Boston Travel Reflections

If asked what city shaped me the most in life, the obvious answer would seem to be London. After all, I lived as an ex-pat there for three years and drone on relentlessly about my time overseas to all who will listen (or pretend to listen.) But, in reality, the city that originally altered this unexpected life of mine was Boston.

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Meet Your Protagonists

Scott and I have known each other since the 1980’s. Both budding musicians who lived around the corner from one another, we would spend hours making and talking about music. In our small houses in North Syracuse, New York, we would challenge and inspire one another.

Scott, although two years younger, often took the lead role in motivating me. His dedication to music itself was stronger and more sophisticated than mine. Both of us of modest means, to put it mildly, Scott was part of the local youth symphony. He also had private music teachers who required him to look beyond the school band music. Conversely, I blindly practiced trumpet exercises for hours each day.

Don’t get me wrong, our high school ensembles were remarkable. However, the repertoire that Scott was exposed to transcended the niche of educational literature. They were true masterworks. With a combination of vinyl records and cassette tapes, I began my true journey into classical music in Scott’s small room in his house around the corner from me.

Why Boston?

During my first two years of undergraduate school, my life was consumed by practicing, studying, and listening to music at the music library in Northern New York State. I also began summer trumpet studies with the Principal Trumpet in the Syracuse Symphony, George Coble. He introduced me to the performing philosophies of Charles Schleuter, the longtime Principal Trumpeter for the Boston Symphony Orchestra. These strategies helped to maximize efficiency during my hours of daily practice. In addition to marveling at the golden tone of Mr. Coble, I became obsessed with listening to Boston Symphony recordings and would later travel to the Boston suburb of Newton to take a lesson with Mr. Schleuter.

Scott continued to make leaps and bounds in his trombone playing and he was accepted into The New England Conservatory of Music (NEC), in the heart of you guessed it, Boston, Massachusetts! With an opportunity to study with his trombone idol, Norman Bolter, Scott embarked on the next step of his musical journey two blocks from Boston Symphony Hall.

Your Reverse Travel Guide

It is my sincere belief that travel, no matter how near of far, is most important and memorable when strong memories and human connections are made in its midst. I take relatively few travel photos and I do not keep notes or a travel journal. Read why here.

This “reverse travel guide” will provide you a feel for Boston, as well as stories from some of my many memories of this great city.

Getting To Boston

Boston is actually an easy city to access and traverse, IF you don’t drive. Sure, you CAN drive, but what you will find is a spider web of thoroughfares, many leading to unexpected one-way roads and very little municipal parking.

As one of America’s oldest cities, urban planning did not historically occur in a strategic manner, but rather developed over time. The Big Dig, one of the most expensive, controversial, and lengthy public works projects in recent decades, has made what used to be nightmarish bearable and allowed development in an area that was not historically prosperous.

Logan Airport and ‘The T”

Boston’s Logan Airport, is a bit of an underrated gem. The terminals have recently undergone some nice upgrades. It is also unique for the beautiful harbor view and many modes of transportation from its island-like location. I liken it to San Francisco International Airport and New York City’s LaGuardia Airport where you descend rapidly with a great view of the cities. You truly know that you have arrived, sometimes in a spectacularly bumpy manner.

The “T” is Boston’s subway (and sometimes above ground) public transportation system. It is quite old, and in my opinion, a bit tricky at times. It also breaks down quite a bit, which causes reroutes and delays. That being said, it is incredibly convenient to all desired destinations. Other than walking, the “T” is the way to go by all accounts.

My “Getting To Boston” Story:

As a not-so-confident college student, I was afraid of everything new. [Read about that here.] Scott encouraged me to visit him at NEC and I did. I was anxiety-ridden throughout, especially as I neared the city. All I could think about was finding the nearest parking lot and unclamping my hands. Unable to get out of my own head, my anxiety was high for three days. Scott encouraged me throughout my weekend-long stay, but he could not truly understand my panic.

Trembling while traversing is the best way I can describe my first visit to Boston. If my understanding of anxiety hadn’t developed so strongly over the intervening thirty years, my embarrassment would still be palpable. I survived that first trip in tact and it gradually led me to take more and more risks throughout my life. That weekend in Boston was part of a process of learning to push through fear. The rewards have been endless.

The Back Bay

The New England Conservatory is situated in The Back Bay area of Boston, which is one of the city’s most well-known tourist destinations. The area is serviced by five east-west streets:  Beacon Street, Marlborough StreetCommonwealth AvenueNewbury Street and Boylston Street. In addition to its beautiful brownstones, it is the home to Copley Square, The Hancock Building(s), The Prudential Center, Old South Church. The Christian Science Plaza, Boston Symphony Hall, and more.

My Back Bay Stories:

I have numerous stories about the Back Bay. It is the area that I enjoy the most. As an avid city wanderer, this area could not be more perfect for my aesthetic. The aforementioned brownstones contrast with the greenery, the banks of the Charles River, three music conservatories, numerous restaurants and bars, tall buildings, and abundant people watching.

Many tales stand out to me from the dozens of times I have visited that area. The first was back in 1999 or 2000. Like any friendship that lasts over thirty years, Scott and I had a few misunderstandings and disagreements. For reasons not worth mentioning, things came to a head outside of a high-end Italian Restaurant on Newbury Street. We shouted at one another like two lovers having an embarrassingly heated quarrel. The bottom line is that we both later realized the ridiculousness of the situation and our friendship is as strong today as it has ever been. Such is the nature of human connection.

In contrast, my second anecdote is an experience a few years back with my good friend Andrew. Having attended the Berklee College of Music for a short time in the 1970’s, Andrew had not been back since. We stayed in a nice hotel in the heart of the Back Bay, two blocks from his former music school. He was in heaven.

What better experience than to relive one’s younger days by walking around the old neighborhood. It was heartwarming to witness his joyful visage as he searched for his student apartment, spoke to locals about all of the changes over the decades, and took in a rush of memories and emotions. In a twist of irony, we began the afternoon at the same restaurant where the aforementioned argument with Scott had taken place years earlier. The night drew to a conclusion with us meeting up with Scott a couple of blocks from Andrew’s old college apartment. Life is often circular.

The Charles River, The Esplanade, and Cambridge

The Charles River meanders through Boston and also separates it from neighboring Cambridge, home of Harvard University and The Massachusetts Institute of Technology (MIT). There is so much to cover with these areas that it would require another post. These three sections of greater Boston are filled with greenery, parks, world-famous regattas, universities, ethnic restaurants, college bars and just about everything you could want in a great American city. The Esplanade is also the summer home of the world-famous Boston Pops Orchestra. If you really want to have some fun and live on the edge, try to insist to a Cambridge local that it is really part of Boston!

My Esplanade Story:

Again, I could go on forever, but my most memorable human connection to this area was a Fourth of July Fireworks display at The Esplanade with the Boston Pops accompanying. On a beautiful night in 2003, I was accompanied by a good friend who had traveled with me from England. It was my turn to share my culture with her, rather than the other way around and it meant a lot to me.

With perfect weather, a great orchestra, and wonderful company, it was the most memorable 4th of July celebration of my life to that point. The fireworks seemed as if they were going to land on us. I was mesmerized by the synchronization of the music, the smell of the dissipating smoke, and the kindness of all of those around us in the packed audience. This was the essence of Independence Day in one of America’s great, historic cities. And, I was able to share it with someone meaningful to me from another country.

Boston Harbor, Quincy Market/Faneuil Hall, and The North End

Once again, these areas could, and maybe will, merit their own post. Although it commences here, my favorite walk is not the famed Freedom Trail. I prefer to begin somewhere near the Quincy Market/Fanueil Hall Marketplace area, a super-touristy spot that still possesses an air of excitement. There is also a busy indoor and outdoor food market worth checking out, if you can stand the crowds.

One can then walk across the street underneath Interstate 93 and stroll along Boston Harbor, looking at the boats and watching the airplanes take off from the airport across the way. I have also taken dinner cruises in Boston Harbor with student groups that I have supervised. The views of the Boston Skyline are phenomenal and the children love it.

The New England Aquarium is also nearby and it is one of the best of its kind anywhere. It is also extremely kid-friendly. A stroll north on Atlantic Avenue brings you to The North End, which boasts Boston’s Little Italy. The food is phenomenal, and in many places it is also authentic. I won’t dare recommend any one place, as I don’t want to take the chance of getting whacked! (I jest, I jest…)

My Boston Harbor Story:

Boston Harbor’s Long Wharf

Once again, I have visited this area more times than I can recall. Trips with students [see my post about the joy of traveling with students here], times with friends, family visits as a youngster [see my post that includes a childhood Boston visit with my Dad here], and more. But, the one visit that has the most recent significance was with my family.

We only had a day or two and I wanted to show my wife what all the fuss was about. It was September or October. The weather was turning colder and we stayed south of Boston in nearby Plymouth, Massachusetts, home of the famous Plymouth Rock. (If you haven’t seen it, I won’t spoil the surprise.) Boston was a day trip with no itinerary. Basically we were taking a family road trip from Plymouth. [I describe how much family travel means to me here.]

The details of our road trip are of little significance to the story. The bottom line is that with dozens of possibilities for a day in Boston, our family time together was what was most important. We strolled part of The Freedom Trail, saw a couple of tourist attractions, wandered along the piers, ate lunch in Little Italy, and made our way back to the parking garage.

Filled with love and content to only spend half a day, we jumped into the car and headed back to the hotel in Plymouth. We shared a simple dinner and spent more time together laughing and relaxing. I reflected on my times in Boston as a single person, as well as my fun times with Scott and others. A sense of calm washed over me as I relished the fact that I had now shared my love of the city with my family. It was more meaningful than I could have imagined.


In My Unexpected Life, I share stories, thoughts, and simple ideas to entertain and possibly inspire others to become more connected with each other in conversation, food, travel, and more…no matter how big or small those experiences may be.


  1. what a great story …… did Scott stay in the Hotel room one night or am I thinking of someone else??

  2. What a great way to give a sense of a city, thank you for your stories and your city expertise! There’s something really special about sharing a place you love with people you love – I recently got to take my fiancé to the park my brother and I played in all the time as kids, and your final paragraph reminded me of that.

    1. You are so right! Even with small places (like the park you mention) that have meaning to you, it is so meaningful to share them with important people in your life. Thank you for reading my post!

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