Expert Advice

6 Things To During A Long Weekend In Boston

From food to Fenway

Raeanne V
A Hilton Grand Vacations Owner and her travel party at Boston Common while on vacation

Take a fun weekend trip to the charming city of Boston, Massachusetts. This New England city is small but mighty with tons of fun things to do. Here are six fun-filled ways to spend a long weekend in Boston.

A Hilton Grand Vacations Owner and her friend on Newbury Street in Boston 

1. Shop ‘til You Drop

Newbury Street is famous for its shopping and dining. This picturesque, tree-lined street stretches about a mile, from Massachusetts Avenue to the Boston Public Garden. The shopping ranges from affordable fashion retailers like T.J. Maxx and H&M to upscale shops like Chanel and Ralph Lauren.

Need a break from shopping? Dine at one of Newbury’s wide array of restaurants and cafes. There are plenty of outdoor seating options, making it a great spot to people watch and enjoy the atmosphere. Some classic spots are:

  • Sonsie, a relaxing American bistro and wine bar with an eclectic menu
  • Stephanie’s on Newbury, which serves up award-winning comfort food with an elegant twist
  • J.P. Licks for a Boston summer staple: local homemade ice cream

For more summer fun, visit Newbury Street on a Sunday for “Open Newbury,” where the street is closed to vehicles so that pedestrians can enjoy the full width of the street.

A pond at Boston Public Garden on a sunny day 

2. Enjoy A Taste Of Nature

Boston Public Garden, a tranquil oasis in the heart of the city, is the perfect place to take a break from sightseeing. Pause beneath a weeping willow for some shade as you enjoy the views of the Garden Foot Bridge and the swan boats passing by.

Boston Common is a historic park located close to the Public Garden. It was established in 1634, making it the oldest public park in the United States. This park features walking paths, gardens and playgrounds where you can take a stroll, have a picnic or enjoy the scenery.

Nearby, Cheers Boston is an intimate neighborhood bar — the kind of place where everyone knows your name. This Boston pub is an icon and served as the inspiration for the famous TV show “Cheers.”

Faneuil Hall and Quincy Market in Boston at night 

3. Experience Classic Boston Eats

Faneuil Hall is referred to as the home of free speech and served as a meeting hall in downtown Boston. But to local Bostonians and visitors alike, this historic marketplace is known for souvenir shops, restaurants and food halls, including the famous Quincy Market Colonnade.

Quincy Market houses a variety of goods, such as fresh seafood, baked goods and gourmet fare. Order classic New England staples like lobster rolls or clam chowder. If you’re looking for a night out on the town, Ned Devine’s is a popular spot to dance to live cover band music.

Stop at Boston’s famous North End, just a quick walk from Quincy Market. This neighborhood is known for its vibrant Italian-American culture and traditional Italian cuisine like pasta, pizza and pastries. A Boston must-visit is Mike’s Pastry on Hanover Street, which is famous for its cannoli.

Boston skyline from the Charles River 

4. Bask In The Beauty Of The Charles River

The Charles River Esplanade is a scenic park that stretches along three miles of the river’s shoreline. The esplanade a popular destination because of its wicked views of the Boston skyline.

I ran along it almost every day as a Boston University student. The views are so scenic that it makes a 5k more bearable.

Kayaking the Charles River allows you to take in the views of Boston classics without worrying about the hustle and bustle of tourists, college students and city-goers. Enjoy views of the Prudential Center, John Hancock Tower, MIT and the Longfellow Bridge.

There’s also the Hatch Shell, an outdoor amphitheater for summer concerts, movies and other public events. Check out the summer Hatch Shell events here.

A Hilton Grand Vacations Owner and her friend at Fenway Park on a trip to Boston 

5. Play Ball At Fenway Park

You didn’t really go to Boston if you didn’t go to Fenway Park. Take a tour of the ballpark or catch the Boston Red Sox take on their opponents. Feel the energy of the crowd as you sing along to “Sweet Caroline” during the seventh-inning stretch.

Whether you’re going to a game or exploring the neighborhood, Fenway offers plentiful food options and Beantown pubs that will keep your spirits high. Time Out Market Boston features a curated selection of the city’s best food, drink and cultural offerings in one convenient place. The market features over 15 different vendors, ranging from Italian, French, Korean and Japanese. Or try Tatte Bakery, a cozy yet chic cafe known for its delicious baked goods, sandwiches, salads, coffee and tea.

Looking for a night out at Fenway? Fan favorites include the Lansdowne Pub, Bleacher Bar, Lucky Strike, Loretta’s Last Call and Game On!

A Hilton Grand Vacations Owner enjoying sushi while on vacation in Boston 

6. Have Some Indoor Fun

In case of rain, here are some ways to spend a day indoors. My absolute favorite restaurant in Boston is Oishii, located in the South End. This Japanese restaurant is known for its high-quality cuisine, elegant atmosphere and excellent service. Oishii has received numerous awards over the years, including one of Boston Magazine’s best sushi restaurants in Boston. My must-haves at Oishii are the salmon on fire, Toro truffle roll and chocolate lava cake.

The Museum of Fine Arts is one of the largest museums in the United States, housing a collection of over 500,000 works of art from around the world. Discover the museum’s permanent collections of Van Gogh, Rembrandt and Monet.

Or visit the beautiful Isabella Stewart Gardner Museum, known for its Venetian-style architecture, stunning courtyard garden and exceptional collection of international art.

It’s easy to convert Club Points to Hilton Honors™ Points and stay at the Hilton portfolio in Boston. So what are you waiting for? Plan your trip and get packing for a wicked fun vacation.

Read “How I Redefined ‘Work From Home’ And Spent An Unforgettable Month In Hawaii” to see how Hilton Grand Vacations helps me travel my way.

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Hilton Grand Vacations Owner Raeanne surfing while on vacation in Hawaii

Raeanne V

Raeanne’s been an Owner since 2019. One of her highlights of ownership was using her ClubPoints to WFH (work from Hawaii) for three nonconsecutive months. Follow Raeanne to satiate your travel bug for adventurous vacations.

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