We have a wedding to attend in Siena on July 6th and would like to develop the trip around this. We are thinking of flying into Rome, then to Florence, Siena for the wedding, somewhere else in between and then departing from Milan. We would depart the States on June 30th and depart Milan on July 14th. Money isn't an object. Train travel or car rental for transportation and hotel and restaurant recommendations greatly appreciated.

If you're flying into Rome, I would stay there 4 nights, then to Siena (I think you can do this by bus, search here for Rome to Siena) for 2 nights, bus to Florence and 3 nights there, train to Venice for 4 nights. Do a few searches here for hotels in each city and you'll get more information than you know what to do with. But I'd get going, that's not very far away and is high season. A lot of places will already be completely booked.

I agree with SusanP: Rome, Siena, Florence, Venice, Milan. You need to make decisions quickly and book some hotels. If Venice doesn't pan out, consider one of the lakes or additional time in Tuscany.

If money is not an issue, and they still have rooms, Albergo del Senato is a must in Rome. A room with a view of the Pantheon (as in you can almost reach out and touch it), gracious staff, elegant room, delicious breakfast, wonderful views from the rooftop bar. We're going back in August!
As a suggestion for an itinerary, what about picking up a rental car on the way out of Rome, spending a night in Orvieto then drive through Umbria and Tuscany to reach Siena exploring more of the area between wedding activities. Then drive to Florence of the Chianti Road, S222. Get rid of the car on the way into Florence, then continue the rest of trip via train if you don't want to get another rental car since you can't drive it into Venice. We thought the drive across from Venice to Milan pretty ho-hum.

I thnk 4 nights in Venice might be a little too long.
I would add an extra night each in Rome and Florence.

I agree with nanabee, Rome and Florence have too much to offer to stay that long in Venice. Check out web: www.limoinitaly.com for more help
SH

I would skip the heat an crowds of Venice at this time of year. Why not keep your original plan of going to Rome and Florence first, then to the wedding in Siena. From there you could consider going to the Riviera di Levante, staying in Santa Margherita Ligure or Camogli, and going on to Stresa on Lake Maggiore or Orta on Lake Orta - from either of these it's easy to get to Milan Malpensa Airport. This could be done by picking up a car as you leave Florence, or train. If you search for Santa Margherita Ligure, you'll find lots of hotel suggestions.

With a car, I've stayed at Hotel Villa Scacciapensieri on the outskirts of Siena, and Hotel Cenobio dei Dogi in Camogli. Both were nice and had easy parking on the hotel grounds:

http://www.cenobio.com/

http://www.villascacciapensieri.it/

If money trully is no object, you might consider staying at Hotel Splendido in Portofino:

http://www.hotelsplendido.com/

Adding time in Rome (never a bad idea) won't work here because they're arriving on July 1 and the wedding in Siena is on July 6. That's why I suggested the number of days that I did. (They also don't have time for Rome plus a drive through Umbria & Tuscany before Siena.) And 4 nights in Venice is certainly not too long! I admit, however, that I overlooked the fact that they are leaving from Milan, so I suppose it would be better to spend 3 nights in Venice and the last night in Milan for their flight the next day.

Thank you for the great responses. I'm researching all of them. Are there any restaurant suggestions? Good food and wine always enhances the experience and anyone's favorites / recommendations are appreciated.

ttt