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9 Day A Week in a Tuscan Castle 2019
time 9 Days / 7 Nights

Spend a week driving in a Tuscan wonderland! With the incredible Montegufoni Castle as your home base, you are never more than an hour's drive from any of Tuscany's lovely cities, towns and villages. Visit as much of the region as you like, or spend as much time as you like taking in the beautiful grounds of this medieval castle.

inclusionAt a Glance
  • Departure from US
  • Arrival in Tuscany!
  • Florence Walk & Talk Tour
  • Pisa & San Miniato
  • Siena & Volterra
  • Wanna Be Italiano Cooking Class in Florence
  • San Gimignano & Certaldo
  • Chianti with Wine Tasting
  • Departure to US
dates Itinerary
Click on the plus sign for full day description.

Buon Viaggio!  You're off to Italy! 

Whether you arrive in Florence or Pisa - welcome to Italy! Head to the car rental office to pick up your car, then check in to your exciting week at the Montegufoni Castle.

After you check in, take some time to explore the beautiful grounds and take in your first view of the Tuscan countryside.

Tonight, have dinner in town.

In Italy, breakfasts are usually quick (unlike dinner). The cafes in the gas station shops are similar to simple delis in the USA. They are quite good and frequented by locals as they prepare fresh pastries and cappuccinos to start your day.

Florence is only a 30 minute drive from Montegufoni Castle.

We suggest taking the Florence Walk & Talk Tour during which you will see Piazza della Signoria with the town hall Palazzo Vecchio, the Duomo, the Baptistery with its ‘Gates of Paradise’, Giotto’s independent bell tower, Brunelleschi’s Dome, Santa Trinita and Orsanmichele Church, Pontevecchio Bridge and the secret Vasari Corridor, as well as famous shopping streets and the Oltrarno - the fourth and last district, the manual crafts neighborhood.

This tour is not included in the price above. Please let us know if you'd like to add it to your itinerary.

The rest of the day is free for you to explore this city of the Renaissance.

Since you won't enter any monuments or museums in the morning, take the afternoon to enter your favorite ones or just walk around the city at your leisure.

Tonight, you can either have dinner in the city or in a small restaurant less than 10 minutes from the Castle.

Today, drive over to the home of the famous leaning tower, Pisa! Piazza dei Miracoli is the square that contains the Leaning Tower, Monumental Cemetery, the Cathedral and Baptistery, which are considered among the most beautiful sights in the world. After many years of work to re-stabilize the tower, it is now open to the public. Be sure to get your tickets as soon as you get there for a time later in the day. Every 30 minutes, a group is allowed to climb the tower and take pictures.

Also, take some time to walk through the old town. Those small winding streets are proof that Pisa was once a city with canals, very similar to Venice. It's soft and shallow earth is why many of Pisa’s buildings are leaning.

In the afternoon, visit the small Tuscan town of San Miniato. This town is historically important because it was one of the main stops along the path from the rest of Europe to Rome. (Ever heard of the saying all roads lead to Rome? It was true a long, long time ago!) San Miniato is also recognized as a town of Slow Food and home to the truffle (black and white mushrooms that grow underground).

Tonight, we suggest having dinner a small, local restaurant in San Miniato.

This morning visit one of Tuscany's major cities, Siena, home of the famous horse race, Il Palio. You can explore the city on your own, or at 11am take a guided Siena Walking Tour to visit the major attractions including Piazza del Campo, the true heart of the town, the Palazzo Comunale (Town Hall) and the majestic Basilica of San Domenico. The tour includes admission to the Cathedral.

This tour is not included in the price above. Please let us know if you'd like to add it to your itinerary.

Grab lunch, then drive over to Volterra, a city dating back to the 8th Century BC.

A cool story about Volterra: In the Second World War, when the Germans were coming to invade the city, the people of the town tore up all the stones from the streets and filled the main entrance to the city, blockading themselves in and the Germans out. Because of this, they were able to preserve the gate that was thousands of years old, as well as the city inside, from being destroyed as so many other historic sites were during the war.

There is a wonderful little shop that sells glass plates and vases, but the amazing part is the glass floor, that shows the ruins of an ancient road beneath it. Also, be sure to see the well preserved Ancient Roman Theater from the 1st century BC.

Grab a quick breakfast on your way in to Florence. At 10am, meet up with your guide for an exciting market visit and cooking class!

This tour is not included in the price above. Please let us know if you'd like to add it to your itinerary.

After the cooking class, the afternoon is free. You can explore the city on your own, take another Florence Day Tour, or just head back to the castle for a relaxing evening.

As a UNESCO World Cultural Heritage site with a well-preserved medieval style, San Gimignano is one of Tuscany's most popular smaller cities.  In the summers it is packed with tourists, eager to get a taste of history... and its D.O.C.G. Vernaccia wine.  But since you will be traveling in the off-season, you will have more time and space to take this city in for yourself. 

Certaldo is a great little city with a lot of history.  From the new town, you can take a cable car up to the old, fortified town.  Certaldo is famous for its onion.  In fact, it’s a part of their town seal, with the motto "By nature I am strong and sweet, and still like I those who stay and those who work."  Even the famous Italian author Giovanni Boccaccio wrote about it in his 6th book of the Decameron.

Tour the Chianti Classico area one of the Italy’s foremost wine-producing region with its charming views of the Tuscan hilly countryside. Your tour will also include a stop in one of the local vineyard for a tasting of a selection of locally produced Chianti Classico wines.

This tour is not included in the price above. Please let us know if you'd like to add it to your itinerary.

Take the rest of your last day in Tuscany to relax at the castle, and start getting your things together.

Have dinner in the castle, or head out to a nearby restaurant.

Sadly, today you say Arrivederci! to the beautiful Tuscany. Make sure you allow enough time to fill up the gas tank, return the car and take care of any final charges (like the GPS rental). Then make your way to the airport. Hopefully you'll have time for one more cappuccino!

We hope you enjoy this exciting opportunity to stay at the Montegufoni Castle and explore the gems of the Tuscan region.