DAY TRIP: Portland, ME

Hello bloggers, readers, and Thursday!

Today I’m going back in time to Monday 1/2/17. I still can’t believe its 2017; and that 10 years ago I graduated high school?! And 6 years ago, college?! Okay fast forward again to Monday.

Yes, my me and Andrew’s Monday Funday Adventure. We both had Monday off, it was fairly nice out, and it was my last day of the long weekend… So what better than to go on our first day trip in 2017!

We were brainstorming different ideas and places until Andrew suggested we go back to:


We had gone last August, Andrew planned it for my birthday and both of us loved it out there! You can read our Maine Adventures HERE



The Piscataqua Bridge to know we’ve made it into Maine!


Love this guy entirely too much!


Entering Downtown Portland #wemadeit


I personally love Portland not only because it’s right on the water but I love the brick buildings in their downtown and the mesmerism cobblestone streets. Their downtown is actually quite large, filled with stores, shops, retail, bakeries, restaurants, bars & taverns- you get the idea.



It’s actually even larger than I thought. The last time we came we explored the 2 parallel streets but this time we went even deeper and noticed it extends back even further.



We also went back to the same spot we took pictures last time by the water-



And these were from the summer

And then one last picture before dinner time by the cobblestone streets.


We were debating on going to the same restaurant we went to last time; DiMillios (omg, I loveddd it there)

But we decided to try somewhere new which I always am down for new


My haddock and Andrew’s salmon were cooked to perfection. We also had some oyster meatballs- delicious. Very happy we tried this place!

And just like that, it was 6PM, pitch black out so we headed back to home bound.

It was a perfect little day trip!

xo, JJ


51 thoughts on “DAY TRIP: Portland, ME

    • lovejennyxo says:

      Salmon is definitely a favorite of ours…. weird question but do you like yours seared or grilled lol I was just having this conversation with Andrew last night and I was saying I like mine seared because I love the softness of it. But I think hes more of a grilled type.


  1. ayrgalaxy says:

    Every time I see Portland I’m like “Heeeyyy…oh wait… nevermind.”
    But if I remember correctly, birds and bridges creep you out. We have both of those and a lot of them lol.

    I love it that you guys call it downtown Portland too lol. And it also sounds the same as over here. E have plenty of little shops all over the city. Both well known and others that are like hidden gems. I love the cobblestone streets though. Our max runs through the city so we have regular streets lol.

    I love the sculptures right in the middle. We have sculptures all over the place too. Omg they sound like sister cities! Lol. Sorry I’m excited lol.

    So cool!! 🙂 and how far is Portland from you guys?


    • lovejennyxo says:

      Thank you, it really is pretty there I think its the color of the brick against the gravel and cobblestone contrast. And then I love that just across the street is the water! Perfect little place! Thanks for reading! xo

      Liked by 1 person

      • afrilly says:

        Very cool! : ) If you’re ever in Canada, you should check out Vieux-Québec in Quebec City. It’s also got the brick, cobblestone, near water, old-timey feel, and it’s /très French/. :p :p


    • lovejennyxo says:

      The food is definitely great here, especially if you’re a seafood lover. I love the East coast for sure, born and raised over here but I do love that each of the coasts are all so different, it makes traveling so much more fun. What places in the East Coast have you been so far?

      Liked by 1 person

      • Melanie and Todd says:

        I have been to the Maryland/Virginia area… did the whole capital scene and the beach! It was fun for sure, new atmosphere since I am from the west coast so I loved it! Still trying to make my way to New York sometime! anywhere there is good seafood and I’m there! Lol



    Awww daytrips are so fun! Never knew about Portland, Maine, but you’re right it’s beautiful :)) cobblestone streets are always special bc they’re unusual & I mean how long have they been there?? Like what historical figures walked on the same street?! that’s what I always think!
    I just moved to North Dakota, so soon we will be taking day trips around the area when the weather allows. Also, that’s a cool bridge — bridges are always fun moments on road trips lol

    Liked by 1 person

    • lovejennyxo says:

      Woah girl, I love that thought (historical figures walking on that same street) So true, now I’m going to be thinking that everywhere I go! I have a friend over in S.Dakota and she literally always snaps me all the snow they get over there! It makes me feel a little bit better about New England weather though lol Is it still like that currently?

      Liked by 1 person

  3. Mackenzie says:

    Whattt I am obsessed. That place looks magical. I didn’t know there was a Portland, Maine! Ahhh I have to add it to my bucket list (which has expanded greatly from blogging). And Oyster Meatballs- you go, my lil foodie, you. So proud ❤ That sounds soo tasty! What a fun day!!!! Ya’ll are too cute.

    Liked by 1 person

  4. K.M. Sutton says:

    I heart this blog post so much especially since I am already homesick! I grew up seventy-five minutes from Portland and always fly into the airport there. If you guys ever stay the night, I highly recommend Top of the East ESPECIALLY at sunset. It is stunning with views of Portland and the ocean. Also The Grill Room and Fore Street are two of my favorite restaurants. Oh and there is a coffee shop called Arabica. So yummy and cozy. Oh my gosh now I am hungry AND homesick 😉 ❤

    Liked by 1 person

    • lovejennyxo says:

      Is Top of the East right in that downtown area? I for sure think we’ll be going back again this summer, we just love it there! Also totally noting those restaurants, we were yelping places to eat but like every place is 4+ stars so it was so hard to just choose one lol so we ended up just choosing the one closest to where we were at that exact moment. Now I feel more prepared for next time 🙂 Thanks for the suggestions theyre always appreciated!!! xoxox

      Liked by 1 person

      • K.M. Sutton says:

        It might be more outskirts of downtown. It is amazing! When I get sick of New York I could see myself moving there.
        Haha it really is! Everything is so yummy! Fore Street does require reservations in advance, though they also do have some tables set aside for walk ins. ❤

        Liked by 1 person

  5. Krista Aoki says:

    I’ve been wanting to go to Portland Maine for a little while now! I rarely make it to the East Coast. Wow, what freaking amazing pictures though! It looks like a quaint town. Aaand you and your boyfriend are so cute!

    Liked by 1 person

    • xoJenny says:

      Portland is surely a must-go! Of course definitely more in the summer months since it’s surrounded by water but its such a great little town! Where do you live if you don’t mind me asking!


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