Home Culture How to Spend a Weekend in Boston, MA

How to Spend a Weekend in Boston, MA

by Yarleen Hernandez
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Boston, Massachusets is one of the most popular cities on the East Coast. There are so many activities to do and things to see in this historic city — going to see a Bruins or a Red Sox game, participating in The Boston Marathon, perusing Boston Common, and indulging in the city’s many delicious eateries, to name a few. Boston is located about four hours from Essex County, and while there is an endless amount of things to do here, you can tackle a decent amount during a long weekend here. We rounded up an itinerary for a weekend in this New England City. Read on for your guide to Boston, Massachusetts.

Getting There

hello boston sign

Boston is only just over a four-hour drive from Hoboken (depending on traffic) and a five-hour train ride from New York’s Penn Station. Flying out of New York or Newark to Logan International Airport will only take about an hour. Boston is a walkable city, so if you choose a train or plane, you won’t necessarily need to rent a car.

The Ivy at Chatham

Where To Stay

boston massachusetts

There are an array of lovely places to book in Boston. You can find hidden gems for as low as $65 a night. But, if you’d like to splurge on a luxurious stay, there are tons of options as well. You can also book a charming Airbnb – either way, finding the right spot for you will be a breeze.

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Boston Harbor Hotel | 70 Rowes Wharf

boston harbor

If you love being near the water, Boston Harbor Hotel is the ideal location for you. It is top-rated and comes with a pool, fitness center, bar/lounge, and patio.

The Whitney Hotel Boston | 170 Charles Street

Located in the beautiful Beacon Hill neighborhood, The Whitney is a boutique hotel that offers sophistication and comfort. The hotel has a fitness center, complimentary bike rental, valet parking, and more.

Four Seasons Hotel Boston | 200 Boylston Street


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The Four Seasons is an internationally recognized place for luxury. The Boston location has a pool, fitness center, bar, and patio.

The Newbury Boston | 1 Newbury Street

Located on Boston’s famous Newbury Street, The Newbury Hotel is a great choice for your stay in Boston. The restored hotel offers a pool and daily continental breakfast for two. It has an incredible rooftop and restaurant — Contessa — which is said to be one of Boston’s most desired dining spots. The restaurant features an Italian menu inspired by the best European trattorias.

The Verb Hotel | 1271 Boylston Street


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This unique and stylish hotel in the Fenway neighborhood plays an ode to rock n’ roll music with its decor and eclectic design. The Verb’s backstage trailers are inspired by rock legends who traveled cross-country on American highways to create the music we know and love today. The hotel’s pool is open all year round and a night’s stay can be as low as $150-$250, depending on when you book. While you’re staying at The Verb, make sure to catch a game at Fenway Park which is only a short walk from the hotel.

Where To Eat

Caffe Nero | 10 Summer Street


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Whether you enjoy Dunkin’ (a favorite among Bostonians) or if you prefer something a bit more authentic, Caffe Nero gives you that cozy coffeehouse vibe without breaking the bank. The coffee shop sells a variety of coffee from all over the world. The classic cappuccino is the best way to start your morning and the flat white is delicious. The establishment hails from the U.K.

Mike’s Pastry | 300 Hanover Street

mikes bakery boston

A Boston staple in the North End neighborhood, Mike’s Pastry is world-renowned for its cannolis. The shop offers nationwide shipping and the cannolis go for $7.50 each. Mike’s Pastry was founded in 1946 by Italian immigrant Michael Mercogliano who wanted to bring the iconic Italian dessert to Boston.

Taberna de Haro | 999 Beacon Street


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This Tapas bar goes beyond the typical Spanish cuisine and provides delectable dishes like the saffron-scented paella and jamon Iberico. The aceitunas and croquetas are a must-try. Taberna de Haro also maintains that the establishment has the second-largest all-Spanish wine list in America with over 300 options to choose from.

The Black Rose | 160 State Street


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This is your classic Irish pub/restaurant which has served Boston for over 47 years. Steps from Boston’s beautiful waterfront, The Black Rose offers a full Irish breakfast every weekend as well as New England fare like lobster rolls and corned beef. You can enjoy live Irish music seven nights a week.

Union Oyster House | 41 Union Street

boston massachusetts things to do

Union Oyster House is Boston’s oldest restaurant, and claims to be the oldest continuously operating American restaurant. Located in a pre-revolutionary building designed in 1714, Union Oyster House was founded in 1826 and has been serving up traditional New England fare ever since. This is also the place where Charles Forster is said to have popularized the use of toothpicks in Boston. Make sure to give Union Oyster House a visit on your trip. The restaurant is conveniently included in Boston’s Freedom Trail and is worth the hype.

What To See

Acorn Street | 1 Acorn Street

acorn street boston

This enchanting cobblestone street in Beacon Hill transports visitors to 19th-century colonial Boston and it’s a place you won’t want to miss. This is where many cooks, artisans, and merchants lived. It’s now one of the most popular spots for pictures in Boston.

Boston Common | 139 Tremont Street

Considered the oldest public park in the United States, Boston Common was founded in 1634 and has served as a stage for free speech for centuries. Martin Luther King Jr. and many other icons have spoken at the park. In December 2022, the infamous bronze sculpture by Hank Willis Thomas titled The Embrace, was installed to commemorate MLK and Coretta Scott King’s hug which they shared after he was awarded the Nobel Peace Prize in 1964. The park offers a carousel, free summer yoga, movie nights, a spray pool, skating lessons, and College Nights at the Frog Pond.

Fenway Park | 4 Jersey Street


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Fenway Park is one of the most well-known landmarks in Boston. It’s been the home of the Red Sox since 1912, and it’s the oldest baseball stadium in major league baseball. Ironically located on Jersey Street, so many baseball greats have played at Fenway including Babe Ruth before he was traded to the New York Yankees starting what many baseball fans believe to be The Curse of the Bambino. It’s a great spot for baseball buffs. HG pro tip: leave your Yankees gear at home.

Film Tour

Go on a walking tour of your favorite films. You’ll see spots from everything from Good Will Hunting (thank you Matt Damon + Ben Affleck), to The Departed to Cheers. So many highly-acclaimed films and TV shows were filmed in Boston.

House of Blues Boston | 15 Lansdowne Street

Take a trip to this famous music joint to catch your favorite artists performing live at the House of Blues and enjoy their signature Southern dishes while you’re there.

The Many Museums

old state house museum

Boston has an incredible selection of inspiring museums to choose from. Among them are the Museum of Fine Arts, the Boston Tea Party Ships and Museum, the Museum of Science, or the Isabella Stewart Gardner Museum.

Newbury Street

Newbury Street is one of the most popular shopping centers in Boston. Located in the charming Back Bay neighborhood, you’ll find hundreds of eateries, high-end boutiques, salons, and so much more. Boston Public Library and Copley Square are also located on Newbury and are definitely worth a visit.

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The Freedom Trail

samuel adams boston

The Freedom Trail is the absolute best way to explore Boston. It’s one of the most recognized walking tours in America that goes on for two and a half miles while you follow the red-lined bricks on the ground. The tour highlights 16 spots of revolutionary history as well as historic sites such as Faneuil Hall, Paul Revere House, Old North Church, meeting houses, and much more. The best part is that these pieces of history are interwoven into the city so you’re taking a historic walking tour and exploring Boston’s current culture all at the same time. You can do a guided tour or you can do a self-led tour at your own pace.

University Tour

Take a tour of the many prestigious universities in the area including the most well-known — Harvard, as well as Boston CollegeMITBoston University, and Berklee College of Music, to name a few.

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