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A Perfect Day Trip to Portland, Maine: The Ultimate Trip Itinerary

Portland, Maine might just be one of my favorite little cities in New England—and yes, it’s totally doable in a day. Whether you’re stopping in on a Maine coast road trip, popping up from Boston, or just looking for an easy New England day trip, Portland delivers with charming streets, great food, and that salty sea breeze you didn’t know you needed.

In just a few hours, you can wander 19th-century brick buildings, try some of the best lobster rolls in the state, and even squeeze in a scenic coastal walk or boat tour. And because the downtown is compact and super walkable, it’s actually one of the best cities to visit if you’re short on time but want to see a lot.

This guide covers everything you need to plan the perfect day trip to Portland, Maine—from breakfast to sunset sails, plus where to eat, what to skip, and a few hidden gems if you have extra time.

Happy travels to Maine!

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Is Portland Maine Worth a Day Trip?

Absolutely. While you could spend a few relaxing days exploring the city (and I wouldn’t blame you), a day trip is enough to get a solid feel for Portland. You’ll get to enjoy the best of the Old Port, try iconic local eats, and soak up the city’s coastal charm—all in one very full but very fun day.

If you only have 12 hours to spare, Portland makes it easy to make the most of them. Great food, walkable neighborhoods, and plenty of tours and attractions that don’t require much advance planning? That’s the dream day trip combo.

How to Get to Portland for a Day Trip

Portland is located about two hours north of Boston, making it an easy drive or train ride for a quick escape.

  • Driving: There’s paid parking downtown, and some free spots if you don’t mind walking a little.
  • Train: The Amtrak Downeaster runs daily from Boston’s North Station to Portland. It takes about 2.5 hours and drops you about a mile from downtown.
  • Flying: If you’re further afield, Portland International Jetport (PWM) is just 10 minutes from downtown. But if you’re planning a full day of exploring, flying in and out same-day isn’t practical.

Where to Stay in Portland

Portland, Maine might be the sweetest town but it isn’t the cheapest to stay in, especially during high season (June-August) where hotel prices can easily rise to over $300 a night.

Perhaps that’s what makes making a day trip to Portland so appealing to many travelers. But if you choose to stay a night there are some great options.

Hotels in downtown within walking distance to shops and restaurants are the most expensive. If you can’t find a hotel that fits your budget consider staying in Kennebunkport. It’s a smaller coastal town less than 30 miles from Portland.

Hotels on a budget

The Westin Portland Harborview
Cambria Hotel Portland Downtown Old Port

Want to save more on your hotel? Hotels near the Portland Airport are the cheapest option but a bit outside the main city center. Many of these hotels are also available with points, which means you could be paying nothing for your nightly rate!

Mid-Tier hotels

The Francis Hotel
The Chadwick Bed and Breakfast

Splurge and stay here

Blind Tiger Portland

Best Time of Year to Visit

Personally I think the best time of year to visit Maine is shoulder season, which runs mid-April to Memorial Day and again September to October. Spring sees the lowest prices for hotels, which can save you hundreds on your accommodations.

If you can, I’d recommend visiting late-April. You’ll have great weather, all the season activities and restaurants will be open, and you’ll pay less with far fewer tourists.

What to Do on a Day Trip to Portland Maine

If you’ve only got one day in Portland, this itinerary packs in the best of the city without feeling rushed. You’ll get a little bit of everything—coastal views, great food, local shops, and even a lobster roll (or two). Here’s how to spend the perfect 12 hours.

Morning: Coffee, Pastries, and a Stroll by the Sea

Start your morning with a stop at Standard Baking Co. This tiny bakery tucked under the Fore Street restaurant is a local favorite. Grab a coffee and a famous morning bun (seriously, one of the best I’ve ever had) and enjoy it by the water. If it’s nice out, head to the Eastern Promenade or drive over to Portland Head Light to enjoy breakfast with a view.

Travel Tip: Standard Baking gets busy early, especially on weekends. The line moves fast, but showing up before 9 a.m. helps you beat the rush.

Mid-Morning: Explore by Bike or on Foot

Once you’ve fueled up, it’s time to explore the city. You’ve got two great options:

  • Guided bike tour: Cruise the coastline, see historic lighthouses, and ride through some of Portland’s most charming neighborhoods. It’s flat, scenic, and surprisingly chill.
  • Culinary walking tour: If you’re more into bites than bikes, a food tour will take you through the Old Port and beyond. You’ll sample local oysters, lobster rolls, and other Maine staples while learning a bit of city history, too.

Both options let you cover a lot of ground without having to plan every detail yourself.

Early Afternoon: Local Shops and Hidden Gems

After your tour, take some time to explore the Old Port. The cobblestone streets are lined with 19th-century buildings and some seriously good shopping.

  • Sherman’s Maine Coast Book Shop: The oldest bookstore in Maine and an absolute gem for readers.
  • The Maine Souvenir Shop: Featuring over 100 local artists—this is where you’ll want to grab a gift (or treat yourself).
  • Sea Bags: Stylish, durable bags made from recycled sails.
  • Dean’s Sweets: Small-batch chocolate made right in Portland.

This part of the day is perfect for wandering without a plan. Just follow the brick sidewalks and peek into any storefront that catches your eye.

Mid-Afternoon: Brewery Break

By now, you’ve earned a drink. Head to Rising Tide Brewing Company. They’ve got a great lineup of IPAs, sours, and seasonal brews. Not into beer? Try Tandem Coffee Roasters for an afternoon caffeine fix.

If you’re more into cocktails, you can also pencil in Blyth and Burrows or Room for Improvement later in the evening.

Dinner: Lobster Rolls + Local Seafood

For dinner, make a reservation at Eventide Oyster Co. It’s one of Portland’s most iconic spots and worth the hype. Their fresh seafood is honestly amazing and unique.

Start with a local oyster sampler (many are harvested just miles from the city) and then try their signature lobster roll—it’s served on a steamed Asian bun and unlike any other.

If Eventide is fully booked, nearby Highroller Lobster Co. is a solid backup with a more casual vibe but just as much flavor.

Optional: End the Day with a Sunset Sail

If you’re visiting in the warmer months, end your trip with a sunset sail aboard a windjammer or schooner. These leave from the docks near the Old Port and offer beautiful views of Casco Bay. It’s a calm and scenic way to cap off your day.

Be sure to check seasonal schedules and book ahead—these sails often fill up quickly in summer and fall.

Things to See in Portland, Maine

Take a boat tour

One of the best ways to experience Portland is on the water. My boat tour was one of my favorite things I did! You learn a lot about the fishing industry (hello, lobster and oysters) and see some of the New England sea life on a boat tour, too. There is no better way to see Cape Elizabeth after all.

Booking a tour in advance will ensure you get a spot on a boat but you can book in-person right before a boat leaves, if there is space available.

Visit the Portland Museum of Art

Come see the collection at the oldest art museum in Maine. The Portland Museum of Art is a great way to spend a rainy afternoon or early morning in the city. They have a wonderful collection for its size, especially in the American and Impressionist collections. And as a bonus the museum is free every Friday from 12 p.m. to 8 p.m.

Travel Tip! Do you have a membership to your local museum? You might have what's called a reciprocal membership to the Portland Museum of Art! This gives you free admission - just be sure to bring your membership card to the museum you are a member of.

take in the views at the Portland Observatory

What was once a communication station in 1807 for the bustling ship harbor is now a unique destination in Portland. Now the observatory gives amazing views of the surrounding city and seaside to visitors.

Keep in mind the observatory keeps some strange hours, so be sure to check before heading over to snag a guided or self-guided tour.

Have a beer at some of the best New England breweries

New England brewery culture can’t be missed on a trip to Portland. You can find dozens of great breweries in Portland and the surrounding areas but some of the best are Allagash Brewing Company and Belleflower Brewing Company. (I also liked Rising Tide and Austin Street!)

>> If you want to do something a little different consider a guided brewery tour of the Old Port.

Shop local

If you like finding unique local products Downtown Portland has plenty of places to find them. One that I always recommend is Sherman’s, Maine’s oldest bookstore. Sherman’s has locations in a few Maine cities (I love the little one in Bar Harbor) but either way supporting this continuing local bookstore is worth the visit.

Some other local shops to add to your list:

Stroll the Old Port

There is nothing more New England than strolling 19th century brick buildings near the fishing docks. Still a working port you’ll find lobster traps, fishing boats, and so much more near the Old Port in Portland. Nowadays the port is full of unique restaurants and shops to wander through.

>> If you want to learn more about Maine’s history you can book this walking tour, which includes the Old Port!

Take a drive to the Portland Head Light

Located 5 miles from downtown the Portland Head Light is a seaside lighthouse completed in 1791. The lighthouse is in the Fort Williams Park. The park is a nice place for a walk, too.

I recommend bringing your morning coffee and pastry from Standard Baking Company out to the lighthouse in the morning. It’s the perfect way to relax with the waves crashing into the rocky shoreline.

Take the ferry to Peaks Island

If you want something local to do try taking the public ferry to Peaks Island for a day trip. Tickets are $14 with a variety of departure times you can choose from. Ferries are operated by Casco Bay Lines which operates passenger and car ferries in Maine.

If you only have a day in Portland I’d probably skip a trip to Peaks Island but if you’re staying a few days and want a slower pace, local activity it’s a great option.

Bike the coastline

See a different side to Portland with a guided bike tour around the coastline. Portland is very flat and easy to ride, making it a great way to spend a sunny day. If you’d rather bike yourself you can DIY a similar experience renting a bike in town, too.

Visit the Victoria Mansion

With construction of the mansion completed in 1860, the Victoria Mansion was a summer home for a wealthy New Orleans hotel mogul. The home is a great example of the Italian Villa style with guided tours. The mansion is well preserved, showcasing 19th century lift in Portland.

More things to do in Portland, Maine

Where to Eat and Drink in Portland

Portland is a foodie paradise with plenty of amazing places to eat and drink throughout the city. The longer you visit the more you can give deep into the rich culinary universe that is Portland but with just a couple of days the highlights will still be exciting.

If you only have a day or two in Portland I recommend checking out a food tour. Joining a food tour will make sure you get to try all the Maine classics, like lobster rolls and oysters.

Best places to get a coffee

Where to get a lobster roll

Get a drink at these spots

Have a meal on a budget

Easy Day Trips from Portland, Maine

If you’re spending more than a day in Portland—or want to base yourself in the city while exploring the Maine coast—there are plenty of easy day trips just a short drive away. These nearby towns and parks offer a totally different vibe but are still close enough to enjoy without switching hotels.

Here are a few of the best day trips from Portland, Maine:

Freeport

Freeport is most famous for being home to the L.L. Bean flagship store, which is open 24/7 and feels more like an outdoorsy Disneyland than a retail shop. But there’s more here than flannel and fleece. Head to Wolfe’s Neck Woods State Park for scenic trails and coastal views, or stop at local spots like Wicked Whoopies for a Maine treat on the go.

Kennebunkport

Kennebunkport has a slower pace and picture-perfect New England feel. Spend your day browsing boutiques in Dock Square, grabbing lunch by the harbor, and ending with a sunset walk on Goose Rocks Beach. This is the place to go if you’re after clapboard homes, cute cafés, and that “I might just move here” energy.

Bath

Small but mighty, Bath is one of the most underrated towns in southern Maine. Stop by the Maine Maritime Museum to learn about the state’s rich shipbuilding history, then stroll downtown for antique shops, bakeries, and waterfront views. If you’re a history lover, this one’s for you.

FAQs

What is the best month to visit Portland, Maine?

The sweet spot for a day trip to Portland is spring through fall, especially during shoulder seasons—late April to early June or September to mid-October. You’ll get mild weather, most restaurants and tours will be running, and you’ll avoid the summer crowds and high hotel prices.

Is one day enough in Portland?

Totally. You won’t see everything, but you can cover a lot in just one day. From strolling the Old Port to squeezing in a food tour or lighthouse visit, a well-planned itinerary lets you experience the highlights without feeling rushed.

How do I get to Portland, Maine?

You can fly directly into Portland International Jetport or fly into Boston and drive about an hour and 45 minutes to Portland. Typically flights into Boston are cheaper but if you otherwise wouldn’t rent a car flying into Portland might be the cheaper option.

Final Thoughts: Planning the Perfect Day Trip to Portland Maine

Whether you’re here for the lobster rolls, the waterfront views, or just need a quick New England escape, Portland is a city that punches well above its size. You can stroll cobblestone streets, sip a local beer, and catch a sunset over Casco Bay—all in one single, satisfying day.

So if you’re wondering whether a day trip to Portland, Maine is worth it? The answer is yes. A thousand times yes.

Pack comfy shoes, make one solid dinner reservation, and just go.

And if you end up wishing you had more time? Don’t worry—you’re not alone. Portland has a way of convincing you to come back.

More Maine Tips and Inspiration

I hope you found this Portland Maine itinerary helpful for your trip! I love Maine and Portland is just the best little coastal town. If you liked this itinerary be sure to check out some other Maine travel inspiration.

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