We love to vacation in Italy and we’ve been lucky enough to return there many times. There are so many places to see in Italy, that deciding where to go is always a challenge. We always want to explore destinations that we haven’t seen. But at the same time, we long to return to our old favorites.

The truth is that there’s never enough time. So if you’re planning a trip to Italy, you should make up your mind that you won’t be able to see everything you want to see in one trip.

Traveling to Italy is easy from most major cities in the United States. Since we’re going to Northern Italy, we’re flying Air France nonstop to Paris and then connecting from there. If you’re not going to Rome or if there isn’t nonstop service to Rome from your home city, consider flying to whichever European city you can fly nonstop to.

It’s only 2-1/2 hours from London to Rome. And depending on when you travel, it may be less expensive to do a roundtrip to some other European city and then buy point-to-point fares to your destinations in Italy.

However you get there, avoid backtracking if you can. Fly into Rome and out of Venice or Milan instead of returning to Rome. Italy train travel is pretty good, but it can be expensive and time-consuming.

Over the years, we’ve learned that the less traveling we do, the happier we are. So we always stay a minimum of two nights in each destination – but more often, three or four. We pick a city that’s central to lots of places we want to go and then use it as a base.

We book all our hotels in advance because the really desirable, affordable ones always fill up fast. For Italy, we like to use booking.com and venere.com. Both these sites have detailed descriptions and photos, and lots of user reviews. Before we make reservations, we usually check tripadvisor just to make sure there are no unpleasant aspects that we don’t know about.

Rome Italy
Trevi Fountain

Driving in Italy is pretty manageable in the country, but don’t even attempt it in the cities. We try to keep our destinations just a few hours apart because we want to stop here or there for a leisurely lunch and do some sightseeing along the way.

We’ve used Avis the last several trips and always had positive experiences with them. Like the guy who wears suspenders and a belt, we take a GPS and also screen grabs of maps. The European maps on our Garmin GPS are pretty accurate. The viamichelin web site is a great place to generate point-to-point maps. It will even tell you the cost of the various routes. There are lots of toll roads in Italy.

On this trip, we’re flying into Genoa and staying in Sestri Levante and Vernazza to do the Cinque Terre. We’re doing this part of the trip by train, and then picking up a car in Viareggio for our time in Tuscany.

We’re using Lucca as a base for the cities in Northern Tuscany, and Siena as a base for the towns in Southern Tuscany. In this way, we’ll have nearly a dozen towns that we want to explore that are less than 90 minutes from where we’re staying.

We don’t want to have the car in Florence, so we’re dropping the car in Siena the night before and taking the train the next morning. Be aware that many car rental offices – particularly outside big cities – close for several hours for lunch.

We made reservations and bought tickets online for the Tower of Pisa and the Uffizi Gallery so we won’t have to waste any time waiting in line. Other than that, we have a list of attractions and appealing restaurants in the towns we plan to visit. But we always allow plenty of time for spontaneity.

The first time I went to Rome, I didn’t see the Sistine Chapel because I decided to have a second glass of wine at lunch and just enjoy the piazza. Years later, when I finally went to the Sistine Chapel, I knew I’d made the right decision. It was, in fact, still there.

With so many places to go in Italy, it’s best to restrict yourself to a single manageable area. If you’ve already been to Rome, consider doing Naples and the Amalfi Coast. If you don’t want to drive, you can see Capri, Ischia, Positano, Amalfi, and Sorrento by ferry – which is absolutely delightful.

If you’re all about art and churches, try a week in Umbria and a week in Tuscany. Or visit Milan and the Italian Lakes. Just be sure not to bite off more than you can chew. Nothing is worse than being on vacation and feeling like you have to stick to a demanding schedule.

We’ll have plenty to talk about when we return from our trip in a few weeks.

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