1st Time in Italy - Advice Appreciated!
 

Three kids and 23 years of marriage and we're finally planning our first trip to Italy - just the two of us! Sept. 23 to Oct. 10. We have only 2 weeks and want to see as much of Milan (I have family there), Venice, Florence and Rome as possible. I have planned the following itinerary but can use tons of advice. Sorry in advance for the long e-mail.
Here we go:
Friday, Sept. 23 - Depart from Toronto.
Saturday, Sept. 24 - Arrive in Milan. I have family in Milan so accommodations and sightseeing is taken care of the first few days. I have to spend about 2-3 days in Milan. I figure starting our trip arriving in Milan (rather than Rome) is a good idea since we can take advantage of family and take an easy pace the first few days in Italy recovering from jet lag.
Sunday, Sept. 25 - Milan
Monday, Sept.26 – Milan
Tuesday, Sept.27 – depart Milan by train to Venice. Any recommendations for accommodations in Venice? (3 star is fine - we are more interested in location than luxury). Is it worth (or even possible) getting off the train in Verona to tour around and then board a train to Venice later the same day?
Wednesday, Sept. 28 – Venice
Thursday, Sept. 29 – Venice for part of day, then take train to Florence. Any accommodation recommendations in Florence (again, location over luxury).
Friday, Sept. 30 – Florence
Saturday, Oct. 1 – Florence
Sunday, Oct. 2 – Florence for part of day then depart for Siena. I know we will want to tour the San Gimignano and Chianti area for a day. Are we best to rent a car in Florence and do the tour by car on the way to Siena OR do we take the train to Siena and rent a car from Siena to do day trips? My itinerary suggests the latter. Any accommodation recommendations in Siena?
Monday, Oct. 3 – Siena
Tuesday, Oct. 4 – rent car in Siena and tour Colle Val d’Elsa, San Gimignano and Chianti area. Return to Siena for the night.
Wednesday, Oct. 5 – Tour Montalcino, Pienza, Montepulciano area and end in Orvieto for the night (return rental car in Orvieto), OR would we be best to drive from Orvieto to Rome the same day? I like the idea of staying and dropping off the car in Orvieto to shorten the day and avoid driving into Rome which I've heard can be difficult. My itinerary suggests this option. Any accommodation recommendations in Orvieto?
Thursday, Oct. 6 – Part of day in Orvieto, then take train to Rome. Any accommodation recommendations in Rome?
Friday, Oct.7 – Rome
Saturday, Oct. 8 – Rome
Sunday, Oct .9 –Rome
Monday, Oct. 10 – depart Rome back home. Boo hoo.

Is this too ambitiuous? Should we drop or shorten time in areas, or add on new destinations? I wish we can add on more days!
Any advice is much appreciate.
Grazie!

"Is it worth (or even possible) getting off the train in Verona to tour around and then board a train to Venice later the same day?"
Yes, it can be done. The is a secure luggage storage room at the train station where you can leave your bags.

Your night count looks pretty good to me, a nice balance:
Milan - 3
Venice - 2
Florence - 3
Siena - 3
Orvieto - 1
Rome - 4

I think that your itinerary looks wonderful. I would definitely return the car in Orvieto and then train to Rome. The rental car place (I think it was Hertz) is right by the train station and there is a funicular right there that takes you to the upper town (where you will want to stay - sorry, don't have a specific recommendation since I stayed in the lower town last time due to a last-minute trip - it was very nice, but the upper town is a better place to stay). Accomodations are pretty reasonable in Orvieto, but you should book Rome ASAP. The last time I was there I stayed at the Daphne Inn Rome and liked it very much. Very clean modern room, great bathroom, great breakfast, they provide a cell phone, and the staff was wonderful. I would go back.

A one day car rental can be expensive. You might find a 3 day to be very little more. I think with 5 people you might need a minivan (cars are small and luggage space tight).

I think the plan to tour Montalcino, Pienza and Montepulciano in one day is a bit ambitious, especially when you remember that small Italian towns close up tightly through the middle of the day.

Colle Val d'Elsa is a sweet little town with not much going on, and perhaps not the best choice for your first trip to Italy. This is one of those towns where you won't even find people on the street through the middle of the day.

Could you possibly rethink your base and stay somewhere in Tuscany where you can easily visit Siena, San Gimignano, Pienza and Montalcino and Montepulciano? Siena is very nice, but it might be possible to place yourself more central to your planned day trips. But, of course, Siena will do.

What is your hotel budget? It's very hard to make recommendations without a price range.

if you want to stay in Siena you will find car parking a pain (they never designed the city for cars). SO either stay outside the city in a local town or put up with having to walk a fair way to the car.

Florence, if you want to cut the price a bit on staying in Florence try to be south of the river and you will see a bit more of the locals area rather than just tourist town.

Driving in Rome is not a problem, its just that romans will know how to park better than you will. I'd dump the car before Rome