“A Day in Series” Boston, MA

Wanting a mix of rich history, scrumptious seafood, and an intense passion for hometown sports team?

Though it’s not necessarily one of my favorite cities, Boston, MA has its charm and wit, and it is a great start to get a taste of true American culture. I mean, it’s where the US history books say it all began.

Not a huge city, it’s easy to squeeze in a weekend trip or day trip, and get 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. (See Back Bay & Downtown) 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.


Not as robust as NYC’s system, Boston does have a train or, The T, which navigates throughout the city, color-coded byline for each neighborhood it serves. Its various lines will either take you underground or sometimes right alongside the street traffic. And it’ll run you about $5-6 USD for an RT ticket, called a Charlie card. As a tourist, understanding the train or even opting for an Uber/Lyft, though expensive, is a far better option than attempting to drive. Even the most seasoned drivers will find themselves frustrated maneuvering alongside the overly aggressive Masshole’s in traffic.

There is also a bus system that accompanies the train system, but in all my years of living in Mass (not many), I’ve never caught the bus.

Your last option, other than walking, is to rent a car and drive but aside from the terrible driving, parking will be quite difficult within the city as most neighborhoods have designated residential parking, and unless you want to spend most of your spending money on garages or parking meters, street parking is scarce.


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.

Unless you’ve been living under a rock, or just not in the United States, you’re probably well aware of Boston’s football team, the New England Patriots, their hockey team, the Bruins, and the Red Sox, their baseball team, arguably America’s favorite sport. You might not run into a player, but it is most certainly a great idea to head to Boston’s Fenway neighborhood to check out Fenway Park, home to the Red Sox. 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. So check it out, regardless if you check out a game or not.

Gillette Stadium, home to the NE Patriots, is in Foxborough, MA, which is a way outside of the city, and not worth the drive unless attending an event.

Boston, being so filled with history, has both walking and boat tours that will be worth your while, as I’ve done both numerous times. To check out more information such as scheduling and pricing of the boat tours or the walking tours, check here. Definitely schedule one of these during your visit, if you’re interested in learning more about the history of the city, affectionately nicknamed, Beantown (which you’ll find out why on one of the tours).

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. With areas like Newbury St in Back Bay and anchor stores of the famous chains, Marshalls and TjMaxx, there is something fabulous for everyone, no matter your budget. When I first relocated to New England, I spent almost every weekend visiting Newbury street. Filled with stores like Nordstrom Rack, Chanel, Sephora and Forever 21 and adorned with local cafes and boutique shops, it’s easy to get lost for hours taking it all in. 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 I also encourage all visitors to check out the Black Heritage Trail and learn a different type of history. 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!

Lastly, being situated on the east coast, Boston and most of New England has a ton of easily accessible beaches! Not the ideal destination for a beach vacation but, it is an option.

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, 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, Slades, Warden Hall, Angela’s Cafe, Red Lantern, Shojo Yvonne’s, Lolitas (Ultimate Fav), James Hook & Co, Boston Burger Co., Flames, Lucy Ethiopian Cafe, Tiki Rock, Bootleg Special, 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>>

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