A Perfect Weekend in Portland, Maine: 3 Day Itinerary
A Weekend in Portland, Maine
Planning a weekend getaway and eyeing Portland, Maine? You’re on the right track to discovering a gem!
We understand you’re searching for that perfect blend of beauty and an engaging itinerary for a weekend in Portland Maine.
As avid explorers of the Northeast, trust us, Portland holds a special place in our hearts, and we’re excited to guide you through its charm.
Whether you’re a solo adventurer or a family on the move, our tailored guide is packed with insider tips.
Let’s embark on this journey together, creating memories in one of the USA’s most picturesque spots!
A Weekend in Portland, Maine Itinerary
We’ve crafted a comprehensive guide to ensure your weekend in Portland, Maine, is unforgettable.
Before we dive into all the details, here is a snapshot:
- Day 1: Local Flavor & Historical Sights
- Breakfast at The Front Room
- Visit Portland Head Light and Fort Williams Park
- Lunch at The Lobster Shack at Two Lights
- Afternoon brewery tasting or art at Portland Museum of Art
- Dinner at Empire Chinese Kitchen, then evening entertainment in the city
- Day 2: Sail, Savor & See
- The Holy Donut to start
- Sailing on Casco Bay
- Stroll through Old Port
- Sunset Cocktails at Top of the East
- Dinner at Eventide Oyster Co.
- Day 3: Nature and Nourishment
- Breakfast at Bayside American Cafe
- Whale Watching or exploring Peaks Island
- Dinner at Duckfat
Day 1 Itinerary for a Weekend in Portland, Maine
Breakfast at 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!
The bacon gnocchi still has Nicholas daydreaming about it. You will not be disappointed. It does get crowded though so be sure to get there early.
Portland Head Light and Fort Williams Park
- 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
Head on over to Portland Head Light and Fort Williams Park – you can go on your own or on a tour.
Personally, we advocate for this tour since you will get WAY more context from their experience from your informative guide.
Portland Head Light is one of the most popular tourist destinations in Maine.
The light, which was first lit on January 10, 1791, is located at the entrance to Portland Harbor and is visible for miles. The area was originally built to warn citizens of coming British attacks.
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, which surrounds the light, is also a popular spot for picnicking, hiking, and visiting the nearby beach.
The light and the fort are both well worth a visit!
On The Rocks at Two Lights
- Cost: $5 Adult Maine Resident, $7 Adult Non-Resident, $2 Non-Resident Seniors
- Hours: Open all year; 9:00 a.m. to sunset daily unless otherwise posted at the gate
On The Rocks is a hidden gem located within Two Lights State Park.
This beautiful spot is home to an iconic lighthouse, sweeping views of the Atlantic Ocean, and dramatic rock formations.
Visitors can explore tide pools, hike along scenic trails, and picnic on the grassy lawn. On The Rocks 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, right there where you can grab a bite while taking in the blissful views.
Parking is a bit cramped so make sure you pack your patience!
Option 1: Afternoon Tasting Portland’s Best Brews
Are you a beer lover? Portland, Maine is home to some of the best craft beer in the country (in our opinion 😎). That’s why we’d recommend taking an afternoon to sample the local brews.
There are so many great breweries in Portland that it’s hard to know where to start. We highly recommend heading to Industrial Way.
On this one small street, you will have 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.
Another fantastic brewery is Bissell Brothers Brewing Company. They are located on Thompson’s Point. They would also be a great place to spend an afternoon.
Plus, Stroudwater Distillery and Rosemont Market & Wine Bar are right next door if you’d like some variety outside of beer!
Please, drive responsibly and make use of Portland’s rideshare or Portland’s Best Craft Beverages Bus Tour!
Option 2: Take a stroll through the Portland Museum of Art
- Hours:
- 10am – 6pm: Weds, Thurs, Sat, Sun
- 10am – 8pm: Friday
- Closed: Mon, Tues
- Cost:
- $18 | Adults
- $15 | Seniors & Students 22+
- Free | Visitors 21 & under*
- Admission is FREE to all every Friday from 4-8pm
The Portland Museum of Art is a world-renowned institution that houses an impressive collection of art from across the globe.
Featuring pieces by Picasso, Matisse, Renoir, and Monet, the museum is a must-visit for any art lover!
Kelsea and Nicholas would not claim to fall into a connoisseur of art category but the beautiful collection made for a fantastic few hours.
In addition to its art galleries, the museum also offers a variety of educational programs, concerts, and special events – make sure you check out their calendar!
Whether you’re looking to view iconic paintings or learn about the latest in contemporary art, the Portland Museum of Art is sure to offer something of interest.
Dinner at Empire Chinese Kitchen
WOW – the flavors coming out of the Empire Chinese Kitchen are bold, beautiful, and sure to leave you wanting more!
We highly recommend checking them out. Make sure you order the Lobster Rangoon – you will not be sorry!
Evening Entertainment
See a show at the Portland Stage – There are some spectacular performances put on in this cozy venue. Make sure to check out the calendar to see what plays/shows are going on when you are in town!
Hockey Game – If you are in Portland October-April, check out the Maine Mariners!
This electrifying ECHL is the affiliate team of the Boston Bruins and the games are right in the downtown area at the Cross Insurance Arena. These hockey games pack a punch and are a fun Maine experience.
Day 2 Itinerary for a Weekend in Portland, Maine
The Holy Donut
Start your day off 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 wait might be long, but you can also book a Donut Tasting Walking Tour to skip the line!
We recommend getting there earlier in the morning so they will still have stock of everything and pack your patience. They move through the line quickly!
Time to Set Sail
In our opinion, the Northeast should always be paired with a sailing experience. There are many great options but we recommend taking a tour on a tall-ship out of Maine State Pier.
Sailing 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.
They have 2-hour general sailing tours and you can bring your own food and drinks (including wine and beer).
Explore the Old Port
After your sailing adventure, you’ll be right on the waterfront and in the Old Port area. We highly recommend taking the afternoon to walk around and pop in and out of the cute shops.
A walking tour is a great way to learn a ton about the rich history of Portland – we recommend this walking tour for a great tour and fantastic laughs!
Sunset Cocktails
The Top of the East is a lounge on the top floor of the Westin with a spectacular view of Portland and the water. This is the perfect place to grab a drink and watch the sunset!
The drinks might be a bit pricy but the view is worth the surcharge.
We recommend getting there an hour or so before sunset so you can be sure to grab a seat with a great view!
We came about 15 minutes before sunset and got very lucky that we got a seat because it was crowded.
Dinner at Eventide Oyster Co
Eventide Oyster Co, a James Beard-winning restaurant, has some of the best seafood in the Northeast.
As you may have guessed from the name, they are known for their extensive selection of both raw and cooked oysters.
Additionally, they have “buns” and a clam bake that receive just as many rave reviews as the oysters.
They offer very limited reservations (typically being released 2 weeks in advance) so make sure you watch their website! No reservations? No worries – they keep a majority of their tables “first come first serve”.
Day 3 Itinerary for a Weekend in Portland, Maine
Breakfast at the Bayside American Cafe
A delicious, hearty breakfast at Bayside American Cafe will set you up for success in your choice of activity for the day.
We recommend ordering the eggs benedict and/or cinnamon roll pancake!
Option 1: Whale Watching
Maine is a great place to go whale watching. Whale watching tours give visitors the chance to see humpback, pilot, minke, and the enormous finback whales up close.
Humpback whales are known for their acrobatic displays, and it’s not uncommon to see them breaching or slapping the water with their tails.
Whale watching season (in Portland) is typically from mid-April through October. Whale watching tours typically last 2-3 hours, and guides will provide helpful information!
Whale watching is an unforgettable experience, and Portland is the perfect place to do it.
Odyssey Whale Watch operates out of Portland Waterfront.
Planning to go? I highly recommend taking a bag of these ginger candies to keep away any seasickness!
Option 2: Peaks Island
You can take a 17-minute ferry over to the wonderful Peaks Island using Casco Bay Lines.
You can grab a golf cart tour or rent a bike from Brad’s Island Bike Rentals and bike around the Island.
Peaks Island was best known as the “Coney Island of Maine”. Now, it is a quaint island that has a 3.7 mile loop around it.
It is a beautiful way to spend the day and make the most of your day trip!
Things to do/see on Peak’s Island:
- Peaks Cafe – great coffee, sandwiches, and Lisa’s famous cinnamon buns!
- Kayak Tour – a beautiful way to experience the island from a different perspective! Half, full, and sunset tours.
- Umbrella Cover Museum – a lovely stop in a unique museum!
- Oceanview Meal/Drinks at Cockeyed Gull
- Battery Steele – A large gun battery from WWII that protected Portland
Dinner at Duckfat
There is no need to fly all the way to Belgium when you have this gem! Duckfat brings the big and bold flavors of Belgium’s delicacy, frites and sauce, to downtown Portland.
Their duck confit is superb! Don’t want a sit-down dinner? You can grab some fries or poutine from the walk-up window!
Best time to visit Portland, Maine
There’s no bad time to visit Portland, Maine. The state’s largest city is filled with interesting things to see and do and there’s always something going on.
That said, the best time to have a weekend visit Portland, Maine depends on what you’re looking for!
June-August is considered “peak season”, with cruise ships coming to the area and many tourists. The summer in Portland, Maine is pretty mild compared to many parts of the country with the temperature rarely getting over 80 degrees.
The summer season also brings many festivals. The Bud Light Kite Festival, Lobster Festival, and Wine Week are just a few!
If you’re looking for fewer crowds and cooler weather, then fall is the perfect time to visit. The temperatures start to cool down in September, making it a great time to explore all that Portland has to offer.
The leaves will start changing colors making an already gorgeous area glow just a bit brighter! We find that October is the perfect leaf-viewing time.
And if you’re a fan of Halloween, then you’ll definitely want to check out the city close to Halloween time – they go all out with many parties and spectacles.
If you’re looking for winter activities, then December is the month to visit. Portland has many ice rinks, and there are also plenty of cozy cafes and restaurants to enjoy when the weather gets chilly.
So no matter what time of year you visit, you’re sure to find something to love about Portland, Maine.
How to get to Portland, Maine
Flying to Portland, Maine
The fastest way to get to Portland is by plane – the airport, Portland International Jetport (PWM), is located just a couple miles from the city center.
The majority of major airlines serve Portland International Jetport from all over the county:
- American Airlines
- Delta
- Elite Airways
- Frontier
- jetBlue
- Southwest
- Sun Country Airlines
- United
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.
Driving to Portland
Portland is just 2 hours (107 miles) from Boston and a beautiful drive!
Check out the first part of our top 21 places to stop when driving from Boston to Acadia National Park – it covers the drive from Boston to Portland!
Train from Boston to Portland
The Amtrak Downeaster is a wonderful way to sit back, relax, and enjoy the sites while traveling from Boston to Portland.
This train ride will take you about 2 and a half hours. A one-way Coach ticket varies from $3 to $30.
Getting Around Portland
Walking
The downtown Portland area is quite walkable! The distance from the Eastern Promenade to the Western Promenade is 2.6 miles (55 minutes) and takes you straight through the Old Port area.
More than likely, you won’t be walking this full stretch at one time but it demonstrates that you are always less than an hour walk (and probably more like 10-20 minutes) from anything in the downtown area.
Now, you will more than likely need transportation of some sort to get to some destinations.
Biking
Portland is a super bike-friendly city! Want to move around a bit faster? Check out their bike rentals. You can rent both regular and electric bikes at any of the 30+ bike stations in downtown Portland.
We suggest downloading the app before you head out!
Driving/Rideshare
For those without a vehicle, rideshare is a great option. Uber and Lyft are both in supply in Portland and would be the best option if you are traveling to any of the awesome Portland breweries.
If you have a car, you will find that Portland is easy to navigate! Parking is easy as well with many on-street parking spots, surface lots, and garage options.
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!
Metro
Lastly, Portland does have a great Metro Bus system that takes you all around the greater Portland area (including the airport).
Check out their website for more information.
Where to Stay in Portland, Maine
We recommend staying in the Portland Peninsula! There are 4 main areas to stay during your weekend in Portland, Maine:
- Art + Government District
- Old Port
- East End
- West End
Art + Government District – Central
Splurge Hotel: The Press Hotel, Autograph Collection
- The Press is a beautifully designed hotel – the theme of “printing press” is wonderfully executed. The rooms and bathrooms are fancy and the perfect place for a weekend getaway.
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!).
Rental Space 1 Bedroom: Chic One Bedroom Apartment In Portland’s Arts District
- Sitting just a block off Congress Street, this rental space is a great location for a couple or solo traveler!
Rental Space 4 Bedrooms: 1st Floor Private Entrance Condo
- Got a big group? No problem! This rental has space for everyone with 4 bedrooms and 5 queen beds – plus, it is just a couple blocks from the main area!
Old Port – Party People
Hotels: Portland Harbor Hotel or Courtyard by Marriott Portland Downtown/Waterfront
- Staying in Old Port will get you a great view of the waterfront and you will be within walking distance of many attractions. It is worth noting, however, that it is a pricey location and there is a lot of noise from the numerous bars and restaurants. These two hotels are the best in the area at providing the most comfort for the price and would be a good stay!
Rental: “Henry” Penthouse Suite or the “Margaret” Penthouse Suite
- Both of these rentals are ~ stunning ~. Imagine waking up, pouring yourself some coffee (or drink of choice), and soaking in the morning sun looking at these views. These would make the perfect, luxurious getaway!
Rental: The Docents Collection
- A rental company that has many great properties in the Old Port area.
East End – Neighborhood Feel
Mostly rentals in this area!
Rental – 1 Bedroom: Panoramic Water, Island & City Views w/Private Roof Deck
- This top-floor apartment has a stunning top deck that rental dreams are made of! A perfect romantic getaway spot. Plus, a great working area if you want to extend your trip a bit!
Rental – 2 Bedrooms: The Globe House on Munjoy Hill
- Historic home with almost as much color as charm! Close to many restaurants and within walking distance of attractions!
Rental – 4 Bedrooms: Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
- Great house for a group. Cute and quiet neighborhood that is within walking distance to so much of Portland.
West End – Bed and Breakfast Fans
- There is a reason many lists have them as the #1 Bed and Breakfast in Portland, ME – their rooms, breakfast, and service is outstanding!
- 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 Mercury is paving the way in a new style of hospitality – they land somewhere in between a hotel and a traditional Bed and Breakfast. You’ll experience high attention to detail in a beautifully restored Victorian home as well as a delicious locally-sourced continental breakfast.
Is Portland, Maine Safe?
Yes! Portland, Maine is safe. In fact, they have one of the lowest crime rates of any major city in the United States. US News puts their crime rating at “lower than average”.
If you have concerns about safety, we always recommend walking with another person and in busy and well-lit areas. Additionally, make sure any bag you are carrying has good zippers and is not easy to pickpocket.
We felt totally safe the entire time we were there!
How many days should you spend in Portland Maine?
Portland, Maine is the largest city in Maine with plenty to do and explore. The town is beautiful, with a rich history – plus, Bon Appetit named Portland the Restaurant City of the Year in 2018 so your taste buds will thank you!
If you can swing it, we recommend a long 3-day weekend. With 3 days, you’ll be able to do some exploring, maybe a tour or two, and visit the most popular sites.
However, if you just have 2 days – you will still have a fantastic weekend in Portland, Maine, and get to see plenty!
Plus, if you don’t see quite everything you wanted, it would be a perfect excuse to come back for another beautiful weekend in Portland!
Stopping through? Check out our 21 top stops when driving from Boston to Bar Harbor/Acadia!
A Great Weekend in Portland, Maine
This is such a wonderful location for a weekend spent exploring. There are a ton of things to do and plenty of great food to taste.
We would highly recommend a weekend in Portland, Maine to everyone! Only have 1 day to explore? Check out our 1 day in Portland, Maine itinerary.
We wish you the best travels, and don’t forget to set your “Out of Office!”
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