I might be biased, but New England is a pretty perfect place to plan a long weekend. The six states that make up this region of the United States offer a little bit of everything – mountainous landscapes, cozy cities, and a sprawling coastline. With fall being one of the best times to visit the area, I’m kicking off my Three-Day Getaway series with perhaps the most well-known travel destination in New England: Boston.

A long weekend in Boston is the perfect amount of time to get a good sense of exactly what this city has to offer. Compared to its East Coast counterpart, New York, Boston is much smaller, making it easy to do a little bit of everything. Depending on the experience you’re after, you could spend the weekend soaking up the historical charm, eating your way through different neighborhoods, or popping in and out of different museums.

Getting There and Getting Around

Boston Logan International Airport is located just a few miles north of the city, making it the easiest way to arrive and depart for most travelers. It is also easily accessible by train and bus through Boston’s South Station, located in the middle of the city.

Despite streets that don’t run in a traditional “grid” pattern, Boston is easy to navigate due to its small size. It is incredibly walkable (and bikeable if you’re comfortable biking in an urban environment!) and the subway (or, the “T”) covers the major parts of the city.

Image via Hotel Management

Where to Stay

Envoy Hotel


Envoy Hotel has a luxury, boutique feel and is located in Seaport, one of the best parts of the city for chic eateries and craft cocktail bars. Most rooms have a view of the water, with intricate custom details and pops of color. Envoy is also home to Lookout, a bar on the top floor with a stunning view of the harbor.

Hotel Commonwealth

Hotel Commonwealth is located in Kenmore Square, very close to Fenway Park and convenient to most neighborhoods in the city. The outside of the hotel itself is filled with charm, and rooms are luxuriously modern. Hotel Commonwealth is also home to two of my favorite picks – Island Creek Oyster Bar and Eastern Standard.

Fairmont Copley Plaza

Fairmont Copley Plaza is located in Back Bay, a central part of the city in close proximity to almost everything. Long known as one of the best luxury hotels in the city, the Fairmont Copley Plaza has been open to guests since 1912 and is rich with elegance and charm.

Explore + Experience

For one of the prettiest strolls in the city, take some time to explore the quiet streets of Beacon Hill with a coffee from Tatte Bakery on Beacon Street. Wander through the boutiques on Charles Street for some of the best boutique shopping in Boston.

Insider Tip: For one of the most picturesque views on Beacon Hill, don’t miss Acorn Street.

For baseball (and non-baseball) fans, Fenway Park is an absolute must! Home of the beloved Boston Red Sox, Fenway is the oldest ballpark in America. The area is filled with Red Sox related fanfare and is also home to a few great spots to eat as well as some of the most popular bars for going out in the city.

Insider Tip: Fenway Park offers tours of the ballpark all year long. If you have a few baseball fans in your group, this tour will show you the ins and outs of the park.

For those looking to get a taste of Boston’s rich history, walk the Freedom Trail. Easy to navigate, this two and a half mile red-lined route will bring you by some of the biggest historical sites in the city.

Insider Tip: The Freedom Trail will bring you into the heart of the North End, a neighborhood known for Italian food. If you need a snack on the way, be sure to stop at Mike’s or Modern Pastry to choose your favorite cannoli!

For local beer fans, Boston is home to three major breweries: Harpoon, Samuel Adams, and Trillium. Head to Harpoon and Sam Adams for tastings and tours. At this time, Trillium does not offer tastings at their retail location, but you can pick up a four pack or visit their beer garden on the Rose Kennedy Greenway during the summer.

Insider Tip: Want more beer? Venture just outside the city to find two amazing taprooms at Nightshift or Lamplighter.

For a cultural experience, take the T over to Harvard Square for an afternoon of exploring one of the most popular “squares” in Cambridge. Grab lunch at Russell House Tavern, pop into a few shops, and then wander around the campus of Harvard University – a beautiful space worth seeing.

Insider Tip: Just outside the city, you could spend an entire day exploring, eating, and drinking in Cambridge. Head to Kendall Square for craft pizza at Area Four, grab dinner and craft cocktails at Alden & Harlow in Harvard Square, and don’t miss Little Donkey in Central Square for unique small plates and drinks.

For those looking to scope out the museum scene in the city, the John F. Kennedy Library and Museum, the Harvard Museum of Natural History, the Isabella Stewart Gardner Museum, the Museum of Fine Arts, the Museum of Science, and the New England Aquarium are some of Boston’s best.

Insider Tip: Museums in Boston frequently have reduced admission prices depending on the day of the week that you’ll be visiting. Be sure to check online before your trip to potentially take advantage of a discount!

Image via Precinct Kitchen + Bar

Eat + Drink

Back Bay: Citrus & Salt, Friendly Toast, Parish Cafe, Precinct Kitchen + Bar, Terra

Fort Point/Seaport: Drink, Lolita, Lookout Rooftop, Row 34

Kenmore/Fenway: Eastern Standard, Island Creek Oyster Bar, Sweet Cheeks Q, Tiger Mama

Long Wharf: Chart House, The Landing, State Street Provisions

North End: Al Dente, Giacomo’s, Mike’s Pastry, Modern Pastry, Quattro

South Boston: Coppersmith, Loco Taqueria & Oyster Bar

South End: Banyan Bar + Refuge, Barcelona, Beehive, Blackbird Donuts, Coppa, South End Buttery

Have you been to Boston? Share your must-do’s in the comments below!


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