I'm in the leave the laptop behind camp. If you're in Italy (and fill in the blank on other countries) on vacation, you're there to enjoy yourself & the country, sights, sounds, food, etc, not feed your email addiction. The world will not fall apart if you don't check in; the emails will be waiting for you when you return.
A few years ago I was doing a river cruise from Moscow to St. Pete. Short of trying to find an i-cafe in those 2 cities (and taking time away from vacation), I literally was not going to have email access for the majority of the trip (none on boat, stop at small towns). I angsted about it at first, but then my UK client said, it's a vacation. Why on earth would you check email?
I made sure all the client stuff was taken care of before I went, and for 2 weeks enjoyed a carefree, email-free time. It was actually quite liberating, and I put that feeling of freedom (ie, not being tied to a computer) almost as high in terms of experience as seeing the sights in Russia!
Since then my game plan is I'll work up until the jetway, and then I'm offline & not available until my return.
I do whatever research I need re: museums, places to eat/drink, things to attend before I go over. Bring a guidebook if I think I need it. Ask the hotel concierge if I have any questions.
OVMV, but it's been great for holidays being email-free. Cheers.