The Perfect 3-Day Portland, Maine Itinerary

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Portland is a fascinating city along the southern coast of Maine and is absolutely worth seeing. Its quaint, everlasting essence is what charms travelers and makes it one of the most cherished places to visit for those in the state.

sunsetting on portland headlight with views of the ocean to the right

The moment you step into this inspiring city, you will be immersed in its glorious history rich in fishing, agriculture, and of course industrial growth.

The perfect amount of time to spend in Portland, Maine is 3 days.

You’ll be able to see beautiful coastal lighthouses, enjoy the delicious food scenes, and walk along the charming cobblestone streets!

How Can I spend 3-Days in Portland, Maine?

For those thinking about spending time in the fun city of Portland, it’s time to break down what a 3-day Portland, Maine itinerary should encompass!

Check out the contents below for a quick overview and read on for all the deets!

Day 1: Portland, Maine Itinerary

Is Portland Maine worth seeing

1. Visit The Old Port & Downtown Area

There is nothing more “Portland-Esque” than visiting the Old Port. This is one of the more historic and traditional attractions in this coastal city and it is going to be a place you will remember.

The brown-colored buildings with welcoming locals everywhere can be heartwarming. Old Port also is lined with cobblestone paths, which just adds another layer of charm.

A few of my favorite stores to browse through were Pinecone + Chickadee, Life is Good, and Maxwell’s Pottery.

This is also a food hub for those who want to take in the sights while enjoying what local eateries are all about. Just stop by, order a meal, and get some of the best food you are ever going to find.

A couple of notable restaurants are Duckfat for some Belgian fries and The Honey Paw for Asian fusion.

This is a delicious part of Portland and a great introduction to what the city has to offer. You will love it as a starting point.

2. Take A Culinary Tour Near Old Port for Lunch

Since you are going to be around Old Port, it’s time to dig deeper into what the region has to offer. This is a complete tour that is going to show the ins and outs of the culinary delights associated with this part of Portland, Maine.

You will learn more about the history of seafood, how it is made, and which meals are must-eat in this beautiful city. There is enough food that you will be filled up for lunch!

The tours are kept smaller for a personalized experience, just make sure you’re wearing great walking shoes like my favorite Bob’s shoe or these slip-on Addidas!

Check out the tour here: Culinary Tour Near Old Port.

3. Visit the Holy Donut for Dessert

After your culinary food tour, head on over to the Holy Donut for a sweet treat. These riced potato donuts are delicious and a must-try when in Old Port. Some of the best flavors are the Triple Berry, Honey Lavender, and Dark Chocolate Sea Salt.

You can continue browsing in Old Port as you snack, or save your donut and drive to the Portland Headlight for a view!

  • Holy Donut | Address: 177 Commercial St, Portland, ME 04101
See the Portland Headlight

4. See Gorgeous Views at Portland HeadLight

The Portland Headlight is located in Cape Elizabeth, Maine, and is a beautiful spot to take in the views of the Atlantic Ocean and Casco Bay. The lighthouse was constructed in 1791 and is still operational today. It’s definitely worth a visit if you’re in the area!

Take your Holy Donuts and grab a spot at one of the picnic tables to enjoy the sea breeze. If you’re feeling active, there’s a trail that takes you over some rocks to see the headlight from the cliffs. The views are simply breathtaking!

For a more relaxing activity, take a walk on the beach and get some amazing pictures of the lighthouse. You’ll definitely want to remember your trip to the Portland Headlight!

  • Portland Head Light | Address: 12 Captain Strout Cir, Cape Elizabeth, ME 04107
  • Free parking in Fort Williams Park
  • Entrance fee into the lighthouse | Adults: $2 | Children 6-18: $1 | Under 6: Free

5. Eat at J’s Oyster

Now it is time to wrap up the day with a good meal. J’s Oyster does it all with its welcoming ambiance, spacious seating, and overall high-quality seafood.

Whatever you order here is going to impress. Whether it is the lobster roll or stew, you will want to fill yourself up with some of the finest seafood in the area.

Nestled right along the water, this is a fun-filled experience for those who want to enjoy good customer service, fun people, and great food. It is the perfect trifecta in that sense and a good way to wrap up day one.

  • J’s Oyster | Address: 5 Portland Pier, Portland, ME 04101

Day 2: Portland, Maine Itinerary

How can I spend 3 days in Portland Maine

1. Check Out Some Local History at the Portland Museum of Art

The Portland Museum of Art is about a 4-minute drive or a 13-minute walk from Old Port. The museum is passionate about providing art for all by including people of all backgrounds to experience its art. There are rotating exhibits, so there’s always something new to see.

One of my favorite things about this museum is that there is a sculpture park that takes you outside. It’s quite an incredible view!

If you’re looking for a dose of culture, the Portland Museum of Art is definitely worth a visit!

  • Portland Museum of Art | Address: 7 Congress Sq., Portland, ME 04101
  • Open Hours | Wednesday – Sunday, 10 am – 6 pm
  • Entrance Fees | Adults: $18 | Seniors + Students: $15 | 21 years and under: Free

2. Go For Burrito at Crunchy Poke

When it is time to eat, you will want to step away from the seafood and try out something new in the form of a Portland burrito. Crunchy Poke is a fun, easy-going restaurant that offers some of the best seafood burritos you are ever going to taste!

If you’re not into seafood burritos, you can also grab a poke bowl to enjoy all the flavors of seafood. Whatever you choose to order, you can’t go wrong!

The place is always welcoming and offers a more authentic seating experience in this small city. You will experience Portland in a way that is unique, memorable, and perfect.

  • Crunchy Poke | Address: 426 Fore St, Portland, ME 04101

3. Get Some Views From the Top at the Portland Observatory

The Portland Observatory is about a 4-minute drive or an 18-minute walk from Old Port and it offers some of the best views of the city. The observatory was built in 1807 and is the oldest standing structure in Portland.

The observatory is open for tours from May through October, and it’s definitely worth a visit. You’ll be able to see the harbor, Old Port, and the Portland skyline from the top.

If you’re visiting Portland, make sure to add the Portland Observatory to your list of places to see!

  • Portland Observatory | Address: 138 Congress St, Portland, ME 04101
Eat a lobster roll in Portland Maine

4. Grab a traditional Maine Lobster Roll for Dinner

When you think of Maine, one of the first things that come to mind is lobster. And what’s a better way to enjoy lobster than in a traditional lobster roll?

A lobster roll is simply a roll of lobster meat, mayo, and celery that’s been chilled. It’s usually served with a side of fries or onion rings.

If you’re in Portland, there are a few places where you can get your hands on a lobster roll. One of my favorites is Portland Lobster Company. They have a great outdoor seating area where you can enjoy your meal with a view of the harbor.

Another great option is DeMillo’s on the Water. They have an extensive menu with a lot of great seafood options. The lobster roll is definitely worth a try!

A third option to get a lobster roll is at Eventide Oyster Co. They serve up some of the best seafood in the city, and the lobster roll is no exception. It’s definitely a must-try if you’re in Portland!

  • Portland Lobster Company | Address: 180 Commercial St, Portland, ME 04101
  • DeMillo’s on the Water | Address: 25 Long Wharf, Portland, ME 04101
  • Eventide Oyster Co. | Address: 86 Middle St, Portland, ME 04101

5. Visit Bubba’s Sulky Lounge For Dancing Fun

When you are on a trip, you will want to have a bit of relaxed fun. This is where Bubba’s Sulky Lounge comes into the equation with its welcoming patrons, fun-filled tunes, and inviting ambiance.

Whether you are thinking about grabbing a drink after dinner or having a bit of fun dancing, there is something for everyone here and that is what makes it appealing. You’ll also find a plethora of antiques as that’s one of Bubba’s favorite hobbies!

Portland is home to several of these places but there is nothing better than spending time at Bubba’s.

  • Bubba’s Sulky Lounge | Address: 92 Portland St, Portland, ME 04101

Day 3: Portland, Maine Itinerary

How do people spend 3 days in Portland Maine

1. Grab Breakfast at Hot Suppa

Hot Suppa is a southern breakfast restaurant about a 5-minute drive or a 20-minute walk from Old Port. The restaurant is known for its creative breakfast dishes, and it’s definitely a must-try if you’re in the area.

The atmosphere of the restaurant is cozy and comforting. It’s the perfect place to start your day.

My personal favorites are the chicken and waffles and the mother clucker, which is boneless fried chicken served with cheddar curds and biscuits. If you’re looking for something sweet, try the french toast. It comes spiced with vanilla, cinnamon, and nutmeg, yum!

No matter what you order, you’re sure to enjoy your breakfast at Hot Suppa. It’s definitely one of my favorite breakfast spots in Portland!

  • Hot Suppa | Address: 703 Congress St, Portland, ME 04102

2. Head To Peak’s Island For Exploration

It’s the last day of your 3-day Portland, Maine itinerary! One of the coolest places to visit is Peak’s Island. This is one of the most breathtaking parts of the coastal city and an experience you are going to thoroughly enjoy.

Peak’s Island is accessible through a ferry and is quite the sight during the warmer months. It is rich in greenery, has open spaces, and offers a look at a historic part of the region in the form of a WW II outpost. The area is dripping in history due to this reason.

Even if you are not a history buff, the visual appeal of Peak’s Island is reason enough to want to visit it.

You can rent a little golf cart and drive around the whole island or hang out on the beach. One of my favorite activities was driving around the neighborhoods to peep the adorable coastal homes – they also have names!

Make sure to check the Peak’s Island ferry boat schedule so you can plan accordingly!

  • Peak’s Island | Address: 20 Island Ave, Portland, ME, United States

3. Eat Lunch At Bao Bao

You can grab lunch at Peak’s Island, but if you are returning to the main part of Portland for lunch, check out Bao Bao, another well-established restaurant that offers quality food using the best recipes.

Bao Bao is a dumpling house where you can order dim sum or dumplings. This starts with wonton soup, pork and scallion dumplings, or beef bulgogi dumplings.

The crisp, mouthwatering taste of their menu items will make you want to stay there and keep eating. It is one of the biggest allures of Bao Bao because the food is fantastic and the atmosphere is welcoming.

  • Bao Bao | Address: 133 Spring St, Portland, ME 04101
sunset at bug light park

4. See the Sunset at Bug Light Park

If you’re looking for a beautiful spot to watch the sunset, look no further than Bug Light Park. The park is located in South Portland, Maine, and offers stunning views of the harbor.

Even more than the views it offers, Bug Light Park also has a great history of being the site of shipbuilding activity during WWII. The lighthouse was built in the late 1800s in Grecian style and was dubbed “Bug Light” due to its small size.

You can participate in some activities like picnicking, kite flying, and boating at Bug Light Park, but one of the best times to visit is in the evening when the sun is setting.

The park is a great place to relax and take in the beauty of nature. It’s definitely a favorite spot in Portland!

  • Bug Light Park | Address: South Portland, ME 04106
  • Open Hours | Every day,  6:00 AM – 9:00 PM

5. Grab A Drink At Liquid Riot

When it comes to ending your day, you will want to grab a drink at Liquid Riot. This is one of the best gourmet bars in the region and an experience that is an attraction all by itself.

It all starts with the housemade beers and spirits. It is a setting that is a different take from other establishments in the city making it one-of-a-kind in that regard. Some of the beers include Spaceman Spiff, Stereotropic DIPA, and Special Ale.

The long rows of seating, elegant lighting, and charming staff will ensure you have a good time. This is a wonderful place to drink with family and friends while traveling.

  • Liquid Riot | Address: 250 Commercial St., Portland ME  04101

Map of Things to do in Portland, Maine

Key: Yellow – Day 1 | Blue – Day 2 | Green – Day 3 | Pink – Accommodations

Extending Your 3-Day Portland, Maine Itinerary

How many days should I spend in Portland Maine

1. Take a Coastal Tour

Since Portland is one of the most appealing coastal cities in Maine, you are going to want to take advantage of its elegance with a coastal tour. It takes you from the Portland Headlight up north into Bar Harbor and through to the Bass Harbor HeadLight.

This all-day tour will showcase the coastal beauty from end to end. This includes the flowing blue water, rich greenery, and inviting coastal landmarks. It is an experience that is going to engulf you and can be quite the setting during the warmer months of the year.

Book this tour if you want an all-encompassing tour guide to see the beautiful coast of Maine! Check it out here: Coastal Tour

2. Head to Bar Harbor + Hike in Acadia National Park

If you would rather take your time exploring northern Maine, take a 1-hour drive up from Portland, Maine to spend some time in Bar Harbor. There is plenty to do in the small town, from hiking and biking trails to visiting the local shops.

Don’t forget to drive through Acadia National Park! The park has some of the most beautiful scenery on the east coast. Make sure to stop at Jordan Pond House and try a popover with jam.

There are plenty of hiking trails to choose from in Acadia National Park, but make sure to head out earlier so you can see the views! A couple of my favorite hikes are the Bubble Trail, an easy to moderate trail, and the Beehive Trail, a moderate to difficult trail.

Overall, Bar Harbor is a laid-back small town to spend a few days in and is the perfect home base for exploring Acadia National Park.

  • Portland to Bar Harbor Drive Time: 1 Hour
  • Jordan Pond House | Address: 2928 Park Loop Rd, Seal Harbor, ME 04675

Read Next: The Ultimate 10 day New England Road Trip Itinerary [Portland to Boston Drive]

3. Take a Road Trip Down to Boston

If you have a few more days to spare, take a road trip down to Boston and check out this amazing, historical city! There is so much to do and see in Boston–you won’t regret stopping by.

One of the coolest things to do in Boston is to walk the Freedom Trail where you take a self-guided walk through some of the most historical sights in American history: Park Street Church, Granary Burying Grounds, Old South Meeting Hall, Faneuil Hall, and so much more!

If you’re into whale watching, you can also take a boat tour to the Stellwagen Bank National Marine Sanctuary. You can also take a short trip to tour Harvard University (and claim that you went there).

The drive from Portland down to Boston is about 2 hours long.

Take a road trip rom Portland Maine

Where to Stay for a 3-Day Portland, Maine Itinerary

Hyatt Place Old Port

When it is time to find a place to stay in Portland Maine, Hyatt is never going to go wrong. This is nestled in Old Port making it easier for you to tour the area, take in the great seafood options, and make the most of your trip.

Since you will want to spend time in the downtown area and around Old Port, this is a good place to stay. It will keep you close to the key areas while also ensuring you can branch-off later too.

The hotel itself has a long list of amenities, is well-known, and remains clean year-round.

  • Hyatt Place Old Port | Address: 433 Fore St, Portland, ME 04101

Portland Regency Hotel

The Portland Regency hotel is in an ideal spot as it is central to everything. This makes it ideal for those wanting to visit different areas of Portland without having to steer too far away from where they are staying at night.

The hotel is well-located, offers exceptional service, and makes it easy to enjoy your stay in a spacious room. The brand is appreciated locally for its luxury and you are going to get to make the most of it by staying here.

If you want a central location, this is a hotel to have on your list.

  • Portland Regency Hotel | Address: 20 Milk St, Portland, ME 04101

The Press Hotel

This is a recommended place to stay for those who want to stay central in the city but also have a bit of money to spend. The luxuries associated with The Press Hotel are different from the other options and that makes it far more enticing to some people.

The gorgeous rooms, long list of facilities, and overall ambiance is nothing to scoff at. You will appreciate it as soon as you walk through the front door.

This is a hotel with a purpose and a beautiful place to spend 3 days in Portland, Maine.

  • The Press Hotel | Address: 119 Exchange St, Portland, ME 04101
best time to visit Portland Maine

The Best Time to Visit Portland, Maine

When visiting Portland, it’s never a bad idea to time your trip to perfection. The summer months are perfect in Portland making every day a breathtaking one. However, summer is the high season for Portland is between June and August, so you might find more crowds during the warmer months.

The temperature tends to hover between 65°F-73°F. This is comfortable, breezy, and works well at all times of the day. You also have less rain to deal with and that makes Portland, Maine quite appealing to those visiting and heading outdoors to places such as the beach.

September and October are also good months to visit as the temperatures are still in the 70s, there are fewer crowds, and you get the beautiful fall foliage and bright colors!

Getting Around Portland, Maine

When it is time to plan your 3-day Portland, Maine itinerary, it’s important to pinpoint how you are going to handle transportation.

If the transportation is not planned, you will have a stressful time getting from one part of Portland to the next. While it is a small city, you do need transportation to get the most out of it.

While in and around Old Port, you could walk to most of the sites. To get from the airport to your accommodation, you can take a Lyft or Uber.

You could also take the Portland METRO Bus to get around the city as well. This works well when you are in the downtown area and/or looking to get to places that are a few minutes away.

We personally rented a car when we visited because we were planning on visiting other cities as well. This may be the most efficient option for you, too, if you would rather not worry about figuring out the METRO stops or ordering Lyfts/Ubers.

Look at all of these options based on what your budget is so you can fully enjoy your 3 days in Portland, Maine!

Seeing Peaks Island in Portland Maine

How to Pack for a 3-Day Portland, Maine Itinerary

With temperatures in the 70s, you can get away with shorts in Portland. You’ll definitely want a jacket for when you visit the coast or see the gorgeous lighthouses! I would highly recommend comfortable walking shoes so your feet can fully enjoy all the walking you might choose to do.

3-Day Portland, Maine Packing List:

Final Thoughts on Your 3-Day Portland, Maine Itinerary

As you begin to plan things out, you will want to have this all-encompassing 3-day Portland, Maine itinerary on hand at all times.

Whether you are thinking about heading to Commercial street or eating at Bao Bao, planning with a purpose is key. This guide should act as a wonderful way to enjoy your time in the bustling city of Portland without missing out on its main attractions.

This is a city with an unrelenting elegance that is impossible to ignore. You will enjoy your time along the coast with its scenic views, tourist-friendly eateries, and gorgeous weather. Whether you are into museums or lighthouses, this is a place dripping in historic relevance.

Visit Portland, Maine, and enjoy an itinerary that brings a smile to your face!


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My Favorite Travel Tips + Resources

Here is a quick glance at all my go-to travel tips and resources that I use to plan every trip! For more information, check out my travel resources page.

  • Booking flights: I use Google Flights to check all routes and find the best flights. Then I compare them with Expedia (for reward points) and Skyscanner (for the lowest prices) before I book.
  • Accommodations: I love budget-friendly rentals or booking at a hotel where I can earn points. For hotels, I go through Booking.com or book directly with Marriott (for points + rewards). When I travel internationally, I’ll book through Hostelworld for very budget-friendly stays. For vacation rentals, I usually look through Airbnb, but you could also use Vrbo. Expedia also has some great bundles for hotels, flights, and car rentals altogether.
  • Transportation: For travel in the United States, I love renting through Expedia with Enterprise or Thrifty. They have been consistent and provide the best customer service. For international travel, I’ll book through Rome2Rio or Eurail for trains or bus fares.
  • Travel Credit Card: I book all my travel (flights, hotels, car rentals) through my favorite travel credit card. I also use this card for everything on my trip including dining, excursions, and souvenirs. Apart from earning 5x more points towards free travel, there are amazing benefits: no foreign transaction fees, trip cancellation/interruption insurance, trip delay reimbursement (so I can book worry-free), fraud protection, emergency assistance – it’s really a great deal! Check it out here!
  • Vaccines and Medications: Check the CDC website for updates on necessary vaccines to enter a country, including updates on Covid-19 and recommended places to visit. I recommend getting all the vaccines you need before you go!
  • Tours + Experiences: I absolutely love my tours! Everything from eerie walking ghost tours to food tours, I’ll usually book something every trip either through Viator or GetYourGuide. I also love LastMinute.com for very affordable tickets to theaters and other experiences in Europe.
  • What to Pack: I almost always travel by backpack. For products I like, check out my packing guide page for all the things I take with me on different trips.