To fully appreciate Boston, you need to visit the city at various stages of your life and at various seasons of the year. I first visited Boston on a family vacation when I was 7 or 8 years old. Boston was a multi-day stop on a greater tour of the New England area that included stops at Mt. Washington, Sturbridge Village, and Fort Ticonderoga. We still talk about that trip thirty years later. Boston’s a great place to visit as a family—there’s historical sites, there’s cultural sites, there’s sports sites, and there’s great neighborhoods connecting all the pieces. It’s exploring those great neighborhoods that makes a return trip to Boston as an adult worthwhile.

On an April 2021 trip to Boston, I realized that I knew very little about the city. I’ve always thought that Boston shared characteristics with Philadelphia. Both cities were a hub of colonial activity. Both cities had bad baseball and football teams (I should put an emphasis on had, for Boston anyway). Both shared a proximity and rivalry with New York City.

Both cities have hard scrabble, blue collar citizens that proudly carry a chip on their shoulder…or so I thought. Here’s the thing with Boston in 2021—it’s not the Boston of 2000 or the Boston of the 20th century. Boston, along with San Francisco, is the preeminent American cosmopolitan city. It’s the city that foreign visitors should see as America’s “best foot forward” city. From public transportation to new public and private investment to glistening neighborhoods to a burgeoning microbrewery, coffee, and restaurant scene, to even their sports teams, everything in the city feels world class. I felt sad returning to Philadelphia. I felt like my “brother” city went off to college and became a success and I was stuck living in my highschool past. That Philadelphia is one of poorest cities in America never really bothered me until I started driving back from Boston and began to wonder about life in a wealthy city like Boston.
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A good example of Boston’s superiority? Philadelphia has a block called Delancy Place (between 20th and 21st Streets) that I consider the nicest block in Philadelphia—it’s Philadelphia at its residential peak yet it’s a block compared to say the Park Slope section of Brooklyn which is an entire neighborhood. But…then…there’s…Boston. The ENTIRE city looks like Delancy Place—solid, renovated, clean Brownstone after Brownstone, block after block, street after street, neighborhood after neighborhood, for the entire city. You think South Boston (or Southy) is full of seaport workers and fishermen? No way. It’s completely yuppified and I don’t mean that negatively. The Seaport District is a completely revamped neighborhood home to tech companies, microbreweries (Harpoon and Trillium), and other commercial initiatives. It’s the equivalent to a buildup you see in Singapore or Dubai.
Our Boston 2021 trip started from the South. We spent a night in Riverhead, Long Island, New York and caught a morning ferry from Orient Point to New London, CT. We made a stop in Attleboro, MA for my wife to catch up with a hometown friend. First stop in Boston was the city's renowned microbrewery of all microbreweries, Sam Adams. The brewery is located on the southern side of Boston and gave us an introduction to the slow surface street driving around Boston. Once you leave the interstates, expect the driving to slow to a crawling pace, not because of traffic but because of traffic lights and winding through small towns and neighborhoods. It's been a long time since I drank a Sam Adams lager and I'd forgotten how good a beer their flagship lager is - the city even has a world class microbrewery. The site itself is relatively small - there was an outdoor sitting area, an indoor bar area, and a small giftshop. By small I mean compared to Yuengling's giftshop which has all sort of memoriablia and their band on everything. Sam Adams had some shirts and some glassware and that was about it. Tours are available but if you've gone on one brewery tour, you've gone on all brewery tours.
From Sam Adams it was a nice zig and zag drive over to the Dorchester Heights / South Boston area. During the Colonial Era, Dorchester Heights provided a panoramic view of the area and down to harbor. Now it's a relatively high end neighborhood. We then drove on W. Broadway through the South Boston area. I was expected this area to be a little rough. A bit like Philadelphia's Kensington neighborhood and well...it's not quite rough. The neighborhood's hard reputation has given way to upscale dining and bars. The primary drawback to this neighborhood today is you may have a ten minute walk (or longer) to the nearest T station.

From here we drove around Boston's Seaport / Innovation District. As I stated above, it felt like a public/private works project you'd find in Singapore - it's similar to the Marina Bay Financial Centre although with a bit more dining and drinking options. Philadelphia talks about projects like this conceptually...Boston get's it done.
We made The Lenox Hotel, in Boston's Back Bay area our home base for three nights. The Back Bay area may be the finest residential and commercial district in the U.S. The hotel is a block south of Newbury Street, the neighborhoods primary shopping and dining thoroughfaire. The ground and basement level of brownstones have been turned into restaurants and boutiques. With COVID-19 going on, restaurants had expanded their outdoor seating from patios into the street. Walking the area felt like being transported to Paris.
Block after block after block looked like the photos below. It was a joy taking Annie out for a walk three times a day and heading in different directions to see more of the neighborhood but each area looked the same - amazing.
A block north of Newbury Street is Commonwealth Avenue. This street doesn't have the shopping or dining of Newbury but it does have a wide median that acts as a park. There's a center walkway with greenery on both sides. There's monuments along the walkway as tributes to famous Bostonians. The image on the below right is a tribute to fire fighters.
At the eastern end of Commonwealth Avenue are Boston's two great green spaces - Boston Commom (below) and Boston Public Garden (further below). Boston Common feels like a giant park with views of the state capitol building, a few monuments, a bandstand and baseball fields.
Boston Public Garden is slightly smaller but it felt like there was more going on. There's a giant pond in the center of the park and the bridge that crosses the pond provides stunning views. We walked through this garden a couple of times during our time in Boston.
Boston Common and Boston Public Garden are lined with expensive real estate, however, it's also the site of the Bull and Finch Pub, the bar that inspired the TV show Cheers.
The bar is located down a flight of stairs and as a restaurant above but unfortunately there was no Sam Malone inside slinging drinks. One final shot of Make Way for the Ducklings, a favorite sculpture in Boston. The ducks get dressed in various costumes throughout the year. Our visit coincided with the traditional timing of the Boston Marathon and thus the ducks were in their running gear.
On Sunday morning I ordered a breakfast sandwich from Mike & Patties, then walked around the Chinatown and Theatre Districts before grabbing a coffee at George Howell and walking back to the hotel through Boston Common. Very clean city.
In the late morning we took the T over to the historical area. We saw the site of the Boston Massacre before walking around the Faneuil Hall area. Faneuil Hall was still closed due to COVID-19 but we were able to eat a bowl of clam chowder from Union Oyster House, a place the Kennedy's frequented. The one thing that Boston does not do better than Philadelphia is city halls. I like the Boston's modern take on a city hall but it has nothing on Philadelphia's Greek Revival, French influenced city hall.
Photo recreation below from a family vacation to Boston when I was a kid and in April 2021.
The Red Sox had an afternoon game at Fenway Park so I walked over here from the hotel. I expected there to be a bit of a crowd along Landsdowne Street, a bar street behind the stadiums outfield wall, but it was relatively sedated. Bostonians were taking the COVID-19 protocols seriously and the state had some serious controls in place. Everyone we saw, and I mean everyone, was wearing a mask OUTSIDE. In parks, no one else around, people were wearing masks.
From Fenway I caught a T ride down to Coolidge Corner, a bustling intersection, in Brookline. Like every other place in Boston, it was nice. I walked the main commercial street then caught an Uber over to Cambridge and walked around the Harvard campus. A few thoughts on the Harvard campus - I really like that it's on the water, there was a nice green space on the southern side of the campus. The rest of the campus I thought was just ok. There's a lot of history here but as a campus, I think Princeton's a little nicer. I'd prefer being in Boston over the town of Princeton, but Princeton's campus is tough to beat. Harvard has a sprawling campus with the Harvard Business School being located across the Charles River but the historical campus area is relatively compact and centered around Harvard Square, a tree filled quad. I walked around Brattle Square and JFK Street before catching another T ride back to Beacon Hill. On a future visit to Boston, I'm going to take a deeper dive in the Cambridge and Somerville area - I'll likely book an Airbnb in Somerville.
From the Charles T station I walked across the Longfellow Bridge to take a few shots of Boston and the Back Bay area with the Charles River in the foreground. I will say this about Boston, the city does not have a great or iconic skyline. It's a relatively low city. I think that's help the individual neighborhoods look so amazing and if that's the tradeoff for not having an impressive skyline, then that's a good tradeoff to make. As is, the shot of Back Bay from the Longfellow Bridge may be the city's definitive skyline image.
From the bridge I walked down Charles Street through the Beacon Hill area, then once again, cut through Boston Public Garden.
I spent the final day in Boston working from the hotel. I always have a bit of extra adrenaline when I work from a new location. I hoped to work a few days in Boston but the city is expensive. It's not a place to travel to for work if you need to personal pay for the travel. I originally planned to spend two days working in Boston but after checking hotel prices, that got cut to one day. In the late afternoon I walked over the South End neighborhood. One more great neighborhood to see before driving home the next day.