Raise a glass to Annapolis’ past on a two-hour guided pub crawl that links colonial rum, whiskey distilling, and Prohibition-era stories to the city’s most iconic watering holes. Expect brief walks, historic stops by the State House and Ego Alley, and recommended drinks at each venue.
More ways to explore the area's outdoor wonders
The cobblestones of downtown Annapolis click underfoot as the harbor breeze pushes a hint of salt through narrow streets. On this two-hour pub crawl you move between low-lit bars and corner taverns where brick walls still hold the outlines of colonial conversations. Guides stop the group by the State House and Ego Alley, pausing to point out how a sailor’s rum ration and a legislator’s whiskey shaped the town’s public life.
Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for all fitness levels; requires short periods of standing and brief, flat walking between venues
Wildlife
History
Annapolis rose as a colonial port and state capital; its rum trade and later distilling fueled local economy and political life, while Prohibition-era smuggling left enduring stories.
Conservation
Support local businesses and historic preservation; avoid littering, use public recycling where available, and practice responsible drinking to minimize impact.
Reserve your spot on the Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Carry a valid photo ID
Proof of age is required at all stops—keep your ID accessible to speed entry and avoid delays.
Stay hydrated between drinks
Bring or buy water between tastings to pace alcohol intake and keep focus during historical talks.
Wear comfortable walking shoes
Cobblestones and wet sidewalks are common—closed-toe shoes with good traction make the route easier.
Plan your ride home
Book a taxi or note public transit options before the tour ends; downtown can get busy after evening crawls.
Valid photo ID
Required for alcohol service and venue entry.
Comfortable walking shoes
Protects you on uneven cobblestones and in crowded bars.
Reusable water bottle
Staying hydrated makes the tour safer and more enjoyable.
Light rain jacket
Spring showers are common—pack a compact rain layer for outdoor stops.
spring