Just over 300 miles from NYC, a trip to Portland, Maine is likely just how you picture it… which is, filled with lighthouses and lobster rolls.

This historic sea town marries the old world and the new world — from its cobblestone downtown streets to a bustling dining scene, it’s unclear if the region is better known for its classic New England maritime vibes, or its modern, world-class food scene. We say you don’t have to choose; it’s called Vacationland for a reason, after all.

To get here, the drive from NYC to Portland, ME clocks in about five hours. Or hop on a plane: direct flights from offered by JetBlue JFK take just over an hour, and tickets are really reasonably priced.

Where to Stay in Portland, Maine: the Francis Hotel & Spa

Sun-filled room at the Francis Hotel & Spa in Portland, Maine. The hotel is on the National Park Service’s Registry of Historic Places. All photos by Erin Lindsey/Escape Brooklyn.

Blending historical charm and modern amenities, the Francis Hotel & Spa was originally a palatial home for a wealthy family, created by architect Francis Fassett around 1881. Starting in 2015, the current owners (two brothers from Maine) spent two years restoring the Francis after it had been abandoned for over a decade, making sure to preserve original details while adding beautiful new touches. It’s notably on the National Park Service’s Registry of Historic Places; several rooms have incredible details like ornate tiling on floors, original doors, wavy glass windows or beautifully detailed crown moulding.

Each of the Francis’ fifteen guest rooms are unique with slightly different features — but all feature work by local artisans, from custom-built furniture and lighting fixtures to the art hanging on the walls. (We stayed in the Terrace King, which featured a private deck.) Linens and bedding are soft and comfortable; bathroom products are from Malin + Goetz. A beautiful one-room spa onsite offers treatments like deep tissue and therapeutic massages as well as body wraps and scrubs.

Several food and drink themed packages are available to guests, including Tandem Breakfast in Bed or an in-room “brewery crawl” with samplings from Portland’s local breweries. Other bonuses include pet-friendly rooms, superb Covid safety measures in place, and a 24/7 text concierge so you can always be in touch for assistance or even local recommendations.

Best of all is its location, in the charming Parkside neighborhood, steps away from some of Portlands best shopping, meals, and drinks. Slightly removed from the Old Port and the crush of its (#basic) tourists, you’ll love feeling like a local when you can wake up and walk across the street to grab breakfast from Portland’s very best coffee shop, Tandem.

What to Do in & Around Portland, Maine: Visit Portland’s Iconic Lighthouses, or Daytrip Up the Maine Coast

Personal favorite: Spring Point Lighthouse in Portland Maine.

Portland stands as one of the few working waterfronts left in the United States; wandering through the Old Port district in Portland, Maine is a must. With cobblestone streets, 19th-century brick buildings, and fishing piers, you’d swear you’re stepping into a movie set if it wasn’t for all the tourists. With that in mind, a visit to Old Port is best in the morning, before it swells with people.

But if living in New York City, or living through a pandemic has taught us anything — better adventures are further afoot, away from the crowds and preferably outdoors. We got you.

Definitely plan to visit some of Portlands six lighthouses; each one feels straight out of a Wes Anderson flick. Fifteen minutes from town, Portland Head Light is the most iconic and well-known lighthouse; it’s also the oldest. Head here for sunset, and if you’re lucky enough to be there when Bite Into Maine food truck is too, grab a lobster roll. (Note: you’ll need to pay for parking to visit the lighthouse.) Personal favorite Spring Point Lighthouse is delightfully uncrowded, free to park, and incredibly photogenic. Plan your visit around sunset, and stroll out to the lighthouse — accessed by walking across a rocky break wall over the water — where you’re guaranteed some seriously ‘Grammable photos. To visit more or all the lighthouses, check out Visit Portland’s roundup, which includes an itinerary to easily visit each one.

Another delightful jaunt from Portland is to Peaks Island, accessible by an $8, fifteen minute ferry ride from Old Port. Once on Peaks Island, swim from the public beaches, rent a golf cart or wander around the 3.7 mile loop. (Note there are no services on the island; pack a picnic!)

Last, Portland is the portal to the rest of Maines rugged coast — with its beautiful rocky beaches, sleepy fishing towns and roadside lobster shacks. If you have the time, a day trip up the coast to Bailey Island delivers all of these things. Without stopping, the drive is under an hour, but it’s likely you’ll be tempted to stop and take a million photos on the way. Set your GPS to Land’s End, a cute gift shop located at the very end of the island. On the way out, stop for a hike at Devil’s Back or the Cliff Trail; then reward yourself with a delicious lobster roll from Gurnet Trading Co. Definitely pop into the aforementioned Land’s End, where you can stock up on all the Maine-themed souvenirs you didn’t even know you needed — including lobster themed everything, local crafts, candy, etc. Just beyond the shop, stroll to the shoreline with its rocky beach and soak in the stunning view.


Where to Eat and Drink: the Best Restaurants in Portland, Maine

Mr. Tuna Sushi Trailer in Portland, ME whose daily location you can find via their Instagram.

When staying at the Francis, you’re well situated to get in line first for the best coffee in Portland, just across the street at Tandem Coffee. The coffee shop housed inside an old gas station serves up baked goods and yummy breakfast sandwiches as well. An additional “must have” for Portland breakfast (or lunch) is Rose Foods, whose specialty of bagels and fish and the perfect ingredients for an indulgent and delicious breakfast — or to take on the road for a picnic. Also, prepare to spend extra dough on a souvenir because they have the best branded merchandise ever — it’s impossible to leave empty handed.

Lunches and dinner recommendations are pretty interchangeable — but honestly, who’s keeping track because most people come to Portland to eat their weight in seafood, all day every day, right? (For non-seafood recommendations, see below.) First up, Eventide Oyster Company came very highly recommended and has a delicious lobster roll – the portion is small though, so best order a ton of oysters as well. Less traditional and equally lovable is Highroller Lobster Co., whose menu ranges from your classic lobster rolls to lobster grilled cheese, lobster tacos, lobster Rangoons, lobster corndogs — you get the point. The topping choices are a fun add-on too; our personal favorite was the lime-jalapeno mayo. Last, Mr. Tuna goes the non-traditional route and serves up absolutely delicious sushi. Try and grab a spot at their 16-seat sushi bar in The Portland Public Market, or find out where their mobile sushi bars will be parked via their Instagram.

It’s a crazy concept, but, it is possible to get burnt out on lobster. Walkable from the Francis Hotel & Spa, check out Pai Men Miyake for delicious ramen that’s perfect for chilly nights in Portland — or Chaval, a brasserie with Spanish & French inspired seasonal cuisine. Grab a seat on its lovely patio, weather permitting. In the downtown/Old Port area, Otto Pizza, Central Provisions, Fore Street and Honey Paw all came highly recommended.

Last but not least, Portland is home to nearly 20 breweries; top highlights include Allagash Brewing Company, Bissel Brothers, Lone Pine Brewing and Oxbow Brewing. For a full roundup of Portland breweries, check out Thrillist’s Portland Maine Brewery Guide with recommendations on what to drink at each stop of their Portland brewery crawl. Cheers!