Graduation Gift Trip to Italy

Be sure to hit the Galileo Museum in Florence.

Personally, I would want more nights in Venice otherwise, the itinerary looks good. Can you drop a night in Orvieto and add one to Venice?

Sounds great! Do you have tickets yet? I ask because most flights out of Venice are very early AM.
My suggestions are - taking one night from Moneglia and adding it to Venice.
While in Florence, day trip to Siena by bus. It takes you into the town and you don't have to worry about parking.

A great way to see Siena and San Gimignano from Florence is with a company called WALKABOUT FLORENCE. We did 2 of their tours - THE BEST OF TUSCANY and THE CHIANTI WINE & FOOD SAFARI. Both were top notch. You can see photos and read reviews on TripAdvisor, but go the the walkaboutflorence.com website to book - don't book thru TripAdvisor which uses Viator, a 3rd party booking company - support the company directly. We spent 3 weeks in Italy and those 2 tours were the highlight of our trip. We never needed a car. You'll also wish you did at minimum of 3 nights in Venice, which still isn't enough as it only gives you 2 full days. Italy is our favorite European country - you will have a great time.

There are a couple of items in your itinerary that strike me as inefficient. First, Pisa and Lucca are very close to one another and are much closer to Florence (about 1 hour) than to Moneglia (about 2 hours). My suggestion would be to visit them together in one day trip from Florence, although you could also stop to visit them enroute from Moneglia to Florence. Second, Chiusi is a huge detour to pick up a rental car for a stay in Colle di Val d'Esla. It would make more sense to pick up the rental car in Florence and then visit Chiusi (if that was your intent) enroute from Colle di Val d'Elsa to Orvieto.

Thanks for all the great ideas everyone! Venice was cut to 2 nights because after I checked the cruise ships in port schedule the other days in Venice would have been 4 ships in port. The 2 days we are in Venice there is only 1 cruise ship in port. We are flying out of Venice in the afternoon so we plan to get up early in the am our final day and do a last look around before the cruise ships unload. I wish we could add another 3 weeks to the trip but as Rick says..."Assume you will return!" Venice will be back on the list for sure since we have never been to Rome. We will be back to Italy! LOL. We chose Moneglia to get away from the tourist crowds as best we can in the evening. We were hoping for a more authentic experience in small non tourist town. The car rental was nearly $400 cheaper in Chiusi than in Florence so that is why we are going to take the time to get there from Florence. I am also hoping it will be easier driving out of Chiusi than Florence. Not sure when we will visit Pisa and Lucca or Siena/San Gimignano yet. Probably from Florence however the Palio is in Siena in early July. Not really interested in visiting during that event. We may it Siena later in the trip. Any other ideas for Science or Engineering or Geology stops in this itinerary? We were looking at Saturnia for the hot pools.

For engineering check out the Duomo in Florence. Watch PBS “The Great Cathedral Mystery” for context regarding the engineering mystery. You can climb the dome and see the herringbone pattern used. It’s really quite fascinating how this dome was built with limited technology by someone who had no engineering training. Modern engineers and brick layers recreated the dome in Florence to test their theories.

Hard to believe there's a $400 difference in car rental rates. Are you trying to rent an automatic instead of a manual? If you haven't already, check rates with Auto Europe. Colle di Val d'Elsa is a relatively short drive from Florence, whereas it's a longer drive from Chiusi plus a 2 hour train ride to Chiusi. You'll spend half a day of your trip just collecting the rental car in Chiusi. If you decide to go that route, you might want to make a full day of it and visit Montepulcinao and Pienza on the way back to Colle di Val d'Elsa.