Help with Itinary

With 3 weeks, you can do SO MUCH more and not feel rushed at all. First off, 7 days in Rome seems a little long. Don't get me wrong, you can easily fill 7 days, but Italy has so much more to see. Second, 7 days in Florence is definitely too long. If you were planning on using it as a home base to the rest of Tuscany, I would consider Sienna instead (much more charming), or maybe an agriturismo with a car. Third, why 3 days in Padua? It is 30 minutes away from Venice which you plan on staying 4 days in. Why not combine the two stops and extend your stay in Venice with side trips to Padua?

With 3 weeks, my trip would look like:

Rome 5 nights.

Sorrento 4 nights (side trips to Naples, Capri, Amalfi, Pompeii)

Sienna 4 nights (side trips to Florence, Lucca and San Gimignano)

Either Cinque Terre or Milan 4 nights (Or skip this section and add nights to other spots.)

Venice 4 nights (side trips to Padua and Verona)

I really like Jared's plan and agree that those are all places that you'd probably enjoy! I really like the idea of using Siena as a base for side trips to Florence, etc. I vote for Cinque Terre rather than Milan.

Some of this itinerary will depend on where you fly into and home from. If you haven't already purchased your tickets, fly into Rome and home from either Milan or Venice.

Also, since you're traveling in June, I'd get your itinerary settled so you can make hotel reservations--it's a busy time in Italy!

Your schedule looks good, giving you a good amount of time to explore Rome. A week in Rome is fine, giving you time to explore the whole city. You can even take day trips to Ostia Antica, Tivoli, and even Pompeii (to really make a long day trip of it) if you choose. A week in Florence seems a little lengthy; don't get me wrong, it's fine since you'll be doing day trips in between. However, if you like hiking, you can use some of this time to head to a place like Cinque Terre (or even Milan or one of the Lakes if you're more interested in either of those). Also, why 3 days in Padova? I definitely enjoy Padova, but 3 days may be a little lengthy. Since Venice is right there close by, why not head over? I might suggest something like this:

-7 days in Rome
-1 travel day to Cinque Terre (it would be a lengthier trip, but you can stop and visit Orvieto on the way if you wish)
-3 days in Cinque Terre
-1 travel day to Florence (on your travel day from CT to Florence, Pisa and Lucca are on the way;; you can store your luggage, if packing heavy, and have plenty of time to explore both towns to make a full day of this travel day... a half day in each town)
-4 days in Florence (includes a full day's day trip to Siena, and possibly another day trip to San Gimignano and Volterra, depending if you've gotten to see everything you want in Florence)
-1 travel day to Venice
-4 days in Venice (use one or two days to side trip and visit Verona and Padova)

So... that gives you your 3 weeks (21 days). I'm not sure if you have extra days for flying in and flying out on the end of that 3 week period, but if not, it can be worked in. Again, this is just a suggestion. Depending on what you want to see and do and how you want to travel you could visit and stay in a town in Umbria or go down south the Amalfi coast for a few days or (again) head up to Milan and the Lake District or even the Dolomites. It's all up in the air, but this itinerary is one way you can do it.

Or if you like extended stays with minimal travel, just do 7 days in Rome, 7 days in Florence, and 7 days in Venice, and you can take day trips from each place if you want to explore further..

One thing you will notice on itinerary questions is that you will get two types of advice. In one camp will be the people who will advise you to pick a limited number of places and stay there for a longer period of time. Sort of like what you have planned above. Others, like myself, prefer to take in as much as possible and we like to move around. With the exception of a few places I don't spend more than 2 or 3 nights in a place.

With three weeks you can see most of Italy. 7 days in Rome is too much. I think 4 or 5 days is perfect, you can see all the major sights in 4 days. Likewise, I think 7 days in Florence is too much. Plus some of the places you mentioned (Siena, San Gimignano) are worth at least a night on their own. Siena and San Gimignano are gorgeous at night. I also think 4 days in Venice is too much as well.

With three weeks here is a list of the places I would want to see in no particular order. Lake Como, Venice, Cinque Terre, Florence, Siena, San Gimignano, Lucca, Assisi, Rome, Sorrento, and Palermo. I probably wouldn't be able to see all those places but I could get to most. This list also doesn't include day trips from places like Sorrento to Capri, Amalfi, Pompeii, Naples, Paestum, etc...

My 2 cents is see the country, don't limit yourself to a few places, especially if this is your first time to Italy. Who knows when you will be back so you may as well see as much of it as you can.

I heard that the train from Naples to Sorrento is dangerous for pick pockets? Is it safe to ride the train to Pompeii?

Just be aware of your bag and surroundings and you wont have a problem.

Thank you for your comments.