With its cobbled streets, historic brownstones and clusters of cute cafes, Greenwich Village is as charming and alluring as urban quarters come. Let the neighborhood beguile you (over drinks) as you explore the Village's past via its most storied establishments—the local pubs.

Meet your guide in Washington Square Park and hit the pavement with a stroll down winding streets as you seek out a watering hole to wet your whistle. Cozy up to the bar for a welcome shot, and sip on drink specials as your hilarious guide regales you with entertaining anecdotes and little-known facts.

En route to your next saloon, spot Village landmarks like the townhouse of Aaron Burr—third Vice President of the United States, who is probably more famous for dueling Alexander Hamilton—and the apartment from the hit TV show Friends. Pull up a barstool at the next tavern, and get in on the historical fun as your guide leads you in laugh-out-loud reenactments of major NYC events, complete with costumes and props.

At your fourth and final destination, test your Big Apple aptitude during a trivia quiz over a cocktail or a pint, and then turn the tables on your guide, testing his or her knowledge with an entertaining round of history improv. Before your tour concludes, be sure to pick up pointers on the best places to continue your evening exploration of New York's finest and friendliest drinking establishments.