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.
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
Additional food and drinks, tips/gratuities for your guide
Your hotel in Florence city centre
Your hotel in Florence city centre
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.
Travelers 18+ must show proof of COVID-19 vaccination. Children 6-17 must present a negative COVID-19 test (PCR or lateral flow) conducted a maximum of 72 hours prior, proof of recovery dated up to 9 months, or proof of vaccination. For further information, please review COVID-19 Health & Safety at https://www.urbanadventures.com/en/about-us/covid-19-customer-info
If you have any issues on the day of your tour, please call +39 320 250 3173
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.
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