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

The meeting point will be confirmed after booking


We accept most major credit cards and payment forms. Please see the bottom of our website for the payment types accepted.

Most of our customers enjoy having the benefits of a private tour. You have your own guide. You can have rest stops when you like. We can tailor the tour to suit your needs and preferences. We always choose the best guide for your needs, whether you are a family, an art school, or a company doing an incentive event.

All our tours except our Sex, Drugs and Renaissance tour are kid friendly. When doing a private tour with us, you have your own guide, so tell us in the notes of the booking the ages of your kids and we will tailor the tour and choose a guide that’s great for kids for you. We also have 4 special kids’ tours in Florence.

No large bags or backpacks in museums, in churches shoulders and knees must be covered so bring a scarf to cover your shoulders. IF it’s a walking, bicycle or a countryside tour make sure to bring comfortable shoes.

It’s important for everyone to bring their ID

student or children for the museum

All tours are conducted in English only unless otherwise noted or requested. Other languages available for all private tours on request.

We recommend arriving 15 minutes before departure time for all tours and services

We are offering mainly Private and some Semi-private tours at the moment. We do not offer many semi private small group tours anymore due to the consequences of the Covid-19 pandemic. The difference between Private and Semi-private is that the private tours are fully private tours with your own guide and the Semi-private are small shared group tours where individuals can join others.

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


7 reviews 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.

  2. David Boyko

    Great day with Marissa on a 1-day tour of Tuscan highlights. Good information on the history and culture of the region and towns, plus tips on what to look for/ stop in on the towns we visited

  3. Marla Garrett

    This tour was amazing! Three wonderful villages. Amazing tour guide and driver. Delightful lunch and wine tasting. Just a perfect day! Five stars!

  4. Sylvia

    Our Artviva walking tour of Florence in June 2022 was led by a guide named Martina. She was extraordinarily knowledgeable, pleasant and adept at leading our group. She also spoke English very well, so there was no language barrier. The portable tour microphones were a great help as well. All in all we were quite pleased with our experience.

  5. Linda Meek

    We loved our tour!!! Everything was perfect and as promised!! I have used your company before and when my 12 family members decided to go to Italy I used your group again. Ella, our same tour guide from 3 years ago, was fantastic and fun! The drivers were wonderful and informative too. I will highly recommend your tour company to my family and friends.

  6. Linda Hudes

    Alessandro was our outstanding guide. His knowledge of Siena and San Gimignano greatly enhanced our appreciation of the area. From the vineyards to the olive trees to the artistic masterpieces, Alessandro provided both an overview and cogent details of everything we saw. He clearly loves his work and has mastered the subject. Also, a wonderful person to spend the day with

  7. Isabella Hankins

    If you do nothing else, do this tour! This was my second time doing it, and I would do it again. Our tour guide, Alessandro was fantastic. His knowledge was amazing! Our driver Louiggi was the best! This was the highlight of our 10 day stay throughout Italy-and, we did a lot!

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