Re: Best Beginners sailing grounds?
From a beginner: I started in 2010 with ASA 101, 103 & 104 lessons in Santa Barbara within an 8-day period. Slept on the boat; sailed during the day. Terrific experience! During the 2011 season we time-shared a sailboat out of Belmont Harbor in Chicago. Another great experience - but everything said above about the perils of Lake Michigan is true. We learned a lot! Last January we rented a cottage for a week in the Florida Keys that came with a 23' Com-Pac. We sailed most every day on the bay side. Great time! This past June we spent two weeks in the San Juan Islands; first week was with an instructor so my spouse could complete ASA 101, 103 & 104; second week it was just the two of us hopping from harbor to anchorage. Fantastic!
What I am saying is that it is hard to go wrong - every experience we have had has been challenging and immensely satisfying. Plus, I think we have gained by sailing in different waters.
But if I were to pick one of these spots, it would be the San Juans. The land masses of the Islands buffer the winds and wave heights of the Pacific, so it is rare to have to manage anything over 15 knots (though I do remember being out on the deck reefing the main in 24+ knots). The scenery is spectacular. You can alternate between harbors one night (with showers) and anchorages/moorings the next. As a beginner, you'll learn currents and tides in ways you won't on Lake Michigan; every day is a different docking or mooring/anchoring experience, and that's good experience.