving rush and all the puppies I get to see when I come back!

Travel is one of those things that people say truly makes you richer because of the experiences you have, not because it’s something you can physically hold or place on a shelf. Now, pictures you can keep—and I took so many! 📸


These are some pictures from the VRBO Artist Apartment we rented out on the West Side of Portland. At around $99 a night, it was a steal! The hosts are so amazing too and gave us a map and some inside intel on places we HAD to check out while we were there, especially restaurants. It was a 1 bedroom apartment with a bathroom, kitchen, dining and living room. All the amenities, but no tv. Which we actually loved! It made it easier to focus on writing, reading and spending time together instead. ❤️

I have to say, Portland, Maine is a great location. You can explore the city and if you tire of doing that, you can venture out to the Kennebunks, which are only 30 minutes away, Freeport and home of L.L Bean, which is only 20-30 minutes away, and other places like Brunswick, Bath and more! For the first two day leg of our trip, we stayed in Rockport, Massachusetts, which was only a 2 hour drive from Portland. It made it very convenient getting from destination to destination and the contrast couldn’t have been better!

When I planned mine and Tim’s trip, I picked Rockport and Portland because they are so different. Rockport has a definite small, Cape Cod vibe, whereas Portland is very spread out and bigger city. Tim also pointed out that our rentals, both through VRBO, couldn’t have been more different! The first was a cozy attic apartment over an ice cream parlor and the second was an apartment walkup in the West End of Portland, which had 10 foot ceilings! Tim would notice this, being taller than I am! 😂 Anything I call “cozy” gives him a concussion!

Both VRBO owners were PERFECT to work with. If you haven’t tried the service out, DO. It gives you a more unique experience and can be a lot more affordable than a hotel.


Tim and I have both said that one of our favorite things we did on this trip was visit Portland Head Light in Cape Elizabeth, only about a 12 minute drive from Portland. The actual lighthouse observatory was closed since November and much of this time of year is their off season, but the views were breathtaking along the cliffs and recreation area and there were less people around, so less people to avoid getting in your perfect shot! 👍🏻 If you happen to go in the summer, their rates are super affordable! Only $2 admission into the lighthouse! 😱 That’s crazy! And it is the most photographed lighthouse, the first one in our country commissioned by George Washington himself, so if you go to see ANY lighthouses, make it this one! 


For coffee, our patrons recommended Omi’s Coffee, just down the street from where we stayed. It was pretty good. There are also quite a few Coffee by Design chains in town as well as Dunkin Doughnuts, which got their start up this way in Massachusetts. They are literally on EVERY corner. For doughnuts to go with your coffee, you have to make a stop at The Holy Doughnut on Exchange Street. They are POTATO DOUGHUTS.  I know, sounds strange, but it’s the type of flour they use, so the consistency is a lot like a cake doughnut, which I’m a fan of. (Sorry, Krispy Kreme. 🍩) I had a fantastic lemon doughnut and Tim really liked the maple or maple bacon.

When we took a day trip to The Kennebunks, we stopped at a place called Jake’s Seafood. 


DO NOT PASS GO. DO NOT COLLECT $200. Just get yourself a lobster roll and thank me later. They’re about $17.50 with a side, but so worth it. It’s the food of Maine! If you come up here and don’t like seafood, I’m sorry, this trip is wasted on you. You can get your lobster roll traditional style in mayonnaise and cold like I did, or warmed and with butter like Tim did. DELICIOUS.

If you go into Freeport, a trip to L.L Bean is necessary. Take pictures with the boot. Explore all the stores, including home, ski and snow and hunting and fishing. 

Also, if you plan on driving a lot, I would say budget between $30-$50 for tolls, that being on the higher end. If you have an itenerary and sort of plan where you want to go, you can save by not doubling back or just knowing where you want to go.



Another great thing we did just before coming to the airport was checking out The Waterfront Fresh and Flea Market in Brunswick, Maine. It’s a little past Freeport. They do this Flea/Fresh Market most Saturday’s from 9-2. There were so many cool antiques that I sadly couldn’t fit in my suitcase to take home and so much delicious looking fresh vegetables, cheeses, and pastries and candies! It is definitely worth a stop and you can sample and buy some authentic Maine made products!

I am sad to leave Portland, but excited to go on our next adventure! Here are some other noteworthy mentionables:

1. Silly’s Restaurant

40 Washington Avenue

(Brunch on Saturdays, burgers and so many organic vegetarian options!)

2. Otto Pizza

Pretty much anywhere in Portland

(It’s a Portland chain, but so good! We had the Chicken and Basil Pie.)

3. Portland Art Museum

(Most hours are 11-8 and Fridays were free from 4-8!)

4. The Flea For All

585 Congress Street

(This place had some awesome vintage selections and everything was in great shape! Furniture, clothes, knick knacks and more!)

Goodbye, Portland! We’re going to miss you! 💋 

Have you been to the New England area? What are some recommendations you have? And better question, where should Tim and I go on our next trip?! 

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