For international travelers, Boston often gets overshadowed by New York and Chicago, which is a shame because it tends to be the same people who find that the USA “lacks history.” Nowhere proves this reputation wrong more than Boston — a city filled with a rich intellectual history. On a visit, it is impossible not to immerse yourself in the stories of revolution and transformation that seep out of the neighborhoods. Although, it isn’t merely a city of the past. Today’s Boston is known for being home to growing opportunities, incredible boutiques and local restaurants, and neighborhoods that are bursting with energy thanks to the incredibly loyal residents. Boston is a place I have returned to over and over again throughout my years in the USA, and it’s charm never fails on me. From the seafood to the art (it was, after all, dubbed the Athens of America in the 19th century), this is a city that I have no problem spending time exploring. To help you plan your next trip, here is my Boston City Guide…
When To Go: Generally, the best time to visit Boston is from June to October when the pretty temperate weather makes touring around on foot a joy. The last time I was there was in November and it was f-r-e-e-z-i-n-g, although the blue skies still pushed me to wander.
Getting Around: Boston is definitely a walking city, and you can easily plan your days by finding strolls between stops. To speed things up, the MBTA is Boston’s public transportation system, and it’s a great way to get around quickly and cheaply. (Look for a “T” in a circle for a subway stop.)
Eating & Drinking
I might not be a massive breakfast person, but I can’t start a day without a strong cup of coffee. When in Boston, the perfect coffee can be found in the North End — the city’s Little Italy. Start your morning at Caffe Vittoria the city’s first Italian cafe and admire the vintage espresso machines and coffee makers, while sipping your cappuccino. For the total North End experience, walk a couple of steps to Mike’s Pastry for what many describe as the best cannoli you can find outside of Italy. Other breakfast stops that came highly recommended are South End Buttery which features a wide selection of breakfast items, Tatte is apparently the spot if you are looking for a local’s favorite and, for those who find themselves in Cambridge, Sofra Bakery and Cafe offers Middle Eastern cuisine that transforms breakfast into the most exciting meal of the day.
Lunch can often be combined with ticking off some of the city’s most famous experiences. Quincy Market is right on the Freedom Trail and offers plenty of options for food including the classics: clam chowder, Boston Cream Pie, Bostonian baked beans with brown bread, and lobster rolls. Although, James Hook and Co is considered by many to be the place for the most delicious lobster roll in the city.
In previous trips to Boston, I had never explored the city’s Chinatown which meant that I never had before experienced Winsor Dim Sum Cafe — officially the best dim sum I have had in the United States. It was cheap, fast, and drool-worthy and they sat my lonesome self at a table with three other couples. This whole area is worth some time in your itinerary as it is the third-largest Chinatown in the United States, (after New York and San Francisco) and the only surviving ethnic Chinese area in New England. On the opposite end of the spectrum, on the 52nd floor of the Prudential Center, Top of The Hub provided the background for a romantic dinner of seafood, live music, and 360-degree views of the skyline.
No trip to Boston is complete without experiencing the Freedom Trail, a 2.5-mile-long path that passes by 16 locations meaningful to the history of the United States — particularly during the American Revolution. Places such as Boston Common (which used to be a community cow pasture right in the middle of town), the Old South Meeting House (where the Boston Tea Party was planned), the Paul Revere House, and the Bunker Hill Monument are all stops on the route. Slightly surprisingly, my personal favorite stop was the USS Constitution, an active naval vessel that was first launched in 1797 and which you can board and explore. Most of the stops are entirely free, and the trail is marked by a red brick line, allowing you to guide yourself (use this for more information on each stop) and learn so much about the founding over the country while not needing to dip into your travel budget. Score!
After you have got your history fix, stroll through Beacon Hill, a 19th-century neighborhood that is the most pleasant neighborhood in the city. Dream of owning one of the gorgeous townhomes that sit on narrow cobblestone streets, lit by gaslight lamps. If you want to make the most of this neighborhood, opt to do this self-guided walking tour. If not, at least take a peek at Rouvalis Flowers, Louisburg Square, and Acorn Street — one of the most photographed streets in America. Continue your walk through the Boston Public Garden, a beautiful green park adjacent to Boston Common.
One of the reasons I love spending time in Boston is due to the extensive array of museums on offer. The Museum of Fine Arts is free (well donation-based) after 4 pm on a Wednesday making it an excellent opportunity to see one of the most impressive art museums in the country on a budget. I can’t believe I still haven’t been to The Isabella Stewart Gardner Museum which is designed like a 15th-century Venetian palace and filled with an incredible collection of pieces from all over the world ranging from paintings to sculptures, tapestries, letters, and tiles — but it is my number one priority for when I return. (If you are lucky enough to be named Isabella, admission is free!) The Boston Public Library is iconic and offers a free art and architecture tour of this gorgeous historic building which I highly recommend. Last but not least, inside the Mary Baker Eddy Library, you can find the Mapparium, an enormous, inside-out glass globe built in 1935 that is undoubtedly one of the coolest things I have ever seen.
Ahhh – the shopping. Newbury Street reminds me of shopping in England, no malls in sight; instead, you walk outside, stopping to peruse into boutiques and luxury stores as you please. If that isn’t enough for your wallet, Charles Street is another area filled with aesthetically-pleasing boutiques. For sustainable spending, Follain is a Boston-based clean beauty shop, Olives and Grace offers a variety of small batch housewares made by local artisans, and Paridaez is stocked with elegant, minimalist women’s wear made in New England. One of the largest used book shops in the country, Brattle Bookshop has two floors of general used books, while a third one is dedicated to old and first edition books. But, the open lot outside is where the bargains can be found, with an assortment of carts featuring books that cost as little as one dollar.
Have you ever been to Boston? Do you have any recommendations? Let me know in the comments below so I can add them to my list for next time!
– See more of the city in my Boston Travel Guide vlog