How I Spent 48 Hours in Boston

By Published On: September 9th, 2023

My best friend and I were lamenting the end of the summer a few weeks ago when it occurred to us that we hadn’t taken a single trip together at all this summer. As that realization sank in, we immediately took to the Internet to search up interesting places that we could go for a long weekend that were within a four hour radius. We bounced off of a few places in New England, but eventually decided on a spot that neither of us had ever been to before: Boston, Massachusetts.

My expectations of Boston were similar to that of New York City. I expected the city to be busy, bustling, and the traffic to be insane. While Boston did cover all of those bases, I also found it to be a beautiful city rich with history, interesting architecture, and lots to see and do.

We arrived on Friday afternoon after a relatively painless three hour drive (I had been expecting much worse considering that it was the start of Labor Day weekend). We chose to stay in The Westin in the Seaport District in South Boston, which allowed us to see an additional part of the city that we may not have ventured to otherwise.

The seaport is a beautiful area that offers the best of both worlds, with restaurants, bars, and shops lining the streets in addition to parks and beaches overlooking the Boston harbor. We spent Friday night exploring the Seaport District and popping in and out of the upscale shops there.

Saturday morning we hit the ground running, with our first stop being the New England Aquarium. The aquarium boasts a huge glass tank that is spiraled by a multilevel walkway, which allowed us to see the various fish and mammals in the tank all the way through the aquarium. The highlights had to be the enormous green sea turtles, African penguins, and dwarf seahorses. Although, I must admit that a memorable moment was also getting to stick my hand in the touch tank and pet a cownose ray, which is a type of stingray commonly found in the Gulf of Mexico.

Following the aquarium, we set off towards downtown, but quickly got sidetracked by an artisan market in Wharf District Park. There we found a variety of vendors selling everything from jewelry to glass blown animals and handmade bags. My favorite vendor, however, was a company called Liquor Wicks.

Liquor Wicks is a company that specializes in creating eco-friendly candles out of liquor, wine, and beer bottles. They work with local suppliers and source their liquor bottles from local bars and restaurants that don’t have recycling programs.

A genius idea, indeed, and I ended up purchasing two candles (and would’ve bought many, many more if I didn’t have to carry them with me for the remainder of the day).

Next, we headed towards Quincy Market and made various stops in the shops there. While wandering through the Quincy Market area, we came across the Sam Adams Downtown Boston Taproom. Feeling faintly hungry and especially interested in drinking a flight of beer, we immediately went inside (because you can’t go to Boston without paying good ‘ol Sam Adams a visit). The taproom is spread across three floors, with the top floor being an open rooftop with plenty of seating overlooking part of the Freedom Trail and the Samuel Adams statue.

At this point, we were sweating from walking around in the sun, so we opted to sit inside and enjoy our lunch in the luxury that is air conditioning, rather than on the rooftop. We each ordered a sandwich (Caprese on Ciabatta for me and a Roast Beef Panini for my friend) and enjoyed our flight, which was made up of their Sour Hour (on the sweet side, but good), Cherry Wheat Ale (very good), Rice and Shine Lager (not a fan), and Golden Pilsner (eh, tasted like your average beer). (I should make note that I am not a beer connoisseur of any kind.)

Effectively fueled back up, we walked through the Government Center and made our way towards Boston Common and the Boston Public Garden. We spent some time wandering through Boston Common, observing a large group of people protesting for fair wages along Tremont Street, kids playing in the Frog Pond at the center of the park, and an organization raising awareness for suicide near Beacon Street.

Another thing that seemed to be a recurring motif was the appearance of various colorful cow statues popping up around the entire Boston area. After seeing them in different areas, we finally decided to look up what their purpose was. Apparently, the cow sculptures were created by 75 New England artists as part of a “CowParade” to support The Jimmy Fund and the Dana-Farber Cancer Institute. Art for a good cause, indeed.

Next, we walked over to the Beacon Hill area and took in the old architecture and the small, cute shops that line Charles Street. After wandering around there for a while, we called an Uber and made our way back to our hotel where we recharged for a few hours in the afternoon.

Later that evening, we set out for West End where we had dinner at Banner’s Kitchen and Tap, just outside of TD Garden. Banner’s is a multi-level sports bar complete with a wall of televisions of varying sizes behind the bar that are broadcasting games of every sport you can possibly imagine. While I was initially overwhelmed by the sheer amount of screens that were pointed at me, I grew used to it, and even found myself keeping up with multiple games at once while we ate dinner.

In keeping with the theme of being in a sports bar, we decided to stock up and share a bunch of appetizers, rather than ordering actual entrees. We ordered the soft pretzels with beer cheese, loaded potato tots, and bourbon bbq wings.

After Banner’s, we headed back towards our home base in the Seaport District and made a stop at Cisco’s Brewers, which is a seasonal pop-up outdoor bar that offers a variety of their beer, wine, and liquor. I ordered a cocktail made with their Nantucket blueberry vodka, club soda, and a lime/mint mix. It was perfectly sweet and fizzy.

At this point, we were rather tired and decided to call it a night, so we walked back to our hotel and promptly fell asleep.

On Sunday, we slept in until mid-morning before getting up to check out of the hotel. Before heading home, we made our way over to Newbury Street in Back Bay. Every Sunday from July to October, The City of Boston closes Newbury Street to vehicles in an event aptly called “Open Newbury Street.” This means that vendors can set up in the road along the street and restaurants can expand their outdoor seating outward to accommodate more customers. Newbury Street was incredibly crowded while we were there, but it was nice to see so many people mulling about, purchasing items from vendors, and enjoying the beautiful weather.

From there, we made a not-so-quick stop at Shake Shack for lunch (the line was very long) before we headed back to the parking garage and started the three hour drive home.

Overall, Boston far exceeded my expectations! It’s definitely still a city, but has the vibe of being small and quaint in a way that many cities attempt to attain, but never quite do. Boston is rich with history and offers tourist attractions without feeling too touristy – meaning you can be a tourist there and not stick out like a sore thumb in the way in which many do in New York City. Our time there was limited, so we were unable to explore too much of the city, but that’s a blessing in disguise because it means that I get to plan a trip back to do more exploring! Boston, I’ll see you again soon.