Visit this historic hilltop town in Tuscany during the Bravio delle Botti.
Itinerary
Fly Condor to Florence via Frankfurt
Rent a car from Avis, drive 1.5 hours south to Montepulciano
Stay Dimora dell’Erbe first few nights, Casa del Fauno rest of the week
Visit friends, tour agriturisomos, enjoy Bravio della Botti week
Drive back to Florence and spend 1 night at NH Collection Palazzo Gaddi
Fly home via Frankfurt
Travel
Excitement about Condor Air’s reasonable prices for business class international tickets quicky turned to frustration as gate staff showed no interest or urgency in preparing plane. Pilot and copilot felt the same and were publicly upset with the lax, slow moving employees. This led to leaving 60 minutes late and many passengers including us with extremely tight connections. This got even more frustrating when Condor rebooked us, without asking, on a much later flight, resold our seats, and wouldn’t allow us on board our scheduled flight. So after 5 hours waiting around in Frankfurt we boarded our short flight to Florence. When we arrived in Florence my son’s baggage didn’t arrive so we filled out the form along with many other people at the baggage counter and headed out.

The airport shuttle that runs every 30 minutes showed up just as we arrived at the bus stop making it a quick trip to rental car area about 5 minutes drive away. We were second in line at the Avis counter – there was only one agent, friendly, but in no hurry and a line of about 20 people behind us that likely waited an hour or more. Car rental facility is clean, modern and you get your keys at the counter, find your car and exit the lot and were on our way.
Easy drive using Google maps to Florence with the car’s Airplay. Maps lets you know where the speed cameras are and came in helpful. Tolls were about 7 euros paying with cash or card.
Montepulciano Arrival
Francy, our contact at Dimora dell’Erbe was super communicative on WhatsApp checking to see how flights were, giving us directions, helping with parking lot suggestions and would meet us at the property. We parked outside of town and walked through the charming old town to get to the apartment. Francy met us and checked us in and then we walked down the street to our friends contrada (neighborhood) which was hosting dinner. Andrea had brought a special wine in honor of my son who was traveling with us. It was from the same year as he was born and he was excited to get to taste it and cheers with us.
As we walked home we got our first glimpse of a team practicing running the wine barrel up the steep streets of Montepulciano.

Tuesday I woke up early and walked around town watching the sunrise and enjoying the quiet morning.


Mid morning we met up with our friends and drove out to look at the first agriturismo property. It was interesting and we learned a bit about the restoration process. The afternoon involved shopping for clothes and things that were lost by Condor and then in the evening dinner and sparking wine tasting.

Jetlag continued to wake us up early and my son joined my Wednesday early walkabout. After which our group began what became our daily meet up at Caffè Poliziano for breakfast with several cappuccinos and americanos.




That afternoon we walked down toward the Sanctuary of the Madonna di San Biagio and then across the white road (gravel road) to Montefollonico. This was a great hike across the valley and then up to the town in the heat of the day. We found a great spot for lunch and then called a taxi to return us back to Montepulciano. Hike was about 10 miles.







Late afternoon we toured a small boutique hotel for sale which was quite nice but right on a busy road so not very peaceful.
Thursday was time for O to drive the itinerary so he had us up early and after breakfast and espresso we drove about 30 minutes to a tree to tree and zip line course. We read about an old mercury mind where you ride in mine carts so we drove over to check it out. The tour was only in Italian but we were there for the mine cart ride so signed up. After about an hour of following a guide into the mine and listening to him in Italian describe things in what seemed like excruciating detail, we asked when we get into the train. Oh we don’t do that anymore as they always were derailing.




Back in Montepulciano area we met our friend for drinks at the farm Podere Il Casale, a really cool farm and restaurant with a panoramic setting and incredible views. The owners are friends of our friend so we spoke with the owner about their property.
Friday we visited more agriturismos in different areas. That evening we met up with friends at another contrada for Florentine steak which is only served rare and charged by the kilo and cooked over an open flame. A great way to spend the evening with new friends and their families.






Saturday, after breakfast and espresso at Caffè Poliziano, we went down to the park at the entrance of town for a workout on the mini soccer turf field in the 80 degree heat. In the afternoon we stopped by De’ Ricci Cantine Storiche for a wine tasting and to wander around their cellar dating back to the Etruscan period.



That night was a special night were friends and family that had moved away came back to town for the celebration and to reconnect – a reunion of sorts. It was a great evening.

Sunday is the culmination of the week with the wine barrel race. The morning starts with selection of the starting positions. Then each neighborhood sends a delegation dressed up walking up to the top of the town from the Municipal building to the Cathedral waving flags and drumming.
The barrels, which weigh is about 80 kg each, are rolled by two athletes for each district, the “spingitori” (pushers) along with an uphill slope and through the roads of the historical center. The finish of the Barrel Race is in front of the Cathedral, in Piazza Grande.
The history of the Bravìo dates back to the end of the XIV century, specifically to 1373, when the Municipal Statute determined the Palio (prize) rules. The Bravio delle Botti seems to have been established in honor of San Giovanni Decollato, patron saint of Montepulciano, celebrated on August 29th.
The Bravìo horse race occurred until the XVII century and was abolished for public order reasons. The recent history of the Bravio starts in 1974 when Father Marcello Del Balio had the idea of transforming the old horse race into a barrel race.
We watched the procession from our apartment windows and on the street and then made our way to the cathedral square at the finish line to watch the race.





While our friends’ neighborhood didn’t win, we enjoyed the crowd and watching the runners coming up and into the square and then falling over in exhaustion – and then the medics reviving them. The night continued with dinner and wine. We didn’t make it out too late that night but sat on the street and chatted with groups as they came by for the disco put on by the winning contrada.
Monday we checked out of the apartment and drove back to Florence. O loved the apple juice and looked up the producer who was just outside town. We made a little detour to visit the factory store and buy a few bottles to bring home. Then we drove back by the agriturismo we liked the best and made a circle around the area and then back to the freeway.


Traffic was slow and the trip took 3+ hours vs. expected 1.5. Dropped the car at the rental office which was simple with someone in the lot so just parked and walked to the taxi stand and got a ride to our hotel in Florence, NH Collection Palazzo Gaddi which was great and nicely located.
O and I had a quick pizza across the street and then walked to the Leonardo da Vinci interactive museum for a quick stop. Nice small museum that’s hands on. Then we walked through the main tourist streets packed with English speaking tourists. It felt like Disneyland and a shock to the system after our week in Montepulciano.


We met up with a friend of a friend who is a boutique hotel consultant and turned out to be a really nice and interesting guy. He is an athlete that participates in the calcio storico which is a mix of mixed martial arts, rugby and football.

After drinks and discussing hospitality in Italy, we walked to Buca Mario, which was full but when your friend knows the owners, a table magically appeared, and we enjoyed a massive Florentine steak and some incredible wine.




The next morning we were up early for our flight back home. Florence airport was easy to navigate and we were at the gate within minutes and enjoyed a smooth ride home.



