Three Days in Maine: Things to Do and Places to Eat 

Whether you envision the quaint, calm New England coastline or daydream about a soft lobster roll that runneth over, you’re more than ready to book a vacation to Maine. The only problem is, you’re not quite sure where to begin your long weekend.

That’s fair enough: there’s plenty to do and see in the Pine Tree state. On top of that, there are many towns and cities dotting the coast that will give you all of the traditional northeastern vibes you crave.

To help narrow things down, here are two of our favorite destinations to help you plan your next trip up north. Pack your bags and arrive with an empty stomach because it’s time to go to Maine.


3 perfect days in maine itinerary
Image Credit: Mike Durkin, Flick (CC BY-SA 2.0)

For a three-day weekend, Kennebunkport is a great place to visit: it’s a convenient 90 minutes outside of Boston, which makes it easy to reach by plane and subsequent rental car. The town has everything you could want in a quiet northeastern getaway, especially its selection of cozy bed and breakfasts. That rental car will come in handy if you choose to stay in a bed and breakfast outside of town, too, so you can get around and see everything this gem of a town has to offer.

What to Do

There’s plenty to do while you’re in Kennebunkport, and you’ll find activities for the entire family to enjoy. For example, your kids will love the Seashore Trolley Museum, where they can hop aboard an electric trolley and explore other types of electronic transportation. Older kids might enjoy a kayaking tour around the coastline and toward Porpoise Point, potentially catching a glimpse of the ocean mammals.

Then, of course, there are the grown-up activities. From hiking, to lobster fishing, to antiquing, you’ll have no trouble keeping yourself busy if it’s just you, your friends or your significant other. The best thing is, most of these activities won’t require reservations or much of a traditional tourist’s time schedule, so you can see it all without rushing — vacation vibes, indeed.

What to Eat:  

The northeast is known for one thing: seafood. Your trip to Kennebunkport won’t disappoint if that’s what’s on your vacation menu. Fall and winter trips will certainly call for a bowl of lobster chowder. While you’re in Kennebunkport, Condé Nast Traveler suggests a hearty bowl at Hurricane, where extra-large dining room windows give you a picture-perfect view of the rocky coastline while you eat fresh seafood.


weekend in maine itinerary

Portland, Maine, is another great destination for a three-day weekend. Its close access to lush, leafy outdoor landscapes make it an ideal destination in fall, when leaves begin to change colors. Book flights directly into Portland’s International Jetport, or take the two-hour drive from Boston to arrive at your seaside destination.

What to Do: 

Portland’s attractions range from athletic, to artsy, to outdoorsy. For starters, a summertime trip to the area might have you seated in the stands at Hadlock Field, where you can cheer on the local AAA baseball team. There’s no more quintessentially summer activity than that.  

Nice days might also beckon you to visit the nearby Casco Bay Islands. A Portland-based ferry will charter you out to the island, where you can take part in a slew of outdoor activities. Rent a bike, sign up for stand-up paddle boarding lessons or simply go swimming in the waters surrounding the pristine island. 

Of course, not every day on your trip will be perfect. If it’s rainy, gloomy or otherwise not outdoorsy weather, visit the Portland Museum of Art. The city may be small, but it has a nationally renowned museum with highlights from the likes of Renoir, Monet and Homer.

What to Eat: 
Portland was named America’s Foodiest Small Town in 2009 by Bon Appétitmagazine, and things have only gotten better since then. Most of the show-stopping dishes are — you guessed it — inspired by the sea. Try fresh oysters at Eventide Oyster Company, or grab a spoon and ladle into the famous seafood chowder at Gilbert’s Chowder House.

Portland’s also a great destination if you love sampling freshly brewed beer. The Allagash Brewery is Portland’s highest-ranked tourist destination on TripAdvisor, and for good reason: guests can venture inside for free brewery tours or sign up for tastings of year-round and seasonal brews. If you have a new favorite, grab a few to go and sip responsibly at your hotel or bed and breakfast.


These are only two examples of all that Maine has to offer. There are many towns with just as much charm, including Bar Harbor, Camden and Rockport. You’ll likely be able to find comparably exciting activities, tasty food and friendly locals in any of those destinations, too. All there’s left to do is plan your travel, book your lodging and get going: Maine is waiting, and a three-day weekend will be enough to show you just how special this New England state is.


Kacey is a lifestyle blogger for The Drifter Collective, an eclectic lifestyle blog that expresses various forms of style through the influence of culture and the world around us. Kacey graduated with a degree in Communications while working for a lifestyle magazine. She has been able to fully embrace herself with the knowledge of nature, the power of exploring other locations and cultures, all while portraying her love for the world around her through her visually pleasing, culturally embracing and inspiring posts.

Follow Kacey on Twitter and subscribe to her blog to keep up with her travels and inspiring posts!

Share ThisShare on FacebookPin on PinterestShare on Google+Tweet about this on TwitterShare on StumbleUponShare on RedditShare on LinkedIn



  1. I would love to check out the Acadia National Park in Maine I heard it was absolutely gorgeous, have you been?

  2. Portland looks pretty amazing, with the lighthouse and all. I like such posts which give the highlights in a city for 2-3 days because that’s usually the amount of time i have to spend in a city. Thanks for sharing!

Leave a Reply

Your email address will not be published. Required fields are marked *

CommentLuv badge

This site uses Akismet to reduce spam. Learn how your comment data is processed.