Boston for Beginners: A rookie’s take on Boston’s must-sees (and must-eats)
I ventured to Boston last month to attend a travel conference, and it’s such a fantastic city - rich in history, filled with green spaces, and incredibly walkable, with clean and convenient public transportation.
This is only my second extended visit to “Bean Town,” the first being a few years ago with my niece. On that trip, we took full advantage of everything this charming city has to offer. Coming from the younger states out West, we were especially captivated by simply wandering the historic, narrow streets lined with red brick rowhouses in the North End and Back Bay.
There are a few Boston highlights we think are absolutely not to be missed.
Cannolis
When I told people I was heading to Boston, everyone I talked to mentioned the cannolis and the rivalry between two iconic pastry shops - Mike’s and Modern. My niece and I devoted ourselves to understanding this cannoli face-off. We jumped right in on our first morning to begin our research. We traveled on the T, Boston’s rail system, to the North End (aka Little Italy) and found Modern Pastry Shop first. Modern has a more traditional selection of cannolis with a choice between three fillings - classic ricotta, vanilla or chocolate. After one bite, I knew we would be spending a good deal of time in the North End. The next day (or was it later that same day?), we strode into Mike’s. Mike’s has veered from tradition offering a large variety of fillings and flavors, such as amaretto, espresso, Dubai chocolate and limoncello to name a few. Each day we taste-tested at least one cannoli, so devoted to our investigation we were. Our conclusion (and this may be contentious) . . . Modern for the win!
Freedom Trail
With all that cannoli tasting, we knew some exercise was in order. We immediately jumped on the Freedom Trail right there in Little Italy. It is easy to identify - just follow the double row of bricks embedded in the sidewalk. Walking this trail is a great way to see the most of the major historical sights in Boston including Paul Revere’s house, the USS Constitution (Old Ironsides), Bunker Hill, and many other sights significant to our country’s beginnings. One of my favorite things was wandering through the different burying grounds and reading the sometimes unusual encryptions on the gravestones.
Boston Duck Tour
Some of the best advice we got pre-trip was to go on a Boston Duck Tour. If you aren’t familiar, Duck Tours are city tours traveling through historical sections and unique neighborhoods of Boston all from a WWII-style amphibious vehicle land that is comfortable on land and water. This entertaining tour narrated by a conDucktor gets interesting when the Duck drives down the ramp and right into the Charles River. The tour is full of great stories and a lot of laughs. Don’t miss it!
Boston Common
There are nearly 300 parks and green spaces sprinkled throughout Boston. It give this city a healthly feel. I always try to incorporate an “urban hike” into my travels and Boston offers so many options. For this trip, I was staying close to Boston Common and was able to get out for a walk early one morning and only encounter a handful of friendly runners and dog walkers. It was lovely to watch the morning light creep into the view and spend some unhurried moments taking in the statues.
The Embrace statue in Boston Common
Fenway Park
It felt essential to catch a baseball game at Fenway Park. Imagine my delight when I realized the Red Sox would be playing the Yankees while we were in town. Talk about classic rivalries! The energy in that stadium is electric! Multiple times throughout the match-up, the crowd would spontaneously start chanting, “Yankees suck!” (I’m told this is a standard Fenway cheer no matter who the Red Sox are playing.) But, security only tolerated so much bad behavior. We watched one mouthy Sox fan get sternly escorted out. It was a great night - always fun when the home team wins!
Cape Cod
I have read quite a few Elin Hilderbrand books (aka author of many perfect beach reads). Several of her books are set on Nantucket Island near Boston. I badly wanted to visit Nantucket during our trip to see this magical place for myself. Then I looked at the price of accommodations. Yikes! We opted for a day trip to Cape Cod instead. It was a beautiful sunny day of lounging on the beach at Wellfleet. We treated ourselves to fried oyster po’ boys at the Beachcomber Restaurant, a Wellfleet institution. Speaking of restaurants, between both of my trips to Boston, I discovered some great places to grab a bite to eat.
Wellfleet, Cape Cod
Good Eats
Isabella’s - a small, intimate Italian restaurant on the North End. Easy to pop in for cannolis post meal!
Gray’s Hall - on Broadway in South Boston. A wine bar known for creative and amazingly flavorful small plates.
The Nautilus - a lively bar and restaurant in Seaport with delicious offerings from the land and from the sea.
Kava - a cozy Greek taverna on the South End with authentic and delicious Mediterranean cuisine.
Buttermilk and Bourbon - a Back Bay hot spot right on Commonwealth Ave that serves a terrific brunch on the weekend.
Row 34 and Select - Row 34 in Seaport and Select in Back Bay are the places to go for seafood in general and oysters in particular.
Sail Loft - located on the North End waterfront. Serves classic New England seafood and has a wicked good chowder.
Boston is the kind of city that invites you to slow down, wander, and savor the experience, whether you are following the Freedom Trail, lingering over a cannoli, or catching a game at Fenway. It is approachable, full of character, and easy to fall for on a first visit.
If Boston has been on your list, this might be your sign to go. And if you would like a little help turning inspiration into a well-planned trip, I am always happy to help you get started.
