The Best Things To Do in Portland, Maine
Whether you’re here for a day trip or a week long vacation, there is plenty to keep you busy in the heart of Vacationland! We know our guide to the Best Things To Do in Portland, Maine will help you plan the perfect Portland, Maine experience.
Things to See & Do:
Portland Head Lighthouse @ Fort Williams Park in Cape Elizabeth, Maine: A quick drive across the Casco Bay Bridge from downtown Portland, sits the most photographed lighthouse! With its famed red roof, this beauty offers a picture-perfect backdrop for your Maine Instagram photos. We highly recommend walking the coastal trail and dropping by Bite into Maine’s food truck for our favorite lobster roll in Maine!
Lobster Boat Experience: Lucky for us, there are 2 great options in town. Both Lucky Catch Lobster Cruises and Rocky Bottom Tours offer a great time on board an authentic lobster boat to experience the day in the life of a Maine lobsterman. This is a must do activity whenever we have visitors in town! Nothing beats getting out on the water and hauling trips. So wicked fun!
Explore the Casco Bay Islands: Casco Bay Ferry lines operates from Commercial St. in downtown Portland and services the major islands of Casco Bay. Peaks Island is the closest to Portland, at just a 15 minute ferry ride from Commercial St. Grab tickets same day at the terminal window and enjoy a day exploring the island. The ferry is pet friendly too! Once on Peaks, we recommend grabbing wood fired pizza from Il Leone and seafood (a beer & haddock sandwich is our fav) from Island Lobster Co. Casco Bay Lines also offers a mailboat cruise each day at 10am that cruises through the bay stopping at all of the islands with the day’s mail and goods. If you have the time, this is a great escape!
Old Port Shopping: Explore our favorite shops around the Old Port including Skordo for cooking spices, salt and peppers, and Seabags for tote bags made from recycled Maine sails! Window shopping up and down Exchange St. is also one of our favorite ways to spend an afternoon.
Portland Museum of Art in Portland’s Arts District offers beautiful rotating exhibits worth checking out. Fun fact - admission is free due to local sponsorship every Friday evening so take advantage if you can!
Spa Day at Akari: We love this retreat in the heart of the city and highly recommend a facial! You can also get massages and hair services here too. Truly a hidden gem in the heart of the Old Port.
Visit Freeport: About a 30 minute drive north, lies the cute village of Freeport and the home to L.L. Bean. Explore the flagship store (fun fact - the store is open 24/7, 365!) and surrounding campus + great outlet shopping throughout the village. We love stopping into Maine Beer Co. and Mast Landing in town for a beer too. Bradbury Mountain is also close by for hiking, especially in the fall.
Portland Sea Dogs Game: The feeder team to the Boston Red Sox is located right here in Portland. Nothing beats a summer evening at the ballpark with a beer and hot dog in hand at Hadlock Field.
Haulin’ Traps aboard The Lucky Catch, July 2021
Where to Eat:
Must Do Food Stops include Maine potato donuts from The Holy Donut (they have a great new location on Commercial St.), Happy Hour at Via Vecchia or one of our other favorite happy hour spots, and oysters at Eventide
Portland’s Washington Ave area in the East End is up and coming “foodie row” and we highly recommend checking out The Shop for oysters, Forage for Bagels, Portland Pottery Cafe for brunch, Izakaya for Japanese tapas, and inventive BBQ at Terlingua (they have a great patio).
Food Truck Picnic on the Eastern Prom is the go to spot in Portland’s East End for an award winning line up of food trucks. On any given day, you can find the city’s best trucks lined up serving lunch. This is a great spot to picnic with sweeping ocean views over Casco Bay. Vy Banh Mi is our favorite truck in the city right now!
Lobster Rolls - Check out our Best Lobster Rolls in Maine blog post for a listing of our favorites.
Our favorite spots for a date night include Fore Street, Street & Co, Scales, Wayside Tavern, and EVO. Scales also gets our vote for best seafood dinner with a view. For a fun night out with friends, we recommend Crispy Gai on upper Exchange St. for fried chicken, Bao Bao Dumpling House in the West End, and Yosaku for sushi (great outdoor patio!). Some of our other recommendations include Becky’s Diner for breakfast, Hi-Fi Donuts for breakfast sandwiches and donuts, and Honey Paw for dinner.
Lobster Roll at Luke’s Lobster in Portland at sunset
Where to Drink:
Maine Craft Beer: Fun fact - Portland has the most breweries per capita of any U.S. city! We love creating our own brewery crawl through Portland’s East Bayside neighborhood to explore the amazing local breweries. Some of our favorites in this area include Austin Street, Rising Tide, Belleflower, Lone Pine, Goodfire, and Apres for hard seltzers. We also love Portland Zoo for a fun tasting room experience. Allagash Brewing is another famous Maine brewery to check out, though they are located outside of the downtown area, about a 15 min drive away. And finally, Novare Res Bier Cafe on Exchange is a fun tasting room in the heart of the Old Port where we can try all the local beers plus many “from away” too.
Local Coffee Shops: Our favorites include Tandem Coffee & Speckled Ax. Tandem Coffee offers great pastries (both sweet and savory as well!). Order ahead of time with the app for easy window pick up. Speckled Ax has 2 locations in Portland and we love the Commercial St. spot across from the Maine Narrow Gauge Railroad. Grab a breakfast sandwich there too!
Wine Tasting: If beer isn’t your thing, we love trying new wines at Grippy Tannins. Schedule a tasting ahead of time at this neighborhood bottle shop and you won’t be disappointed. Wines by the glass are also available. If you’re visiting in the summertime, we also recommend booking a wine sail with Wine Wise. It’s a beautiful opportunity to sail through Casco Bay sipping and learning about wine. Note - these tours will up well in advance, so reserve online before your trip!
Kombucha: Urban Farm Fermentory in East Bayside is a great stop to add to your brewery crawl to enjoy a flight of kombucha. Root Wild on Washington Ave. serves up some delicious ginger and blueberry kombucha that we love taking in cans to go as well.
Hard Cider: Washington Ave’s Anoche Cidery serves up an impressive list of on draft hard ciders. It’s located next to Oxbow’s Tasting Room and the Duckfat Frites Shack making this a perfect afternoon stop to sip and bite.
Spirits: Portland is home to quite a few distilleries as well. We love checking out Hardshore on Washington Ave for gin cocktails. Maine Craft Distilling down the street is also a great spot for drinks and a heavier food menu.
Aboard the Wine Wise Wine Sail, Summer 2021
Where to Stay:
The Press Hotel: Located in the former Portland Press Herald (local newspaper) building, sits the beautiful Press. Their in house restaurant, Union Kitchen, is also a great visit.
The Canopy Hotel: Located in the heart of Portland on Commercial Street, sits the city’s newest and hottest hotel. Their rooftop bar, Luna, offers sweeping ocean views and an inventive snack and drink menu.
The Francis: Located in Portland’s West End, across from the famous Tandem Coffee, sits this beautiful boutique style hotel. Their in house restaurant, Wayside Tavern, is also a must visit for date night.
Views from the Luna rooftop bar at The Canopy Hotel
