Wanting a mix of rich history, scrumptious seafood, and an intense fan base for the local sports teams? Boston, MA certainly has its charm and wit, and it is a great start to get a taste of American culture.
The largest city in Massachusetts and 21st largest city in the US, you’ll have no shortage of activities to fill a weekend or even day trip, while gathering the overall essence of what is to be seen and tasted! Like most major US cities, Boston is divided into sub-communities and each has its own personality. Some are more worth visiting than others. Check below for a breakdown of my Boston must-do’s and download a printable bucket-list, to guide you through the city as you check off each activity- A Day in Series-Boston.
Boston is a very walkable city. You could easily get around by renting a bike at Blue Bikes! Or you could use a ride sharing service like Uber or Lyft. Boston also has a train system, the Massachusetts Bay Transportation, also known as The T. The T navigates throughout the city, color-coded byline for each neighborhood it serves, with the Red Line, Orange Line, Blue Line & Green Line. There’s also the Mattapan Trolley. Its various lines will either take you underground or sometimes right alongside the street traffic. See below for fare information or click the link above to find out more information such as stops, how to get a pass (can be purchased at any train station) or other FAQs.
1 & 7 day (& Monthly) Passes are also available.
Like most major cities, parking can prove to be difficult, and oftentimes expensive, and driving is not for the faint of heart- so though not impossible, not really recommended! If you decide to drive, check to see if your hotel or Airbnb offers parking, if not, beware that all street parking is not created equally as most neighborhoods require resident stickers for overnight parking ( a quick google search will point you in the right direction). Boston is a pretty “small” city but despite this navigating may be a bit confusing- definitely leverage services like Google Maps!
Also- download app Park Whiz. Park Whiz helps you to find discounted rates for popular parking lots across the city (available in multiple cities) I’ve scored spots for $17 that were originally $40-$54!
Getting to that rich history, delicious food, and sports culture I mentioned above, Boston does have a lot to offer to create a jam-packed weekend itinerary.
If Boston does anything, they’re going to have rowdy fans and an intense sports culture. From the New England Patriots (football) , The Bruins (hockey), Celtics (Basketball), and The Red Sox (baseball)-this city is pretty much in a frenzy, year round! Whether you are a sports fanatic or not (or like me, have a strong disdain for the Patriots)- it is still fun to partake in a game or the overall experience! You may not run into a player, but it wouldn’t hurt to head to Fenway Park, home to the Red Sox in Boston’s Fenway neighborhood! The stadium and area surrounding is overpriced just like any stadium you’ll go to, but it’s a really cool field, especially for those with an affinity for stadiums. Gillette Stadium, home to the NE Patriots, is in Foxborough, MA, which is a ways outside of the city, and not worth the drive unless attending a game, concert, or other vent! TD Garden, where the Bruins & Celtics play, is a really cool arena if checking out a game or any of the other concerts, events, ice shows, family shows or even wrestling events that are hosted there!
Boston, being so filled with history, has both walking and boat tours that are definitely worth checking out! To check out more information such as scheduling and pricing of the boat tours or the walking tours, check here. If time permits, definitely add one of these to your agenda, whether to learn more about the city’s history, where it got it’s clever nickname, Beantown, or just to tour the neighborhoods! I also encourage all visitors to check out the Black Heritage Trail and learn a different type of history.
Shopping is probably one of my top 5 favorite activities to do and Boston happens to be one of my favorite places to do it. Head down to Newbury Street where there’s something for everyone, from high end stores like Burberry or Chanel, a Sephora and Zara and even more affordable retail locations like Forever 21 and TjMaxx. There are also a ton of local shops and boutiques as well as varying restaurants and cafes.
A visit to Boston’s Faneuil Hall Marketplace and Quincy Market will produce more shops and boutiques as well as cool bars and eateries.
Back Bay (Newbury), Fenway, and Faneuil Hall aside, Boston has a lot more to offer. From the New England aquarium, Paul Revere House, Boston Commons, Boston Public Gardens, museum of science, and MFA, amongst a million other things, there is so much to do. All of the things above are some of my most recommended activities, but . And if you are a beer lover there are endless opportunities to do beer tastings, I’d suggest a tour at the Samuel Adams Brewery!
Being situated on the east coast, Boston and most of New England has a ton of easily accessible beaches! You can stay local at Carson Beach & Castle Island, head to Gloucester (Wingaersheek or Stage Fort Park) Beach, M Street Beach, Orient Heights Beach, Crane Beach, or check out Revere Beach-there are plenty of options as long as the weather cooperates. You can also head down to Rhode Island (check out my Newport blog here), catch a boat to visit charming Martha’s Vineyard, or drive up north to Maine! (Head to my IG for highlights on New England adventures- including Boston, Newport, Maine & Martha’s Vineyard)
Looking for something fun & unusual? Check out Trillfit, Boston’s original hip hop workout party!!
If time permits, I’d suggest adding a few day trips a bit outside of Boston, from the Parlee flower farms in Tyngsborough, MA, a trip down to Cape Cod for beaches & seafood, or even visiting the vineyards in Newport, RI- there’s not shortages of New England adventures!
Now for the good stuff, clam chowder, lobster rolls, and some of the other best seafood you can ask for, Boston is your place.
Legal Seafoods, a local chain and hometown favorite is really good and very pricey, but I would suggest going to a local joint if you had to choose one over the other. Visiting Boston’s Seaport district, along a stretch of water in South Boston, you’ll be matched with a string of sleek restaurants, hotels, and bars, with a waterfront view. One of my favorite places to go, I bring all of my guests to the Seaport. Fit with its own Legal Seafood, it also has delicious Mexican food options with either Temazcal Cantina or Rosa Mexicano, both great options. The local joint I mentioned above for one of the best lobster rolls? It’s in the seaport, Yankee lobster. Rated 4.4 stars, there’s no-frill or glam, with all of the focus being put into the taste of the food.
Famous for its Italian background and tight streets, you MUST visit the North End, a neighborhood in Boston, home to Mike’s Pastries where it’s imperative you get one of the infamous cannolis. Don’t let the long line fool you, it moves quickly and it’s worth the wait. As with most cities and popular restaurants, someone will always claim there’s a better, less popular option to go to, but don’t listen-or go to both, Mike’s is a must-visit. Aside from Mike’s, the North End has a ton of authentic Italian restaurants to choose from. Pricey, yet worth it.
A list of more of my fav places to eat in Boston: The Barking Crab, 753 South, Slades (Black-Owned), Warden Hall, Angela’s Cafe (East Boston), Darry’s Corner Bar & Kitchen (Black-Owned), Suya Joint (Black-Owned), M&M BBQ (Black-Owned), Red Lantern, Shojo Yvonne’s, Lolitas (Ultimate Fav), James Hook & Co, Boston Burger Co., Flames, Lucy Ethiopian Cafe, Down Home Delivery (Black-Owned), Tiki Rock, Bootleg Special, Urban Grape (Black-Owned/Wine), Citrus & Salt, The Broadway, Yellow Door Taqueria, Osteria Nino, Blossom Bar (Great Cocktails), and The Coast Cafe.
Not really comparable to a LA or NYC, Boston does still offer a robust nightlife and has different options dependent on the vibe you’re looking for. Some of my favs are Good Life, Kingston, Cure, and Alibi, located inside the Liberty Hotel, an old jail repurposed, but maintaining its jail cell doors adorned with mug shots of celebrities who’ve spent time behind bars.
For a more ‘chill’ vibe, there are spots like Darryl’s, the W, or Hojoko that I love to go to for a simple night out.
There is so much to do and see in Boston, but fitting it all in during a short or extended weekend is doable. Staying in a hotel or Airbnb in the South Boston or downtown area puts you right near the action and catching the train leaves you flexible and avoids Boston traffic and parking. When you plan to visit, avoid the winter months, December-March, to truly enjoy your trip. Hit with tons of snow and below freezing temps, you don’t want to risk being stuck in Boston due to canceled flights. Fall is my favorite season in New England, though the city truly comes alive in the summer.
**A hotel that I stayed in and loved is the Courtyard Marriott South Boston and an Airbnb I absolutely recommend can be found HERE.
Download my “A Day in Series” Bucket-List: Boston edition HERE <<A Day in Series-Boston>>