To be clear, this is not just 10 things to do in downtown Boston, as that would imply you could and should do any and all of these activities whenever you want in whatever order you want. No, no. This is a very precise walking itinerary perfected over the course of five years, designed so that you arrive at each destination at the perfect time to enjoy it most.
Whether you are traveling, trying to get out of your campus bubble, or just looking to share a full and happy day on the town with friends, family, or your love interest, this itinerary will be just what you need.
To make it easier for you to plan less and enjoy more, I’ve created an interactive Google map to guide you throughout your day.
1. South Station (11 AM)
South Station, not only beautiful, is the hub of Boston public transportation. Wherever you’re coming from, you’ll probably start here. Enjoy the bustle and architectural majesty of the Financial District as you make your way to Chinatown.
2. Q Restaurant, Chinatown
You’ll want to grab an early lunch at this hot pot restaurant, because if you don’t hustle, you just won’t get a table. In case your mind is in the gutter, hot pot has nothing to do with illicit activities. Hot pot is a type of East Asian cuisine in which you cook noodles, meat, and vegetables in boiling broth in the middle of your table.
Preparing and eating hot pot is messy, but cute messy, making it a good place for early dates. I recommend you order a split bowl with the Mongolian vegetable broth and the tomato broth and get a watermelon smoothie to drink.
If you fail to get a table, Pho Pasteur across the street is a fine fallback.
3. Boston Common
A Boston landmark, the Boston Common is a great place for people-watching. Make sure to walk by the Frog Pond, an ice skating rink in winter and wading pool in summer, to visit the Robert Gould Shaw memorial sculpted by Augustus Saint-Gaudens, and to stop at the Brewer Fountain next to Park Street Station.
4. Beacon Hill
Beacon Hill has always been one of the wealthiest parts of Boston, and its brick sidewalks, imitation gas lamps, elaborate door decorations, and stunning townhouses make it picturesque.
5. Boston Public Gardens
In the glorious warmer months, the swan boats and the musicians on the bridge are a must. When it’s chilly, just wander and try to find the monument to the inventor of anesthesia. I also recommend bringing bubbles.
6. Boylston Street or Newbury Street
Boylston Street and Newbury Street are equally lovely walks to Copley Square. Boylston is the way to go if you find crowds or a high density of boutiques overwhelming, as I sometimes do. Whichever way you go, you must stop into Restoration Hardware, a former natural history museum turned luxury home decor store filled with lust-worthy design, elegant artificial flowers, glass elevators, and glamorous chandeliers.
7. Copley Square
Oh, Copley Square. Definitely most joyful during the summer, just like the rest of Boston. (People think we’re grumpy, but we’re just cold most of the time.) That said, whatever time of year, it is a beautiful area surrounded by great shopping, with stunning hotels and churches reflected in the glass of the John Hancock tower.
8. Copley Library
Reminiscent of the Library of Congress, Copley Library, the first large public library in the country, is filled with beautiful mosaics, marble staircases, John Singer Sargeant murals, excellent study rooms, a cozy café, a sunny European courtyard, a tea room, rotating exhibits, and a diorama room!
9. Top of the Hub
Located on the 52rd floor of the Prudential building, the Top of the Hub restaurant offers sweeping views of Cambridge, Downtown Boston, the Blue Hills, and the Harbor Islands. Not only does it have amazing views, but, BONUS, it also has pretty good food.
It is important to arrive here around three or four PM because that is neither lunch nor dinner, meaning that you can sit in the main dining room instead of the slightly less exciting lounge area while only ordering tea and cookies. You can get 12 fresh-baked cookies for $15, a great deal for a group, all with the best views in Boston. I’ll also note that every time I have gone in the afternoon they have told me the wait was an hour and have seated me within five minutes, so just be a teeny bit patient!
I recommend you pretend you’re looking for your table or getting lost searching for the bathroom so that you can walk through the whole restaurant and see all the views before someone scolds you. I do it every time.
Bonus: Max Brenner
You’re probably too full at this point, but if you’re still energetic, go shopping at Marshall’s, Nordstrom Rack, Lush, or whatever else pleases you, then go to Max Brenner, a chocolate-themed restaurant, for dinner. Their savory dishes are delicious, but their abundance of desserts, muted Willy Wonka decor, and chocolate cocktails are the real show-stoppers.