Welcome to Portland, Maine, the land of lighthouses, lobsters and fabulous food, set on a peninsula extending into beautiful Casco Bay! Maine’s largest city certainly doesn’t disappoint! The long, cold winters help the summertime in Maine feel extra special, with streets overflowing with outdoor patios and music from microbreweries! No matter if you’re a history-lover, art-buff, foodie, beachcomber or all of the above you’ll find something to love in this tiny city by the water with it’s small-town charm!

Located just 2 hours north of Boston and 4 hours from New York City, Portland is a summer-getaway for many from the hustle and bustle of nearby big cities. The two major sections of Downtown Portland are the Arts District, covering most of Upper Congress Street to the West End, and the Old Port, located along the cobblestone streets, fishing piers, and waterfront streets. Both areas are extremely walkable and bike-able, with many streets closed off to car traffic & many bike racks and walking paths available. If you’d like to explore outside the city, there is a ferry out to Casco Bay and the many tiny islands there. You can also utilize a rental car or Lyft service to nearby attractions like Freeport, ME (home of the giant L.L. Bean store and other shopping opportunities), Portland Head Light in nearby Cape Elizabeth, or to just drive along the coast for more scenic vistas and little towns!

Portland International Jetport (PWM) is the largest airport in this small state. While there are some non-stop or one-stop flights from most major cities, the majority of people fly into Boston for more flexibility, then rent a car or take the train to Portland. We love this route because it allows for a fun little road trip on the way! Our favorite mid-way stop is nearby Portsmouth, NH for lunch! If you did fly into Portland, the easiest way to get to your hotel is to take a cab or call a Lyft. It will only take about 10-15 minutes to get in to town and will cost about $20-40. There is also a public transportation option, the Metro #5 bus, but check online for the latests schedule.

A city occupied by Native Americans as long ago as 11,000 BCE, Portland has a long and rich history. Eventually colonized by the Europeans, its port location made it a strategically and economically important city and helped Portland (back then actually part of Massachusetts) play a key role in the American Revolution. The next few centuries saw various ups & downs (often caused by changes to the fishing or shipping industries) along with great triumphs and sorrowful tragedies for Portland. ne in particular was The Great Fire which decimated a huge swath of this burgeoning town. Mainers are made of tough stuff and they would continue to thrive and have rebuilt over and over. Today Portland is still an active port & fishing town, but it is also known for a young population with an incredible culinary scene, fabulous breweries, tons of art, and very scenic surroundings!

Portland has a rich history in industry, fishing, agriculture, and Americana - and that isn’t even the half of it! If you’re a history-buff, you can spend days exploring Maine’s maritime history and the lighthouses & forts that dot the coast. Seeing the mingling of preserved 19th & 20th century architecture and modern marvels keeps their culture cutting-edge in the city’s Downtown. If you love the outdoors, be prepared to explore Casco Bay and its tiny islands and the rocky coastline, maybe by bike or by sailboat! And if you’re more an indoors-y person, Portland is definitely for you too! You’ll be spending your days exploring cute cobblestone streets filled with quaint local shops and art museums with collections to rival larger cities. Plus you can eat your meals at award-winning local restaurants & breweries every day!

The best time to visit this coastal city is June- August. Although summer is peak tourist season, the season’s cool temperatures - with highs seldom climbing above 80 degrees - are hard to beat. We’re also partial to a fall visit up the coast, with great brisk weather filled with changing leaves. Wrapped up in an autumn sweater is the perfect way to enjoy outdoor breweries!

Of course when you think of Maine, you probably think of lobster — specifically steamed lobster and lobster rolls. If you’ve read Blueberries for Sal as a kid (or to your kids!), you’ll know blueberries are from Maine too! There are tons of local farmers raising a plethora of the best produce and livestock in the area. The fresh seafood, produce, and livestock is one of the main (haha get it) reasons Portland has one of the best culinary scenes in the country right now! Tons of James Beard nominated chefs are creating truly special dishes from the best ingredients … so savor every bite!

L.L. Bean is a Maine-based clothing (and everything but the kitchen sink) store in nearby Freeport, ME … so it’s the perfect thing to buy to take home and remember your time on the coast! Other great souvenirs include maritime antiquities, blueberry jam, whoopie pies, & locally made candies. Plus, you can never go wrong with a kitschy lobster keychain!

Lean in to your inner L.L. Bean meets J.Crew catalogues for inspiration! Mainers dress for comfort and the weather. Comfortable walking shoes, shorts, & jeans are the norm with layers for the evening when the temperature drops. Even the hottest day in August might be cool enough for a windbreaker on the water at night! In the winter, consider warm socks and gloves with a puffer coat and wool hat.

Portland is the closest U.S. transatlantic port to Europe and still is one of the largest fishing ports in the nation … providing nearly 90% of the nation's lobster supply - roughly 40 million pounds annually! Food is serious business in this town - with one of the highest concentrations of James Beard chefs of any city in the country. So, go ahead and indulge a little! One thing to keep in mind, especially if you’re visiting in the summer, is that you’ll likely be waiting a little bit for the best meals! Due to Maine’s laid-back nature many of the restaurants don’t take reservations and instead have a walk-in queue. So, put your name in & explore the cute shops or maybe a nice waterfront vista while you wait!