Portland, Maine is a destination that combines historic charm with modern amenities, offering visitors a rich and varied experience. Whether you’re strolling through the Old Port, savoring fresh seafood, or exploring the scenic coastline, there is something here for everyone and Portland promises a memorable visit.
This guide provides dining, hotel, and activity recommendations from myself as a local who's lived here for 10 years. Whether you’re a history buff, a foodie, an outdoor enthusiast, or someone looking to relax by the sea, Portland has something to offer.
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I'll continue to update periodically, especially as I continue to try more of the best restaurants in town!
The Old Port is the historic waterfront downtown area of the city. There are tons of great shops ranging from touristy gift shops to stores owned by local makers and artists. You'll also find dozens of amazing restaurants and bars. The views along Commercial Street are not to be missed!
A lovely trail that has amazing views of Casco Bay. There's nothing like watching the sun set over the sailboats in the bay with a picnic in the grass. In the summer there is also a food truck park with local eats which you should definitely try - my favorites are Falafel Mafia and Mister Tuna!
In the spring through fall, the market is held every Wednesday and Saturday morning. Dozens of amazing local farm and vendors. Fresh produce, meats, dairy, honey, flowers, preserves, oysters, bread, and more! Pro tip, arrive early (opens at 7 am) for best pickings and a smaller crowd.
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Tours
Want to learn more about the city's history, culture, and architecture? Go on an educational walking tour!
There are a few companies that offer sailboat charters in Portland. Below is my favorite company (might be biased though because I got married on their ship the Bagheera)! Sails are offered spring through fall. You are also welcome to bring your own snacks and alcoholic beverages. They even let guests help to hoist the sails! I would recommend the sunset sail for epic Maine vibes.
If you're looking for another charming area to visit besides the Old Port, you can take the ~ 15-minute ferry ride over the Peaks Island. The island is within the municipality of Portland and offers bike and golf cart rentals. Go for a swim from one of the many sandy or pebble cove beaches and take in the beautiful scenery of Casco Bay and surrounding islands. Peaks deserves its own guide, but below are a few of the top places to explore.
Great half or full day trip from Portland with loads of quaint, coastal charm. Have a picnic lunch, swim in the coves, go for a bike ride, and explore the WWII fort.
Iconic historic lighthouse, and it's the oldest one in Maine! Gorgeous views from all over Fort Williams Park. You can also explore the fort and have a perfect picnic here.
Great spot for views of both the lighthouse and Fort Gorges. Another nice picnic spot. You'll drive through the Southern Maine Community College campus to get to Spring Point.
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Tours
Want to see all of Portland's lighthouses and learn from a local along the way?
Calm, quiet beach loved by locals. Willard Beach parking lot fills quickly, but there is some limited street parking, as well as parking at the Southern Maine Community College campus.
A National Historic Landmark, open May 1 through October 31. Beautiful historic mansion with original, unique interior.
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Tours for Foodies
The food scene in Portland is just incredible. My top restaurant picks are below in this guide but there are also a few great food tours available in town for those that want to add to their Portland food experience.
Portland has so many great hotel options in the heart of the Old Port that are super walkable. All the major brands are available (Hilton, Hyatt, Marriot, etc.) and there are some lovely boutique hotel options as well!
I've focused on hotels in the Old Port here so that you can be within walking distance to the best parts of downtown!
Gorgeous hotel in the heart of downtown. We stayed here during our wedding weekend and our room was beautiful, very spacious, and comfy, with a quiet courtyard view and the ocean in the background. Excellent service, delicious drinks from the bar, and private valet garage parking were all great perks of this hotel!
Excellent walkable location downtown with a free airport shuttle! Many of our family members have stayed here when visiting the area and they have all enjoyed their stay here.
Bright and sunny hotel at a great downtown location. Our family members that have stayed here love this cozy option just a quick walk to the waterfront.
Upscale condo hotel in a historic building within walking distance to all of the Old Port.
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Where to Eat & Drink
One of the biggest draws to Portland is the epic food scene. Portland rates as having one of the highest number of restaurants per capita, with over 300 restaurants in this small city! It's been my mission since as long as I've lived here to try somewhere new every single date night! Below are just a few of my favorites, this list could be much much longer!
The duckfat fries and milkshakes are something else... You won't be sorry you tried these. Tasty sandwiches and salads are great for a chill lunch spot.
My absolute favorite breakfast spot. Fills up fast, so get there early or try ordering take out! I love that they serve half sized dishes because I always want more than one dish! The stuffed french toasts are incredible!
Order ahead if you can on the weekends! Super popular, exceptional bakery that sources the highest quality ingredients for their breads, breakfast pastries, and sweets.
I love Bard's mission to source the highest quality coffee beans and to share farmers' stories. Great window counter seating for people watching or getting some work done.
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Other Helpful Tips
Getting Here and Getting Around
If you can, I'd recommend flying into Portland (PWM). The airport is small and very easy to navigate, and only 10 minutes away from downtown. However, airfare to get here can be a bit more expensive since it's such a small airport and doesn't have a lot of direct routes.
Flying into Boston is usually a little cheaper and there are many more direct flight options here instead. You can take an express bus from Boston Logan Airport right into Portland with no stops for $34 one way or $60 round trip. The ride is about 2 hours on a comfortable coach bus. Rental cars are also always an option, but public transportation and Uber/Lyft within Portland is very good and the downtown area is super walkable. There are also bike rentals located throughout downtown.
If you have a rental car, most hotels offer valet or paid parking garages, which can be a little pricey. All on-street parking in Portland is free from 6 pm until 9 am Monday-Saturday, all day Sunday, and on major holidays. Use the Passport App to pay for parking during the day.
Book Early
The Old Port can get busy during the summertime, especially on the weekends or when there is a cruise ship in port.
I would definitely recommend booking your hotels several months in advance if you want to visit during peak season as room can be pricey and hard to come by for summer weekends.
Making restaurant reservations in advance is also a good move as wait times for a table can be close to 1-2 hours for popular spots.
Food Trucks
Like food trucks? Download the Food Truckalico app to see where all the best food trucks will be each day of your visit!
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I am an avid travel enthusiast with extensive experience planning trips for myself and husband, friends, family, and colleagues. Once inspiration for a trip strikes, I become fully immersed in the planning process, and now, I am excited to help others create their dream adventures!
My journey into travel planning began with a life-changing trip to Iceland, where my now-husband proposed. Since then, I have been the go-to travel planner for my circle, constantly urged by friends and family to pursue this professionally. Today, I am thrilled to share my passion for travel planning and itinerary building with you.
I specialize in crafting travel experiences that seek out epic landscapes and nature. Whether it's adventurous hikes, cycling, mountain biking, camping, RVing, horseback riding, snorkeling, or scuba diving, I have a knack for finding the best spots and activities to make any trip unforgettable.
I particularly enjoy slow travel and own a Class C RV, which I have driven across the United States along with my two dogs. I am well-versed in using tools like RV Life Pro to plan detailed road trip itineraries, ensuring every journey is smooth and enjoyable.
Based in the Portland, Maine area, I am a strong advocate for loving where you live. Maine holds a special place in my heart, and I would love to show you all the incredible experiences this beautiful state has to offer.
