Re: Im buying a big boat! But i have never sailed
I hadn't sailed before either so took some dinghy lessons then bought a 34 foot Hunter. My problem was the boat was in Puerto Rico and I lived in Barbados. Couldn't find a crew so I took precautions (EPIRB, auto-pilot, good GPS and charts etc.) and single-handed her back to Barbados. Of course, the Caribbean isn't as busy as the English Channel or the ICW (for you US folk) but I never went below deck at night and cat-napped up top in full gear. I also kept a VERY close eye on the weather so I could run for one of the islands in case of trouble. One year later, I reversed the process as I got a job in the Bahamas - again, single-handed. She is still there and I'm going back for 3 weeks sailing starting tomorrow (yippee!) (currently in Saudi). Common sense, good precautions and a safety first attitude will take you a long way but no trip is ever the same twice. Italy should be do-able with the right planning and precautions and you only live once. Go for it and enjoy!