The best lobster rolls! This food truck is also conveniently located at the Portland Head Light, the famous historic lighthouse with incredible views. If you want to stay in Old Port, Highroller and Luke’s are two other great options.
Amazing Mexican BBQ, particularly the brisket and pulled pork!
Incredible hoagies! Check out their sister-restaurant Benny's (Philadelphia Italian restaurant) for cheesesteaks!
Amazing Italian food! Try the radiatore and the local mussels.
Our favorite Mexican restaurant in Portland. Great brisket and drinks.
Japanese small plates and donburi, Maddie recommends the takoyaki!
Hawaiian shave ice - shaved ice on top of ice cream with homemade syrups. Maddie recommends the Cayman combo with a snow cap and toasted coconut, and Paul recommends anything with lime or the lemon-ginger ice cream base if it’s available.
A fantastic bakery! Highly recommend the orange brioche roll.
Great pies - get a blueberry pie while you're in Maine!
The best bar in Portland. Come for daiquiris, stay for the mind eraser.
Maddie's favorite cocktail bar! They also serve a Maine staple - red snapper hot dogs. It’s directly across from Eastern Cemetery, established in 1668.
Fun cocktail bar that feels like being in your grandfather's basement.
Awesome basement cocktail bar spinning vinyl - very cozy!!
Great cocktail bar with delicious snacks!
Board game bar and cafe!
Check out the Maine Oyster Festival in Freeport on the 28th!
If you have time on Saturday morning, we recommend taking a stroll through the Portland Farmers' Market. You'll find a large variety of produce, flowers, and artisan goods.
Walk around the Old Port in Portland for some shopping, bars, and restaurants and get a feel for this old commercial fishing port!
Take a tour on a lobstering boat and experience lobstering firsthand! You can also purchase the lobster you catch and take it over to Portland Lobster Company for a fresh lobster dinner. Also recommend checking out a seal or whale-watching tour!
See the beautiful historic lighthouse and walk around the cliffs for beautiful views of Casco Bay and the Atlantic!
Tour this historic home built in 1858.
Hop on a ferry and head over to Peaks Island! You get a beautiful view of Casco Bay on the way. We really enjoyed the walk to the Fifth Maine Civil War Museum. If you don’t want to walk on the island, rent bikes or a golf cart in advance.
Brewery focusing on farmhouse ales and saisons. There is also poutine provided by Duckfat!
Store selling cool nature-themed shirts, sweatshirts, and accessories from local artists. Maddie is a fan of the frog shirt and Paul loves the birds of prey.
Eclectic home goods, a great gift shop!
Cheese shop! What more could you want?
Great place for comics, board games, graphic novels, and all other nerd stuff!