Whether it's your first time to Boston or not, a trip to the North End is always a good call. Take a stroll on the freedom trail past Paul Revere's house and the Old North Church. If you are in the area for lunch stop by Galleria Umberto's for a quick slice of Sicilian Pizza and an Arancini (cash only). If you're feeling seafood, then head to Neptune's for oysters and a lobster roll, but get there early as a line forms fast.

While the argument for best cannoli in Boston is a hotly debated topic, usually divided into Mike's vs Modern, neither are Beth and Matt's pick. Instead head to Bova's bakery which has the added benefit of accepting credit card or if you want to sit down and enjoy an espresso or a cocktail, then stop by Cafe Paradiso which has one of the most underrated cannoli in the city.

No trip to Boston would be complete without stopping by the famed ballpark. While the on field product might be bad, it's still worth checking out the area. If the Sox aren't in town then head over to Bleacher Bar to have a drink while also looking into the stadium.

If you're looking for a place to eat dinner near the stadium, head over to Hojoko for a funky, Japanese inspired cocktail bar and restaurant.

Part of famed landscape architect, Frederick Law Olmstead's emerald necklace, you might recall the Boston Public Garden from the park bench scene in Good Will Hunting. Take a ride on the swan boats if the weather permits, and take photos at the Make Way for Ducklings statues.

Across the park is the Newbury Hotel whose top floor restaurant, Contessa, offers stunning views of both the park and the Back Bay neighborhood. Reservations can be tricky to come by but if you go during the hours between food service, you can easily grab a drink at the gorgeous bar.

Located in Somerville's Union Square, not too far from where both of Matt's parents grew up, this two level outdoor market is home to a brewery, a James Beard nominated wine bar, two cocktail bars and a number of food stalls and shops.