Portland, Maine Travel Guide

How To Wear A Tunic Sweater
By Jess
13 Jun 2019
Visit Ogunquit, Maine for a seaside cliff walk and charming shops.

While Portland is a great destination regardless of where you live, I especially love that it’s such a short trip from Boston. A city that’s so close (an hour and a half or so by car) and can actually feel like you’re a flight away is the most ideal feeling for a weekend getaway. I can’t help but think of Portland as Maine’s version of Newport: there’s a lot of history and charm, with enough small shops and award-winning restaurants to keep you here for weeks—all located directly on the water. My favorite parts? The abundance of fresh oysters and lobster and the encouraged happy hours!

To Eat

  • Drifter’s Wife – A current hot spot for a truly delicious meal. While you’re there check out the restaurant’s sister wine shop, Maine & Loire.
  • Fore Street – A must! Reservations book up very far in advance but I think this is the best pick for quintessential Portland — farm to table ingredients, rotational offerings and a cozy, upscale vibe.
  • Eventide – It’s worth the wait for this lobster roll alone! Trust me — the constant crowds of people don’t lie.
  • Duckfat – Although deemed a tourist hotspot, the poutine at this quaint, yet well-known spot is really (really) great.
  • Blythe and Burrows – The best craft cocktail bar I might have ever been too. You know those places where the bartenders are like artists? Like that, in a super cool speakeasy atmosphere.
  • The Shop – Only the best oysters from the well-known Island Creek Oysters. Sit out on their open patio located up a few blocks from the bustle of downtown.
  • Scales – Great location and views and a fantastic menu.
  • The Holy Donut – Another Portland must! The Maine Blueberry is my favorite.
  • Sur Lie – Great for happy hour and tapas.

To Stay

Perkins Cove is a relaxing stop outside the city of Portland, where sailboats and tulips are abundant.

To Do

Wine Tasting – Portland may be known for its craft beer, but at the city’s newest wine bar, Grippy Tannins, you can enjoy a number of wines in an ultra chic and comfy setting.
Portland Museum of Art
The Portland Observatory
Boat Rides and Whale Watches – While there’s too many to list here, Portland offers many boat cruises and whale watches, if you’re interested in soaking up as much ocean-time as possible.
Live Music – My favorites were the Thirsty Pig and Portland Lobster Co.
Perkins Cove – A short drive out of the city will bring you to Ogunquit, Maine, home of Perkins Cove. Go here for a stroll along the cliff walk (also very Newport-esque), cute shops and multiple restaurants to indulge in casual summer food from whole lobsters to burgers.

Shop at Pinecone and Chickadee in Portland, Maine for everything from tarot to vintage Polaroid cameras.


Flea-for-All – A large vintage market, fun to treasure hunt through.
Exchange Street – From clothing to souvenirs, ceramics and stationary, this busy little street has something for everyone. And when shopping gets exhausting, head into the Thirsty Pig or Blythe and Burrows for a craft beer or cocktail.
Pinecone and Chickadee – This fun-to-explore shop offers a variety of fun items, including VHS and Polaroid cameras!
Strata – Walk up a few blocks from the bustle of Old Port to the ‘Black Boxes’, where you’ll find this shop, a dream come true for the home chef in your life. The craftsmanship of this culinary knife shop and whetstone sharpening service is pretty impressive, even if you aren’t going home with a hefty Japanese knife.
Mulxiply x Campfire Studios – Located in the micro space next door to Strata, this space offering jewelry and leather goods from Mulxiply and ceramics from local brand Campfire Studios is bound to be the perfect spot to pick up something for a loved one, or yourself, on your trip.

Stop by the Thirsty Pig in Portland, Maine for live music, hot dogs and pretzels and local beers.

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  1. Chelsea wrote:

    So glad this was posted! I’m going to Portland in September with my sister and will definitely be using this guide, thank you!

    6.13.19 | Reply
    • Jessica Lambi wrote:

      That’s great– I hope you have an amazing trip! — Jess

      6.17.19 | Reply
  2. Rach wrote:

    I’ve been wanting to go to Portland, Maine. Thank you for this travel guide!


    6.13.19 | Reply
    • Jessica Lambi wrote:

      Of course, so glad that you enjoyed it! — Jess

      6.17.19 | Reply
  3. Dee wrote:

    The fresh seafood sounds incredible!

    6.13.19 | Reply
    • Jessica Lambi wrote:

      Some of the best in New England, in my opinion! 🙂 — Jess

      6.17.19 | Reply
  4. Anne wrote:

    My hometown! I think Fore Street is a little overrated, and the Streets have better restaurants – Street & Co, Scales, Standard Baking, etc. But if you can get a rez, I wouldn’t turn it down.

    If you have access to a car, get off the peninsula! Go to Woodford F + B for mussels and fries, the Proper Cup for coffee (Tandem is also great on Congress!), Riverside for all of the breweries (Foundation, Austin Street, Allagash, et alia) and Tony’s Donuts (SO MUCH BETTER than Holy Donut; this is my hill to die on). Then walk/run Baxter Boulevard, accessible from the East End path, to burn off all that food.

    You can even go over the Casco Bay Bridge to South Portland/Cape Elizabeth. Get bagels from Scratch, ice cream from Red’s, and then enjoy an Italian sandwich from Amatos at Fort Williams/Portland Head Light, the oldest Lighthouse on the Eastern Seaboard.

    Love my city.

    6.20.19 | Reply
    • Jessica Lambi wrote:

      All great suggestions! Thanks for sharing! — Jess

      6.21.19 | Reply
  5. Jill wrote:

    I love Portland! I have a lot of family in Maine so I have been frequently. I absolutely love the restaurant, Duck Fat. Have you been to the restaurant, Central Provisions?


    6.23.19 | Reply

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