Thanks for all the input folks, your words are very inspiring. I have owned one or another Cat 36 since 1986 and I know the boat like the back of my hand. I have repaired or replaced every system over 20 years and can singlehand it as easily as my Miata. It is the absolute perfect boat for me ( as long as it's a pre 1992 before they destroyed the great nav station in place of an "aft cabin"....yuch!) I figured that knowing the boat so well would inspire more confidence when attempting new sailing grounds. My retirement idea is to find and buy a second 36 (this one would be shoal draft) in the northeast in the Spring, spend the summer upgrading her rigging and installing needed equipment and then head south down the ICW with the snowbirds. Looking at a few years of sailing the islands and then who knows. Would probably keep my current 36 in LA. Might have to rename them Tweedledie and Tweedledum. My first question was "will the boat handle it?" and you've answered that for me, thanks. I thought it might work as my prior owner took my boat to Acapulco & back. Yeah, I know I could find a better boat for the trip, but true love is a funny thing.