We managed to find Greta at the car rental fine, get to the car and after some initial starting problems we were on our way. What should have taken 80 minutes to get to Montepulciano from Florence took 120 minutes due to a combination of poor navigation from Matt (even though we had a world class orienteer in the back seat) and some crazy roads. I guess the Florentines just didn't want us to leave! We eventually made to it our accommodation after going through the centre of town along very narrow roads (which I wouldn't recommend) and headed down to the hotel owners delightful restaurant for dinner. AND we made it back in time for extra time of the World Cup final.
The next day we started with a light run, explored Montepulciano for a few hours and then headed to a nearby vineyard for some wine tasting and a tour. We got to taste this dessert wine which takes 13 years to make and costs €60 per 100ml. Delicious and very thick! When we got back to Montepulciano we did some more exploring and wine tasting around town and then headed out for dinner at a crazy Italian/80s restaurant with two old chaps playing very loud music. It was great!
The next morning we had a late start and meandered our way to our next nights accommodation through Siena. In Siena we walked around and chilled out reading our books in this walled off park.