How To Spend A Weekend In Boston: A Local’s Guide

(Last Updated On: September 15, 2022)

Hey everyone and welcome back to The Abroad Blog! Today’s post is going to be all about Boston, Massachusetts. Boston is very special to me because this is not only my home city, but it’s one of my favorite cities in the world. I’ve met so many travelers over the years who’ve visited Boston in the past as part of a New England leaf peeping trip, or in conjunction with a visit to NYC, as they’re only 4 hours away from one another! I’ve also met a lot of people who are interested in visiting Boston on a weekend trip! Boston is the most historical city in the United States, and with a downtown that’s easily walkable, it’s the perfect place for a weekend trip. So, this post is going to cover how to spend a weekend in Boston!

Disclaimer: This blog post is sponsored by Aloft Hotel Boston Seaport District. Aloft was kind enough to host me for a night in exchange for a feature on my blog and on my Instagram, @nicole.rosania. I had the most wonderful stay and am so excited to share more about Aloft later on in this post. If you plan on visiting Boston, I highly recommend booking a room here. As always, all opinions are my own!

What to See During A Weekend In Boston

Although Boston is considered a small to mid-size city, there’s SO much to see! I’m just going to touch upon a few highlights…

Watch A Red Sox Game At Fenway Park

A visit to Boston wouldn’t be complete without a visit to Fenway Park. Not only is Fenway the oldest pro baseball stadium still in use (it was built in 1912), it’s also a huge part of our culture here in Boston. No where else in the US will you find a stadium that belts Sweet Caroline during the 7th inning or loves Fenway Franks as much as we do!

Acorn Street & Beacon Hill

Beacon Hill is my personal favorite neighborhood in Boston. It’s full of brownstones with colorful doors, pretty archways, and lots and lots of dogs. Talk about charming. I highly recommend taking a stroll through Beacon Hill, with a photo stop at Acorn Street. Acorn Street is the most photographed street in Boston, so be sure to check it out and you’ll see why!

Shop At Faneuil Hall

This is a classic. Honestly, Faneuil Hall is pretty touristy. This is the part of Boston where you’ll find balloon animal makers, street performers, restaurants, a few bars, shops, and more. I do recommend seeing it – especially the Quincy Market, but no need to spend all day here. Quincy Market does have some of the best clam chowder in the city though!

Spending winter in New England? Faneuil Hall features a giant tree each December and puts on a fun Christmas experience every year called Blink!

Seaport District

The Seaport is Boston’s newest neighborhood. It’s the up and coming area in Boston home to all of Boston’s trendy restaurants and bars. This is also where you’ll find the Aloft Hotel, but more about that later!

Boston Common & Public Garden

The Boston Common is a must-see, especially after a stroll through Beacon Hill (discussed above). The Boston Common is America’s oldest public park and has had a wide variety of uses throughout the years. It was first used by the Puritans as farm land and later to train British cavalry during the Revolutionary War. The Common has also been used to punish people, including hangings of some of the accused witches during the Salem Witch Trials – which if you’d like to learn more about, you can in this post about how to spend a spooky day in Salem.

The Public Garden sits adjacent to the Common and is one of the most stunning parts of Boston! I highly recommend walking through the Public Garden. Be sure to check out the Make Way for Ducklings statue and the swan boats here!

Shop On Newbury Street

Newbury Street is home to most of Boston’s luxury stores. Here you’ll find Burberry, Kate Spade, Lily Pulitzer, Cartier, and more! This whole street is lined with a bunch of shops, and a few hidden gem restaurants as well.

Pro-tip: Looking for a hidden, aesthetically-pleasing cafe to grab coffee at? Check out Cafe Susu beneath the Suit Supply shop!

Isabella Stewart Gardner Museum

Ugh this museum is a dream. Its atrium is one of the most Instagrammable places in Boston, so grab your camera and check it out! This museum is any travelers dream as it’s filled with paintings, sculptures, and tapestries from Europe, Asia, and the Americas, all originally owned and collected by the queen, Isabella Stewart Gardner, herself.

Pro-tip: Entry tickets are $20 for adults and $13 for students.

Museum of Fine Arts (MFA)

The Museum of Fine Arts, or MFA, in Boston is one of the largest art museums in the world. It has more than 450,000 pieces of art from all around the world, making it one of the most comprehensive galleries in the Americas. If you’re a member of the MFA, entry is free. Non-members must pay $25 to enter!

Visit The Aquarium & Do A Whale Watch

Boston Harbor is famous for many reasons. First, the Boston Harbor islands provide wonderful summer day trips and escapes from the city. If you’re looking to go beyond the harbor, I recommend a New England whale watch! Many people are able to see humpback whales off the coast of Massachusetts each year.

I also recommend checking out the New England Aquarium during your weekend in Boston! There’s a massive tank in the center of the aquarium with a spiraling ramp leading you up each of the floors.

Walk The Charles River Esplanade

The river that runs through Boston is called the Charles, which separates the city of Boston from Cambridge. When spending a weekend in Boston, definitely go for a walk along the river on the Esplanade. If you’d like to get your feet wet, grab a kayak or sailboat and go for a ride!

Pro-tip: Cross the river and head into Cambridge to explore Harvard Square. This is where you’ll find North America’s oldest university, in addition to dozens of restaurants and shops.

Do A Ghost Tour

Since Boston is such a historical city, I couldn’t recommend doing a ghost tour more! This past weekend I was lucky enough to experience a ghost tour through Boston Ghosts, which is a branch underneath US Ghost Adventures. US Ghost Adventures offers tours all across the US, although I think Boston is the perfect place for a tour! We walked 1.5 miles around downtown Boston, learning all about history and paranormal activity along the way. Definitely check them out if you’re looking for a nighttime activity to do during your weekend in Boston!

Where To Eat During A Weekend In Boston

Trattoria Il Panino

Located in the North End, this is one of my absolute favorite Italian restaurants in the city. First, their wine is delicious. Second, this restaurant serves all of their authentic pasta dishes in pots & pans! And they are TO DIE FOR!

Cisco Brewers

Cisco Brewers is headquartered in Nantucket, but they have a fun pop-up right in the center of the Seaport! It’s outdoors-only, so definitely keep an eye on the weather before you go, but prepare to have a blast. This place can be packed in the summer months, but I promise you their frosé will be worth the wait!

Envoy Lookout Rooftop

The Envoy is a luxury hotel located in Boston’s Seaport, and they also happen to have a fabulous rooftop bar. The bar is called the Lookout Rooftop and is known for their fun cocktails and tasty appetizers. Although this rooftop is most popular during the summer months, don’t be afraid to go here in the winter! Envoy offers both igloos and iceboxes for guests to hang in that overlook the skyline.

Committee

Committee is a high-energy and upbeat restaurant located right in the Seaport on Boston’s waterfront. Not only is the decor here super hip, the menu is unique because it is all Greek-Mediterranean influenced. Be sure to try the chicken and waffles!

Pink Taco

Also located in the Seaport, Pink Taco is a newer restaurant offering a trendy aesthetic and delicious Mexican food. Be sure to try their cocktails – some are served in a pineapple!

Lolita

Lolita is one of my favorite restaurants in Boston! Located in the Fort Point neighborhood, adjacent to the Seaport, Lolita is another authentic Mexican restaurant that provides a “neighborhood cantina feel”. The interior of the restaurant will make you feel like you’re underground. It’s dark and dramatic, with pops of red, and even a huge stained glass accent wall! The best part? They give out green apple cotton candy to everyone for dessert!

Citrus & Salt

Look no further than Citrus & Salt for your next Instagram. Located in Boston’s Back Bay neighborhood, Citrus & Salt is a Baja Coast Mexican inspired eatery. As the name suggests, they too are known for their fun cocktails!

Buttermilk & Bourbon

Located in Back Bay, this New Orleans-themed southern restaurant is to-die-for. My absolute favorite dish here is the honey buns. I think about them all the time to be honest. Also, get a drink on the rocks.

Stephanie’s On Newbury

As I mentioned above, Newbury Street is known for its luxury shops, but don’t overlook the restaurants located here! One of my favorites is Stephanie’s because of its all-American menu and ideal location for people watching. I recommend sitting outside on their patio and checking this place out for brunch during your weekend in Boston.

Union Oyster House

Union Oyster House is a classic Boston eatery. Founded in 1826, this place is Boston’s oldest restaurant. The Union Oyster House serves seafood and other New England specialities, and is also conveniently situated right on the Freedom Trail!

Dick’s Last Resort

Okay, this place doesn’t have the best food in the world, but I had to put it on this list because it’s so fun! Dick’s Last Resort is actually a chain, but they have a location right in Boston’s Faneuil Hall. Dick’s is known for its sarcastic and obnoxious employees, so prepare to be insulted here.

Where To Stay For A Weekend In Boston

Aloft Hotel Boston Seaport

Need a place to stay for a weekend in Boston? Check out Aloft Hotel Seaport District! Located right in Boston’s booming Seaport district, across from the Lawn on D, this hotel is in an ideal location for a weekend in Boston. Aloft is an urban gem surrounded by sights, nightlife, restaurants, and attractions. Aside from its coveted location, Aloft’s interior is a dream. It’s chic and colorful lobby pairs nicely with its loft-inspired, cozy rooms. There’s also a pool, gym, and restaurant for Aloft’s guests to enjoy.

Aloft was nice enough to host me for a night at their hotel in Boston, and I couldn’t recommend a stay here enough. As mentioned above, I was easily able to walk to all the shops and restaurants in the Seaport, and had the best time exploring the hotel. My favorite part about my stay was definitely the view of Boston! I stayed in a corner room, so I had 180° views of the city, overlooking both the Seaport and downtown Boston’s skyline.

Thank you again Aloft Hotel for hosting me and sponsoring this blog post! I hope you all book a room here next time you’re in the city and have a great weekend in Boston!

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