6 Must-Do Activities to Add to Your Portland, Maine Bucket List

There is still plenty of summer left to enjoy. If you find yourself visiting Maine, you are definitely coming to the right place. There are so many wonderful sights to see and things to do in our small but bustling waterfront city, especially with these last couple of warm months ahead. From sailing the Casco Bay to a classic ball game, we’ve pulled together a few can’t-miss items to add to your Portland, Maine bucket list!

Picnic on the Eastern Promenade

sailing casco bay

The Eastern Promenade, just on the other side of Munjoy Hill, is breathtaking to say the least. This area of the city is full of unique history and sights to see. You can enjoy 180-degree views of the vast Casco Bay, dotted with sailboats, ferries shipping out to the rocky, forested islands, and the historic Fort Gorges. There’s even the tiny East End beach where you can bring your dog or kids to play.

Our recommendation? Order takeout from one of the many incredible restaurants in town and enjoy a meal al fresco on the hill, in true Portland fashion!

Portland Observatory

While you’re on the East End, be sure to check out the historic Portland Observatory. The last standing maritime signal tower in the country, this landmark was used in the 1800s to monitor ships coming into the harbor. The base is now a free museum, where you can learn about the history of Portland and the Observatory, but you can also purchase tickets to walk to the top of the tower for an amazing bird’s eye view of the water.

Sail the Casco Bay

couple enjoying a sunny sail
Photo by Jon Ashley

While enjoying the view of the coast from above may be beautiful, there is truly no better way to experience the coast than by sailing the Casco Bay. Get up close and personal with the gentle waters surrounding the city!

Book a trip on our sailboat, the Eleanor Hawkes, which holds up to 6 guests; or, book a charter on our cocktail cruiser, the Calista Ann, which holds up to 12 guests (with a minimum of 8) for an intimate group feel.

Whichever boat you choose, you can enjoy a lovely 2-hour sail through the calm waters of the bay. We offer multiple trip options for you to choose from, including private charters or even private parties. Book your tickets online today!

Victorian Mansion Tour

If you can believe it, there is just as much history in the West End of Portland as there is in the East End! There are many ways to explore this part of town, including horse-drawn carriage tours, fire truck tours and boat tours, but the best way to experience the rich history of the West End is by foot. There are endless centuries-old Victorian mansions that are still lived in today, each with a plaque including details about the year built and who it belonged to. Be sure to walk down to the Western Promenade – on a clear day, you’ll catch a glimpse of the enormous snow-capped Mount Washington!

Portland Museum of Art

Head downtown and you’ll find the architectural home of the Portland Art Museum. Considered by many to be one of the best in New England, you’ll find some incredible collections and very famous pieces housed here. The range of art and mediums is so vast, you could spend an entire day exploring each section of the museum.

Sea Dogs Game

Whether you’re passionate about baseball or passionate about stadium snacks (Sea Dogs biscuits, anyone?), it’s worth heading to the locally notorious Hadlock Field for a Sea Dogs game. The Portland Sea Dogs are a Minor League team, but many players that start here go on to become Major League stars. Hanging out at Hadlock is a fun, unique way to spend a few hours the way the locals do!

There are so many activities to immerse yourself in when you visit Portland, Maine – from sailing the Casco Bay to enjoying an afternoon of art. Let this bucket list be a jumping off point for many adventures to come!

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