Things to see and do
By Land:
Historic Pub Crawl of Annapolis:
For our guests in search of more Annapolis history offered in a relaxed and unconventional setting, we highly recommend the Historic Pub Crawl of Annapolis.
For more than three centuries, travelers and locals alike have been quenching their thirst in Annapolis' many historic pubs and taverns. From our founding fathers to pirate rogues, anyone in need of food, drink or entertainment found their way into our many historic bars...and you can too!
Enjoy a guided two-hour pub crawl around the darkened streets of Annapolis and some of our most infamous and historic drinking establishments. Relax with a cocktail while learning some of our most interesting and colorful history as told through the tales of our historic taverns.
Drink in the history, crawl out the door! Schooner Woodwind:
Annapolis By Bike:
Love to pedal? Love nature? Then check out Annapolis By Bike, where renowned environmental writer, and local history expert Steve Carr offers visitors to Annapolis an unique environmental and historical experience as they pedal around the 300-year-old national landmark on a bicycle, checking out a wide assortment of environmental projects and learning about one of America’s most historic colonial-era cities located along the shores of the majestic Chesapeake Bay.
Capital City Colonials:
For our guests who got a taste of Annapolis' history on our Historic Pub Crawl, but still want more, we recommend Capital City Colonials. Thier colonial-clad characters are poised to guide you through history. While on your feet or in a seat, Capital City Colonials can entertain you on your visit to Annapolis. Whether you are traveling solo, in a pod of family or friends, or a gaggling group, they have choices that promise to wag your tail.
Discover Annapolis Tours:
For those guests that are mobility challenged, but would still like to see Annapolis by day, Discover Annapolis Tours offers a climate controlled trolly tour that presents a great overview (and vistas) of Annapolis and the United States Naval Academy. Tours depart across from 36 Market Space and 26 West Street in Annapolis • Phone 410-626-6000.
By Sea:
As featured in the hit movie Wedding Crashers! Climb aboard their two beautiful, wooden 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland. Annapolis is "America's Sailing Capital" in the heart of the Chesapeake Bay. Help raise the sails, steer the boat, or simply sit back and relax as "Woodwind" sails from the historic waterfront, past the Naval Academy and cruises into the Chesapeake Bay. Departs from Marriott Waterfront Hotel • Phone 410-263-7837
Pirate Adventures on the Chesapeake:
The best daytime on the water attraction for children and families in Annapolis. An unforgettable experience aboard the pirate ship, Sea Gypsy in the Annapolis Harbor. 311 Third Street, Annapolis, MD 21403 • Phone 410-263-0002
Liberte, the Schooner:
Sail aboard a magnificent 74' schooner for your next event or celebration. 49 guests, full beverage bar. Located next to Chart House restaurant • Phone 410-263-8234
General Info on Visiting Annapolis:
Annapolis Visitor's Bureau
