Tuscany

Trip Itineraries
16
 available
Vineyards and Villages
About

A land of medieval hilltop towns, beautifully rolling countryside dotted with vineyards, and silver olive groves.

Few destinations are as romantic as Tuscany. Dotted with wine-soaked villages, spectacular medieval hill towns, and vibrant cities packed with a wealth of historical treasures, Tuscany is one of the most beloved regions in Italy.

No visit to Tuscany is complete without exploring its countryside. Many of the small towns have remained unchanged for centuries. Step inside the gates of San Gimignano, discover the remains of the Etruscan Acropolis in Volterra, or explore the hilltop town of Cortona, where you will find the famous Etruscan Academy Museum. Culture vultures interested in awe-inspiring art and medieval architecture can visit cities like Pisa, Lucca, and Sienna.

Wine lovers can tour the vineyards of Chianti, a mountainous area of Tuscany well-known for its wines, ranked among the best in the world. For the wine connoisseur, the Brunello wine in Montalcino will be essential as well.

Life in Tuscany is slow-paced. Never hurried, the locals truly embrace the simple life and small things that bring joy. You will find them enjoying the simplistic and rustic Tuscan cuisine and consuming wine in small family-owned trattorias where time passes slowly.

Highlights

When in

Tuscany

  • Snap a photo in front of the world-famous Leaning Tower of Pisa.
  • Get the blood moving with a hike through the countryside.
  • Go on a Wine Tasting Tour in the Chianti region and discover centuries-old vineyards and gorgeous villas.
  • Explore narrow winding streets in the medieval town of San Gimignano.
  • Join a Tuscan cooking class and learn how to make everything from tiramisu to ragu.

Popular Day Tours

This is just a small example of the 100's of tours and activities we can provide throughout Italy.

Customized tours

Family Heritage

There is a rich history of Italians immigrating to the US, resulting in many of today’s North Americans having roots in Italy. We can help you discover the village your family originated, where we can look into old records and perhaps find written evidence of your ancestors. In some cases, we may even be able to introduce you to distant relatives you didn’t even know you had!

Heritage
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Customized Tours

Family Heritage

There is a rich history of Italians immigrating to the US, resulting in many of today’s North Americans having roots in Italy. We can help you discover the village your family originated, where we can look into old records and perhaps find written evidence of your ancestors. In some cases, we may even be able to introduce you to distant relatives you didn’t even know you had!

Heritage
Customized Tours

Family Heritage

There is a rich history of Italians immigrating to the US, resulting in many of today’s North Americans having roots in Italy. We can help you discover the village your family originated, where we can look into old records and perhaps find written evidence of your ancestors. In some cases, we may even be able to introduce you to distant relatives you didn’t even know you had!

Heritage
Customized Tours

Family Heritage

There is a rich history of Italians immigrating to the US, resulting in many of today’s North Americans having roots in Italy. We can help you discover the village your family originated, where we can look into old records and perhaps find written evidence of your ancestors. In some cases, we may even be able to introduce you to distant relatives you didn’t even know you had!

Heritage
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Customized Tours

Tuscan Treasures: Siena and San Gimignano

Your driver will take you to the two most famous medieval settlements in the middle of Tuscany: Siena and San Gimignano. You will see Siena’s historical center and monuments and find out its secrets. You'll learn about the Palio of Siena, which is not just a horse race but an enshrined tradition. After walking, you will eat Sienese cuisine in a typical “trattoria” in the city’s center. Then you will go to San Gimignano, a village that has been declared a UNESCO World Heritage Site for its attractiveness and medieval features. San Gimignano is on a hill overlooking a valley and its historical center comprising towers and unique architecture. Discover the village and investigate their Saffron and Vernaccia wine.

Medieval Towns
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Customized Tours

The Leaning Tower of Pisa and Lucca

Pisa and Lucca are two of Tuscany’s most historic towns. Your driver will help you learn the history and traditions of the towns and then show you the squares and monuments in Pisa: the Piazza dei Miracoli with the famous Leaning Tower, the Cemetery and the Cathedral. You will then eat lunch before exploring Lucca, a walled city of art and Renaissance style. Your guide will walk with you along the town walls and show you the roofs, alleys, house-towers, places of worship and palaces of officials. Then you will go to the town center to see Piazza Anfiteatro, Guinigi Tower, St. Martin’s Cathedral and antique shops.

The Leaning Tower
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Customized Tours

Chianti Villages and Vineyards

Chianti Classico is one of the most well-known wine regions in the world, for good reason. Located in the middle ofTuscany, this area spans between Florence and Siena and includes fourteen cities. You will see rolling hills, vines, olive trees and oak forests, among small medieval villages and farmhouses. On this tour with your knowledgeable local driver, you will see the small town of Castellina in Chianti and then view the Quercetto winery for a tour of the property, vineyards and cellar followed by having a meal and tasting wine. After lunch, you will visit Sant’Agnese to taste wine. Your driver will then take you to Monteriggioni to see its medieval walls and fortifications.

Chianti
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Customized Tours

Val d’Orcia: Montepulciano, Pienza, and Montalcino

A beautiful day spent touring one of the most breathtaking wine regions in the world. Your first stop is a winery, where you will tour the cellar, view their vineyards and taste their wine! Then you will see older parts of Montepulciano and go to Piazza Grande for the next wine tour. You will not only gain knowledge of winemaking but also tour their Etruscan-age cellar. After lunch, your driver will take you to Pienza to view this hilltop Renaissance city and taste gelato at gelateria "Buon Gusto." From Pienza, you will be driven to Montalcino to taste the wine of a Brunello producer and tour their cellar.

Val D'Orcia

Trip Itineraries

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