After landing at Florence Airport, pick up your reserved car (according to the instructions you will receive before departure). This will give you freedom of movement and allow you to reach places less accessible by public transport. The program depends on your arrival time. If you arrive in the evening, check in and have a seat in one of the countless bars, either near your hotel or perhaps in Piazza della Signoria with a breathtaking view of Palazzo Vecchio. If you have more time, I have prepared a walking tour of the most important monuments of Florence, where you can admire the palaces, churches and squares of this Renaissance jewel of Tuscany.

Head south to your destination, Montepulciano, the "friendliest city in the world". Before you get there, stop in Siena, which would be a shame to miss. You can easily spend several hours in this historical gem and still have something to admire. Have lunch in one of the many trattorias and then head to Montepulciano, where you will stay. You will have the whole next day for the city, but if you have the time and inclination, head out in the evening to the narrow streets surrounded by stone palaces and taste some of the excellent wines offered here at every turn.

You'll dedicate this day to exploring the town where you're staying. It's sure to win you over with its authentic atmosphere. And not just that! The rolling hills, vineyards, and the paths between them are not only a feast for the eyes but also invite you to take a short walk. If you have the time and inclination, put on your shoes and head along the dirt roads towards Montefollonico. You don't have to go all the way there, after all, it's almost eight kilometers, just a short distance is enough to enjoy this beautiful landscape up close. 

You will travel through the picturesque landscape of the Val d'Orcia valley to the town of Pienza, where Enea Silvio Piccolomini, the future Pope Pius II, was born in 1405. He later decided to rebuild his native village and had an "ideal city" built. Although the plans were not fully realized due to his untimely death, an example of medieval urbanism remains here, now under UNESCO protection. After the tour, you will soak in the thermal springs and end the day with a glass of unique and appreciated wine in the village of Montalcino.

Once again, you will pass through the impressive Val d'Orcia with its olive groves and typical cypress trees scattered in the rolling landscape, which is a UNESCO World Heritage Site. After about a quarter of an hour, you will reach the small town of Montichiello and then head to Bagni San Filippo, thermal springs almost unknown to tourists, flowing down travertine cascades. In the evening, say goodbye to Montepulciano with a visit to one of the wine cellars and enjoy your last evening in this charismatic town.

The program for this day depends on your departure time. Either you head directly to the airport, or you take the opportunity to stop in Monteriggioni for one last Italian coffee with something sweet to go with it.