If you want to stay in the USA, try Maine, Chesapeake Bay or the San Juan Islands. Maine is beautiful, but with a short sailing season. The three hazards in Maine are lobster traps, rocks and fog. Most all of the charter boats have chart plotters on them to help with the navigation, some with RADAR. It is prudent to build in a couple lay days in case the fog is really thick and you don't feel safe to move around. You can buy live lobsters at most marinas for cheap!
The Chesapeake Bay offers a wide variety of sailing venues and I would recommend making St. Michaels a must stop. The weather here can be a bit dicey with T-Storms. Just remember that if your boat gets hit by lightening, and you are still alive, don't move - you've got a good spot! <img src="http://www.traveltalkonline.com/forums/images/graemlins/Yikes.gif" alt="" />
The San Juan Islands are also cool cruising grounds. The area gets fog, too. Also, you need to mind the currents in some spots. Other than that, navigation is pretty straight forward and the islands are close together.
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