Private Tuscany Tour: The Original Best of Tuscany Tour

The first and original Exclusive Best of Tuscany Tour. A Private Tuscany tour that takes you to the region’s most stunning hilltop towns: Siena, San Gimignano, and Monteriggioni.

The Ultimate Private Tuscany Tour Experience

Experience divine Tuscan life on our exclusive private tour of Tuscany and its treasures.

See the Best of Tuscany on this private full-day guided trip from Florence!

In your comfortable private vehicle, you’ll traverse lush vineyards, rolling hills and 3 of Tuscany’s most charming hilltop towns.

Drink Chianti Wine, Eat Italian Food 

You’ll be living the Tuscan dream on this day-long tour of Tuscany. You’ll break for lunch and taste iconic Chianti wine from Tuscany’s renowned vineyards in a beautiful Tuscan estate.

Discover Siena

Beautiful Siena has gorgeous views over the countryside and the famous Piazza del Campo.

Explore San Gimignano

The town of the fine towers, bustling with boutiques and great gelato!

Visit Monteriggioni

A small jewel of a hilltop town. Monteriggioni is a pretty medieval hamlet with fortifications and watchtowers.

Relaxed time to explore the towns

Take your time to wander and shop in each town without feeling hurried.

Lunch at a Tuscan estate, including a wine tasting

A delicious Italian style Tuscan lunch and the finest local wine.

Hear the fascinating history and stories of each town

Your personal guide will fill you in as you travel through Tuscany.

Stunning views of the Tuscan landscape

See the very best of beautiful classic Tuscany. Rolling hills, shimmering olive groves and glorious vineyards.

Tasting Wine & Extra Virgin Olive Oil

Enjoy the great tastes of Tuscany.

The scenic route through Tuscany

Take in Tuscany’s picturesque countryside while learning the territory’s deep and ancient history. Our (very) small group Tuscany tour will guarantee that you get the most out of your experience. That means spacious minivans and small groups, and a fun guide eager to share the region’s history. We’ve designed this tour to give you the chance to meet and get to know your fellow travelers and guide. We want you to feel comfortable asking questions, to share your own stories, to stop for pictures. We know the best highway stops for those iconic Tuscan shots, so be sure to bring your camera!

Small town charm – Tuscany Tour

Enjoy free time to tour Tuscany’s 3 most famous medieval towns on your own. Stroll through Siena’s historic city centre, a designated UNESCO World Heritage Site. See the soaring medieval towers of San Gimignano. Visit Monteriggioni, known as the Gateway to the Middle Ages. In each town, we’ve given you free reign to spend the time the way you want. Visit churches and museums. Wander the cobblestone streets and narrow stone alleys. Unwind with an afternoon gelato at the world’s best gelateria.

A Typical Italian Lunch

You’ll taste a gourmet lunch of local Tuscan specialties and homegrown ingredients. Yes, that means real extra-virgin olive oil and Chianti’s finest wines! And if you have allergies or dietary requirements, don’t worry, just let us know. Tuscan food has something for everyone.

Click here if you prefer to do the tour as part of a semi-private small group.


While You’re in Italy, Why Not Try…?

The Florentine Steak Experience

Masterpieces of the Uffizi Gallery Tour

Vinci, Pisa & Lucca Tuscany Tour

Pasta Making & Cantucci Baking: Vegan-Friendly Villa Cooking Class with Beautiful Views

Tuscan food and wine

Tour Details

Sites Visited in this tour:

  • San Gimignano
  • Siena
  • Monteriggioni
  • Tuscan Estate/Wine Estate in San Gimignano area


  • A wonderful English speaking guide
  • All transfers from/to Florence
  • Wine tasting at typical Tuscan estate
  • Typical Tuscan light lunch
  • Visit to Siena historical center
  • Visit to the hilltop town Monteriggioni
  • Visit to the beautiful hilltop town of San Gimignano

Not included:
Optional gratuities

Runs rain or shine

Meeting Time 8.15 (15 minutes before the tour starts) 

Start Time 8.30

9 hours

Start Location:

End Location:

Dress Code:
Comfortable shoes, casual dress

Important information
Vehicles are not able to enter into the walled cities of the ancient hilltop towns so there is some walking involved. Children are welcome on this tour however we are not always able to provide car seats and by law children cannot ride on a parent’s lap. Please contact us ahead of time if you are travelling with small children.


Meeting Point

In our office at Via dei Sassetti 1, Florence


General faq
We keep our group sizes small, but on occasion may need to increase. We rarely go over our group size maximums. We believe strongly in high quality experiences with great guides. But sometimes due to extenuating circumstances it’s not possible to keep the group as small as we would like. More often on all our small group tours you will find our groups are smaller than our published maximums.

Yes, children of all ages are allowed on the tour. Infants require a car seat.

Please contact us for private tour options

Yes, just let us know what your dietary requirements are and we will update the venue.

Typical Tuscan lunch at an estate. We can accommodate any dietary requirements or food allergies.

Yes, you will have free time in each town to explore on your own.

We use a 9-seater minivan

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1 review for Private Tuscany Tour: The Original Best of Tuscany Tour

  1. Lisa Malachowsky

    ArtViva was a new tour company to us recommended by folks we met at dinner in Florence. It did not disappoint. Our tour guide Ben was very knowledgeable and interesting. Almost everything relates to Dante somehow! The only thing missing was more information about olive harvesting to make olive oil.

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