Small-Group Tuscany Grand Tour: Siena, San Gimignano, Chianti, Pisa, And Lucca

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Tour Details


From medieval hill towns to walled cities, from the vineyards of Chianti to the Leaning Tower of Pisa, see the very best of Tuscany in just one day on this small-group 12-hour guided tour. You'll visit Siena, San Gimignano, Lucca, Pisa, and Chianti, and enjoy a Tuscan lunch, a gelato tasting, a wine tasting, a winery tour, and an evening 'aperitivo'.


  • Small group ensures personal service
  • Step back in time on a history tour
  • Lunch included
  • All-inclusive tour
  • Informative, friendly and professional guide

Know More about this tour

Your tour departs from central Florence at 8am: be sure to arrive at 7:45am in case of accidents. Climb aboard your comfortable minivan with your tour leader and small group of no more than 16 peopleand relax as you cruise in air-conditioned comfort to your first stop, Siena, about an hour from Tuscany.

Here your guide will lead you on a walking tour through Siena's medieval center. Wander the Piazza del Campo, home to the annual Palio horse races, and admire the city's striking cathedral: explore quiet backstreets as you learn about the different districts which compete in the Palio. Enjoy a surprise tasting of a local Tuscan specialty, before you hop back in the van.

It's about 45 minutes' drive to your next stop, the staggering hilltop town of San Gimignano, with its high walls, narrow streets, and medieval tower-houses. The skyline is unforgettable, as is the atmosphere, and you'll have free time to explore at leisure or shop for souvenirs, before enjoying a gelato tasting.

From here, it's a short drive to a historic winery, set in an ancient villa with medieval tower. Here, savor a classic Tuscan lunch, taste some of Tuscany's famous Chianti wines, and learn about wine production as you tour the vineyards and the cellars.

The views from the minivan window are particularly lovely as you cruise through the Tuscan hills to the historic city of Pisa. Here, you'll have time to admire the glorious landmarks which line its Piazza dei Miracoli (Miracle Square), including the Duomo, the Baptistery where Galileo was christened, and, of course, the famous Leaning Tower. Please note: tower tickets are not included as there are usually long lines to climb the tower. If the line is short, it may be possible to buy them in Pisa.

From here, it's under half an hour to Lucca, another beautiful walled town that's rich in history, art, and food. Led by your guide, you'll visit the major landmarks before enjoying a relaxed aperitivo perhaps a Spritz? - in the Piazza dell' Anfiteatro (Amphitheater Square).

After thisit's about an hour's drive back to Florence, where you'll arrive around 8pm, in time for a relaxing dinner.

Inclusions for Small-Group Tuscany Grand Tour: Siena, San Gimignano, Chianti, Pisa, And Lucca

  • Small-group tour
  • Tour leader
  • Round-trip transportation by comfortable, air-conditioned minivan
  • Guided walking tour of Siena
  • Surprise tasting
  • Gelato tasting
  • Tuscan lunch
  • Winery guided tour and wine tasting
  • Aperitivo

Exclusions for Small-Group Tuscany Grand Tour: Siena, San Gimignano, Chianti, Pisa, And Lucca

  • Gratuities (optional)
  • Hotel pickup and drop-off

Additional Info

Confirmation will be received at time of booking

Minimum drinking age is 18 years

Please advise any specific dietary requirements at time of booking

A moderate amount of walking is involved

Not wheelchair accessible

Cancellation Policy
  • If you cancel within 3 calendar days (72 hours) of the scheduled departure time, the cancellation charge will be 100% of the undiscounted tour price.
  • If you cancel between 4 to 7 Calendar days before scheduled tour departure,the cancellation charge will be 50% of the undiscounted tour price.
  • If you cancel at least 8 calendar days in advance of the scheduled departure time, there is no cancellation fee. You will receive Full Refund for the paid amount.
  • Please note that in case of No show, the cancellation charge will be 100% of the listed tour fare.
  • Please note tours booked using discount coupon codes will be non refundable.

Write A Review

8 Traveler Reviews

  • Except that it was a bit squuezy in the 9-pax vehicle, everything was great. Very relaxing and the guide was very patient, attentive, and enthusiastic in his work. Keep up the good work Ricardo!

  • Our tour leader was great! San Gimignano was great and I really enjoyed the time we spent in this village. However on this tour I would suggest less time be spent in Pisa and Luca.

  • Excellent tour, Highly recommended. Very nice and informative guide.

  • We absolutely loved this tour. 4 towns and a winery tour seems like a lot to do in one day, but the tour was so well organized that we were truly able to enjoy all these areas without feeling rushed. Our guide Chris was excellent - I can and #39;t recommend him highly enough. Wonderful!!

  • I was kind of skeptical in joining such a tour that would visit so many places in one day, as I usually prefer rather relaxed and slow-paced experiences. Well, thank god I joined it! Discovering the whole Tuscany would probably take you a lifetime, but I was staying in Florence only 3 days and this tour turned out to be the best opportunity to really have a sense of true Tuscany. From the most renowned and magnificent places, such as Siena and Pisa, to enchanting San Gimignano and charming Lucca, not to mention the wonderful winery we visited, you really can breathe the authentic Tuscan essence, feeling immersed in it for a full day.
    The transfers from one place to the other vary in length but I felt them as part of the adventure: the landscapes you drive through with the minivan are gorgeous! Vineyards, olive groves, gentle hills... well, in a word, Tuscany!
    And, by the way, even though at the end of the long day you might feel tired, it still felt like a relaxed journey. I think this is all due to the very small group and the professionality and passion of our guide.
    The wonderful memories - and hundreds of pictures! - from this tour will be the best souvenir we'll bring back home from this Italy vacation. Thank you!

  • Wow! Never seen so many beautiful places in one day before!
    Our group was only 8 persons so it felt almost like a private tour, and this does make the difference in a full day trip like this. All the locations are well worth a visit like this. Wonderful Siena, quaint San Gimignano and Pisa with its leaning tower are classic destinations in Tuscany, cannot miss them, and that's because they really can fill your eyes with beauty. But I had never heard about Lucca, before reading about it on a great Tuscany guidebook, and trust me, you'll be surprised by its history and charm, plus the fact that it's definitely less touristy.
    Add to this a wonderful ancient winery in a medieval villa and castle, with a nice lunch and great Chianti wines - that can inspire a little nap during the following transfer to Pisa - and a fun and knowledgeable guide like Cristian, and you've got the perfect Tuscan day!

  • Fantastic tour, seen lots of incredible things in Tuscany and great guide!
    It's a full day tour, about 12 hours, so quite long, but definitely worth it if you are not spending many days in Florence and Tuscany and want to discover the most of it in the shortest time.
    I've seen other similar tours around but with much bigger groups, and didn't want to end up in a 60-seat coach following a flag: this is the only small group tour of this kind I've found we were 8 people on our tour!. More expensive, but a totally different feeling: at the end of the day you feel you've found new friends among the other passengers, and especially talking about our great guide Cristian.
    Siena is magic and our local guide there, Benedicta, was knowledgeable and extremely passionate about her town.
    The free time in the little jewel hamlet, San Gimignano, was much appreciated as this is a very small medieval village and you can stroll around by yourself at your own pace.
    The Chianti winery you visit is immersed in the vineyard hills of the wine region, with a medieval tower you can sometimes climb gorgeous views from up there, an authentic ancient cellar still used nowadays and good quality wines you get to taste some of them. You also have lunch here, with delicious Tuscan cold cuts and pastas.
    The leaning tower in Pisa is... well, the leaning tower, as you've seen it in thousands of selfies, but much more impressive pictures don't do justice to its dramatic leaning and with a gorgeous square, cathedral and baptistery around.
    I had read another review about Vinci being a pointless stop... well, I cannot say anything about Vinci as right before leaving with the tour the local company that runs it informed us that the Vinci stop would be replaced by a visit to Lucca... and Lucca proved to be an unknown to me magic treat! What a lovely quaint medieval town! We even had an aperitivo in its unique amphitheatre square! Not to be missed!
    So, all in all, it's not been the most economic thing I've done in Italy, but it's the first one i would do again!

  • Was really disappointed with this tour:
    Siena - This was brilliant, the tour guide was from the area and had brilliant local knowledge

    San Gimignano - This is self-guided. You get a little information driving to this location, but are on your own when you arrive approx 1 hour. Beautiful place, although it was very busy.

    Chianti Winery tour / lunch - Disaster!! I actually found this part embarrassing! The lady from the winery clearly doesn't do tours - very little information, and at one point we were shown upstairs to a virtually empty room with some old machines that had nothing to do with the tour. It was cringe-worthy. The lunch was fine with tasting of 4 wines.

    Vinci - Pointless stop. We went to both museums, one of which is currently under construction. Unless you have an interest in engineering, there is nothing at this stop for you approx 1hr This was also self guided.

    Pisa - Leaning Tower 1hour. This was fine - time for a walk around the square or trip up the tower. This was also self guided.

    I would not recommend this tour - there are so many other trips out there with good reviews. Really regret taking this one.
    PS - The tour guides were lovely, the tour itself, and the information provided did not live up to expectations!

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