The Perfect Weekend in Portland, Maine

The Perfect Weekend in Portland, Maine

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Portland, Maine has wiggled its way to the top of our list of favorite cities in America. In fact, I debated even writing a blogpost about it because I’m scared the secret will get out! But, when we find a great place that encourages tourism, we want to share it with you.

This city has to much to offer: great coffee, local breweries, delicious food, beautiful parks, history, and more. However, what really makes this place stand out to us is the people. Some of the nicest people we’ve met across America are the people in Maine. Not gonna lie, it sort of surprised us because New Englanders don’t have the most hospitable reputation across most of the USA. But alas, it’s true. These people are incredibly welcoming and smile at you when you pass on the sidewalk. When you order a cup of coffee they ask about your weekend and genuinely want to know what fun adventures you had on your days off.

But don’t take our word for it, visit Portland, Maine and see for yourself! To get you started we’ve compiled a list of must see places in the city. Do keep in mind that while Portland is the biggest city in the state of Maine, it’s a hop, skip, and a jump away from loads of other adventures including Acadia National Park and picture perfect coastal towns like Camden, Maine. If you have more than just a couple of days in Maine, we'd encourage you to day trip out of the city to some these other noteworthy places.

Without further ado, here is our guide and itinerary to the perfect weekend in Portland, Maine.

When to visit Portland, Maine

I don't know about you, but the first thing that comes to mind when I think of Maine is snow. I'm not much a fan of winter, but goodness do I love Portland in summer and fall! While cold, snowy winters are common here, their short summers and gorgeous falls more than make up for the crazy cold weather. That being said, if you're planning a vacation to Portland, you'll likely want to visit during the more moderate weather days.

Infographic of Portland, Maine average temperatures and rainfall provided by NOAA.

I'd highly recommend visiting between the months of May to September. That being said, we've visited Portland, Maine in mid-late October and the days were cool and brisk, much more fall-like than winter-like. June, July and August offer the most moderate days as well as the days with the most sunlight, therefore to get the maximum amount of fun in a day in Portland we'd recommend visiting one of those months.

Where to stay

Everyone has different accommodation preferences when it comes to vacation. Some prefer the flexibility that an Airbnb offers while others prefer the luxury of a hotel or the quaintness of a bed & breakfast. No matter what you prefer, we've rounded up a list of the highest rated hotels, Airbnb's and bed & breakfasts in Portland, Main city limits.


When we're on the go and/or on a budget, Airbnb is the perfect option. Since we travel a good bit, having a little extra space + a kitchen that an apartment or house offers is pretty nice.

Airbnb option 1: Downtown apartment w/ parking | Sleeps up to 4
Airbnb option 2: Modern studio apartment w/ parking in perfect location | Sleeps up to 2
Airbnb option 3: Sunny West End Oasis | Sleeps up to 2


All of the hotels listed here are close to Portland's nightlife and many delicious eateries. Due to the prime location, all of these hotels are business level and above. Portland is a pretty affordable city making it a great place to splurge on a nice hotel if you usually stick with more budget friendly options. We always find that has the best rates. To explore all the hotel options in Portland, Maine, checkout here.

Hotel option 1: The Westin Portland Harborview | 4 star hotel
Hotel option 2: Portland Hyatt Regency Hotel and Spa | 4 star hotel
Hotel option 3: Hyatt Place Portland - Old Port | 3 star hotel
Hotel option 4: The Press Hotel | 4 star hotel

Bed and breakfasts

Is there anything more New England that staying in a bed and breakfast? The Portland area has several wonderful options and these are our top bed and breakfast recommendations in the city.

B&B option 1: Blind Tiger
B&B option 2: The Chadwick Inn
B&B option 3: The Inn of Carleton

What to do in Portland, Maine

Portland Head Light at sunrise, Portland Maine
Sunrise at Portland Head Light, Portland, Maine

If you're visiting during peak season (aka when there isn't snow on the ground), I'd recommend spending as much of your time outside as possible. This city is pretty walkable with lots of parks and trails throughout, not to mention the several blocks of historic streets and waterfront. Here's our list of must-do things when visiting Portland, Maine:

Where to eat & drink

Bag of potato donuts from the Holy Donut, Portland, Maine
Iced lattes outside at Tandem Coffee, Portland, Maine

Oh man, there's not short to great food and drinks in Portland, Maine. There are so many incredible places to try that unfortunately our weekend itinerary won't be able to touch on even a fraction of them. Here's quick rundown of the Portland area's more notable food and drink establishments.

Breakfast and brunch

The Holy Donut - Potato donuts featuring seasonal flavors
The Front Room - Quaint brunch spot serving comfort food and cocktails
Tandem Coffee (Congress Street) - Coffee + biscuits set in an old gas station
UNION Restaurant - Sophisticated brunch spot serving American fare
LB Kitchen - Fresh, healthy options for breakfast and lunch
Forage Market - Industrial chic café serving breakfast sandwiches on fresh bagels

Lunch and dinner

Forage Market
The Lobster Shack at Two Lights - Seafood with a beautiful lighthouse and ocean view
Hugo's - Sophisticated farm-to-table food in a beautiful, warm setting
Duckfat - Sandwich shop known for its duck-fat belgiun fries
East Ender - Quaint neighborhood restaurant serving American fare and craft beer + cocktails
Street & Co. - Simple but upscale seafood restaurant
The Honey Paw - Asian inspired food in a bright and lively setting


Alagash Brewing Company - Belgium style brewery offering guided tours
Austin Street Brewery (Fox Street) - Craft beer with an open indoor/outdoor space
Portland Hunt + Alpine Club - Scandinavian cocktail bard serving small plates
Blythe & Burrows - Vintage maritime themed bar
Root Wild Kombucha - Is kombucha more your evening drink of choice? This place is for you!

Weekend itinerary

Eastern Promenade, Portland, Maine


Sunrise at Portland Head Lighthouse

Grab a warm jacket and blanket and head to Portland Head Lighthouse to watch the sunrise over the Atlantic. Before you leave the park be sure to read the plaques outside the lighthouse detailing its interesting history.

Breakfast at The Holy Donut

Did you know you donuts could be made from potatoes?! Me either. This donut shop has not only perfected the most delicious dough but has also mastered the art of creative, seasonal flavors.

Coffee at Tandem Coffee Roasters

This local coffee roaster is the perfect place to grab a cup of coffee in the morning (it's one of our favorite coffee shops in America, too). With not one but two locations in town, you're never far from good coffee. Side note: their cafes do not provide wifi. If you're trying to work while traveling this can be a bummer. But if you're on vacation, enjoy the lack of connectivity and talk with your friends or S.O.

Take a walk around town

Like much of New England, Portland is very historic. Situated right on the water this town fulfills all your New England dreams. Cobblestone streets, historic architecture, tree lined paths, and more! While some areas of town are is a bit touristy, it's not so overwhelming that you should by-pass it. If you want to see the waterfront and the most historical buildings in town, be sure to take a stroll down Commercial Street.

Lunch at Forage Market

Flower shop, coffee shop, and FOOD! Seriously, three of my top five favorite things under one roof. Grab a table in their cozy little shop and try one of the delicious sandwiches made fresh in house. Don't forget to grab a bouquet of flowers on the way out!


Take a walk to Eastern Promenade to take in Portland's best views of the boats drifting in and out of the bay. Located on the edge of town but just minutes from the city's center, this park is the perfect place to let the dog run off-leash (in certain areas) or sit on a park bench and enjoy the sunshine and a good book.

Austin Street Brewery

Grab a beer at one of Portland's most popular breweries, Austin Street! With a bright, welcoming indoor space and expansive outdoor porch with tables, this is the perfect brewery to kick back and enjoy a beer with friends. They host rotating local food trucks to keep you fed and happy while you're chatting with friends and sipping a beer. Be sure to check their website for their food truck schedule.

Dinner at The Lobster Shack at Two Lights

Finish the night at one of the best seafood restaurants around! Not only will dinner be delicious but you'll be enjoying it with views overlooking the ocean. The restaurant is located on the beach right next to a lighthouse so you know you'll be getting the most Maine experience possible! You have the option to pick your own lobster or choose from one of the menu's other items such as the crab roll. Don't forget dessert either! With homemade pies and whoopie pies aplenty, you'll leave satisfied and full.


Coffee at The Proper Cup

Every day should begin with coffee (or at least that's our opinion). Start your second day in Portland at The Proper Cup to grab a jolt of caffeine to take with to our second stop of the day.... (keep reading below.)

Walk around Back Cove

With coffee in hand, head to Back Cove to enjoy the 3.5 mile walking/biking path that follows the water. Because the city is located to the east of Back Cove, this is the perfect place to take in the sunrise.

Brunch at The Front Room

After a walk around Back Cove you'll probably have worked up quite an appetite. Head on over to one of Portland's most popular brunch spots, The Front Room! Everything on the menu looked delicious, but I can only testify that the Eggs Benedict tasted as good as it looked because that's what I ordered. The restaurant is tiny so be prepared to get to know your neighbors a bit (don't worry, the good food more than makes up for the lack of personal space!). This cozy little spot is the perfect place to close out your weekend in the city.


This list only scratched the surface of what all Portland, Maine has to offer. For being a smaller city, it's full of options to keep you busy and entertained for much longer than a weekend. If you've been to Portland we'd love to hear your suggestions of places to see and things to try on our next visit in the comments below!

Happy travelin', y'all!

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Hi! We're Chris and Sara a husband and wife video making, storytelling, travel loving duo with a passion for sharing travel tips, tricks, and inspiration with others.
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