Finally taking my honeymoon, 5 yrs later in Tuscany

All, I lived, studied and worked for only 10 months in Florence and swore I would go back with my then boyfriend, now ten years later husband. Our plans are to fly into Florence, rent a car then head to Cortona for two nights, stopping by Poppi along the way, then possibily staying in Siena proper for 2 nights or outside for extended stay and daily travel (4-5 nights? thinking Montepulciano) trying to visit; Montepulciano, Montalcino, Pienza, San Gimignano, Volterra. Definitely a night or two in Lucca, back to Fiesole for two nights (taking in some of Chianti) then dropping the car off and Firenze for 4 nights, fly home next morning out of Florence. I'm an artist and my husband and I are both wine lovers so a lot of these places were chosen with that in mind, but I'm starting to feel a nearly 5-6 place stay is too much for only these few days we have, a total of 14 nights. Any other intinerary ideas to help me organize this trip better would be greatly appreciated.