Portland, Maine Summer and Fall Travel Guide

This post is particularly special because it’s about the place we both call home – Portland, Maine. We feel fortunate to live here year-round, but our love for this coastal city truly intensifies during the warmer months. With that in mind, we’re thrilled to share our personal recommendations for an unforgettable summer or fall trip to Portland, ME.

In this post, we’ll be sharing our top recommendations for where to stay, eat, and drink, as well as the best activities to do while you’re in Portland, ME during the summer or fall. Whether you’re looking for a boutique hotel, a trendy new restaurant, or a scenic outdoor adventure, we’ve got you covered. We can’t wait to share our insider tips with you and help you make the most of your time in our beloved city. Welcome to Portland, ME!

Do

• Old Port: Portland’s historic Old Port district is filled with cobblestone streets, local shops, and delicious restaurants. Spend an afternoon wandering the streets, browsing the boutiques, and stopping for a bite to eat.
• Portland Head Light: This historic lighthouse is located in Cape Elizabeth, just a short drive from downtown Portland. It’s a picturesque spot for a stroll or a picnic, with stunning views of the ocean and the surrounding cliffs. If you don’t feel like packing food, Bite into Maine has a food truck at the lighthouse, or The Lobster Shack at Two Lights is nearby, and essentially right on the rocks of the ocean shore. 
• Eastern Promenade: A park located on a hill overlooking Casco Bay, the Eastern Promenade (the “Eastern Prom”) is a great spot for a walk, bike ride, or picnic. There are also tennis courts, a playground, and a beach for swimming. On the weekend, food trucks line the street with options like a sushi hand roll and mini donuts. If you are staying in the Old Port, we recommend getting there by taking the walking trail along the water beginning from Commercial St. to the East End beach, and then up the hill to the Eastern Prom. 
• Portland Schooner Co. Sail: Leaving right from the Old Port, go for a short sail throughout the Casco Bay. At least as of the date of writing, you can also bring your own food and drink, including beer and wine. If you are going with a large group, this company also offers private charters. Visit the website here. If you don’t want to worry about bringing your own drinks, see our next recommendation.
• Wine Wise Events’ Sails: A unique and favorite summer activity in Portland, ME. This guided sailing tour allows guests to enjoy Casco Bay while sampling a selection of wines and snacks. Check out the schedule here.
• Visit the local beaches: There are so many great beaches to enjoy in the summer. For our recommendations, check out Our Favorite Beaches Close to Portland, Maine post.
• Visit the nearby islands: There are lots of islands easily accessibly by ferry leaving from downtown Portland. You can visit and grab a drink on each of Great Diamond (Diamond’s Edge or the newest, Crown Jewel), Peaks (which has the most restaurant options), and Chebeague (Chebeague Island Inn). There are also sea kayaking options available on Peaks. Find the Casco Bay Lines schedule here.

Eat and Drink

Given that this is our hometown, and with so many fantastic dining options to choose from, we had a REALLY hard time narrowing this down, and thought this section was worth its breaking into multiple posts.

• For food and dining recommendations, check out this guide.
• For morning breakfast and brunch recommendations, visit this guide.
• For drink recommendations, check out this guide.

Stay

• Canopy by Hilton: Located on Commercial Street on the edge of Portland’s historic Old Port district. The Canopy hotel has multiple restaurants, including one of the only rooftop bars in Portland, Luna Rooftop Bar. 
• Longfellow Hotel: Located in Portland’s West End. As you step into the beautifully decorated lobby, you’ll find the Twinflower Café in the morning, which transforms into the Five of Clubs bar in the evening. For an even more relaxing experience, visit the on-site Astraea Wellness Spa.
• The Weldon: Located in Portland’s West End, The Weldon offers beautifully designed apartment-style suites with full kitchens, record players, and luxury touches throughout. Guests enjoy access to a modern fitness center, cozy lounge, and easy walkability to the Old Port, arts district, and waterfront.
• The Westin Portland Harborview: A modern hotel located in a historic building with stunning views of the harbor. The Westin features comfortable rooms, an enclosed rooftop bar, and a fitness center.
• Portland Harbor Hotel: Located near the waterfront, this hotel offers the ideal location for exploring all that Portland’s historic Old Port District has to offer.
• Other: There are lots of hotels in Portland. Prices tend to be higher during the summer and early fall, so if these aren’t available to you, we just recommend staying in the Old Port. 

Thank you for visiting our site! We may make commission off affiliate links (at no further cost to you), but we would never recommend a place we don’t genuinely want to recommend.

Tips for Portland, ME

• Leave your heels at home: The city is laid back, but also some of the streets are cobblestones, which makes walking in heels a potentially hazardous activity. That said, if you’re coming for a bachelorette party or girls trip and want to get dressed up, that would not be abnormal. Just proceed with caution.
• Make reservations early: Portland is known for its restaurants, and they book up quickly. We cannot stress enough the importance of booking reservations as early as possible.
• Skip the rental car: Portland is a very walkable city and parking can be a challenge. Uber and Lyft are both available and recommended for exploring. If you are visiting other cities outside of Portland, then you might want a car.

If you have extra time to explore on your trip, be sure to check out our other Maine itineraries and travel guides:

• Kennebunk and Kennebunkport, ME
• Ogunquit and York, ME
• Portland, ME Winter Guide
• Portland, ME Family Friendly Weekend Guide
• More coming soon!

– Karen and Kasey