If you’re road-tripping through Maine or exploring New England, Portland is a must-see destination that makes for the perfect day trip. Whether you’re seeking coastal charm and fantastic food or just want to explore a picturesque town, this seaside city has it all. Here’s how to spend one day in Portland, Maine, with recommendations for where to stay, the best things to do and explore, and where to eat.
Staying longer than a day? Check out my Ultimate Guide to Portland, Maine!
Morning: Stop at Portland Head Light
If you’re driving into Portland, start your day at Portland Head Light, one of the most iconic lighthouses in Maine. Located just a few miles outside of downtown Portland in Fort Williams Park, this stunning lighthouse offers views of the rocky coastline and is a great place to take pictures. Take a walk along the cliffs, explore the park, and grab a lobster roll from the food truck on site.
Check-in: Where to Stay in Portland, ME
Once you arrive in downtown Portland, check into your hotel if you plan on staying overnight. If you’re looking for a more budget-friendly option, the Holiday Inn is a great choice. It’s centrally located and has comfortable rooms and bikes for exploring the city. We stayed here during our visit and had a great experience.
For a more upscale option, consider staying at The Press Hotel. This chic, boutique hotel is housed in an old newspaper building. It’s within walking distance of the best shops, restaurants, and bars in Old Port.
Afternoon: Explore Old Port
After checking in, wander around Old Port, Portland’s historic waterfront district. This charming neighborhood is filled with cobblestone streets, brick buildings, art galleries, and boutiques.
For lunch, you have two options. You can stop by The Shop by Island Creek Oysters for fresh oysters and a relaxed atmosphere, or head to Eventide Oyster Co. for their famous brown butter lobster roll. Both are excellent choices to get your fill of Portland’s local seafood scene.
Late Afternoon: Scenic Walks and Waterfront Views
Once you’ve explored Old Port, walk along the Eastern Promenade for views of Casco Bay. This scenic waterfront park is a great place to relax and take in views of Portland’s coastline.
If you have extra time, consider hopping on the ferry to Peaks Island, where you can explore by bike, take in more ocean views, and get a taste of island life without leaving Portland.
Evening: Dinner
I have two favorites for dinner in Old Port: Via Vecchia or Scales.
Via Vecchia is a lively restaurant with a gorgeous ivy-covered exterior and a dark, stylish interior. The ambiance is perfect for a fun night out, and the menu features delicious Italian dishes. My favorites are the veal chop and the hot and dirty martini.
If you’re craving Seafood, Scales is perfect. It offers fresh catches, a lively atmosphere, and beautiful waterfront views. Be sure to get the tuna crudo and oysters for an appetizer!
Make a reservation for these two restaurants in advance- both places can be tough to get into!
Post-Dinner Drinks
Old Port has two great choices for after-dinner drinks. You can head to Blyth and Burrows for expertly crafted cocktails and a speakeasy experience, or opt for The Porthole if you’re in the mood for a laid-back vibe with waterfront views and live music. We went to The Porthole before dinner and went back after because we loved it so much.
With its historical charm, beautiful coastal scenery, and amazing food, Portland, Maine, is the perfect day trip destination for anyone traveling through Maine or New England. Make sure to add Portland to your road trip itinerary for a memorable day in one of Maine’s most beloved cities!
