For lovers of art, architecture, and beauty, Italy is the place to go. There are so many stunning Italian destinations to visit that it is hard to choose. On our last Italian holiday, we decided to stay in the Tuscan countryside. The Hotel Castillo di Casole provided the most incredible Italian "home" for us. The hotel architecture, amenities, and service are amazing. It was also the perfect location for us to explore Tuscany and its many charming towns. For any art lover, the Medieval and Renaissance art and architecture is astounding. We focused on several small towns including Mensano, Monteriggoni, San Gimignano, and Siena. I was in heaven exploring each one not just for the art and history but for the food as well!
Hotel Castello di Casole
Hotel Castello di Casole is located in Casole d’Elsa just west of Siena. This luxury five-star hotel proved the perfect spot not just because of its proximity to so many of the quaint, beautiful towns but also because it felt like we were living on our own grand Tuscan estate. The hotel has been ranked #2 resort in Europe by Conde Naste Traveler and #1 resort in Europe for families by Travel and Leisure. It is one of my favorites in all of Italy and maybe in all of my travels. For any lover of luxury, you will fall in love with this Tuscan gem.
WOW is the best way to describe Castello di Casole. Driving up the Cypress tree lined road to the main building is exactly what I imagined when thinking of Tuscany. The hotel actually dates back to the 10th century when it was called Querceto Manor. Throughout the centuries, it hosted many of the Sienese aristocracy. In the 20th century, it was owned by Luchino Visconti, a well-known Italian film director. In 2005, Timbers Resorts bought the property and began restoring it. It is magnificent.
The feel of the hotel is right out of a wonderful Italian movie. The hotel features 41 suites. If you’d rather your own larger house, villas surrounded by vineyards can be rented which includes rights to the amenities of the hotel. We stayed in the Suite Magnifica. We had a gorgeous view of both the countryside and the hotel inner courtyard. The room was decorated in very soothing, earthy colors reflecting the blue of the Tuscan sky and the green of the Cypress trees. We loved the room!
The hotel offers so much to do on site! The infinity pool provided us many afternoons of relaxation after sightseeing. The view from the pool of the countryside and vineyards was breathtaking. The Essere Spa located in a stone vaulted section of the hotel provides many services. Need more to do? The hotel offers art classes with a local artist, cooking classes and a fitness center. My daughter had an hour or so long painting lesson and brought home a beautiful original work!
There are three options for dining: The Bar Visconti which provides drinks and lighter meals (We loved the Bar!); Ristorante Tosca with a mix of traditional Tuscan food with a modern twist; and Pazzia which offered the best thin crusted pizzas and salads. We honestly could have never left the hotel. The comfort of the room, the relaxing pool, the delicious restaurants, and the friendly, helpful staff made for an incredible stay. But there is so much to see in this part of Tuscany so we ventured out every morning and spent the later afternoon at the pool!
This medieval hill town located in the Siena province of Tuscany became a UNESCO World Heritage Site in 1990. Walking up the main street feels like you have just stepped back into the 13th century. The medieval architecture and towers are amazing. There are two main piazzas- Piazza Duomo and Piazza della Cisterna. During the middle ages, the town’s important families built about 72 tower houses. These were a symbol of their wealth and power. Today 14 are still standing. It is a must to climb one while visiting.
In Piazza Duomo enter the Palazzo Comunale. It is here that you will find a tower to climb- The Torre Grossa (which means big tower in Italian). This is the only tower in town open to the public. Before climbing you can visit a small museum in the Palazzo Comunale which has beautiful works by Sienese and Florentine artists of the 13th-15th century. It is also the tallest tower in the city. There are 218 steps so be ready to climb. Today the wood steps have been replaced by modern steel stairs. We were all tired from the climb but the view at the top is impressive and well worth it.
The Duomo of San Gimignano (also called Collegiata di San Gimignano) is a treasure not to be missed. The entire interior of the Duomo is covered in frescos which have never needed restoration. The paint and color are the orginal from the 1300s and remain bright today. There is a little damage from WWII bombings but otherwise these frescos seem like they were just painted. The Duomo has small windows so little light has affected them over the centuries. The frescos begin with the stories of the Old Testament on one side of the alter followed by stories of the New Testament on the other side. Each wall has three rows of frescos and should be looked at starting on the left side. The Old Testament frescos are believed to be done by Sienese painter Bartolo di Fredi. The New Testament are thought to be the workshop of Simone Martini. Do not leave the Duomo without visiting the Chapel of Santa Fina. The remains of Santa Fina, who is the patron saint of San Gimignano lie under the altar here. This small chapel is an incredible example of Renaissance art. The three main artists were Florentine masters: Guiliano da Maiano (architect), Benedetto da Maiano (Sculptor) and Domenico Ghirlandaio (painter) The chapel is fabulous. End your visit with a leisurely walk down the main street where there are wonderful shops, restaurants, and gelaterias to enjoy!
This walled medieval castle played an important role during the middle ages. I love this stop! The castle was so well known and respected that Dante mentioned it in “The Divine Comedy.” The castle is located in the province of Siena between Siena and Colle Val d’Elsa. It was built between 1213-1219 on a hill overlooking the Cassia Road. Its primary purpose during the middle ages was defense; the castle was the lookout for enemies approaching Siena. The fortified castle is unique in that the walls are perfectly circular due to the natural curve of the land rather than precise building. The walls include 14 towers and two gates. Soldiers were able to walk the entire wall. Today you can walk on parts of it too.
To visit, park at the bottom lot and walk up toward the Franca or Romea Gate. This gate faces the direction of Rome while the other gate, The Florentine, faces Florence. Enter through the Romea Gate and walk toward the town center, The Piazza Roma. This was the heart of the village during the middle ages even serving as a huge vegetable garden producing food for its medieval inhabitants. Located on the Piazza Roma is the Church of Santa Maria Assunta. This small church is an excellent example of both Romanesque and Gothic architecture. If you are visiting Monteriggoni in early July make sure to check out the Medieval Festival held there. It is very well known and transforms the entire area. You will feel like you have time traveled back into the middle ages.
No trip to Monteriggoni is complete without a meal at Ristorante Il Pozzo. Located on Piazza Roma, this restaurant has been serving lunch and dinner for 40 years. The name alludes to Dantes’ reference of Monteriggoni in “The Divine Comedy.” The restaurant features a charming garden as well as indoor dining in a typical rustic Tuscan room (with arches and white stone walls). No matter where you choose to sit, the restaurant is fantastic. Monteriggioni was one of my favorite sports with its medieval history but also because of this delicious restaurant. We had a long, leisurely, Italian lunch here. It was worth the trip!
The tiny village of Mensano is off the beaten path of tourist but so utterly charming! This tiny medieval village (with about 185 residents) is located a very short driving distance from Castello di Casole. Situated on top of a mountain, this village and its walls date from 1100. The buildings are all charming and exhibit Etruscan influence in their architecture. During the summer, the village hosts many classical concerts, street parties, even donkey races. The Pieve of San Giovanni Battista (or the Church of Saint John the Baptist) is one of the best examples of Romanesque architecture featuring thick stone walls, 3 naves, and 14 capitals with subject for sacred inspiration. The church is attributed to a Pisan architecture Bonamico. In 2013, “The Three Tenors” performed a concert in the church.
As we walked around Mensano, there was an air of peacefulness. The village is so beautiful. This is another town where you will need to park at the bottom and walk. Your walk will be rewarded when you arrive at Osteria del Borgo, an authentic Tuscan restaurant. The meal here was incredible- very casual and just amazing, delicious food and wine. The people at the restaurant and all of Mensano are so friendly which made our visit even better!
Siena is undoubtedly one of the prettiest and interesting city to visit in Tuscany. We were fortunate to be there during the Palio, a horse race held twice a year. The city offers so many amazing sights for visitors. The historic center is a UNESCO World Heritage Site and is one of Italy’s most visited places. The medieval architecture is amazing.
The Cathedral of Siena (or Duomo) is a must for any lover of medieval architecture. I love this Cathedral. It was started in the 12th century but not completed till the 13th century. It is a masterpiece of the Romanesque/ Gothic style of architecture. The Sienese had a very large scale plan for the Cathedral but ran out of funds due to plague and war so they created a smaller version. It’s still massive! The façade in itself is incredible. The exterior and interior are all decorated with white and green/black marble. These are the symbolic colors of Siena. It’s seems a bit overwhelming but it is truly stunning. It is hard to decide where to look first with the marble, the columns and many statues. But what I love is the floor.
There are countless mosaics that appear throughout the floor all telling stories. It took 6 centuries to complete the 56 mosaics. The mosaics are made from one piece of white marble and filled in with black stucco. Colored marble is later inlaid into the decoration. Many are covered for most of the year but for a brief time after the Palio they are all uncovered. We were so lucky to see them. They are absolutely gorgeous. Topics include: The Story of King David, The Wheel of Fortune, She-Wolf of Siena (the symbol of Siena), and Moses Drawing Water from the Rock.
The Piazza del Campo
The Piazza del Campo is the town square of Siena. It is shaped like a shell with the Palazzo Pubblico (1297) and Torre Del Mangia (1325-1344) located there. The Palazzo Pubblico was the place that the republican government met. The Torre del Mangia means “The Tower of the Eater.” This alludes to Giovanni di Balduccio, the first bellringer, who was thought of as cheap and idle. It is the exact same height as the Cathedral representing the idea that Church and State were equal.
The Palio is one of the most amazing things I have experienced while traveling. I drag my husband and kids to a lot of things but this one they were all amazed by. A little history of the Palio first. The Palio is a horse race that was first run on August 16, 1656 in Siena. It is a huge part of the Sienese people’s lives. It takes place twice a summer- once in early July and once in early August. The race occurs around the edge of the Piazza del Campo where a thin layer of dirt is laid down on the ground. The town is divided into contrade, which are different areas of the city.
Today there are 17 contrade. At one point, there where 59! 10 of the contrade participate in both the palio’s pagent and race. Each contrade has their own symbol: Eagle, Snail, Wave, Panther, Forest, Tortoise, Owl, Unicorn, Shell, Tower, Ram, Caterpillar, Dragon, Giraffe, Porcupine, She-Wolf, Goose. Its so colorful walking around the town because each contrade decorates their streets with their flag bearing their symbol. It’s so festive! We each had a favorite.
The entire event lasts over 4 days with two practice runs a day. The actual race is on the last day. Each jockey wears the colors of their contrade and rides their horse bareback. There are many traditions that occur throughout the event including masses to bless the horse and jockeys as well as a large parade with historical costumes. The race lasts about 75 seconds. A horse can cross the finishes line without its jockey and that contrade still wins.
We were blown away by the entire Palio experience. If you can experience it, it is truly memorable. My family thought it was the coolest thing we saw on our trip. To be a part of an event that dates back centuries was truly a unique experience. I can’t wait to go again! Just like I can't wait to go back to Tuscany. This special part of Italy bring history to life. The combination of the wonderful Hotel Castello di Casole and the art and food of Tuscany make for a fabulous, luxurious, unforgettable trip.