Itinerary Suggestions, Please. Trip finally booked!

After 2 years in the making, I have finally booked our trip to Tuscany for the first 2 weeks of August. I know it will be hot, so please do offer suggestions for proper attire as well!

I have our locations planned for our trip and hoping you can offer suggestion as what to do in each area. I need advice on taxi services in some areas when we do not have a car, as well as train tickets. Can i purchase train tickets in advance? And for longer travel between cities, are there fast train options? I'm also interested in the Firenze card so we can skip lines while in Florence. Can the Firenze card be purchased in advance online?

Here is our itinerary for our 15 day trip:

Day 1:Saturday: Fly into Milan at noon. Take train to Monterosso in CT. Stay in Monterosso 3 nights.
Day 4:Tuesday: Train to Florence. Stay in DT Florence near Duomo 3 nights. Day trip by train to Pisa/Lucca.
Day 7:Friday: Rent car at Florence Airport. Drive to Radda Chianti. Stay 1 night.
Day 8:Saturday: Drive to Buonconvento. Stay 5 nights. Do day trips with rental car.
Day 13:Thursday: Drive to Florence to drop rental car. Train to Venice. Stay 1 night in Venice.
Day 14:Friday: Train to Milan. Stay in Milan 1 night.
Day 15: Depart from Milan for trip home.

We are interested in visiting the museums and historic sites, very interested in wine and food. Like staying off the beaten path. Even though I am certainly a tourist, I like to stay away from "touristy" areas and restaurants when possible/recommended. We want to see and experience a lot, but also want time to relax and enjoy our time. Hot air ballooning and horse back riding seems like nice things to do, if possible. But any suggestions are welcome, especially for our day trips while based in Buonconvento.

Grazie!
 
Additional Itinerary Suggestions? And Train Tickets.

Thank you, Donna Denise!

I appreciate your recommendations for wine tastings. We will make certain to stop in those places!

While traveling in different cities/towns, we are interested in visiting the museums and historic sites and very interested in local food as well. We prefer to stay off the beaten path (vs. touristy areas and restaurants) when possible/recommended. Might you have any suggestions given our itinerary? Although we want to maximize our sightseeing, we don't want to try to cram in too much. We would like to relax as well. Knowing that we will use Buonconvento as our base for 5 nights, have you suggestions for day trips (in addition to the wine tastings and visiting Murlo)?

Can you tell me for our train tickets (both long trips and short), can we purchase tickets in advance?
And for longer travel between cities, are there fast train options?

I'm also interested in the Firenze card so we can skip lines while in Florence. Can the Firenze card be purchased in advance online?

Grazie!
Ian
 
Top