Things to Do in Portland, Maine

By VI | Disclosure: I use affiliate links

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When I’m in the mood for ocean breezes, a dash of maritime charm, and incredible food, I head to Portland, Maine—and I think you’ll love it too. I always find myself drawn to the harbor, where I can watch boats drift by before heading out to explore the lighthouses or grab a bite in the Old Port. Whether you’re planning a romantic weekend, a family escape, or just a quick coastal day trip, you’ll find that Portland makes it so easy to relax and explore. My favorite part? I love how the city’s connection to the sea shows up everywhere—from the art on the walls to the seafood on my plate.

Portland, ME Highlights:

For Foodies: Explore the Old Port District – I always make time for this neighborhood. You’ll love the cobblestone streets, the mix of modern bistros and lobster shacks, and the smell of salt in the air as you wander.
For Lighthouse Lovers: Visit Portland Head Light – This iconic spot never gets old. I’ve taken more photos here than I can count, and I know you’ll be just as taken with the views and the dramatic coastline.
For Art Enthusiasts: Tour the Portland Museum of Art – I like ducking in here on rainy days or quiet mornings. You’ll find local and international pieces that really capture the soul of the region.
For Adventurers: Take a ferry to the Casco Bay Islands – I’ve hopped on the ferry just to feel the wind and take in the scenery. You can explore the islands at your own pace—you’ll feel like you’ve stumbled onto your own secret world.
For Beer Lovers: Visit award-winning breweries – Portland’s craft beer scene is fantastic. I’ve done a few tasting flights around town, and I think you’ll be impressed with the creativity and variety on tap.

Best Time to Visit Portland, ME

From May to October is when I try to visit. The weather is mild, the ferries are running, and outdoor dining comes alive in the warmer months. I’ve spent summer evenings on patios with a view of the water, and I always think: this is exactly what a coastal getaway should feel like.

How to Get to Portland, ME

By Plane: I usually fly into Portland International Jetport (PWM)—it’s just 10 minutes from downtown, and you’ll be at the harbor in no time.
By Train: I’ve taken Amtrak’s Downeaster from Boston, and it’s such a relaxing ride. You’ll step off the train ready to explore without the stress of traffic.
By Car: If you’re up for a road trip, I-95 takes you right into town. I’ve driven up from Boston in just about 2 hours—and if you’re coming from NYC, plan on around 5.5 hours with breaks along the way.

Where to Stay in Portland, ME

The Press Hotel – I love the creative touches here—it used to be a newspaper building! You’ll enjoy the boutique feel and the walkable location.
Portland Harbor Hotel – This one’s got that elegant, nautical style I adore. You’ll feel close to the harbor and wrapped in New England comfort.
Black Elephant Hostel – For something colorful and budget-friendly, this hostel is a fun option. I’ve recommended it to friends traveling solo or in groups, and they’ve always had a great time.