Hotel Pickup
Leave your hotel's name on the public notes for our guides to pick you up at centrally located hotels in Florence.
Private Florence Tour: Hill Towns in Tuscany

Get out of the city and spend some quality time sightseeing around the medieval towns of the dreamy Tuscan countryside, with a local guide by your side. Your full-day tour will take in two of the most charming townships, Siena and San Gimignano, with a lunch stop at a boutique winery and plenty of free time for you to explore. We’ll chat history, see incredible architecture, admire Instagram-worthy views, and drop in on artisan shops to discover locally made products from the region.


  • Get out of the city for the day and soak up the sights and smells of the picturesque Tuscan countryside

  • Visit the stunning historic towns of Siena and San Gimignano and browse artisan shops selling locally made products

  • Dig into an included lunch of seasonal produce at a beautiful boutique winery, with wine and olive oil tastings

  • Enjoy arguably the most beautiful panorama in Tuscany from the Piazzale Michelangelo

Local English-speaking guide and driver
Transport in a Mercedes air-conditioned van
Lunch of seasonal produce at a beautiful boutique winery
Wine and olive oil tastings
Pick up at your hotel
Additional food and drinks
Tips/gratuities for your guide.
Important Information
What is included in the tour?

Local English-speaking guide and driver, transport in a Mercedes air-conditioned van, lunch of seasonal produce at a beautiful boutique winery, with wine and olive oil tastings, pick up at your hotel

What isn't included in the tour

Additional food and drinks, tips/gratuities for your guide

Where do we meet?

Your hotel in Florence city centre

Where does the tour end?

Your hotel in Florence city centre

What is the duration of the tour?

8 hours

What is the minimum group size for this private tour?

This private tour is priced for a minimum group size of five travellers. A lesser number of travellers may still book this private experience but will be charged the base rate for five travellers.

Are there any Covid-19 vaccination requirements?

While we strongly recommend that all travellers are vaccinated against COVID-19 to reduce the risk of transmission and avoid putting undue strain on healthcare services, vaccinations are not a requirement to join an Intrepid Urban Adventures tour. For further information, please review COVID-19 Health & Safety at

What if I can't find my guide?

If you have any issues on the day of your tour, please call +39 320 250 3173

Can I cancel my tour?

Free cancellation up to 24 hours before activity


After meeting your driver and tour leader in your hotel lobby, head off in your own private vehicle for a scenic drive through the rolling hills of the Chianti region, crowded as far as the eye can see with vineyards and olive groves. If you’re looking for heaven on earth, we think you may find it here. First up, make your way to the town of Siena, stopping at the Basilica of San Domenico. Inside the church are the relics of Saint Catherine, the patron saint of Siena. Take a stroll to the Piazza del Campo to see the political centre of town where the famous horse race ‘Il Palio’ is held twice a year. From there, meander towards the Gothic Cathedral, which boasts an impressive collection of artworks by Michelangelo, Donatello and Bernini. Along the way, pass by a delicatessen that sells wild boar salami – if you fancy it, we can step inside for a tasting.  Then, it’s onward to lunch at a boutique winery surrounded by the Chianti hills and vineyards. You’ll get to taste the wine, as well as that famous extra virgin olive oil with seasonal produce.   Your second stop is the beautiful walled town of San Gimignano, a UNESCO World Heritage site that’s known as Italy’s medieval Manhattan because of the 13 towers that dominate its skyline as you drive towards it. The town gained importance during the Middle Ages when it was a stop on the major pilgrim route between Italy and France, known as Via Francigena (the road to France). The townsfolk produced silk and cultivated saffron that still grows around its foothills. Another important industry that still exists here today is that of Vernaccia di San Gimginano, a white wine of the area. Your tour leader will tell you about the history of the region and fill you in on where to find the best artisanal stores, coffee shops, and gelato spots. You’ll also get the chance to check out a selection of artisan stores selling locally made products and stroll the winding streets, admiring spectacular views of the valley beyond. Afterward, meet your chauffeur for the transfer back to your accommodation in Florence. On the way, we’ll stop for one last magnificent panorama at Piazzale Michelangelo, where we will gaze upon spectacular views of the city that you won’t forget in a hurry. Before you go, don’t forget to ask your local guide for tips on what else to see, do and eat during your stay in fabulous Florence. 

We reserve the right to change both the route and places visited within the tour. Food inclusions are subject to change, dependent on availability on the day.

Private Florence Tour: Hill Towns in Tuscany
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