Boston Standard

Plan a romantic dinner date at the Green Street Grill. This restaurant has been a fixture in the city since the Great Depression, and is a local favorite that's known for putting a new spin on comfort foods and all-time favorites. After dining on one of the eatery's signature dishes, stick around for drinks; Green Street is proud to feature an award-winning cocktail menu and a variety of craft beers.

The Black Rose is the best place to grab a pint in Boston. Touted as the city's premier Irish pub, the Black Rose offers traditional Irish cuisine and beverages. Enjoy favorites like fish n' chips and corned beef along with a pint of Guinness or the bar's own sangria. This popular nightlife hangout also features live music 7 nights a week.

Live comedy is the ticket at the ImprovBoston Theatre. Stand-up comedians, improvisational shows, and sketch performances are hosted here five nights a week, providing comedic entertainment to thousands of people annually. If you have an interest in being a performer, ImprovBoston hosts classes for those willing to learn.

Follow the red-brick road, otherwise known as Freedom Trail. The trail stretches 2.5 miles and leads the way to 16 historical sites that are significant to American history. Some of the sites and attractions include the Boston Common, the Old State House, the Bunker Hill Monument, the Paul Revere house and the site of the Boston Massacre.