Planning a Trip

The hardest part about planning a trip to Tuscany & Umbria is deciding what not to see or do. The two regions are only about the size of New Jersey and Delaware, respectively, but together they contain more than a handful of the most significant monuments on Earth and more can't-miss attractions and experiences than we could ever fit in this guide. The number one regret I hear from returning tourists is that they just didn't have time to see everything.

With such a variety on offer, Tuscany demands that you know what your interests are and plan accordingly. This is especially true when it comes to timing your trip. If you love the idea of seeing the Palio, driving through fields of sunflowers and lounging by a pool in the vineyards, then obviously summer is the right choice for you. But that would be a bad time to visit for those who, say, prefer to spend time admiring Renaissance masterpieces and strolling through romantic alleyways. They would walk away with a much more fulfilling experience in February, rather than battling the crowds and the heat in July. Food buffs and wine connoisseurs should aim for the fall, when the grapes are on the vine, the truffle season is underway, and the harvest is in full swing. Most importantly, by scanning the list of festivals that follows, the choice might be made for you, and you won't have that horrible sensation of flying home one day before the start of an event you've always wanted to see.

Fortunately, a trip to Italy in this day and age does not require the advance planning it once did. By all means, if you intend to come in high season, book your hotel and rental car well ahead of time, and particularly your tickets to major attractions. (I mentioned the Palio, for example. The best seats sell out more than a year in advance.) From flights to hotels and train tickets, you'll always save money by booking ahead. But things like currency, communications, and transportation are truly a breeze compared to what they were even 10 years ago. There's very little to plan out in advance.

That said, you can never plan too much for your health. While Italian pharmacies are generally similar to American ones and the hospitals are even excellent in many cases, it's always a good idea to have a good supply of prescription drugs, and make sure all of your insurance ducks are in a row.