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A Week in a Tuscan Wonderland
time 9 Days / 7 Nights

Chianti area (7 nights)

Escape the world and relax in a Tuscan wonderland!  Your very own private VILLA, grounds and gardens are all yours to explore!   Also, try venturing out into Tuscany’s charming cities and towns which are no more than an hour’s drive away!

This package includes a car rental and private villa accommodations for 7 nights.

Below we have listed our top suggestions of private tours to add on as you wish. You can decide to have every day at leisure, explore on your own, add a private guide for each suggested tour or even hire a private chauffeur driver. 

Customize the package and make it YOUR dream vacation!

Click HERE to look at our selected villas in Tuscany. 

inclusionAt a Glance
  • Suggested Itinerary: Departure from US
  • Arrival in Tuscany
  • Florence
  • Pisa & Lucca
  • Siena & San Gimignano
  • Cooking class at a Local Farmhouse
  • Volterra & Certaldo
  • Chianti with Wine Tasting
  • Departure to US
dates Itinerary
Click on the plus sign for full day description.

Board your overnight flight and you're off to your exciting Italy Vacation! 
*Flights are not included in the price of this package.  We are happy to arrange them for you.

Whether you arrive in Florence or Rome - welcome to Italy! Head to the car rental office to pick up your car, then check in to your exciting week at your private villa in Tuscany region.

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

*This is just a suggested itinerary. Tours as mentioned below are not included in the basic package price.  We are happy to arrange them for you or customize the package based on your own interests.

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.

Today you can relax at your private villa or we may suggest driving to Florence and enjoy our private Best of Florence tour.

You will discover Florence's historic center on this walking tour including the Accademia Gallery and the 17ft tall statue of David by Michelangelo. The tour will also include the Baptistery Doors by Ghiberti, coined the “Gates of Paradise” by Michelangelo, the Duomo, the astounding Cathedral of Santa Maria del Fiore and the Brunelleschi’s magnificent Dome.

The rest of the day is free for you to explore this city of the Renaissance and perhaps cross the Pontevecchio Bridge and walk around the famous shopping streets in the Oltrarno - the manual crafts neighborhood.

Tonight, you can either have dinner in the city or hire a private chef that will prepare a delicious Italian meal at your villa.

Today, we suggest driving 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.

For lunch with wine tasting, you may stop at one of the wineries just outside of Pisa. One of our favorite is Fattoria Il Poggio.

In the afternoon, visit the town of Lucca. Walking along all the small shops, you'll come to the circular Piazza del Mercato which is built on top of the remains of the Roman amphitheater. Also, see the Cathedral of San Martino and the Guinigi tower.
The Buccellato is the famous typical cake from Lucca. So don't forget to taste it before heading back to your villa.


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 take our private Best of Siena tour and 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.

Grab lunch, then head over to San Gimignano. As a UNESCO World Cultural Heritage site with a well-preserved medieval style, San Gimignano is one of Tuscany's most popular smaller cities. The town with its characteristic towered skyline is also famous for its wine, Vernaccia, saffron and the precious Santa Fina pottery.

An intimate, authentic culinary experience with a famous Tuscan Chef! Great for beginners and experienced cooks alike!

Head to a fascinating farmhouse immersed in the Tuscan countryside to learn recipes and secrets that you will bring home to surprise your friends and family with a true Italian meal! Your menu may slightly vary depending on the season and the fresh ingredients available. Typically, the menu will be: two different types of home-made pasta from scratch (such as pappardelle and ravioli) and a dessert.

The class will end with a delicious lunch that will prove your improved skills in the kitchen, accompanied by tastings of different wines and a final typical Tuscan dessert wine.

At last, you will visit the wine cellar of a small boutique winery to learn about their wine production.

Visit two of the most captivating villages in the Tuscan countryside: Volterra and Certaldo.

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.

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.

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

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 enjoyed this exciting opportunity to stay at a private villa, live like a local and explore the gems of the Tuscan region.