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Every year in the Fall (usually late September or early October), two of the largest boat shows in the United States are held at the City Dock in Annapolis. The city closes the dock (immediately adjacent to the U.S. Naval Academy) to the urusual throng of weekend tourists, and brings in the most expensive, high tech boats on the market today.
There are usually two shows - one for sailboats followed the next week by another for power boats. The price of admission ($17 for adults and $6 for children) buys you the opportunity to tour some of the most luxurious boats on the market, and to even kick the tires on some more affordable watercraft.
Be prepared - the city is jammed with people during the boat show, especially in city center near the dock. If you're driving, look for alternative routes into town (MD 450 going into the back door of the Naval Academy is a favorite). On the weekend, the city provides free shuttle bus transportation from the Naval Academy football stadium.
If you're a boat person, this is nirvana.
Tip: The best place at the show to "people watch" and just kick back to relax is the 2nd floor of the Waterfront Marriott Hotel, at its bar called Pusser's. Admission is free. Drinks are reasonably priced (even though the hotel is quite expensive), and the 2nd floor outdoor deck affords a view over the entire boat show.