There are lots of places to stay in Annapolis. You can spend a bunch of money and stay at the hotels close to the harbor (Marriot), or a bit further (Loews or Westin up West Street) go further away for cheaper rates. If you are not going to have a rental car and wish to walk around town and the show, then you can find a room or a hotel nearby, but book ahead of time. If you have a car, then you can travel out of the harbor area and find hotels and motels for less money. Back in the late 70's and early 80's when one didn't have as much as a selection, you could always find something at Glen Burnie and then drive every day to the show, but now there are tons more hotels/motels, etc. and selection is better, but don't wait until the last minute. Google the topic and you will find lots to look at. For restaurants I would consider Mikes on the South River and Solomon's Island Road (hwy 2) for eating steamed crabs on paper by the dozens. Or Cantler's (smaller place liked by many). O'Brien's Seafood has to be one of the best seafood restaurants around on Eastport side (across Spa Creek). Same area is the Freight house (used to be a Trumpy plant) which is good for a cocktail if not dinner and a great salad bar. Or try Carol's Creek near the Annapolis Yacht Club (Eastport). The old sailor's bar Marmaduke's is not a Ruth Chris steak house, but Lewne's is considered one of the best places for steak too. A cool hole in the wall sailor's bar is Davis' Pub. These are all on Eastport side. Near the show, good places to eat are McGarvey's (try their crab balls) and Middleton Tavern (a must is their raw oyster shooters). The treaty of Paris down stairs bar is good for an after dinner cocktail. Peanuts is the bartender there - great guy. There are sushi places near the harbor, French Restaurants, Italian Restaurants, up the hill off State Circle is an Irish Pub too. No shortage of places to eat. Also try Sam's in a small little harbor near Bay Ridge Road on the way to some of the larger marinas on that side. For site seeing, there are lots of things to see and the Annapolis Academy is cool. Go to the crypt of John Paul Jones and Prebyl Hall and the Maritime Museum. You can go through the sentry on Gate one (near the show) and tell them you want to walk around. Check out the marina. There are stores abound. Drive across the Bay Bridge on the weekend and look at thousands of boats on the Bay. Have a Yuengling beer for me. Oh, and don't forget to go to the show.