This quaint harbor town is often called "America's Sailing Capital," but you won't need a brochure to tell you that. On sunny days, sailboats and pleasure craft of every description cruise the Severn River, their occupants celebrating the good ole summertime. In fact, so many fancy watercraft tie up at the Annapolis City Dock that locals affectionately call it Ego Alley.
Don't worry though. You don't need your own boat to join in the fun. The city offers plenty of diversions, from sailing to shopping. That's what makes it such a great place for an end-of-summer getaway.
Historic Inns of Annapolis ($175-$350), a trio of storied houses, gets our stamp of approval for a weekend. Completely redecorated in 2006, these three inns pair the elegance of yesteryear with today's modern amenities.
Note: Annapolis is a popular weekend destination. If you don't plan ahead, you may not get a room at one of the prime downtown or West Street properties. A number of chain hotels line nearby Riva Road, located just a few miles west of downtown. Try Courtyard Annapolis or Doubletree Annapolis.
If this is your first trip to Annapolis, start with a tour of the city. Many companies schedule guided excursions. Capital City Colonials counts a fabulous food-and-history tour among its offerings.
One of our favorites is the sunset tour aboard the schooner Woodwind, which leaves from the Annapolis Marriott Waterfront Hotel across from City Dock at 6:30 p.m. Watermark also offers dozens of excursions, from a 40-minute narrated cruise of Annapolis to a Day on the Bay trip to St. Michaels. Adventuresome souls can learn to chart their own course at Annapolis Sailing School, the country's oldest, or Womanship, which has programs for women and individual couples.
You'll see young midshipmen around town in their dress whites, but the U. S. Naval Academy is also a must-see for visitors. Tour the grounds, see a sample room, and visit the chapel where legendary John Paul Jones's crypt lies. Enter on foot at Gate 1, and show your government-issued ID. During the school year, time your visit to coincide with noon formation, which begins at 12:05 p.m. in front of Bancroft Hall.