Best of Italy?

From my first trip to Italy I particularly enjoyed Venice, Verona, and Siena. The list is likely to become much larger in a few weeks on my second trip :-)

Rome. Then Venice, Milano, Ravenna, Ferrara, Florence, Siena, Bologna, Cortona, Todi, Gubbio, Assisi, Spello, Montalcino, Frascati, Naples, Paestum, Rieti, Orvieto, L'Aquila, Matera, Siracusa, Taormina, Palermo, Agrigento, Cefalu. About 50 more.

Cortona. Sorrento. Montepulciano. And, of course, Rome and Florence.

I lived in southern Italy for four years, so I was able to visit everything from Rome on down. Next month I am hitting Rome, Florence, Pisa and Venice, seeing the main tourist sites with everyone else, and ending with a week in Paris. My final destinations for Italy in a year or two will be Cinque Terre, Lake Como region and Milan and that will be enough of Italy for me for a while. What is it that you want to see in Italy? Once you've decided on that, then this site can help answer questions you may have on your itinerary/arrival/departure/hotels/transportation and such.

How long is your trip? One week? Four weeks?

Go to the website of some famous tour company. For example the ones linked at the bottom below. Look where they go in their various tours.

I'm not saying you should join one of their tours. I, for example, don't like to be herded like a sheep in escorted tours. However their websites or brochures will give you an idea of the top destinations in the country. Then, if you want, you can organize your own independent tour to those same destinations.

https://www.ricksteves.com/tours/italy
http://www.globusjourneys.com/Vacation-Packages/Tour-Europe/Italy-Vacations/
https://www.insightvacations.com/us/destinations/italy
http://www.perillotours.com/italy/tours-of-italy/index.html

Siena is my favorite. Followed by a bunch of V's - Venice, Volterra, Varenna, Vernazza. Rome, Montepulciano, Montalicino, Bolsena, Vetrella,

We enjoyed the 3 large cities we visited equally- Venice, Florence and Rome.
Of the small towns we visited I think I'd say Montepulciano and Assisi were our favorites.

I haven't been everywhere in Italy but of those cities I have visited my favorites are: Venice, Florence, Sienna, Cortona, Assisi, Volterra, Sorrento, Stresa - in that order. I'm one of the weirdos that wasn't enthralled with Rome so it didn't even make the list.

Rome, Vatican , Florence, Pisa, Venice and Cinque Terre. My personal favourite out of these cities are Rome, Cinque Terre and Venice. All three are amazing and unique, and are definitely worth a visit. Of course you should visit a more quiet and relaxing part of Italy like the Tusacan countryside. You can consider the Amalfi coast as well, I hear its amazing!

When you visit Rome, I would recommend you visit the Catacombs of San Callisto and the Hadrian’s Villa, on top of the typical tourist must dos like the colosseum! Also, if you are looking for a more unusual experience, you may be interested in a street art tour by Mekomy. It was pretty cool to see a different side of this grand city!

Ditto Roberto. Assuming that you've never been, go to Rick's "Best of Italy in 7, 14 and 21 days" tours. They are all based around Venice, Florence and Rome which are all world class sights. Then buy Rick's "Pocket" books for the three cities (everything you need to know, and a lot more, for a first timer is inside for planning purposes and carrying with you as your guide to the sights. His books save you enormous amounts of time and money - I cannot emphasize this enough!!! You have "masterpiece" maps with brief explanations of the significance of what you are seeing, you will never need to stand in long lines, sleep and eat and stroll at night with the locals, on and on. If you choose V-F-R get a Eurorail Pass, pack light, wear moneybelt - all you need are in the books. If you "wing it", which is what it sounds like you might do, you will be very frustrated in Italy. Good Luck.

You don't need any type of railpass in Italy, tickets are inexpensive. For fast trains, if you can plan ahead, you can save a lot by buying super-economy or even economy tickets. These fares go on sale 120 days ahead but allow no or few changes. I got a 9€ ticket from Milano to Venice, but I can't change day or time without buying a new, full fare ticket. Check Trenitalia for schedule.

I am another one who didn't particularly care for Rome. My Italy travels have not been extensive but my picks would be:
Venice for the atmosphere
Florence for the art
Vernazza for the beauty (but that was before the floods)
Lake Como for the beauty
Sorrento for the beauty

For a first trip, I'd stick with the Big Three: Rome, Florence Venice. More time needed for Rome and Florence than Venice. I've been at least a half dozen........maybe nine times, and I've branched out now, but those are the places to visit on a first trip, assuming you've got ten days on the ground, not counting departure day since flights to the U.S. generally leave in the morning.

First two trips flew into Milan because we had family weddings in the North. Never liked Milan -- seems like a big Wall Street. Then I started flying into Rome and saw the Old Sites! Love the Vatican/St. Peters and of course all the famous Roman sites! Florence, Renaissance Art, and like Rome, beautifuil Piazzas and fountains, food, gelato! Venice, Romance! I've now fallen in love with Sicily! Who would have thought it, when family in the North look down their noses on anywhere South!!

With adequate time (at least 10 days on the ground) you can fly into Venice, train to Florence, then train to Rome. Depart for the U.S. from Rome. Next trip, you might want to do some of the other cities mentioned, but with 4 days in Florence you can do a day trip to Siena.

One thing I want to mention: You've been advised to look at tours and see where they go. You cannot cover the ground a tour compay covers in the same time they do. They have a waiting bus, very well scheduled stops, pre-purchased sites tickets., etc that you can't really do on your own. I don't do tours because I don't like someone else telling me where to eat lunch/dinner and at what time I need to get up and get on the road! LOL.

Hands down, Rome; after that, Ravello. In Sicily, Taormina, Siracusa and Palermo.

Yes first time, the Rome, Florence, Venice route is unbeatable. All in a nice straight line connected by hourly high-speed trains. They are all very different from one another, and if you have time, nice day trips by train or bus an hour away. Rome-Orvieto, Florence-Siena, Venice-Padua. Fly into one and out the other.

Agree with Chloe about Sicilian faves! But that's for a second trip to Italy, not a first.