How to plan a trip to Italy

Photo in Fornillo by Nicki Positano — instagram.com/nickipositano

For years people have asked me for some help around planning their trips to Italy. So many people in fact I figured I’d just write up a piece on it for anyone’s benefit.

I don’t professionally organize trips to Italy, I just know how to do it from first-hand experience. I first went to Italy in 1989 and lived in Rome for a year. Subsequently I went back to Italy for a number of reasons at least 100 times in the past 30 years. I once owned a company based in Firenze (Florence) and went there every other month for years. I’ve been to hundreds of Italy’s cities, towns, and villages and have done so across a number of price points both for personal and business travel.

This post is simply some of the advice I’ve given to people over the years who were looking for some help. Perhaps it could be helpful to you or someone you know looking for some insight when the time comes to plan a trip to Italy.

This article is organized as follows:

1. Advice for the first time traveler to Italy.
2. Train travel.
3. When to go.
4. Advice for the returning visitor to Italy.
5. Regional and city advice.
6. An idea for the luxury traveler.
7. An idea for the adventurous traveler