How To Spend 2 Days In Portland, Maine
If you’re craving coastal charm and fresh seafood, then Portland, Maine, is calling your name. My husband and I just spent 2 days in Portland, Maine, and absolutely loved it!
You can experience a lot of amazing things in just a weekend in Portland. Whether you’re relaxing by the lighthouse at sunset or devouring fresh lobster rolls, I know you’ll leave Portland wanting to come back for more!
How To Spend 2 Days In Portland, Maine
Where to Stay: The Portland Press Hotel
We stayed at The Portland Press Hotel and thought it was perfect for our 2 days in Portland. It’s a boutique hotel housed in a former newspaper building. The rooms are cozy and filled with nods to the building’s past. It’s a great location, within walking distance of so many restaurants, shops, and the harbor.
Travel With Angela Hope Tip: As a travel advisor, I have a partnership with The Portland Press, so if you book a stay through me, you’ll get perks like early check-in/late check-out, room upgrades, welcome amenities, and complimentary breakfast. Booking a stay through me is a complimentary service—meaning no extra cost to you!
Day 1
Breakfast at Tandem Coffee + Bakery
Start your 2 days in Portland, Maine at Tandem Coffee + Bakery. The coffee is strong and the food is delicious. Be sure to try the malt coffee and savory-loaded biscuit.
Morning: Walk Around Old Port & The Waterfront
After breakfast, spend the morning wandering around Old Port, the heart of the city. There are cobblestone streets lined with cute boutiques and fun shops. Then stroll along the waterfront and take in views of the harbor.
Lunch: Bite Into Maine
Head to Fort Williams Park for lunch at the Bite Into Maine food truck. This is one of the top lobster roll spots in Portland! Their rolls come in several styles—traditional, Maine-style with mayo, or Connecticut-style with warm butter. Whichever one you choose, you can’t go wrong. We tried a few lobster roll spots and this was by far my favorite!
Afternoon: Cape Elizabeth, Fort Williams Park, Portland Head Light
Just a short drive from downtown Portland, Fort Williams Park in Cape Elizabeth is home to the iconic Portland Head Light, one of the most photographed lighthouses in the country. It’s the perfect spot for a scenic walk or picnic, with plenty of grassy areas and trails along the shore.
Dinner: Central Provisions
For dinner, make a reservation at Central Provisions, one of Portland’s most popular restaurants. Their menu is tapas-style, with small plates that are perfect for sharing. We ordered the bluefin tuna crudo, chopped salad, peekytoe crab, CP fries, bone marrow toast, goat campanelle, and caramelized sheep’s cheese. I loved everything, but my tops were the bluefin tuna crudo, peekytoe crab, and bone marrow toast.
Dessert: Gross Confection Bar
After dinner, head to Gross Confection Bar for dessert. This spot was SO good and had such a fun vibe. It’s a dimly lit space, specializing in dessert and dessert cocktails. We got the crumb brulee and warm brown butter cake. The warm brown butter cake is topped with aged parmigiano reggiano which might sound odd, but it was delicious.
Day 2
Breakfast: Union
If you’re staying at The Press Hotel, I would recommend eating at their restaurant, Union. Their dishes are creative takes on classic dishes, filled with fresh, locally sourced ingredients. I loved their crab benedict.
Morning: Ferry to Peaks Island
After breakfast, head to the ferry terminal and buy ferry tickets to Peaks Island. You’ll take a 20-minute scenic ferry from the city. The island is super peaceful and has beautiful coastal views and charming houses. On the island, you can rent a bike to explore the island or just walk along the shoreline. Ferries depart every ~60-90 minutes (ferry schedule found here).
Lunch: The Highroller
When in Portland, you can never have enough lobster rolls! After you’re back in town, head to The Highroller for lunch, where they serve up some of the most creative lobster rolls in town.
Their rolls come loaded with fresh lobster, and you can choose from sauces like lime mayo, charred pineapple, or classic drawn butter. Plus, they’ve got other seafood goodies like lobster grilled cheese, crab rangoons, and killer fries. Grab a local craft beer or their homemade soda to wash it all down.
Afternoon: Explore the Eastern Promenade
After lunch, spend the afternoon strolling along the Eastern Promenade. This scenic park runs along the coast and has gorgeous views of Casco Bay. You can walk, bike, or just relax on the grassy hills. If you’re up for more adventure (weather permitting), rent a kayak and paddle around the bay!
Dinner: Eventide Oyster Co.
If you’re a seafood lover, head to Eventide Oyster Co. for your last dinner in Portland. Eventide is known for its oysters (hence the name) that come with unique “accoutrements” (my favorite was the horseradish ice and Red Wine Mignonette).
If you’re not a raw oyster fan, don’t worry—they also have a delicious lobster roll on a steamed bun that’s to die for. Their tuna crudo and fried oyster bun are also a must!
Travel With Angela Hope Tip: Eventide does not take reservations. Head there during off hours to wait in line to put your name down for a table. They will send you a text message when your table is ready, so you can explore the city while you’re waiting!
Planning a trip to Portland, Maine?
Be sure to check out my Portland travel guide filled with recommendations for where to stay, how to get around, what to do, and where to eat/drink.
Or if you don’t want to spend time planning, I offer travel planning services!
