After picking you up from your hotel in your own private vehicle, your tour will begin with, what else, but 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.  

Our first stop will be the pretty, walled town of San Gimignano, 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 guide will tell you about the history of the area and fill you in on where to find the best artisanal stores, coffee shops, and gelato spots. Then you will have some free time to go and explore for yourself. You’ll also get the chance to check out a selection of artisan stores selling locally made products and stroll the winding streets towards spectacular views of the valley beyond. 

We’ll then continue to Monteriggioni, a fortified hamlet strategically built between the two rival towns of Florence and Siena. Dante called the town the ‘crown jewel of Tuscany.’ Spend some free time enjoying lunch where you can choose from a panino and glass of wine, or stop by a local restaurant for a plate of local pici (thick, hand-rolled pasta) with fresh tomato, basil and garlic sauce, or pappardelle with a ragu of wild boar. After you eat, we would highly recommend that you tackle the town’s original wall (it’ll be great for your digestion!) and be rewarded with gorgeous views of the Elsa Valley. 

Next up, we’ll make our way to the town of Siena, stopping at the Basilica of San Domenico first. Inside the church are the relics of Saint Catherine, the patron saint of Siena. We will 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. Then we’ll meander towards Gothic Cathedral which boasts an impressive collection of art works by Michelangelo, Donatello, and Bernini. On the way we’ll pass by a delicatessen that sells wild boar salami. If you fancy it, we can step inside for a tasting. 

Then we’ll meet our chauffeur in the Piazza del Duomo for another scenic transfer, this time 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. 

This tour is priced for a group size of five travellers. Smaller groups may still book this private experience but will be charged the base rate for five travellers. If you're looking to book a group larger than five travellers, please contact our local team at info@florenceurbanadventures.com.