Boston City Guide
Fenway Park

If there is one city in the world that I have spent more time in than New York City, it would definitely be Boston, Massachusetts. I have had so many friends move there over the years that I have become a pro at the NYC to Boston travel route. While I know Cambridge and some of the outer cities aren’t technically part of Boston I’m considering anything on the T line fair game with this city guide. Fall is definitely the best time of year to visit, the winters can be brutal! The first time I visited it was so cold out the parking meters had stopped working! So make sure to bring your preppiest New England clothing, your Patagonia jacket and explore Boston.


Boston is very easy to get around. If you have a car it’s a little more difficult to park but it is doable. Just allow extra time to find parking. Otherwise you can get most anywhere you need to go on the T or bus system. And if you need a late night ride or don’t want to take the train Uber is also widely used in Boston.


• Get some history on the Freedom Trail
• Walk along the Harbor and stop for a Lobster roll
• See the penguins at the Aquarium
• Wander Beacon Hill’s beautiful brownstones
• Relax on the Common
• See the Green Monster in historic Fenway Park at a Red Sox Game
• Visit the MFA and Isabella Stewart Gardner Museums
• Explore Harvard and Cambridge
• Run or rent kayaks on the Charles River (maybe spot a Regatta)
• Sit in the sun on the Esplanade

Boston City Guide
The Charles River


• The Shops at Prudential Center
• Newbury Street – Back Bay
• Fanueil Hall Marketplace
• Harvard Square – Cambridge
• Charles Street – Beacon Hill

Boston City Guide
The Aquarium


Wagamama’sMultiple Locations
Fanueil Hall Marketplace – 1 Faneuil Hall Sq, Boston, MA
• Italian in the North End
Top of the HubInside The Shops at Prudential Center, 800 Boylston St, Boston, MA
• Stella – 1525 Washington St, Boston, MA
South End Buttery – 314 Shawmut Avenue, Boston, MA
Carrie Nation Cocktail Club – 11 Beacon St, Boston, MA
Envoy Hotel Rooftop70 Sleeper St, Boston, MA
Grendel’s Den Restaurant – 89 Winthrop St, Cambridge, MA
J.P. Licks Ice Cream – Multiple Locations
The Friendly Toast – 1 Kendall Square, Cambridge, MA
Diesel Cafe – Davis Square, 257 Elm Street, Somerville, MA
Flour Bakery – 190 Massachusetts Ave, Cambridge, MA
dwelltime – 364 Broadway, Cambridge, MA

Boston City Guide
View from the Top of the Hub