Tuscany: The Original Best of Tuscany Tour

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

The Ultimate Tuscany Tour

Do you want to experience the real Tuscan life? Drink wine, soak up the rolling hills and stroll in the hill top towns? Look no, further, this is the only Tuscany Tour you need!

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

Our Best of Tuscany tour has rolling hills, lush vineyards, and food to die for. We’ll take you to three of Tuscany’s most charming hilltop towns in an accompanied day trip from Florence. Break for a dream lunch at a beautiful Tuscan estate, and enjoy an exclusive tasting of Chianti’s finest wines.

Small Group, Private Transfers – Covid-19 note*

ArtViva has only high quality small group tours. Usually you’ll either be in a car or a minivan as you travel through the Tuscan countryside. No big buses, or groups of 100 plus like some tours! *For this reason in the current months we are unable to run the small group semi-private version of this tour as we are not able to maintain social distancing. Please book a private tour from the calendar if you wish to join us this summer.

Visit Siena

The first stunning hilltop town of the three we visit.

Visit San Gimignano

The Manhattan of Tuscany. A wonderfully atmospheric small hilltop town.

Visit Monteriggioni

A small jewel of a hilltop town. Monteriggioni is a quaint, charming, medieval hamlet.

Free time to explore the fabulous medieval hilltop villages visited

We always make sure you have enough time to wander and wonder without making the day too long.

Lunch at a Tuscan estate, including a wine tasting

A delicious Italian style Tuscan lunch and wine to wash it down.

Fascinating stories to bring the past to life while you travel between towns

A great guide with your small group.

Classic Tuscan landscapes and iconic views

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

Tasting of top-quality Tuscan olive oil

Enjoy the great tastes of Tuscany.

Private mini-bus transport – no large buses!

Enjoy a serene ride through the hills! No horrible large crowds or stuffy buses.

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 Dream 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. Tuscan food has something for everyone.

The Best of Tuscany Tour – prefer a private Tuscany experience?
Click here for an exclusive private Best of Tuscany tour!


While You’re Here…

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


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24 reviews for Tuscany: The Original Best of Tuscany Tour

  1. Desiree Moore

    Our tour guide was excellent. We all agreed that her blend of information and warm personality helped to make our day the best of our 6 days in Italy. We greatly enjoyed her company. The geography is stunning, our lunch and hosts at the winery were flawless and of course, the towns we saw speak for themselves. This was the first time for 2 of our group to be traveling to Europe and the first time to Italy for all of us. We loved our day and I can’t think of one thing that any of the 4 of us said that we would change about it. Thanks for the experience

  2. Jean Warriner

    We just returned from Italy and I just wanted to follow up and say that we had a great “Best of Tuscany” tour.. We loved the small group size and the great selection of Tuscan towns, too. Our guide really gave us a very good tour, not wanting us to miss anything. He was informative, funny, and very pleasant to listen to. The tour of the winery and the lunch provided were both very well done too

  3. Melissa Eikenberry

    We had a great time on our tour of Tuscany! It was a highlight of our visit to Italy. Of course the scenery alone is worth the trip but we particularly enjoyed the visits to the two smaller towns. The tour of the winery was wonderful, we learned a lot! Also really enjoyed the opportunity to sample wines and food. Our tour guide was also very good. We really appreciated her commentary throughout the tour. She also helped us by recommending good local restaurants in Florence. We ate at two or three of her suggested places and they did not disappoint!

  4. Richard and Sharon Zarek

    It’s hard to say what we liked best. The whole tour was WONDERFUL. We especially enjoyed visiting and touring and EATING at the wonderful Tuscan farm we visited. That was a real highlight, thank you! And, we enjoyed Siena so much that we spent another 1.5 days there on our own. We certainly would contact you again if we have the wonderful fortune of returning to Italy. Tuscany was a favorite place. Thank you for helping to make our trip to Italy so memorable

  5. Rita Kenny

    A wonderful day, particularly the farm – a real insight to rural Tuscany life, we loved it! Thank you, Walking Tours of Florence your charm, humor and information.

  6. Madeleine Haas

    This tour has certainly lived up to its name, “The Best of Tuscany”.The rolling hills and pastel palette countryside will be forever a part of my wonderful memories of Italy. The food and wine at the farm topped off the experience. Our guide brought the medieval times to life with his vivid descriptions and knowledge. Thank you for an unforgettable experience!

  7. Kirsten Ford

    We had the most amazing day on our Best of Tuscany Small Group Tour. Incredible to experience such a wonderful slice of Tuscany – well organised, wonderfully knowledgable and lovely tour guide, amazing food and wine. And, of course, Tuscany was absolutely picture perfect! Thank you for a day which was a definite highlight of our time in Italy.

  8. Kim Fulcher

    Fantastic customer focus at every facet of this trip, from booking to pre-tour communication to our wonderful guide. Small group, interesting and knowledgeable commentary and just a general fun vibe made this the best tour I did in Italy. The guide was totally invested in everyone in the group getting the most out of the day and his warm and inclusive style broke the ice almost immediately. Lunch at the Palagetto was excellent with a tour of the winery included and the last stop of the day at San Gimignano meant an ice cream frim the “best gelato shop in the world” (if that’s not true it’s pretty close). I learned alot, laughed alot, ate alot and would highly recommend this tour to people wanting a personal and comfortable Tuscany experience. Worth every penny.

  9. Jane Whitnell

    We were a group of 5–several in the group are world wide travelers and somewhat hesitant about enlisting on this tour–by the end, we were all so happy, informed, and excited about our day. Our guide was so informative on the history and current day of the Best of Tuscany tour. She fit right in with us and is a fabulous asset to your business. She sent us on our way with several other restaurant and site recommendations. Marissa was the best guide ever!!

  10. Charles Ponder

    Artviva was a great choice for tours. The Tuscany tour was the highlight of the trip to Florence. The small group tour beats larger tours any day. Our guide was knowledgeable and friendly. Highly recommend this tour. Will use Artviva on future trips!

  11. Marion Holmes

    Great day with Amanda touring Tuscany. Very good mix of cultural and historic sites plus modern winemaking tour and lunch at Palagetto winery ( not a villa as listed in online info, but nice nonetheless).

  12. S. Anderson

    We did this as a private tour since we’re a family of 5 (kids 20, 18 & 15). Spent an amazing day with our guide Eleanora and excellent driver Florian seeing Siena, a neat small winery for a tasting, and San Gimignano. Picked up at our apartment in Florence in a nice clean Mercedes van, we headed to Siena, while Ella provided a great background of the area and it’s history en route. Ella studied in Siena and knew what highlights to see during our time there. Lunch and wine tasting at I Balzini were excellent. Spent some time with the owner/winemaker learning about his wine and got a tour of the grounds and bought a case which was promptly shipped back to the US. Ended the day walking thru San Gimingano. All said a great day spent with an excellent guide. Definitely recommend this and would do it again.

  13. Don Rush

    My family of five people took this tour in July 2019. To start, we loved our tour guide, Ella. It felt like we had a relative in Italy who was happy we decided to visit and wanted to show us all of the good things in Tuscany. She was very friendly and articulate. We enjoyed the lunch stop very much and the small towns along the way were something we never would have seen otherwise.

  14. Alyson VanderToorn

    Our tour of Tuscany was a wonderful day of exploring and eating, from sampling delicious ricciarelli cookies in Siena to the “best gelato in the world” in San Gimignano. The highlight was a tour of a winery followed by a “light lunch” paired with 6 wines! Our guide, Alessandro, was energetic and full of stories.

  15. Cynthia and Steve Come

    Easy to book and would recommend to anyone (well, not families with kids as I just don’t think young children would really get it). Enjoyed seeing highlight towns of Siena, San Gimignano, and Monteriggioni with a great driver to get us there and an awesome guide in Elanora to explain significant and interesting details. Highlight is lunch, wine, and olive oil tasting at Azienda Agricola Casamonti in Chianti. Delicious and educational. Not the least expensive tour, but worth every penny for this well-organized and hassle-free day.

  16. Christopher Corsig

    The tour was great. Ben, our guide was extremely knowledgeable about Tuscany, wine, food and the history the area. Well worth our time and we would recommend to all looking for a unique small group experience. The lunch and wine tasting was also excellent!

  17. Catherine Antrim

    It was great from beginning to end, just like our entire visit to your special Italy. The driver was experienced, friendly and knew the area well. Our guide was friendly, very knowledgeable and shared her love of the country Italy as well! Our stop at the vineyard was PERFECT and the guide there was fabulous ! Loved our small town visits, love the Tuscany region and the day was so special that we hope to return to Italy in the near future! I would definitely recommend this group and this great daytrip tour!

  18. Mike Strange

    This trip was from Florence and driver and guide were early to pick us up. Our guide was great! I can highly recommend Ben. He had a LOT of information about where we were going, lot of history of the area and had lived in Sienna, thus know a lot about the city and the culture. Lot of great information during the entire trip and he kept talking and answering questions as we drive from place to place. Really enjoyed this tour and ask for BEN!


    There were 4 of us on this tour, parents and adult children. We all enjoyed the tour. Lunch at the winery was amazing (we all agreed). We all wish more time was allotted for Sienna. We liked the other towns but Sienna deserved more. Our guide was fun and knowledgable.

  20. Gregory Karrip

    It was the best tour to date. Our guide, Paul was outstanding, friendly, knowledgeable and flexible. We also thoroughly enjoyed our lunch and the tour. It was a perfect day, thank you! We will tell our friends who come to Italy.

  21. 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.

  22. Jamie Tharp

    This tour was amazing. Amanda is a very excellent guide. The visit to each city was prefaced by a mini history lesson, explanations were detailed but not lengthy. The winery lunch and tour was fantastic even though it was after the harvest. Loved every minute!!

  23. Victoria Sullivan

    My mother, sister, and I had an absolutely lovely time on The Exclusive Original Best of Tuscany Tour. Our tour guide was Ben and he was terrific! Ben was very knowledgeable about Tuscany and had a great sense of humor. He picked us up in the morning in a private car and we started the tour in Siena. Siena is absolutely stunning and my only wish is that we would have had a lot more time there — we loved it! From there we quickly stopped in Monteriggioni which was very historic and interesting. We then had lunch at a winery near San Gimingnano which was lovely. The food was just okay, but we really enjoyed the winery itself and of course the variety of wine! We all purchased a few bottles of the red reserve. We had some time in San Gimingnano but thought it was a bit too touristy. Overall, we would certainly recommend this tour to others and we had a trip of a lifetime! Thank you, Ben and Artviva!!

  24. Chelsea Babbert

    I booked this tour on recommendation from a client of mine. I’m so glad I did!! Alex was the BEST guide of any tour we took during our trip. He was hilarious, very informative and made the whole day fun! We’re not big-group-tour people and were very happy when there were only two other people besides our driver, Michele and Alex for the day. It made the whole experience more personalized. I love Tuscany and we only had one day to experience the area on this trip-so this was perfect. I cannot recommend this tour and guide enough! We’ve told everyone back home about it! Thank you again, Michele and Alex!!

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