04/05/2011 03:40 pm ET | Updated Jun 05, 2011

Annapolis Bar Crawl

Annapolis is America's sailing capital. Founded in 1649, this historic haven is the capital of Maryland and home to the United States Naval Academy. From 1783 to 1784, the Colonial town was briefly the Capital of the U.S. During the summer and autumn, midshipmen, locals and tourists congregate at the bustling city dock where people-watching is a popular pastime. Local boaters call it "Ego Alley" after the sailors' perpetual parade of pricey toys. Here are my top three picks:

Downtown Annapolis

Pusser's Caribbean Grille
A trip to Annapolis undoubtedly requires a rum stop at Pusser's Caribbean Grille. During the sailing season, its prime waterfront location induces a constant weekend party atmosphere. At Pusser's sidelines, you'll be part of the Ego Alley action; just don't fall in the drink after a few too many. Their extensive menu includes flavorful traditional Caribbean fare with the freshest seafood available and Chesapeake Bay favorite dishes. This thriving bar and grill got its name from Pusser's Rum, which was first served on board British Royal Navy Ships. A couple of must-order island-style rum drinks are Pusser's Painkiller and the Jamaican Me Crazy. If you're looking for a little refinement, try the Mango Martini, and if you want to go overboard, the Bushwacker will do it.

Armadillo's Bar & Grill
Armadillos has been an Annapolis staple for ages. With a prime Dock Street location, this popular bar is right in the thick of Ego Alley activity. If you're looking for nightlife, drink specials and live music upstairs attract droves of people. Meet your friends, grab a downstairs booth, listen to the DJ and order a couple of beers with a burger. During a summer weekend, entertain yourself outside with a cocktail and watch the never-ending outdoor party scene. Locals and tourists mix and mingle at this hopping bar & restaurant, where blaring music pulsates into the early morning hours. On Friday nights, check out the live band upstairs; the cover charge is $5.00.

Stan and Joe's Saloon
Two Annapolis locals, Stan and Joe, hung their shingle out for business in 2007. For two years straight, the lively bar was voted the best happy hour in town. After a day of sailing head on over to this happening watering hole; a super-friendly staff serves tasty open-flame-grilled burgers and steaks. The seafood is the freshest to be found; start with Jumbo Lump Crab Balls or Mrs. Fletcher's Crab Dip. For more crab, order the house specialty, Jumbo Lump Crab Cakes. There is never a cover for live local music. When it's warm, alfresco drinking and dining can be found on the back patio.

For a guided 2-hour pub crawl, purchase a $20.00 ticket ( which does not include drinks), here.