Things To Do

Fenway Park

Catch a baseball game at the oldest active ballpark in MLB. Make sure you get a fenway frank and for the love of god do not wear a yankees shirt :)

Faneuil Hall Marketplace

Combination of nice and touristy shops, restaurants and street performers. Boston's promenade if you will.

North End

Boston's Little Italy. Dare I say the best italian food you will ever eat. All the restaurants/pastry shops are top notch. But the following are some of my favorites: Trattoria di Monico, Mike's Pastry's, Modern Pastry's and Bovas

Boston Common and Boston Public Garden

Beautiful parks, photo ops with the "make way for ducklings" sculptures and swan boat rides

Boylston Street

Lots of high end shops and restaurants and location of the Boston Marathon finish line!

Boston Public Library - Central Library

I know I know who wants to visit a library but this one is incredibly beautiful!!

Newbury Street, Commonwealth Avenue, Malborough Street

Quintessential Boston... beautiful brownstones, high end shops and amazing restaurants

Copley Square

If you want to stay in Boston I recommend staying in this area as it is very central to all the must sees

Charles River Esplanade

Walking/biking path along the Charles River

South Boston Waterfront

Really cool rooftop bars and good restaurants

Boston Duck Tours Prudential Center Departure Location

Infamous sightseeing tour in Boston, you'll see them everywhere!! Cruise around Boston and Boston Harbor in these WWII style amphibious vehicles with a sprinkle of history.

Museum of Fine Arts, Boston

Museum of Science

Isabella Stewart Gardner Museum

Legal Sea Foods - Long Wharf

Get some authentic New England Clam Chowdah

Luke's Lobster Downtown Crossing

My go to place for a lobstah roll!

Salem

If you are staying on the Northshore, I HIGHLY recommend going to Salem, MA in October. Salem is known for being one of the oldest colonial settlements in Massachusetts and it is where the Salem Witch Trials took place. So it gets CRAZY during October/Halloween. You will find everything from haunted houses, ghost tours, witch museums, hocus pocus tours (see some of the buildings/areas from the film), psychics and the arguably the best people watching you will ever encounter.

Farm and/or Apple Orchards

Be basic and check out one of the local farms and/or apple orchards for apple picking or corn mazes. Some of my favorites in the area are Russell Orchards, Marini Farm, Cider Hill Farm, and Applecrest Farm Orchard (this one is new hampshire but not far).