Breakaway on the Bay in Annapolis, Maryland

Annapolis is a Colonial city transported to the 21st century. The heart of the city – from the harbor to the State Capitol – boasts buildings George Washington strolled past. They are now galleries, shops, restaurantsand businesses.

To get the town’s backstory, choose a walk with costumed guides, a trolley tour, a ride in a five-person eco-van oreven a jogging tour. Or download the free AnnapolisNOW app.

Annapolis is the Sailing Capital of the U.S. On a breezy afternoon, there are so many sails on the Bay that it looks like a whiteout on the water. The dock of Annapolis Harbor is nicknamed “Ego Alley” for the constant parade of sailboats, power boats and yachts circling past the promenade. Get in on the action with scenic sail cruises, boat toursor a ride on the water taxi.

Annapolis is home to the United StatesNaval Academy. Guided tours leave from the Armel-Leftwich Visitor Center. You need a photo ID to enter.Plan your visit to see the noon formation when the entire 4,000-member Brigade of Midshipmen assembles in the courtyard of Bancroft Hall before heading in to lunch.

The Chesapeake Bay means seafood and that means crabs. The traditional crab feast involves crabs steamed in beer with a generous coating of Old Bay seasoning, corn on the cob, cole slaw, cold drinks, and many paper towels. The art of cracking the shells and digging out the morsels of delicate meat is best practiced on a long, lazy afternoon with friends. If “picking” crabs is too much work, enjoy crab cakes (broiled, never fried), crab Imperial, cream of crab and Maryland crab soups, crab dip, crab soufflé —you get the idea.

The Visit Annapolis website has a clever, easy, interactive “build your own visit” option as well as several suggested itineraries, links to vacation packages, and other information.

For more travel advice go to www.insightguides.com.