Annapolis has always been a drinking town with a sailing problem! Since merchant ships first sailed into her protected harbor in 1649, Annapolis has been a city where crawling in and out of taverns has been the rule, not the exception!  Travelers and locals alike come to Annapolis to quench their thirst and fulfill their desires in our many notorious pubs, inns and taverns. From American patriots like George Washington, Ben Franklin, and Thomas Jefferson to pirate rogues such as Captain Kidd and Blackbeard; anyone searching for food, drink or illicit diversions found their way into the city's many infamous taverns...and you can too!  Join us on one of our guided 2-hour Pub Crawls or Craft-Brewed Beer Tour...if you think you can handle it! Drink in the history, Crawl out the door!

Tour operate year 'round and in all weather. So, come along and spend an evening with old friends or come along and make some new ones! See and hear about the side of Annapolis that very few know about, while throwing back a few tasty cocktails on a Pub Crawl of Annapolis!

Pubs & Paddles Crawls

Combining the fun of land and water! Annapolis' first and only Kayak Paddling and guided Pub Crawl, all-in-one! Learn more ›

Haunted Pub Crawl

Wanna go out drinking with a long dead barmaid and a ghost whose beer has a head, even though he doesn't? A crawl so spooky, "it'll scare ya sober!" Learn more ›

Twisted History Crawl

The Twisted History Pub Crawl is a 2-hour walking tour (approx. 1/2 mile) into some of the most historic and famous taverns in Annapolis. Learn more ›

Seasonal Crawls

Enjoy a two-hour pub crawl and naughty caroling trip through the streets and pubs of Annapolis led by our own resident beer geek and Bad Santa! Learn more ›