Maximize One Day in Portland, Maine: Perfect 2025 Itinerary

Ready to dive into a quintessentially New England adventure, but pressed for time? We’ve got you covered with the ultimate day in Portland, Maine, a city that never ceases to amaze us!

We absolutely love to visit the Northeast, and Portland, Maine has become our go-to spot. We’ve traveled here several times in the last 5 years – the food, vibes, and beer are epic!

Whether you’re a foodie on the quest for the next delicious bite, a beer lover eager to sip on craft brews, a history buff, a nature enthusiast, or simply in for a bit of everything, Portland delivers.

We know the drill all too well! So much to explore, yet so little time. But fear not! We’re here to guide you through squeezing every drop of fun out of one day in Portland, Maine.

One Day in Portland, Maine Overview

We’ve packed a lot of details into this article on how to make the most out of your one day in Portland, Maine.

Before we dive into all those details, here is an overview of what to see in Portland, Maine in one day :

Morning in Portland, Maine:

• Breakfast Options:
  • The Holy Donut: Famous for Maine’s potato donuts OR a Donut Tasting Walking Tour
  • The Front Room: Known for delicious offerings like bacon gnocchi.
• Morning Activity:
  • Visit the iconic Portland Head Light and Fort Williams Park – go on your own or take this fantastic guided tour

Afternoon in Portland, Maine:

• 4 Options:
  • Walking Tour of Old Port: Explore cobblestone streets, brick buildings, and historical landmarks.
  • Explore Casco Bay: Take a 2-hour private tour on a lobster boat, enjoy the coastline, and bring your own food and drinks.
  • Whale Watching: Look for marine wildlife, including various whale species and dolphins.
  • Brewery Exploration: Visit Industrial Way breweries like Allagash, Foundation, Austin Street, Battery Steele, and Definitive Brewing Company. Consider visiting Thompson’s Point for even more variety.
• Afternoon Snack: Duckfat offers Belgian-style frites and sauce.

Getting to Portland, Maine

Driving from Boston to Portland, Maine

The drive up from Boston to Portland, Maine is a beautiful one, taking just over 2 hours (107 miles). The route follows the coast, offering stunning views of the ocean and rocky cliffs. 

A day trip to Portland is a must for any Bostonian looking to escape the city and experience New England’s coastal charm, or for a Boston visitor looking to see a small, but charming New England city! 

Check out some of the cool stops between Boston and Portland!

Train from Boston to Portland

Taking the Amtrak Downeaster is a great option for travelers who want to sit back and enjoy the scenery. The train ride takes about 2 and a half hours and tickets range in price from $3 to $30. 

From passing by sandy beaches to rolling green fields, there’s always something new to see outside the window. The ride itself is comfortable and convenient, allowing passengers to sit back and enjoy the journey without any stress or hassle. 

Flying to Portland

All major airlines have flights to Portland and you can get great cheap flight deals. In particular, we see low $49 fares with JetBlue and United to Portland regularly!

The airport, Portland International Jetport (PWM), is located just a couple miles from the city center.

You can get to and from the airport via taxis, ride-share services, rental cars, or the METRO. The Greater Portland Transit District METRO provides bus service from the airport to downtown Portland via Route #5. 

How to Get Around Portland, Maine

Walking in Portland, Maine

One of the great things about visiting Portland is the opportunity to explore on foot. The downtown area is small and compact, making it easy to navigate by foot and discover hidden gems along the way. 

Most of the time, you should be a 5-20 minute walk to your next destination.

Taking a walk along the Eastern or Western Promenade, the furthest stretch, allows for stunning views of the ocean and coastline. The 2.6 mile (55 minute) walk will also take you through the Old Port which offers charming brick buildings and local shops, as well as plenty of delicious dining options. 

Whether it’s a leisurely afternoon stroll or a more intentional walking tour, taking a walk in Portland is always a delightful experience.

Biking in Portland, Maine

In Portland, Maine, biking is also a popular mode of transportation. The city has dedicated bike lanes and is continuously improving their bike infrastructure. 

The city has 30+ dedicated regular and electric bike rental locations – check them out here!  We suggest downloading the Portland Bikeshare app before you head out.

Biking in Portland is a great way to explore the charming coastal town and all it has to offer.

Driving and Rideshare in Portland, Maine

If you have a car, you will find that Portland is easy to navigate! There are many on-street parking options as well as surface lots and parking garages. 

All on-street parking in Portland is free 6pm until 9am Monday-Saturday, all day Sunday, and on major holidays.

Outside of these hours and for metered spots, we recommend having the PassportParking App downloaded to make your parking experience seamless!

In Portland, Maine, rideshare options like Uber and Lyft are available and often used by locals and visitors alike. These services offer a convenient and affordable way to get around the city. 

Additionally, using rideshare can be a responsible choice for those who plan on enjoying some alcoholic beverages during their time in Portland.

Itinerary for One Day in Portland, Maine 

Portland Maine is a great place to spend a day – there is so much to see and do! Below are our recommendations for a fantastic day

Perfect Morning in Portland, Maine

Breakfast

Portland, Maine is known for having fantastic food – make sure you start your day off with happy taste buds by trying one of their delicious breakfast spots.

• Option 1 (Kelsea’s Pick): The Holy Donut
  • According to Kelsea, there is no better way to start your day off than with Maine’s famous potato donuts. This donut shop has a lot of hype around it, and we think it is 100% well-earned! Kelsea still daydreams about the Berry Cannoli donut she had. The Dark Chocolate Sea Salt Donut is also incredible. 
  • The line can be long, so be sure to get there earlier in the morning. This ensures they will still have stock of everything. They move through the line quickly so don’t fret if you see it going down the street.
  • You can also take a Donut Tasting Walking Tour in Portland’s Old Port to visit three donut shops and skip the line at Holy Donut.

• Option 2 (Nicholas’s Pick): The Front Room
  • The Front Room is an adorable restaurant tucked into one of the neighborhood streets on the East end. The food is delicious – Nicholas still raves about the bacon gnocchi. You will not be disappointed. It does get crowded though so be sure to get there early.

Morning Activity

Portland Head Light

Portland is known for its Lighthouse and for good reason – it is stunning! We recommend taking a couple of hours and heading over to Portland Head Light. 

Portland Head Light is a beautiful and iconic landmark. The light was first lit on January 10, 1791, to warn mariners of approaching danger.

The light itself is picturesque, complemented by a cute keeper’s house and surrounding green lawns. 

For the best views of the lighthouse, make sure to take the cliffside trail. It is a short walk (about .4 miles one way) and you’ll be rewarded with spectacular views of the lighthouse and the rocky coastline.

Fort Williams Park

In addition to the famous Portland Head Light, Fort Williams Park offers many recreational activities for visitors. Picnic areas and hiking trails dot the landscape, and a nearby beach provides opportunities for relaxation and fun in the sun. 

History buffs can also take a tour of Battery Blair, an old fortified structure where large cannons were once stationed to protect the area. The cannons fire a 12-inch diameter, 1070-pound shell up to eight miles!

Overall, Fort Williams Park offers a diverse array of attractions for all types of visitors to enjoy. If you are in the mood for a meal or a snack, you will find food trucks at Fort Williams Park to grab something. Bite into Maine is the crowd favorite! 

• Cost: From April 1 – November 15 there is a fee for parking in premium spaces in the park. Free parking is available in the Overflow Lot.
• Hours: open year-round from sunrise to sunset

Two Lights State Park

If you have some extra time, we’d recommend popping over to On The Rocks at Two Lights. 

On The Rocks is a hidden gem located within Two Lights State Park. This beautiful spot is home to two iconic lighthouses, sweeping views of the Atlantic Ocean, and dramatic rock formations.

It is a fantastic place to explore tide pools, hike along scenic trails, and picnic on the grassy lawn. Additionally, it is a perfect place to enjoy a sunny day or watch the gorgeous sunset.

There is also a great seafood restaurant, The Lobster Shack, at Two Lights, where you can grab a bite while taking in the blissful views. We enjoyed the fish sandwich! Everything was cooked to perfection!

Parking is a bit cramped, so make sure you pack your patience!

Awesome Afternoon in Portland, Maine

Now that you have taken in the, arguably, most iconic view of Portland, Maine, we have 4 different options for your afternoon! 

Option 1: Walking Tour of Old Port

The Old Port is a historic district in Portland, Maine. It is located on the city’s waterfront and is known for its cobblestone streets, brick buildings, and 19th-century architecture. 

The area was once the center of Portland’s maritime trade and is now a popular tourist destination. Visitors to the Old Port can enjoy a variety of shops and restaurants, as well as many historical landmarks. 

The Portland Observatory, for example, is the only remaining historic maritime signal station in the United States. Other popular attractions include the Portland waterfront park, which offers scenic views of the harbor and Fort Williams Park.

A walking tour is the PERFECT way to learn a ton about the rich history of Portland – we recommend this walking tour. On this tour, you are going to learn a ton about Portland, Maine. 

If you don’t have time for a full tour, we recommend at least checking out the Wadsworth-Longfellow House.

Option 2: Explore Casco Bay

Maine is known for its rocky coastline, and Portland is no exception. Now that you have seen the beautiful coastline from land, see it from the sea! 

The city’s harbor is dotted with large boulders, making it a popular spot for sailing. Portland is also home to a number of small islands, which can be explored by boat. 

There are many great options but we recommend taking this tour out of Maine State Pier.

They have a 2-hour private tour on a lobster boat and allow you to bring your own food and drinks!

Boating will give you an opportunity to see the beautiful coastline from a different vantage point and to experience travel as it was 200+ years ago. 

You’ll sail by the Spring Point Ledge Lighthouse, a great photo opportunity!

Option 3: Whale Watching

In addition to having a beautiful coastline, Maine is a great place to see marine wildlife. Specifically, Portland has whale watching tours that are searching to see humpback, pilot, minke, and enormous finback whales up close. 

In addition to whales, you could potentially see North Atlantic White-Sided Dolphins, sharks, Ocean Sunfish, Sea Turtles, and many varieties of seabirds on this excursion. 

In Portland, whale watching season is typically from mid-April through October. The tours typically last 2-3 hours, and guides will provide helpful information! Whale watching is an unforgettable experience, and Portland, Maine is the perfect place to do it.

Odyssey Whale Watch operates out of Portland Waterfront and is our recommendation for a wonderful whale and marine life-watching experience.

If you do book a whale watching tour, we highly recommend taking a bag of these ginger candies to keep away any seasickness!

Option 4: Brewery Exploration

In our opinion, Portland, Maine is home to some of the best craft beer in the country. So, if you are a beer lover like us, we’d highly recommend taking an afternoon to sample the local brews. 

There are a ton of great breweries in Portland to explore. But if you head to Industrial Way, you will find 5 conveniently located within walking distance.

On this one short street, you will find Allagash Brewing Company, Foundation Brewing Company, Austin Street Brewery,  Battery Steele Brewing, and Definitive Brewing Company all within 500 feet of each other.

It is the perfect place to pop around and sample a few beers from a variety of Portland’s top breweries. 

If you like Belgian-style beers, you’ll want to stop at Allagash. The brewery was founded in 1995 when Rob Tod noticed Belgian-style beers were difficult to find in the United States.

Allagash White, a Witbier with balanced citrus and spice, is by far their most popular beer, but we prefer Curieux, a Tripel aged in bourbon barrels for approximately seven weeks.

If you are more into IPAs, Foundation Brewing is the place for you. Their flagship beer, Epiphany, is the perfect Maine IPA. Citrus, tropical fruit and pine blend to provide you with a sublimely juicy hop experience. Make sure to grab one if you are in the area.

If you also have wine and spirits fans with you, we would recommend going to Thompson’s Point. On Thompson’s Point, you’ll find Bissell Brothers Brewing Company, one of our favorite breweries.

Bissell Brothers is on a mission to change people’s perceptions of what beer and the beer experience can be. If they have Swish, a Double IPA, on tap, order a pint immediately!

Also at Thompson’s Point, enjoy Stroudwater Distillery and Rosemont Market & Wine Bar.

With a focus on curating high-quality spirits, Stroudwater offers cocktails made with their bottles of Bourbon, Rye, Vodka, and Gin. Their mule cocktail made with their delicious vodka was a perfect afternoon delight.

They are all right next door to each other making it a great spot to meander, especially if you are also going to the Children’s Museum and Theatre of Maine right there.

Please, drive responsibly and make use of Portland’s rideshare or Portland’s Best Craft Beverages Bus Tour!

Afternoon Snack

Need an afternoon pick-me-up? Duckfat has you covered! 

Inspired by a Belgian Frites window they came across in Amsterdam, the owners of Duckfat brought back the big and bold flavors of Belgium’s delicacy, frites and sauce, to downtown Portland. 

In the Old Port, you can order a delicious cone of frites with their mouthwatering sauce to go or you can venture over to their own frites window, Duckfat Frites Shack, in the East End! 

Fantastic Evening in Portland, Maine

Sunset Cocktail

Is there a better way to start the end of your one perfect day in Portland, Maine than with a cocktail and a jaw-dropping view? We don’t think so!

The Top of the East is a lounge on the top floor of the Westin. The views are absolutely spectacular – you can see the water as well as much of the cityscape since the Westin is on a hill a couple of blocks back off the water. 

It is stunning and the perfect place to take a break and take in the views. The drinks are a bit pricy but the view is worth the surcharge! 

Be sure to get there an hour or so before sunset since it is first come first serve.

We did not time things quite right and ended up getting there with only 15 minutes to sunset. 

By that time, all the seats were and great viewing spots were taken. We happened to get very lucky that one couple left in the middle of sunset so we could snag their spot!  

Delectable Dinner 

We have 2 recommendations for dinner:

• Option 1: Eventide Oyster Co
  • This James Beard-winning restaurant has some of the best seafood in the Northeast. They are known for their extensive selection of both raw and cooked oysters.
  • Their oysters are fresh and locally sourced. Additionally, they have “buns” and a clam bake that receive just as many rave reviews as the oysters. 
  • They offer very limited reservations (which are released 2 weeks in advance) so make sure you watch their website to grab a reservation! 
  • No reservations? No worries – they keep a majority of their tables for “first come first serve”. 

• Option 2: Empire Chinese Kitchen
  • The bold flavors coming out of the Empire kitchen are devine and sure to leave you wanting more! We have eaten our fair share of dim sum all over the world but we eat here every time we are in Portland, Maine. 
  • They do not take reservations so we put our name on the list and then took a stroll around Old Port which was really delightful.
  • Make sure you order the Lobster Rangoon and try one of their inventive cocktails like their Chinese Margarita made with yuzu juice – you will not be sorry!

Evening Fun

There is a ton to do to wrap up your one day in Portland, Maine! Here are a few options. You can do just 1 or multiple! 

This concludes our itinerary for that one epic day in Portland, Maine.

Where to Stay

There are many terrific places to stay in Portland! For just 1 day, we recommend the following places for a delightful stay: 

Splurge Hotels: 

• The Press Hotel, Autograph Collection: The Press is a beautifully designed hotel – the theme of “printing press” is wonderfully executed. The rooms are the perfect place for a fancy weekend getaway. 
• Portland Harbor Hotel: The Portland Harbor Hotel is located in the Old Port district and is in perfect walking distance to many of Portland’s top attractions. All 101 rooms are exquisitely designed, no 2 rooms are exactly the same!

Budget-Friendly Hotel: 

• Holiday Inn Portland-by the Bay: While this hotel might be a bit friendlier to your wallet, it is still packed with great views, accommodating staff, and helpful amenities (parking and e-bikes!). 
• Courtyard by Marriott Portland Downtown/Waterfront: This Courtyard by Marriott is one of the newer hotels in downtown Portland. It is just off the main area of Old Port, giving it some distance from the noise that comes with the nightlife but closeness to be able to easily walk to many attractions!

Rental with 1 Night Minimum: 

• The Docents Collection: A rental company that has many great properties in the Old Port area. 

Bed and Breakfasts:

• The West End Inn: Nestled in a cute corner of the neighborhood, this Bed and Breakfast will not disappoint! The rooms are spacious and breakfast is sure to start your day off right!
• The Chadwick Bed & Breakfast: There is a reason many lists have them as the #1 Bed and Breakfast in Portland, ME – their rooms, breakfast, and service is outstanding! Be sure to check your dates – they sometimes require a multi-night stay. 

One Great Day in Portland, Maine

This is such a wonderful location for a day trip or a stopover between locations.

There are a ton of things to do and plenty of great food to taste.

We would highly recommend spending a least one day in Portland, Maine to everyone! 

We wish you the best travels, and don’t forget to set your “Out of Office!”