Southern Italy Charter?

[capnmatt]

After chartering in the Virgin Islands and around the Caribbean for the past 15 years I think the time has come to check out the Med. Our final box to tick in the Caribbean is the Windwards and I think that is going to happen next February. Anyway, I am thinking that Southern Italy between Sicily and Tropea would be a nice place to spend a couple weeks, followed by a couple land-based weeks exploring the rest of Italy. Just wondering what challenges we are going to face if we charter in that area?

I think we would plan to charter next summer or maybe the following summer, during the second half of June. I am competent in mostly all aspects of sailing, other than med mooring. I've had to do it only once in St. Martin, but it was in a 15-20 knot crosswind and it didn't go so well (though no damage done other than to my ego). Maybe I could hire a captain for the first day and get some practice... Anyway, what should we expect that time of the year in Southern Italy? Anchorages and mooring buoys or mostly marinas? Will it be tough to find places to drop the hook or tie up? Weather and wind? Do charter companies facilitate one-way charters there such as Polermo to Tropea - for an additional fee of course? I've browsed all of the recent posts here and learned some, now I'm ready to get more specifics about what we are planning. The trip might be a year or two off, but I need to start gathering info and decide if we should try to incorporate a charter or do an exclusively land-based vacation. We could also look into Greece, but I am really interested in Italy for various reasons.

Thanks for any info!

Matt