The Best of Tuscany Tour Overview

The Best of Tuscany Tour is an immersion journey into the heart of Tuscany that weaves together some of the most famous art, the amazing food and wine and the exquisitely beautiful landscapes that have lured travelers here for centuries.

In Florence we stay in the historic core of the city, only steps away from many of the world's greatest artistic masterpieces.  On our travels together, you'll visit our Italian friends: artisans, castle and winery owners, and amazing chefs whom we've gotten to know well through our many years of living in Tuscany.

After the excitement of Florence, you'll have a chance to experience the beauty and tranquility of rural Tuscan life. We’ll stop in the hill town of Certaldo to learn how to cook some classic Tuscan dishes with Giuseppina and her family.

After lunch, we’ll check in to an 11th century castle in the countryside!  Enjoy the next few nights in this beautifully restored jewel in the heart of the Tuscan countryside.  The castle stands as a testament to the enduring spirit of family and tradition - a haven of warmth where every stone whispers stories of the past and every corner echoes with the laughter of those who have graced its halls.

After a leisurely morning, we'll spend the afternoon visiting the fascinating city of Siena with its world-famous Gothic cathedral and medieval streets.  The Duomo (Cathedral) of Siena is, without a doubt, one of the most spectacular buildings that you can visit in Tuscany, but perhaps its greatest treasure is right under your feet! The entire floor of Siena’s Cathedral is in fact one of the most incredible works of art of all time: a spectacular inlaid marble mosaic floor, something described by Giorgio Vasari as “the most beautiful, largest and most magnificent floor that ever was made”.

We’ll also visit the Piazza del Campo where the famous horse race, the "Palio," is run twice a year. The city is composed of seventeen "contrade" (neighborhoods) which are identified by unique symbols and flags, and which compete each year in an intense, no-holds-barred horse race around the main piazza.

This evening we’ll have an aperitivo in an historic Sienese palazzo before enjoying some free time to shop Siena or grab a bite for dinner at your leisure.

As we bid farewell to the castle, we’ll make a stop in  a small village of 250 people that still possesses its ancient walls; it's a jewel that's still unlisted in the tour guidebooks, and we call it home.

Time will stand still as we travel out into the countryside to have lunch with an Italian family at their winery set in the Chianti hills at a beautiful intersection of woods, vineyards and olive groves.  Here you will enjoy a four-course meal paired with outstanding wines, and everything you eat from meats to wines to veggies is from the family's estate.  Alba’s wild boar lasagna is one of the highlights of the trip, and some people have taken this tour again just to have seconds!

Lastly, we transfer to the ancient Etruscan town of Cortona, made famous by the book and movie, "Under the Tuscan Sun."  Cortona has been sitting perched on the hillside for the past 2500 years, and it has survived its 15 minutes of fame without a scratch.  In Cortona we'll be based at one of our favorite hotels in Italy which offers spectacular views of the Val di Chiana valley below, and the best breakfasts you're likely to find anywhere.

And, then, on the ninth morning of our trip, ready or not, we'll take you back to Florence and wish you Buon Viaggio!