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After just one visit, Portland is one of my favorite cities in the Northeast United States! There are so many public parks and outdoor spaces, I felt very safe as a female traveler, and the city’s food and beer scenes are fantastic. So I created this Portland, Maine itinerary and travel guide to help you plan the perfect trip.
The Best Getaways in New England
So I’ve compiled the best activity, accommodation, day trip, and restaurant suggestions for you, and I highly recommend visiting Portland as part of a New England Coastline Road Trip.
Ready to plan a trip? Then here’s the ultimate Portland, Maine Itinerary and Travel Guide!
When To Go
June – August is Portland’s peak tourism season. These are the driest months of the year, and daytime temperatures rarely go above the high 70s. It’ll be in the 50s at night, so bring layers. Summer is also when most of the city’s festivals, art exhibits, and regattas take place. Tourist numbers and hotel prices will be at their highest during these months, so book your tours and accommodation in advance to save some money and ensure availability.
Portland is the perfect place to visit in September – November if you want to avoid the crowds and peep some Fall foliage. Two of the city’s renowned foodie events – Harvest on the Harbor and Portland Beer Week – are held during these months. Temperatures will drop to the 50s in the day and 30s at night, and these are the rainiest months of the year. Vacation home rentals and hotels lower their prices significantly in these months, but some activities and boat tours don’t operate in the Fall.
December – February is Portland’s off-season because daytime temperatures are below freezing, and it’s in the low teens at night. Snow is common, and the city hosts some incredible snow activities, such as ice fishing, cross-country skiing, ice skating, and sledding. Many tours, attractions, and restaurants close or reduce their hours during the winter. If you can brave the cold, then you can score some great accommodation deals.
March – May is Portland’s shoulder season. It won’t start feeling like Spring until May, when daytime temperatures will finally reach the high 60s. Rain is common in these months, so bring rain gear as well as warm clothes. The rain will bring beautiful Spring flowers to the city and surrounding area. Mid-April is the start of the whale-watching season, so boat tours will resume. Tourist numbers and prices will also still be relatively low during these months.
Where To Stay
Portland has some incredible hotels for every budget and preference. From trendy boutique hotels to historic inns to spa retreats, I’ve rounded up the best hotels in Portland.
If you’re camping or bringing an RV or motorhome, I suggest Wild Duck Adult Campground & RV Park. Portland also has some incredible vacation homes.
What To Do
Visit the Portland Head Light
Go on a schooner cruise
Explore the Old Port
Have a picnic at the Eastern Promenade
Visit the Portland Observatory
Do a craft brewery tour
Spend a day at Willard Beach (if it’s warm enough)
Walk out to the Spring Point Ledge Lighthouse
Take a ferry to Peaks Island
Visit the Historic Victoria Mansion
Go on a food tour
Where To Eat
My Favorites: Eventide Oyster Co. (Oyster Bar, $$$), Central Provisions (Small Plates, $$$), Fore Street Restaurant (New American, $$$$), Duckfat (Cafe, $$).
Fine Dining: Hugo’s (Farm-To-Table, $$$$), Grace (American, $$$$), The Corner Room Italian Kitchen & Bar (Italian, $$$).
Seafood: J’s Oyster ($$), The Highroller Lobster Co. ($$), Luke’s Lobster Portland Pier ($$).
Craft Beer: The Great Lost Bear (Gastropub, $$), The King’s Head (Pub, $$), Gritty McDuff’s Brew Pub (Brewpub, $$).
Brunch: Bayside American Cafe ($$), The Front Room ($$), The Sinful Kitchen ($$).
Waterfront Dining: Portland Lobster Company (Seafood, $$), DiMillo’s On The Water (Seafood, $$), Saltwater Grille (Seafood, $$$).
Best Day Trips
Freeport, Maine: The main attraction in Freeport (located just 20 minutes from Portland) is the L.L. Bean Store – a massive shopping complex where you can buy and test out every type of outdoor clothing and equipment you could imagine. Freeport is also home to cute shops and great restaurants. Pro Tip: park in the L.L. Bean parking lot for free and then walk around the rest of the town.
The Kennebunks: The cute coastal towns of Kennebunkport and Kennebunk are only about a 45-minute drive from Portland. I suggest spending your day marveling at the historic mansions, shopping, lounging on a soft-sand beach (if it’s warm enough), and wining and dining yourself.
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Is there anything you’d add to this Portland, Maine Itinerary? If so, share with us in the comments!
For Planning The Rest Of Your Northeast Trip
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Portland, Maine Itinerary
Recommended Tours in Portland
Frequently Asked Questions
Is it worth visiting Portland, Maine?
Yes! After just one visit, Portland is one of my favorite cities in the Northeast United States! There are so many public parks and outdoor spaces, I felt very safe as a female traveler, and the city’s food and beer scenes are fantastic.
What is the best month to visit Maine?
June – August is Portland’s peak tourism season. These are the driest months of the year, and daytime temperatures rarely go above the high 70s. It’ll be in the 50s at night, so bring layers. Summer is also when most of the city’s festivals, art exhibits, and regattas take place. Tourist numbers and hotel prices will be at their highest during these months, so book your tours and accommodation in advance to save some money and ensure availability.
Portland is the perfect place to visit in September – November if you want to avoid the crowds and peep some Fall foliage. Two of the city’s renowned foodie events – Harvest on the Harbor and Portland Beer Week – are held during these months. Temperatures will drop to the 50s in the day and 30s at night, and these are the rainiest months of the year. Vacation home rentals and hotels lower their prices significantly in these months, but some activities and boat tours don’t operate in the Fall.
December – February is Portland’s off-season because daytime temperatures are below freezing, and it’s in the low teens at night. Snow is common, and the city hosts some incredible snow activities, such as ice fishing, cross-country skiing, ice skating, and sledding. Many tours, attractions, and restaurants close or reduce their hours during the winter. If you can brave the cold, then you can score some great accommodation deals.
March – May is Portland’s shoulder season. It won’t start feeling like Spring until May when daytime temperatures will finally reach the high 60s. Rain is common in these months, so bring rain gear and warm clothes. The rain will bring beautiful Spring flowers to the city and surrounding area. Mid-April is the start of the whale-watching season, so boat tours will resume. Tourist numbers and prices will also still be relatively low during these months.
Is Portland, Maine walkable?
Portland, Maine, is a very walkable city. Some of the neighborhoods are too far apart to walk between them, and the beaches are further from the city, but public transportation and rideshares are easy to find and use.
How long should you spend in Portland?
Give yourself at least 3-4 days to explore Portland. This will give you plenty of time to experience the historic downtown, enjoy the food scene, and take a day trip.
What is there to do in Portland, Maine for 2 days?
If you only have two days in Portland, then prioritize these activities:
1. Visit the Portland Head Light
2. Go on a schooner cruise
3. Explore the Old Port
4. Have a picnic at the Eastern Promenade
5. Visit the Portland Observatory
6. Do a craft brewery tour
7. Spend a day at Willard Beach (if it’s warm enough)
8. Walk out to the Spring Point Ledge Lighthouse
9. Take a ferry to Peaks Island
10. Visit the Historic Victoria Mansion
11. Go on a food tour
What food is Portland, Maine known for?
The Best Restaurants in Portland, Maine:
My Favorites: Eventide Oyster Co. (Oyster Bar, $$$), Central Provisions (Small Plates, $$$), Fore Street Restaurant (New American, $$$$), Duckfat (Cafe, $$).
Fine Dining: Hugo’s (Farm-To-Table, $$$$), Grace (American, $$$$), The Corner Room Italian Kitchen & Bar (Italian, $$$).
Seafood: J’s Oyster ($$), The Highroller Lobster Co. ($$), Luke’s Lobster Portland Pier ($$).
Craft Beer: The Great Lost Bear (Gastropub, $$), The King’s Head (Pub, $$), Gritty McDuff’s Brew Pub (Brewpub, $$).
Brunch: Bayside American Cafe ($$), The Front Room ($$), The Sinful Kitchen ($$).
Waterfront Dining: Portland Lobster Company (Seafood, $$), DiMillo’s On The Water (Seafood, $$), Saltwater Grille (Seafood, $$$).
How many days do you need for Portland, Maine?
Give yourself at least 3-4 days to explore Portland. This will give you plenty of time to experience the historic downtown, enjoy the food scene, and take a day trip.
Is downtown Portland safe?
I felt very safe during my entire trip to Portland. But, as with any destination, you need to take precautions to keep yourself safe. Don’t walk by yourself at night, stay in a secure and well-located hotel or vacation home, use slash-proof, lockable, and RFID-protected bags and purses, and always have a charged cell phone with you.
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This post is not a sponsored post, and, as always, the thoughts and opinions expressed in this Portland, Maine itinerary and travel guide are entirely my own. Some of the links in this Portland, Maine itinerary and travel guide are affiliate links, and, at no cost to you, I may earn a small commission from this Portland, Maine itinerary and travel guide.
