I have been two Boston two times. One time, my cousin's boyfriend (now husband) was living and going to dental school there, so we took a road trip to the city. The second time, it was our first stop on our New England road trip. We stayed with my cousin and her husband who live in Weymouth. I love the city. But my cousin, Amy, loves it more, and her words describing the city are truly poetic.
"The word of the Lord by night.
To the watching Pilgrims came,
As they sat by the sea-side,
And filled their hearts with flame."
Ralph Waldo Emerson's opening lines of his poem, "Boston Hymn. There were no truer words written.
Boston is the greatest city in this country. Sure, an exaggeration to some, but it is truly what Bostonians believe. There is a certain swagger in the streets of Boston, perhaps developed over time and adopted after the initial Sons of Liberty, as they strutted across the cobblestones on their way to the South Meeting House.
I digress. To explore Boston properly, one must simply follow the Freedom Trail. You can book a guide or book a bus tour, but if you are moving on a budget, it is a very walkable city.
Let's just pretend you booked a room at the amazing downtown hotel "The Godfrey," which is in the shopping/theatre district and a walkable distance to so many of the city's wonderful sites. There are another amazing hotels, but I'm just pretending you are staying here.
I start at the BOSTON COMMONS & PUBLIC GARDEN. The Commons once had a dangerous past, as criminals were hanged on the square. Nowadays, there are food trucks, water fountains, an ice rink in the winter, gatherings of hipsters, free Shakespeare performances in the summer, and access to the T (the subway system, which you genuinely don't need unless it's cold and rainy and your venturing out of the city/have tons of luggage). There are beautiful views of the dome of the State House and Beacon Hill from the Commons. If you are a lover of history and Instagram-worthy pictures, venture up the hill and wander through the streets of Beacon Hill. Louisburg Square and Acorn street are two of the most photographable places. You can also book a tour of the State House.
Down the backside of Beacon Hill towards the Charles River, is the Esplanade, a beautiful park with a walking/cycling path that winds all around the river. There are often performances there! But you also just see views of the river, and follow the path towards Back Bay for shopping in one direction, or head towards the North End in the other direction. While the shopping is great in Back Bay and it has some amazing row houses, I would opt for the North End myself. It is my favorite part of Boston.
Oh! throughout your travels, you will see a brick path in the sidewalk- that is the Freedom Trail. You can hire a guide, or you can follow it. If you choose to follow it from Boston Common, it will lead you past some great sites: Granary Burial Ground (Sam Adams' & John Hancock's graves), King's Chapel (sign up for the crypt tour if you love creepy things), Old State House, Boston Massacre Site, Faneuil Hall, Paul Revere House & my personal favorite place in all of Boston, the North Church. All of these are along the same path and they are free to stop outside of. If you want a full tour, it does cost money. Recently, the North Church started requiring tickets just to go in. So you can purchase a pass that goes to all of them, or purchase individual tickets for the places you care most about- I recommend Paul Revere House & North Church.
Fanueil Hall is the home of Quincy Market, so that's a good place to stop for lunch! Don't expect to sit and eat a table, because it's crowded, but it is definitely worth the experience. Regina Pizza is a famous and perfectly delicious pizza place in Boston. The original location is in the North End, and I recommend going, but you can also grab a slice at the Quincy Market location.
All along the harbor of Boston is the Harbor Walk, which is a path that takes you all the way around the city. You could literally spend a day just walking the Harbor Walk, which goes all the way into Charlestown, across the Harbor, where Bunker Hill and the USS Constitution are. If you are a nautical person and like to be near the water and see boats, you can literally just do this and stop for food and fun things along the way. The Aquarium is also along the Harbor Walk. OH, and if you like some cheeesey historic fun, you can cross a bridge and stop of the Boston Tea Party Museum, and participate in a reenactment. They also have beautiful tea shop where you can sample teas and eat scones in the middle of the harbor. LOVE IT.
You should end your day with dinner in the North End. There are so many Italian restaurants and bakeries, and the air literally smells like Italian food. Having traveled to Italy, it feels like you are walking around a small Italian town, as you walk around the North End: older Italian guys sitting in folding chair outside of cafes, drinking espressos, Italian grocery stores, religious shrines on every corner, and festivals to saints every other day. Some of my favorite places to eat are: Il Panino (amazing food, lots of seating, prices are more expensive than an Olive Garden, but won't break the bank), Regina Pizza (duh), La Summa (a family-run restaurant filled with black/white family photos), and the famous, cash-only, two-hour wait line, Giacamo's. Just go there at 4, and have an early dinner- worth it. Get dessert at Cafe Vittoria, Modern Pastry or Mike's Pastry, or Bova's. There are always long waits at Modern & Mikes, so I usually get a breakfast pasty at those two.
Lastly, just some other food recommendations in other parts of town: Ice Cream- J.P. Lick's (Beacon Hill), Irish Pub- the Black Rose (near city center), Burger- J.M. Curley's (downtown/theatre district), The Gallows (South End), Coffee- Cafe Nero (downtown) & George Howell (inside the Godfrey Hotel). Also, you can visit the Boston Public Kitchen for amazing local vendors- cider donuts all year long, and more George Howell Coffee. This is near the north end and near Quincy Market. Steak: MOO. Yeah, it's called Moo. If you are in the mood to drop $50 on a steak, then this is the place to go. I know this sound sort of sarcastic, but it's the best steak I've ever had in my life. And the bread! oh the bread. Maybe you could just get the bread and then do a dine and dash?
Don't forget seafood- a lot of people love Union Oyster House for its history and its great seafood. I'm not a seafood expert, but I am a lobster roll expert. So I'm only going to recommend one place: James Hook & Co. It's worth the price, and the best lobster roll outside of Maine. I'm not kidding. Don't try another place, and don't let the outside of the building fool you. Grab one for lunch on your walk around the harbor.
There is just so much more...
Or you can ignore all of this and do a Duck Tour...because those are funny.
I can't hold a candle to Amy's knowledge of Boston. She is quite the tour guide and when we went there, we traversed all across the city with her as our leader.
A few things that she didn't mention that I enjoyed while there were Fenway Park and something really meta, drinking a Sam Adams at Beantown Pub while looking at Sam Adams grave in the Granary Burying Ground.
As a lover of baseball, Fenway Park is a stadium you have to check off your list. It's one of my favorite ballparks (read my ranking here) dues to it's nostalgic feel and passionate fans. I have taken a tour of this stadium on one occasion and the next I watched a game. Both, I recommend doing.
If you have some extra time, take a ferry to Martha's Vineyard for a quaint island feel, some good lobster rolls, and a leisurely bike ride.
Hopefully, Amy's words inspire you to visit Boston!