Portland, ME Travel Guide

Looking for a quick, relaxing getaway? Portland, ME is only a few hours drive from NYC area,

and is the perfect place to unwind, explore and wine and dine!

I just got back from Portland on a lovely little extended weekend with my girlfriends,

and I'll tell you everything we did while we were there to make our experience unforgettable!


We traveled from Long Island, so we took the Orient Point ferry to New London, CT. It was around $100 for the car & driver + 2 passengers and priority boarding. From New London it was about a 3 hour drive to Portland, passing through CT, MA, NH and finally ME. We were honestly expecting the drive to be a little more, scenic and coastal, but it was still cool seeing Moose crossing signs all over (although, no Moose to be found!). We only filled up with gas twice the entire trip, and the tolls were all under $5, but, for convenience sake, don't forget your EZ pass!

Parking in Portland can be annoying, especially in the summer, so I highly suggest renting bikes if its nice enough, or finding an AirBnb with free parking that is walking distance from town (like we did)!

Uber is also available for the too cold, or too hot to walk days

Air Bnb:

We stayed in the CUTEST little apartment, about a 15 min walk from Downtown. The coolest thing about Portland by far is the character of the buildings there. It looks straight out of a history book, complete with cobblestone roads (in Old Port). All of the architecture is amazing, and every house has such a lovely, old fashioned feel; ours featured all original fixtures, beautiful stained glass windows, a fire place, and a balcony! You can stay in the Port City Nest on your next trip to Portland, too!


Gritty’s (you gotta go to gritty's, its apparently a Maine staple, all the locals pointed us in its direction)

Holy Donuts (you gotta try the: Strawberry Mango & Sweet Potato Sugar)

Pai Men Miyaki (you gotta try the: Sake Lemonade, swap a soy egg for raw egg yolk in your ramen!)

Taco Escobar (you gotta try the: Prickly Pear Margarita)

Gelato Fiasco (you gotta try getting it delivered late night from Uber eats!)

Hot Suppa (you gotta try the: Cajun Bloody Mary)

Shipyard/Rising Tide Breweries (you gotta try: Beer flights!)

DiMillos (you gotta try the Tito's Jam and Lobster Mac N Cheese)

Novare Res Bier Cafe (you gotta try the late night CHEESE BAR)

Dutch’s (you gotta grab a chocolate chip cookie to go!)


-Walk around and shop in Portland/Old Port (Lots of great bookstores, like Green Hand & Yes Books) (Mexicali blues is our favorite shop in Old Port, the owners are world travelers and source all of their goods locally on their wanders, plus 1% goes to charity!)

-Hike to some waterfalls (Jewell & Cascade Falls are near Portland)

-Portland Art Museum

-Rent Bikes & do your own brew tour

-Cape Elizabeth, Coast & Lighthouses

-Portland Head Light & Fort William Park

I hope you all enjoyed my travel guide to Portland, ME and are just as ready as I am to plan your next adventure!




Recent Posts
Wander With Us
  • Black Instagram Icon
  • Black Pinterest Icon
  • Black Facebook Icon
  • Black Twitter Icon
  • Black Instagram Icon
  • Black Pinterest Icon
  • Black Facebook Icon
  • Black Twitter Icon