Portland, Maine, is a city brimming with coastal flair, historic buildings, and the small-town charm worthy of an epic New England getaway.

This port city is dotted with excellent eateries and bars, as well as art galleries on every corner, and gives you easy access to southern Maine beaches and state parks.

A long weekend in Portland, Maine, is nothing short of a foodie and adventurer’s dream.

Between the fresh produce markets, the picturesque lighthouses, and the most delicious lobster in the U.S., you may want to stay longer.

In this guide, I unpack the best ways to explore this charming city through an extensive Portland, Maine weekend getaway 3-day itinerary.

Now without further ado, let’s dive into the ultimate Portland, Maine, weekend trip.

Tip: If you don’t have three days, explore the town’s highlights on a day trip to Portland, Maine.

Your Portland, Maine Weekend Trip At A Glance + Map

• Day 1
  • Coffee + Breakfast
  • Cruise or Mailboat to Casco Bay
  • Walk from Commercial Street to Old Port
  • Lunch at Little Tap House
  • Portland Observatory Tour
  • Join the First Friday Art Walk
  • Dinner on the Waterfront

• Day 2
  • Coffee on Congress Street
  • Stroll through the Portland Farmers Market at Deering Oaks Park
  • Go on a Lobstering Tour
  • Catch a Ferry to Bug Light Park + Lunch
  • Beer Tour + Dinner

• Day 3
  • Coffee + Donuts
  • Visit Friends of the Kotzschmar Organ
  • Peruse Portland, Maine’s Bookstores + Lunch
  • Head to The Eastern Promenade + Dinner

Here is a map you can use on your trip.

Click here for a live version of the map!

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Day 1 in Portland

Coffee + Breakfast

Everyone knows a good adventure starts with a delicious cup of coffee and a tasty breakfast.

Portland, Maine is abundant with quaint coffee shops; one chain that you’ll find dotted across the city is Coffee by Design.

Try the one on Diamond Street, where you’ll discover an artisan roastery, coffeehouse, and cupping room.

On Franklin Street, there’s Coffee ME UP, where you can enjoy your specialty coffee beverage with a selection of light pastries, sandwiches, and tasty smoothies.

Cruise or Mailboat to Casco Bay

Once you’re pumped on caffeine, hop on the first ferry to Casco Bay.

You can catch a gorgeous sunrise via a cruise or a mailboat run at 10 am.

And in case you’re wondering, yes, a mailboat is exactly what you think it is — a boat delivering mail to the island.

Locals enjoy commuting to Casco Bay via a mailboat.

The daily runs from Portland, Maine, cost $17 per adult, take about 2.5 to 3.5 hours, and stop at five islands. This should be enough time to explore your chosen destination. 

Wanderer Tip: If a cruise is more your style, charter a tall schooner ship tour and sail the rugged Casco Bay coastline, catching sights of lighthouses, seals, and other coastal wildlife.

Walk from Commercial Street to Old Port

Upon returning to the mainland, stroll down Commercial Street, and discover some of the best spots in Portland, Maine.

Walk along the working waterfront with fishing boats, lobster spots, jewelry, and pottery shops.

Take some time to explore the historic tourist district and learn more about Portland through guided walking tours to Old Port.

You can browse through cute boutiques, art galleries, restaurants, and bookshops.

The charming bookshops range from family-owned stores with a dog-friendly atmosphere selling works by local artists to book shops where you can grab a snack, a coffee, or a beer.

Lunch at Little Tap House

After all that walking, you must be famished.

Head down to  Little Tap House on High Street from Old Port for local delights. The farm-to-table gastropub serves scratch-kitchen cuisine — the fish and chips are delicious and generously portioned.

Wash your meal down with a refreshing cocktail, a light wine, or a mimosa. Ready for your next attraction? That’s great because it’s right across the street.

Portland Observatory Tour

 A skip away from Little Tap House, you’ll stumble upon the Portland Observatory.

The maritime signal tower is the country’s only surviving one of its kind.

From atop the tower, you’ll see stunning views of Casco Bay. Walk a little further, and behold the Portland Museum of Art.

Take a tour of the museum’s extensive collection and varying displays of contemporary art and film, then head over for some photo snapping at the outdoor sculpture park.

Join the First Friday Art Walk

Is it Friday? Then you know what to do in Portland, ME.

Enjoy strolling through the city’s galleries, alternative art studios, and museums, as well as vibing to live music at Congress Square Park.

This art walk also boasts paths lined with pop-ups, coffee shops, jewelry, and pottery vendors.

The event happens every first Friday of the month, and doors open from 5 pm to 8 pm. Oh, and did I mention the entrance is absolutely free?

Dinner on the Waterfront

Portland, Maine’s waterfront is buzzing with fantastic eateries, bars, and bistros.

You’ll be spoiled for choice between the hand-crafted meal on Fore Street, and Boone’s Fish House & Oyster Room—their lobster mac n cheese is delightful.

Boone’s is quite a popular spot attracting large crowds and a lively atmosphere. 

Day 2 in Portland

Coffee on Congress Street 

Kickstart day two of your weekend trip to Portland, Maine, with a fresh caffeine brew on Congress Street.

If you’re in the mood for a casual vibe and a fresh sandwich made at the counter, Yordprom Coffee Shop is the perfect spot for you.

For a more modern aesthetic, Tandem Coffee and Bakery take the cup. Their freshly baked pastries are excellent, and the chai latte may be the best you’ve ever had.

Stroll through Portland Farmers Market at Deering Oaks Park

Shop from Maine’s top farmers and food producers in one stop, surrounded by gorgeous green spaces and expansive water fountains. 

The farmers’ market is open for the summer season on Wednesdays and Sundays from 7 am to 1 pm, May through November.

And in the wintertime, it’s open Sundays from 9 am to 1 pm, December through April, at the Maine Girls Academy gymnasium.

Go on a Lobstering Tour

One thing you must do when in town, even if you’re only spending one day in Portland, Maine, is going lobstering! 

There are plenty of tour providers along the shore. You’ll find Lucky Catch Cruises and Rocky Bottom Fisheries.

Not only do you see the catching process, but you also get to help with measuring the lobster and emptying the traps.

Tip: If all that lobstering gets you hungry, why not join a seafood and lobster walking tour and sample some of Portland, Maine’s favorite local delicacies?

Catch a Ferry to Bug Light Park + Lunch

Kickback and relax to stunning skyline views and gorgeous Portland Harbor vistas at this nine-acre manicured parkland.

Home to the picturesque Portland Breakwater Lighthouse, Bug Light Park is the perfect place to kill time before the next adventure begins.

If you like, you can pack a picnic basket and enjoy a tranquil lunch on the lawn. Or opt for a gourmet lunch at one of South Portland’s famous eateries.

North 43 Bistro serves classic American cuisine, like smash burgers, and has excellent marina views.

For seafood delights, stop by Saltwater Grille for an upscale ambiance and Portland skyline views.

Other things you can get up to at Bug Light Park include biking, saltwater fishing, and boating.

Take a three-hour South Portland bicycle tour and explore four gorgeous lighthouses.

This includes the Portland Head Light, one of the most photographed landmarks in the city. Its white façade contrasts the rocky shores surrounding it and the azure backdrops of the sea and sky.

Nature lovers will appreciate walking the half-mile-long beautifully landscaped Cliff Walk to get to the lighthouse.

Beer Tour + Dinner

Portland, Maine, has the second most breweries per capita in the U.S. after Vermont. 20 breweries and over 700,000 people — now that’s a lot of beer!

It goes without saying that you won’t see all these breweries in one go, so choose the one that serves grub of equal standard.

Some of the best breweries in Portland, Maine, for a seating experience, include Foulmouthed Brewing and Foundation Brewing, with an expansive variety of crafts from sour ales and farmhouse ales to IPAs and porters.

For a mobile beer experience, join a Maine Brews Cruise tour and enjoy delicious craft beer on a biking tour, beer bus, or walk from one spot to another. 

Day 3 in Portland

Coffee + Donuts

A trip to Portland, Maine, is incomplete without tasting the city’s delicious desserts.

Donuts are popular, and there’s nothing wrong with a little sugar rush to start your last day in Portland. 

Try the tasty donut holes at The Cookie Jar in South Portland, or opt for a creative donut made with locally sourced potatoes at the famous Holy Donut on Commercial Street.

The Holy Donut also serves gluten-free and vegan options.

Visit Friends of the Kotzschmar Organ

The Kotzschmar Organ is one of only two municipal organs in the U.S., a true Portland hidden gem.

You can see this colossus by either touring or attending a concert at Merrill Auditorium in the City Hall.

Thanks to the Friends of the Kotzschmar Organ organization, the instrument is still in use, and if you’re lucky, you may catch the annual classic — The Phantom of the Opera.

Peruse Portland, Maine’s Bookstores + Lunch

While Portland, Maine, is often hailed for its lobster rolls and craft breweries, one industry that bears mentioning is the town’s vibrant literary scene. 

The city has about 13 independent bookstores, selling every kind of new, used, and comic book you could possibly imagine.

Check out some interesting spaces like Longfellow Books, Sherman’s, and the cozy Print: A Bookstore.

For lunch, stop by LB Kitchen for something refreshing and healthy to munch on. The bright and colorful eatery serves delicious lunch bowls, salads, and creative smoothies.

Head to The Eastern Promenade + Dinner

The Eastern Promenade is a 68-acre green space on Munjoy Hill designed by the Olmsted Brothers landscape firm, also renowned for creating New York’s Central Park and the Boston Commons.

This expansive lush space offers the best picnic spots and a two-mile scenic hiking and walking trail in Portland, Maine. Catch the kaleidoscopic sunset or kick back on the beach.

The Eastern Promenade is also great for starting your Portland, Maine, day trip to Acadia National Park.

But if you’re running short on time, a hearty dinner and wine at a nearby eatery will do just fine.

Check out Jing Yan for a unique Asian experience. The Front Room and Blue Spoon offer classic American fare and tasty craft beverages.

Where To Stay in Portland, Maine

Now one thing you don’t want to skimp on during your Portland, Maine getaway is the accommodation. The best area to call home is undoubtedly the Downtown / Old Port district.

This part of town is where you’ll find an abundance of luxury chain hotels and budget-friendly Airbnb.

You’ll also be in the heart of the city, allowing you to walk to nearby restaurants, art galleries, and local breweries.

Some places to consider include:

The Press Hotel, Autograph Collection — Embrace the New England atmosphere at this elegance-inspired boutique hotel in the Portland Downtown Historic District. Not forgetting the chic on-site restaurant, where you can enjoy tasty seafood and wine pairings.

Canopy By Hilton Portland Waterfront — If you like shabby chic and contemporary decor with a touch of wooden oak furnishings, this is the hotel for you. Canopy is home to Luna Rooftop Bar, serving great cocktails and waterfront views thanks to its accordion glass walls.

Aloft Portland, Maine — Funky and colorful; and the art-deco furnishings make Aloft one of the best hotels in Portland, Maine. Spend some downtime riding bikes along the waterfront, playing billiards, or cocktailing it up at WXYZ Bar.

Getting Around

Portland, Maine, has sophisticated transportation methods ranging from buses and taxis to ferries and trains.

But the best way to explore the city is by walking or biking along the cobblestone streets downtown and the waterfront.

List of Things To Do in Portland, Maine

Here’s a quick roundup of Portland, Maine’s best things to do. These top attractions and activities make a great addition to your New England road trip. 

Walk Around Old Port — Discover the historical buildings, quaint bookshops, and charming eateries dotted across the Old Port. See the city’s iconic landmarks, from the bustling Commercial Street to the scenic waterfront.

Visit the Portland Observatory — This 86-foot tall octagonal tower is one of Portland, Maine’s trademarks, with excellent cityscape views.

Tour the Portland Museum of Art — Within a two-minute walk from the observatory, you’ll stumble upon Maine’s largest and oldest public art institution.

Stroll Through the Portland Farmers Market — Buy everything from Portland’s local farmers, from fresh produce and baked goods to meats, jams, and sauces.

Explore Casco Bay via a Mail Boat — Enjoy the locals’ favorite way of experiencing Casco Bay via a mailboat run.

Take a Craft Beer Tour Through the City — If there’s one thing you’ll find scattered across Portland, Maine, it’s breweries. There are over 32 breweries for you to choose from.

Walk or Bike Along the Eastern Promenade — Catch the most stunning views of Casco Bay and Portland Harbor.

Marvel at the Portland Head Light — This historical lighthouse along the shores of Fort Williams Park in Cape Elizabeth has spectacular ocean and rocky Maine coastline views.

Enjoy a Picnic at Bug Light Park — Pack a picnic basket, grab an exciting book, and relax on the vast grassy lawn facing the city at this charming park.

Join the First Friday Art Walk — The first Friday of each month belongs to the arts in Portland, Maine, no matter the weather.

Go Bookshop Hopping — If you’re a book lover, the independent bookstore scene in Portland is really something you should take a gander at.

Hop on a Ferry to Peaks Island — Get unparalleled ocean views from Casco’s most populous island. Peaks Island is home to stunning public beaches, art galleries, and museums like the quirky Umbrella Cover Museum.

Go on a Lobstering Tour — Portland, Maine, is synonymous with lobster — lobster bisque, lobster rolls, or an authentic lobster bake. If you’re interested in seeing where the lobster comes from, why not join a lobstering tour?

Hop on a Lighthouse Trolley Tour — Spot Portland’s beautiful lighthouses, from the picturesque Spring Point Ledge Lighthouse to the famous Portland Head Light.

Admire the Kotzschmar Organ — Go off the beaten path and marvel at this gorgeous instrument with over 7,000 pipes.

Portland, Maine Itinerary 3 Days | Wrapped Up

Well, there you have it — 3 days in Maine’s largest and most vibrant city. Visiting Portland, Maine, is a must-add to any foodie’s and adventurer’s bucket list. 

From stunning waterfront views and historical landmarks to scores of quaint bookshops, breweries, and the tastiest lobster rolls in the U.S., you’re set to have a wonderful time.

And if you only have a day in Portland, Maine, explore the city’s highlights via a quirky, vintage fire truck tour.

So what are you waiting for? Pack your bags, book your stay, and gear up to have a fantastic time exploring and eating your way through Portland, Maine.