Once upon a time, a very long time ago, on the 4th of July, I feel in love in Boston. I did not mean to. I didn’t even want to. I knew he and I were too different, and it would never work out, but alas, the heart wants what the heart wants, even when the brain knows better. At the end of a perfect day of exploration, as The Boston Pops Orchestra played the Overture of 1812 and the fireworks burst over the Charles River, we kissed for the first time. It was absolute magic and a perfect moment, that I still treasure.
The ill-fated romance ran its inevitable course. We parted, and I have never seen him again. Yet, that day has always stayed with me, and every time I walk the Freedom Trail through the North End, and stroll the paths of the Boston Commons, I remember what it is like to be young and in love. And, I hope somewhere, he is living his best life.
Perhaps, I also fell a little in love with Boston that day, and that relationship, though long distance, continues today. I love wandering its streets, looking for its secrets. I love watching the boats on the harbor. I love eating lobster at least once a day. I love the rich history and imagining what it would be like to live there. Not forever, the winters are too harsh, but perhaps for a season. Someday.
I first became aware of Boston as child through history lessons, but I was captivated by something every year on PBS. On the 4th of July, after we had shot our fireworks in our yard in rural Oklahoma, we would come in the house. On the television there would be a broadcast of the 4th of July celebration in Boston. The Boston Pops playing while fireworks, far bigger than I had ever seen, erupted over the Charles River.
Being on Boston on the 4th of July was the first thing on my bucket list, long before that was even a term. And, I made it happen! Often, dreams can disappoint. They just do not live up to our imagination. And, yes, I was startled by the massive crowd on the Esplanade, and the struggle to find a place to sit, but overall it was amazing to be there in the place of America’s beginnings, celebrating independence.
Now, that 4th of July crowd is not for everyone, but there is plenty of things for everyone to enjoy in Boston.
Water Taxi
One of the easiest ways to get around downtown Boston is by water taxi. You can take a water taxi from the airport, across the harbor and to downtown. From there you can walk or take a taxi/Uber/Lyft/Subway the rest of the way to your accommodations. This saves a lot of sitting in traffic, and it gives you the absolute best views of the Boston skyline.
Boston Logan Water Transportation
The Freedom Trail
Boston has an ingenious way of helping you see all the historical sites. All you do is follow a red line on the sidewalk, and it will guide you from The U.S.S. Constitution and Bunker Hill through the delicious Italian district in the North End, past Paul Revere’s house and the Old North church, down to Faneuil Hall and finally leading you to America’s oldest public park, Boston Common.
The trail is 2.5 miles, but you need most of the day to enjoy it, if you are going to visit the attractions along the way. Or you could do the north end of the trail one day, and the south end the next, if you want a more leisurely pace.
There a many other things to see along the Freedom Trail—churches, statues, old cemeteries with the graves of famous revolutionaries, but my favorite spots along the trail are:
The USS Constitution: Also, known as “Old Ironsides” and launched in 1797, it is the oldest actively commissioned battleship afloat. And, she’s undefeated. More importantly, she is gorgeous and full of great stories. You can tour her for free, but be aware that you will be required to show ID and submit to a security check, similar to TSA. She is an active-duty ship operated by the U.S. Navy. Be sure to check the hours, because it can change due to active military operations, or the few times a years she is sailed into the harbor.
On my last trip to Boston, I stayed at the Battery Wharf Hotel, where I could see her from my window. Each night, at sunset, I could hear “Taps” and watch the striking of the colors from her and the other ships at the Coast Guard Station next door.
The Old North Church and Paul Revere’s Statue: As you see the spire of the Old North Church peaking above the trees, you can almost hear the words of Henry Wadsworth Longfellow, “LISTEN, my children, and you shall hear of the midnight ride of Paul Revere” and “Of the North Church tower as a signal light, –One, if by land, and two, if by sea.”
Historians question the accuracy of Henry’s account of that ride, but perhaps as you look up at the tower, your mind can imagine the glow of two lamps and hear the hoof beats heading to out into the countryside to warn the militias.
On my most recent trip to Boston, an artist was actively painting the statue and church. I would love to be that person that could pack some paints or at least a sketch book and capture what I am seeing, but alas I have no talent or patience for it. Even though, it does not hold as much magic or artistry, I am grateful to live in the future where I can snap a digital picture to enjoy.
The Italian District: Eventually, you will wander into the Italian District. You won’t need a sign to let you know you have arrived. Your nose will tell you. When you encounter the delicious scent of pasta sauces mixed with freshly baked confections, you will be hungry, even if you just ate. I encourage you to give in, even if you just have some cannoli!
I do not have a favorite restaurant recommendation. I just tend to wander in somewhere, and I have never been disappointed. It can get busy though. I would recommend eating at an off-peak time or making a reservation on busy weekend nights.
5-Star North End Boston Italian Food Tour
Boston Common and Public Garden: Whether you start or end the trail here, this park will provide a nice lush green counter to the city. I think a city is only as good as its green spaces. New York City has its lovely Central Park. Chicago has Grant Park. St. Louis has Forest Park. And, Boston has its Commons. These are all great spaces enjoyed by tourists and locals alike on pretty days. While I love exploring cities, as someone that grew-up in the country, I find that after a few days in a city, I need to find a green space with trees or find a waterfront where I can see the horizon. It recharges my batteries.
While you can certainly navigate The Freedom Trail on your own, if you would like a guided tour, the ones below are highly rated, and have great reviews.
Full Freedom Trail History Small Group Walking Tour
Shortened Freedom Trail Tour-Costumed Guide 1
Shortened Freedom Trail Tour-Costumed Guide 2
Full Revolutionary Story Boston Walking Tour
Boston Waterfront
Just a few blocks off The Freedom Trail, you can find the Boston waterfront. When I don’t know what I want to do in Boston, I end up here, usually in the Long Wharf area. Here you can find the New England Aquarium, whale watching tours, harbor tours and more great restaurants. Or, you can just sit and watch the boats.
My favorite restaurant here is Boston Sail Loft. They have great food and harbor views and some patio seating. I had the Seafood Diablo with lobster, shrimp, scallops, mussels, and calamari, served over linguini with a spicy marinara sauce. I’ve had so many mediocre scallops in my life that I wasn’t even sure I liked them, but these melted in my mouth. I also had a restorative Irish coffee after a very cold Whale watching tour and a great lobster roll at Joe’s Waterfront.
Toward the south end of the harbor, past Roew’s Wharf, you can find the Boston Tea Party Ships and Museum and the Liberty Star. The Liberty Star is a tall ship that offers sightseeing cruises of Boston harbor. Nothing beats hoisting sails and enjoying the coastline or perhaps a sunset.
Boston Harbor Sightseeing on the Liberty Star
Whale Watching Tour to the Stellwagen Bank National Marine Sanctuary
Boston Tea Party Ships and Museum
Getting Around
Walking is a great way to explore and my favorite. However, Boston is big, and you can’t walk everywhere. I have mentioned the water taxi from the airport. They can also get you from one point to another on the harbor. There are also ferries that can take you around the harbor or up to Salem and Glouster or out to Provincetown at the end of Cape Cod.
There are certainly Taxis, Lyft and Uber services available. However, I would never rent a car here unless I was leaving the city, because it will cost you a fortune in parking. Honestly, even if I lived close to Boston, I would park my car at a commuter rail station and take the train in.
Speaking of trains, trains and the subway are one of the best ways to get around Boston. Don’t be scared. I used to be scared I would get on the wrong train and end up God only knows where. But, on my last trip to Boston, I made myself get better at public transit, and I am so glad I did. I saved so much money and time sitting in traffic.
Google Maps can help you know which lines to take, as well as apps like Transit or the mTicket app for Boston area Commuter Rail. You can buy a one or seven day pass at a vending machine at any subway stop. This will give you a Charlie Card that is refillable. A 1-day pass is currently $11. A 7-day pass is $22.50. Even the 7-day pass is cheaper than most Uber rides. This gives you access to ride as much as you want on most lines and some ferries. Longer commuter rail trips might require an additional ticket.
My favorite Tour in Every City
I am a sucker for a hop-on/hop-off bus. It is my favorite tour in every city. Whether it is my first day, and I am getting the lay of the land, or if it is day three when I am tired of walking or want to explore further afield, the hop-on/hop-off bus is great.
If I am being honest (and why wouldn’t I be?), I tend to “hop-on” and not do a lot of “hopping-off”. I like to be driven around and listen to the narration from the driver. I feel like I learn fun local tidbits that I cannot find in a brochure or on my own. If you do want to hop-off, you usually can get a discount on tickets at the attractions along their route.
Boston Hop-on Hop Off Tour
Back Bay Area
The Back Bay Area was new to my on my last trip. I stayed in that area, explored the streets and toured Fenway Park. I also saw the Boston Pops at Symphony Hall. This area is full of colleges. Harvard and MIT are across the river from here, but Boston University, Northeastern University, Boston Architectural College and Berklee College of Music and others are all in this area. I felt like this made it feel safer to walk at night because there were always a lot of college students out and about.
Fenway Park Tours
East Boston
A happy accident led me to East Boston. I was on a work trip, and my co-workers were heading home, while I was staying over the weekend. They dropped me at my Back Bay area hotel, and went to their hotel near the airport, where they realized they had my coat. I was super bummed, because the airport seemed far away, and going to get it was not an errand that I wanted to run.
However, we made a plan that I would retrieve it from the front desk in the morning. Determined to not spend a bunch of money Ubering to the airport and back, I figured out how to get there by subway and saw from the airport terminal it was a short walk to their hotel. Then I got looking around on the map, and I realized East Boston could be a great place to explore.
East Boston is the neighborhood across the harbor from downtown. I had a nice walk along the waterfront and through the neighborhood which is a mix of old and new. I was thinking how cool it would be to live here—near the waterfront and with an international airport that you could walk to!
I finished with lunch and took the subway back to the back bay. Easy breezy. In the end, I was grateful because the accident forced my hand into using the subway, and I found a little more of Boston to love.
Final Thoughts
Boston has a little something for everyone. History. Shopping. Great food. Art. Architecture. Green spaces. Boat rides. It can be crowded during peak times, and the traffic in and out of the city is tough, but totally avoidable due to a robust mass transit system. Also, the towns up the coast (like Salem and Gloucester), as well as Cape Cod are easy extensions to a Boston trip.
I have been to Boston several times, but there is still so much left for me to do there. Have you been? What are your recommendations in Boston?
Other 4 and 5 Star Boston Tours
Purchases from some links in this article pay a small commission to me, but I always recommend things I have booked or would book.
Cardinal Emprise 
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