A week in Tuscany
- pat kelly
- May 30
- 8 min read
How to get here? You can fly into Florence or Pisa. Florence would be a great way to start a Tuscan vacation but we flew into Venice. Since we were traveling with friends who had never been to Italy, we made sure to see both Venice and Rome which was pretty easy to accomplish. Venice was a great start.
Where to stay in Tuscany? Figure out which towns you want to focus on and decide if you are getting a rental car. Tuscany is one of the few parts of Italy where I would want a car to allow efficiently visiting hill towns and it feels nothing like driving in Rome or the Amalfi coast. We mapped out which towns we wanted to see in Tuscany first then tried to find an Airbnb that was convenient but also could host our group of two families. We found a nice place with a pool in an area called Bucine, near 4 places on our list: Florence, Siena, Cortona and Arezzo.
Typical Tuscan towns to put on your list include: Florence, Siena, Anghiari, Arezzo, Cortona, Montepulciano, Pienza, Montalcino, Volterra, San Gimignano, Livorno and Pisa. After doing some research we picked a few to do day trips in our rental car, always planning on returning to our home base for down time in the evening. We had already visited Pisa previously and were not as interested in returning given some of the other options. Similarly we decided to only spend a day in Florence due to the train mishap and I'd previously seen it on a prior visit. When we realized Il Palio was a possible destination, we moved a number of things around to make it happen. This famous horse race in Siena is an event. We eventually narrowed our list (San Gimignano was deemed too touristy!) of small hill towns to Cortona, Montepulciano, Montalcino, and Volterra.
Our Airbnb was an old stone farmhouse like you see all over Tuscany. It was great -olive trees in the back yard and a view of rolling hills all around. The pool should have been great but the flies that populated this land on this week were like something I've never seen before. Any exposed flesh brought a swarm.
We had a plan to hit one town per day and number one on our list was just down the road: Cortona. Some will know this as the town featured in Under a Tuscan Sun. When visiting hill towns in Italy you are accustomed to sweeping views but Cortona stands out. It is a steep climb to drive into town. Once you get up there, the Val di Chiana spreads out in front of you.
The town of Cortona is small but makes a great day trip. We grabbed a quick lunch at Il Cacio Brillo Da Bucci, one of the restaurants on the main square, Piazza della Repubblica, which was pretty empty around noon. It was a great lunch. After you drive up a steep hill to get to this point, from there it was a straight walk up to get to the church that was to be the destination of our Cortona adventure.
It was a steep climb but it wasn't too hot yet and we seemed to be the only people in the town on this day which is an unusual feeling in Tuscany in July.
Some kind of Italian good karma made the kids take the climb as a challenge and no complaints followed us up through charming streets to Basilica di Santa Margherita- the patron saint of Cortona.
The church interior was impressive and peaceful with no one else about. The scenery was even better on the way back downhill. We picked up some groceries in town and headed back to the house to relax and have a glass of wine and a dip, if the tuscan horseflies would allow.
Next day trip on the Tuscany tour was Volterra. Like Cortona, this city has Etruscan roots. It is famous for its city gates. Porta all'Arco dates to the 4th century B.C. and features the weather worn 3 lion heads.
We wandered through the quiet town and had lunch just off the main square, Piazza dei Priori, at Ristorante Etruria. It was great. We skipped the first century Roman theater but I regret this after looking at pictures as it has a very scenic backdrop as usual with Greek and Roman theaters.
We stopped inside Palazzo dei Priori, 1208. The stone exterior dominates the Piazza dei Priori and is embellished with numerous coat of arms, making this piazza very atmospheric. Many would recommend the Volterra Duomo, Etruscan Acropolis or the Medici fortress but we opted for more casual strolling. With young kids, best to not over schedule but we did go to Museo Guarnacci which featured many Etruscan funeary urns. It is worth a visit. We really enjoyed Volterra.
On our next day trip we targeted famous wine towns on a very scenic drive: the Val d'Orcia. We started in Montepulciano. This hilltop town is known for its renaissance architecture and underground wine cellars. We hit Piazza Grande and wandered up the main street dotted with boutiques and local craft shops. In the Piazza, stop by the Well of the Griffins and Lions which was built in 1520. You can see that the lions hold the famous Medici coat of arms which indicates Florence's control over Montepulciano at the time.
For this day trip, we were joined by another family who were along for the remainder of the vacation. Given the kids were young, historical sites, churches and museums sometimes have to be trimmed from your itinerary.
We had lunch at a great spot and sampled some of the local wine: vino nobile di Montepulciano. Afterwards, we wandered down the main corso and grabbed some gelato. This kids do tolerate well.
For once, we were targeting two towns in one day so we hopped in the rental car and headed into Val d'Orcia. It is about a 40 minute drive from Montepulciano to Montalcino with the town of Pienza halfway between. This drive will feature green hills, fields of sunflowers, Cypress trees and hilltop villages. The rolling countryside is what makes this drive famous.
I would have stopped in Pienza if we had a different group (noone was demanding to taste it's famous pecorino cheese), but with all the kids we drove on to Montalcino.
The scenic drive was reason enough to spend a day in this part of Tuscany. Fortunately, both towns we visited were fun and Montalcino amounted to a pretty quick stop. We had to try the local wine, Brunello from Montalcino is felt to be Italy's finest by many experts.
We walked along the walls of the Fortress of Montalcino, built in 1361. It offers great views of the Val d'Orcia and served as the last stronghold for the Republic of Siena. After this, it was back to the farmhouse and another great day in Tuscany was in the books. We brought back wine from these two towns to enjoy.
The next day was our only day in Florence. We should have allowed at least 2 days but a missed train in Venice changed our plans. We started with the obligatory visit to the Duomo.
As an art lover my one day in Florence had to include the Uffizi Museum and the David. Not wanting to overpack the day, we chose not to wait in line for the interior of the Duomo. When viewed from a distance, it dominates the city, dwarfing the buildings around it. We enjoyed strolling around it and the kids had a gelato.
Unfortunately, a skilled local thief watched me place my wallet inside my shoulder bag but not zip the pocket. While I was gazing up at the Duomo, I suffered the standard European vacation debacle and got my pocket picked. I wanted to skip the Accademia but my wife insisted I see the David- the Carabinieri could wait. She was right.
The sculpture is sublime and should be
seen in its original as well as the replica in the piazza. There are a number of other unfinished sculptures by Michelangelo and otherwise it is a quick visit.
After the David, we were off to the Piazza della Signoria where the replica of David sits along with many other great sculptures. It is a great spot to just sit and people watch, surrounded by great art. Amazingly, tucked away behind it sits a small office of the Carabinieri where a funny, chain smoking cop gave me report detailing my shame. It was actually a funny encounter.
The Uffizi, although home to some incredible paintings by Botticelli (Primavera and The Birth of Venus are both fantastic), Leonardo and Caravaggio; my family didn't love it. Not modern enough for my wife and the kids lost focus after a few rooms of old religious paintings. After the Uffizi, it was back in the rental car and home.
The next day was off to Siena for Il Palio. This famous horse race is twice a year (July 2 and August 16) and is a true event in Siena. The ten horses are ridden bareback around the perimeter of the huge main square, Piazza del Campo- which is definitely not an oval. It is unique in that it is shaped like a shell. There is clay thrown down on the cobblestones to accomodate the race. Each horse represents one neighborhood or contrada.
The winner gets a silk banner, the Palio.
We started by touring the town and checking into Hotel Athena. This was a lovely hotel which we needed as adding a day to our Tuscany week (after our airBnB reservation) allowed Il Palio. Siena needs more than a day so fortunately we were able to visit for a few hours earlier in the week, before this last hurrah. After checking out Piazza del Campo we bought a scarf representing a different contrade for each kid.
We climbed the Torre del Mangia for sweeping views of Palazzo Pubblico. We wandered our way over to the Duomo di Siena which is known for its zebra striped marble exterior.
As we were strolled through the narrow streets of Siena earlier in the week, it was much quieter and charming. On race day, things were a little louder. The day includes a historical parade known as Corteo Storico.
We even saw one of the horses being led through the streets before the race. We packed into the central part of the piazza around which all the action happens. People were packed in like sardines and my wife was pretty nervous about the little kids getting trampled but everything worked out. The race is quick and chaotic. Multiple riders were thrown. It is a little hard to get a view, but what a scene!
People spilling out of every building on the Piazza to get a look and it is all over in a minute. One of the recent Bond films opened with James popping into the race which seems about right.
At the end of the race I was amazed to see the true emotion on the faces of the Sienese. This race really means something. People were crying. Others eating with their neighbors celebrating or bemoaning their horse's fate.
The next day we spend the day wandering aimlessly in Siena, which would be a great way to spend 2 or 3 days. We had a great lunch of pizza and house red wine- basically a safe order anyway in the country. We took it easy on this day as next day we had to catch a train for our last stop: Rome.
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