Mag for Miles

E-Newsletter Subscription


Mag for Miles Absecon-Lighthouse



Travel Resources

U.S. Destinations International Destinations
US States International Countries
US Cities International Cities
US Touring Areas International Touring Areas
Top 30 Destinations by Personality Type
Venturers Journeyers
Pioneers Sightseers
Voyagers Traditionals

Annapolis, Maryland

Great Destination:

Value for Money:

Total Stars:

Personality Types that Like it Best

Did You Know … ?

  • The Maryland State House has been in legislative use since 1779, the longest in the U.S.
  • The Susquehanna River pours 19 million gallons of water a minute into Chesapeake Bay.
  • Kunta Kinte, the African ancestor described in Alex Haley’s book, “Roots,” entered America at Annapolis.
  • Chesapeake Bay produces 250,000 tons of seafood a year.
  • The treaty ending the Revolutionary War was ratified in Annapolis (1783) when the city was the U.S. capital.

America’s sailing capital

Annapolis may be small (not even 40,000 residents in the city), but it is big with people who love sailing in all its forms and with those who particularly appreciate American history.

It’s all about location, and the location is Chesapeake Bay on America’s mid-Atlantic coast. Chesapeake is the continent’s largest estuary at 4,500 square miles. Bespeaking the great location, the U.S. Naval Academy was founded at Annapolis in 1845. The bay still serves the academy’s purpose, but nowadays, there also is a lot of sailing on the bay with no more serious intent than the boaters’ pleasure.

Visitors can sail in the bay freestyle or compete in seasonal races several evenings each week. Boaters also flock to Annapolis to watch or compete in high-profile sailing competitions such as the Annapolis Race Week, set for Labor Day weekend (don’t be fooled by the name).

No surprise then, Annapolis is home to appropriate museums — the Annapolis Maritime Museum plus the National Sailing Center and Hall of Fame. Visitors are attracted to the huge boat shows each October, and about 1.5 million visit the Naval Academy annually.

As for American history: The city’s location is tops, but its timing was good, too. European settlers arrived in the mid 17th century, and Annapolis was Maryland’s capital by 1695. Its State House accommodated the U.S. Continental Congress for 10 months in the 1780s.

Today, the city claims it has more 18th century brick buildings than any other American site. About 45 blocks of the city’s historic center now comprise the Colonial Annapolis Historic District, an area suitable for touring on foot or by trolley.

It’s natural for visitors to gravitate to the Annapolis City Dock for relaxation, to enjoy some crab cakes at a waterside eatery and maybe to catch a free summer concert.

Aside from a mind-blowing list of sailing events, Annapolis hosts food fests (crabs and oysters as the stars), a blues festival and a number of street fairs, both the ethnic kind and the generic kind.

Things to do for Venturers

  • Compete in one of the city’s Wednesday Night Sailing Races. The events depart from the Annapolis Yacht Club each week from April through early September. Or, if you are up for it, compete in one of the city’s high-profile sailing races.
  • For an off-the-wall excuse to make a November visit, come for the annual Slaughter Across the Water, in which 450 people participate at one end or the other in a tug of war across the Annapolis Harbor. The event involves a 1,700-foot rope and is the world’s longest tug of war over water.
  • Or, for more to explain at home, participate in the Annual Polar Bear Plunge, an icy January dip in the Chesapeake (for charity).
  • The city offers unusual modes of transport. Try the electric-powered eCruisers (riders must flag these for free rides to attractions); water taxis; a 10-passenger Duffy electric boat, offered for rent with or without a captain, or the Green Pedals electric rental bikes.
  • In May, attend the Chesapeake Bay Blues Festival, or come a little later (June) for the Eastport A Rockin’ festival, designed to showcase local popular music.
  • Work for your dinner — go crabbing. Matapeake County Park and Sandy Point State Park are possible sites near the city. A crabbing license may be required.

Things to do for Centrics

  • Annapolis is called America’s sailing capital, so take sailing lessons. Or, simply charter a boat with a captain and go fishing.
  • Bike, run or walk the 13-mile Baltimore and Annapolis Trail, in Annapolis.
  • Seek out the Kunta Kinte-Alex Haley memorial at Annapolis’ City Dock. It commemorates the arrival of Alex Haley’s African ancestor, Kunta Kinte, who was made famous in Haley’s book, “Roots.” Then, head to the Banneker-Douglass Museum, which focuses on African-American history. Time this right (September) and you can attend the Kunta Kinte Heritage Festival, too.
  • Come to town for a seafood festival. There are several. And eat crab cakes whenever you visit.
  • For laughs (and charity), compete in the .05K Extreme Sports Event, meaning a run or walk — with your dog, if you want — across the city’s Eastport Bridge. It has been called “the least challenging athletic event ever conceived” by Runner’s World Magazine.
  • Be intrigued (pun intended) by the secrets revealed at the National Cryptologic Museum in western Anne Arundel County.

Things to do for Authentics

  • Tour the historic Maryland State House. The U.S. Continental Congress met in the building for 10 months beginning in November 1783, the only state house to serve as the nation’s capitol.
  • Look for astronaut Alan Shepard’s Mercury spacecraft while on your tour of the U.S. Naval Academy. The pilot of America’s first manned space flight (1961), he was an academy alum. Also, see the crypt where naval hero John Paul Jones is buried.
  • Soak up information of interest at the Annapolis Maritime Museum, then take its tour (available seasonally) of the Thomas Point Shoal Lighthouse, which is located one mile south of the city.
  • Take a walking tour of the city with a focus on its colonial past. Or, take a tour by trolley.
  • See street performers and musicians, who provide free entertainment at Annapolis’ waterfront on summer Sundays. If the timing works, also look for the First Sunday Arts Festival, held the first Sunday of every month, May through October
  • Schedule a visit to the National Sailing Hall of Fame and Museum. Then, have lunch in a dockside eatery and concentrate on boat spotting.


Additional Resources

For more information, consult the Annapolis and Anne Arundel County Conference and Visitors Bureau at