Stay Heirloom's City Guide for Guests



The best of the best

Boston, lovingly referred to as Beantown, is the capital of Massachusetts. It’s mainly known for its history, but it’s also a hot spot for restaurants, shopping, and more. The city is home to over 30 different colleges and universities, which means that there’s always something to do.

Curated & Current

We’ve collected our top tips below so that you can get the most out of your trip and leave feeling like a local.

be ready to EXPERIENCE


Back bay

Must Eat: Joe’s American Bar and Grille Must Visit: Boston Public Gardens Must See: The Prudential Rooftop


Must Eat: Committee Must Visit: The ICA Must Drink: Harpoon Brewery

north end

Must Eat: Bova's Bakery Must Visit: The Paul Revere House Must See: Improv Asylum

South End

Must Eat: Frenchie Must Visit: SOWA Market Must See: Wally's Jazz Club


Must Eat: Tiger Mama Must Visit: Isabella Stewart Gardener Museum Must See: Time Out Market

Government center

Must Eat: Mariel Must Visit: Faneuil Hall Marketplace Must See: The Freedom Trail

Boston is so packed with history that around every corner there’s something to learn. Even though it’s called the walking city, we don’t expect anyone to actually walk the whole thing, so here’s a cheat sheet. Visiting these spots is like a history class… with the fun professor who doesn’t give you any tests.


1. The Paul Revere House

Revere is best known for his midnight ride, but he was also a silversmith! Learn all about Paul Revere’s life on an informative self-guided tour.

2. Fenway Park

Need we say more.

3. Boston Tea Party Museum

Float and find out about the unlikely relationship between taxation and tea.

4. Old North Church

A notable stop on both the Freedom Trail and Paul Revere’s Midnight Ride that will shed some light on the American Revolution.

5. Granary Burying Ground

A cemetery that is the resting place of many notable historical figures including John Hancock, Paul Revere, and Sam Adams.


  1. The T tends to run behind schedule, so make sure to allot for extra travel time.
  2. You might think that Mike’s Pastry is the best in the North End, but Modern Pastry is just as good.
  3. Cambridge (home of Harvard) is actually across a bridge which makes taking public transportation not impossible, but kind of difficult. We’d recommend taking an Uber to save time.
  4. All the cross streets in Back Bay (Boston’s downtown neighborhood) follow the alphabet from A-G, which makes finding things easy.
  5. If you don’t want to pay big bucks for Boston parking, park outside of the city at the end of the T line. We’d recommend Alewife and Ashmont on the Red Line.
  6. The most luxurious Newbury Street shops are closest to the Boston Garden, with more boutiques and chain stores as you head towards Mass Ave. 
  7. We love our sports (maybe because we’re the best), so when there’s a game… prepare for a packed city, both on the streets and on the T. Watch out for Fenway and North Station!
  8. You can actually kayak down the Charles River to get the best Boston skyline views.

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