Travel this Land: 48 Hours in Portland, Maine


Portland, Maine is LOTS of fun. That’s how I would sum up our 48 hours there. It’s got small fishing town vibes packed with restaurants and bars that’ll keep you smiling and laughing your whole way through. On our 14-day road trip up the east coast, we spent 2 nights in Portland and loved every minute of it. I’ll break down the details for you.


We traveled in late September, early october. Specifically, we were in Portland from September 27-29th! I’m guessing this city would be even more fun when it’s a little warmer but we had great fall weather and sunshine.

We stayed in the great Airbnb in Cape Elizabeth. It’s not in downtown Portland but it’s a 5-minute uber ride and closer to the Portland Headlight and some pretty cool beaches. If you haven’t tried Airbnb yet, you can get $40 off your first trip when you make an account with this link. We stayed in the upstairs unit of the nicest couple’s house. We had 2 whole bedrooms and a full bath to ourselves. It was perfect.

Here’s a little itinerary of what we did:

Wednesday, September 27th: we arrived in Portland in the evening, checked into our Airbnb and booked it for downtown Portland. We ate at the Porthole where we got the famous twin lobster dinner for like $35! Our waitress showed us how to eat the lobster (we were scared to ask, haha!) and then we went to this cute like bar called Andy’s for I’m not kidding the BEST blueberry pie we have ever tasted. And then headed back to bed, we were exhausted from driving up from NYC. You can tune in to our day here in Nic's fancy travel vlog. 

Thursday, September 28th:
We woke up and went straight to Holy Donut. It’s a famous donut place in Portland that makes potato donuts! They were really great. Then we explored downtown, walked a ton, got to see the cool fishing boats, bought some touristy magnets, and  then headed to the Portland Headlight. It’s one of the OLDEST lighthouses in the country and it was beautiful. It’s a must see! We also got to snag our first Lobster Roll right there. Nic liked it but honestly, I was like eh. It was like TWENTY TWO DOLLARS or something crazy.


We went back to our airbnb until we got ready to head to dinner! We started the night at this secret (literally!) bar called Lincoln’s. It’s really fun and everything there is $5. But you aren’t really supposed to take pictures and tell people about it. So that’s that. :) And then we ate at J’s Oyster Bar and it was decent but it wasn’t anything to be super crazy about it. The food here in Portland wasn't spectacular, but it was normal and the drinks were great so there's that. 

Friday, September 29th: 
We got an early start towards Bar Harbor but on our way out of town we stop at one of the most beautiful beaches in Portland. We enjoyed Trundy Point and set out up Route 1 towards Bar Harbor. If you happen to take a trip like ours, it's a must that you stop at Sarah's Cafe. We had one of the best meals of our whole trip there and you'd really be missing out.