I chose Sorrento for my first ever singles holiday. I felt 6 days was just right - long enough to get the feel for it but not too long if I was unhappy. I was newly widowed and so nervous. My sister took me to the airport and asked how I was feeling and I replied "Don't ask". I spent most of that day dashing to the loo. But it was wonderful. Our group quickly gelled and our tour manager was excellent. He was there for us whenever we needed him but not obtrusive for those who were confident enough to get on and do their own thing. We were only in Italy for 4 whole days but were blessed with wonderful weather and the excursions were excellent. If you're wondering if you're brave enough to go I'd say to you Just Do It - you won't regret it.