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Annapolis as a Vacation Destination


Annapolis, known as the "Sailing Capital of America", is nothing short of a water-lover's paradise. The city lies at the mouth of the Severn River, which provides easy access to the Chesapeake Bay, the nation's largest estuary. As a result, the city offers a wealth of opportunities to explore and enjoy this dynamic maritime environment:
  • Schooner trips: Hop aboard the 72-foot schooner Woodwind for a relaxing two-hour sail or enjoy a Sunday champagne sail aboard the schooner Liberté.
  • Sailing school: Learn how to sail "the Annapolis way" at the Annapolis Sailing School. Kids can attend the KidShip Sailing School, while women may prefer Womanship, Inc., a women's sailing school whose motto is "Nobody Yells!"
  • Sport fishing: Charter a trip on the 55-foot Bounty Hunter or the 46-foot Julie Anne and see what you can reel in.
  • Sunset cruises: Cruise past the Thomas Point Lighthouse, St. Michaels, and more on the 36-foot Gulfstar trawler or explore the West and Rhodes Rivers on the 65-foot, double-decker Richard Lee.
  • Pirate cruises: Sit back and relax as your child learns about life as a pirate. Or join the Watermark's Pirate Crew aboard the Annapolis Harbor Queen for a pirate tour of the Bay.
  • Kayaking: Get closer to the natural beauty of Annapolis harbor with a 3-hour kayaking tour, ideal for families or solo travelers.
  • Overnight sails: Rent the sailing ketch Pintita and spend the night on the water with a group of friends.
Annapolis Sunrise
Not surprisingly, most of Annapolis' popular annual festivals are also centered on the city's nautical heritage, as well as its traditional seafood-based economy:
  • USNA Graduation Week with the Blue Angels Fly Over
  • Maritime Museum Boat Trips to Thomas Point Light House
  • Regatta Schedule
  • Maritime Heritage Festival
  • Lights on the Bay holiday display
  • Spring Boat Show
  • Waterfront Arts Festival
  • U.S. Sailboat Show and Powerboat Show
  • Annapolis Rotary Club Crab Feast
Other festivals also highlight the city's rich history and international population:
  • Maryland Renaissance Festival
  • Scottish Highland Games
  • Kunta Kinte Heritage Festival
  • Maryland Legislature meets in Annapolis from January until April each year
  • Three Century Tours: Guided tours through out Annapolis streets, and gardens
Annapolis from the air Despite the large role played by Annapolis' proximity to the Bay, the city is just as appealing to landlubbers - particularly landlubbers with a deep appreciation for the nation's early history. Annapolis was founded in 1649 and incorporated in 1708, rapidly becoming one of the most important harbors on the East Coast. Its economy was heavily reliant on water trades like sail making and oyster packing, but eventually segued to tourism once Baltimore Harbor surpassed Annapolis' City Dock in economic importance. Today, the city's collection of more than sixty 18th century buildings, including the homes of four Maryland signers of the Declaration of Independence, is the country's largest. In fact, the entire downtown is a registered National Historic Landmark! The Banneker-Douglass Museum and a selection of Kunta Kinte statues are also located in Annapolis, to both acknowledge and commemorate the significant contributions of African-Americans to the city. St. John's College, the third oldest school in the U.S., is also located here and dates back to 1789. Another notable heritage site, and perhaps the city's most famous, is the United States Naval Academy, established in 1845. Over the years, the school has grown from 10 modest acres to a more than 338-acre campus. To take in Annapolis' impressive history, consider one of the city's many tours. You can go by foot, trolley, horse carriage, or boat.

Another major attraction is shopping, thanks to Annapolis' multitude of retail establishments ranging from boutiques and antique shops to art galleries and major department stores. The Annapolis Harbor Center alone offers 50 stores, while the nearby Westfield Annapolis Mall boasts more than 175 stores, along with 6 restaurants and a movie theater. And a number of the city's downtown streets - from Main Street to West Street - are lined with shops and galleries.

The theater is another draw, as the city is home to an impressive selection of live arts groups offering professional performances all year round. These include:
  • Annapolis Chorale
  • Annapolis Opera, Inc.
  • Annapolis Summer Garden Theatre, Inc.
  • Annapolis Symphony Orchestra
  • Ballet Theatre of Maryland
  • Bay Theatre Company
  • Chesapeake Center for the Creative Arts
  • Colonial Players of Annapolis
  • Maryland Hall for the Creative Arts
Whether you're a salty dog or simply in need of a quiet get-away, Annapolis is an ideal destination. And at just 26 miles south of Baltimore and 29 miles east of Washington, D.C., the city is easy to get to, for a day trip or for a weekend stay at one of the city's charming boutique inns or B&Bs. So come to Annapolis and enjoy not only miles of waterfront living, shopping, and dining, but also one of our nation's oldest cities. You'll be amazed at all there is to discover.