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Tuscany - Montalcino / Chianti

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Hi all!

We're honeymooners planning an October 2012 trip, and need tips on the Tuscany leg of our trip! We're interested in the obvious: visiting wineries, wine tasting, seeing beautiful scenary and stopping by quaint towns/villages. All this at an "adequate" pace (not exactly slow-travel, but nothing rushed either).

This is what we have so far (FYI we will have hired a car):

Day 1:
Rent a car in Rome in the morning (10am) and head to Orvietto.
Spend 1-2 hrs in Orvietto, light lunch there.
Head to Castello de Velona (our hotel), check in at 4/5pm-ish.
At night head to Montalcino (town) at 8pm-ish, stopping by Enotteca La Fortezza first.
Then dinner in Grappolo Blu (9pm).

Day 2:
Leave 10am, first stop Fattoria dei Barbi winery. Tour the winery.
At noon, head to Sant. Antimo to see the Gregorian Chants at 12:45pm.
Head to Poggio Antico for lunch and possibly a tour or more wine tasting (1-4pm est.)
Then head to Castello Banfi for a tour and/or wine tasting (4-6pm est.)
Head to hotel. Dinner at the hotel to relax.

Day 3:
Leave 10am towards Montepulciano
Stop at Bagno Vignoni to see the Etruscan baths (on the way)
Pit stop at San Quirico d'Orcia
Visit Pienza
Visit Montepulciano (it's market day there!)
Back to Hotel, back by 5/6pm
Dinner at restaurant outside of town -- Il Leccio at around 8/9pm

Day 4:
Check out of hotel at 9/10am
Head to Montalcino to spend a few hours (it's market day there)
Then continue to drive to Siena, check in at hotel (Palazzo Ravizza) at around 1pm
Spend the rest of the day walking through and getting to know Siena
Dinner at Locanda Garibaldi (9pm)

Day 5:
Drive to Pisa (head there at 9am, spend a bit of time)
Drive to Lucca (lunch here, spend a few hours)
Drive back to Siena arrive at around 6/7pm
Dinner at Antica Osteria da Divo (9pm)

Day 5:
Check out of hotel, head to Florence
On the way to Florence, stop by San Gimignano and have lunch there
Arrive at Florence 4pm-ish

My questions are obviouus,
1. Is the itinerary too rushed?
2. Are dining times OK by Italian standards?
3. Do I need reservations for many of these places?
4. Am I missing any "must see" spots? Should I swap any restaurants, wineries, towns, sights?

Any input would be highly appreciated.

Thanks!

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