Maine Road Trip Stop 1: Portland

Icon Share

SHARE

Advisor - Sydney Getzin
Curated By

Sydney Getzin

  • Arts & Culture

  • City Travel

  • Domestic Travel

  • Food & Wine

  • Road Trip Travel

  • Portland, Maine

  • Maine

  • Local Culture

Advisor - Maine Road Trip Stop 1: Portland
Curator’s statement

Anyone who knows me knows I love Maine. I think about moving there constantly. Sometimes it feels like destiny, sometimes just a pipe dream. Either way, Portland has my heart. Whenever I am in Portland, I have only a small list of priorities: Eat, wander and pretend I live there and quench my thirst with the local tap — and in that order. So THIS is my Portland laundry list. Everywhere I’ve been. Everything I’ve tried. Places that I frequent. Places that I still haven’t checked off my list yet.

The Fora Difference

Book with Sydney to access exclusive perks and experiences on your trip.

Icon Travel Perks
Killer perks

Free upgrades, spa credits and more—we got you

Icon Recommendations
Personalized recs

Customized travel planning for your style

Icon Inside Knowledge
Insider knowledge

Expert advice from people who’ve actually been there

Where to stay in Portland, Maine

Unlock perks by contacting Sydney to book your trip.

Things to do in Portland, Maine

ONGGI @ Washington Ave

Note: If I haven’t yet visited somewhere or done something, you'll see the ☐ symbol.

WANDER.

A must walk: Eastern Prom and food trucks with a view. Beach optional.

Washington Ave: Stop at ONGGI, Strata, Cheesemongers, Post Supply

☐ Free Fridays: 4-8 pm at the Portland Museum of Art

Farmers Market Saturdays: 7 am-1 pm in Deering Oaks Park

☐ If you want to see a lighthouse, Cape Elizabeth and Fort Williams Park are nearby!

☐ Day trip: Peaks Island hopping. Ferry is super easy! Or just ride the ferry without getting off with Casco Bay Lines.

Gifts for you and your loves ones: Blanche & Mimi, Soleil, The Merchant, where we like to pick up new sticker art from Jo Moyer-Battick.

For bowling with beer: Bayside Bowl

☐ When I move: Eight-week class at Portland Pottery (also cute breakfast)

Places to eat & drink in Portland, Maine

Crown Jewel - A destination cocktail bar on Peak's Island, a ferry away from Portland!

EAT.

Stream of consciousness. Everywhere I want to eat depending on what I’m craving. Semi-ranked from top to bottom. But the bottom of the list is still made up of some of my favorite places to eat on earth.

Fore Street - It's farm-to-table famous for a reason. There would not be a Portland, Maine, dining scene without it. Despite the $$$s, it’s worth it. If you like to cook, just witnessing their vegetable pantry will make you drool. Make a reservation. Last time I was there, we had an oxtail caramelized onion tart. Wood-fired squid. Wood-fired Caesar salad. Venison. Duck. For dessert we saved room for the downstairs bakery that supplies breads and sweets to the restaurant …

Standard Baking Co. - The frangipane tart is my favorite. We like to grab a big bag of baked goods to take home on our way out.

Izakaya Minato - The fish is SO fresh. Go with the chef’s table if you don’t want to make decisions.

Pai Men Miyake - My favorite ramen

☐ Regards - LA meets the Maine coast

☐ Papi - Opened in 2023 and the people love it

Leeward - Pasta and veggie forward

Mr. Tuna (food truck) - Handrolls and tataki, please

Cong Tu Bot - Bun for me

Duck Fat Shack - Frites, what poutine dreams are made of

Boda - Thai since 2010

☐ Terilingua - BBQ with a side of patio

☐ Woodford F&B or Wayside Tavern - Better in the winter / cozytown

Belleville - Croissants

Rose Foods - Bagels and lox

Hot Suppa - For brunch

QUENCH.

Okay, so, while I don’t drink beer, the people I love the most do. The brewery scene in Portland is incredible (duh). You really can’t go wrong. These are the two places we frequent most, and one that’s on our to-do list.

The best IPA: Bissel Bros. The substance. Not the movie!

The best saison: Oxbow and fries: Why go to to the original Duckfat location, when you can drink outside or with live music, no lines and still get poutine.

☐ Family favorite: Belleflower Brewing. Fellow dog lovers. Scrugsy.

And now my not-beer drinking list:

For fancy cocktails: Blyth & Burrows (heads up, your drink might be on fire when it’s served to you)

More fancy cocktails, but make it après: Portland Hunt + Alpine Club

☐ Even more cocktails, but on a beach with fried chicken: Crispy Gai

☐ Destination cocktails: Crown Jewel on Peak’s Island. Only open in the summer!

For kombucha: Root Wild. In the summer, try the frosé booch.

For sidra and funk: Anoche Cider Bar

For bottles to take home: Maine & Loire

Best coffee: Moonday on Washington Ave. Maple latte for me.

☐ Local favorite: Lambs in South Portland.

Need to know

Don't just spend time in Old Port. Make sure you explore the West End & Munjoy Hill neighborhoods.

Advisor - Sydney Getzin

Travel Advisor

Sydney Getzin

Get in touch with Sydney

Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can normally expect a response from Sydney within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).

For more inspiration and insider recommendations, visit our Portland, Maine page.

We use cookies to enhance the user experience. Read our Privacy Policy here.