Depart Florence today in the comfort of your own private vehicle with driver, and relax on the drive south (approx. 1hr 45 mins) to Avignonesi, where you'll get to visit an excellent wine producer, Le Capezzine Estate, situated at a few kilometres from Montepulciano, complete with its own villa, chapel and ancient stone wine cellar. The shared visit of the cellar will last approximately 1hr15mins and will take you around a real labyrinth made of wine barrels.
At the end of the wine tasting enjoy a typical 3 course Tuscan lunch accompanied by Avignonesi wines to match each course. Lunch will typically consist of Tuscan Appetizer, choice between pasta first course or meat main course with side dish, dessert, 3 Avignonesi wines, 1 Italian dessert wine (the choice between pasta and meat has to be confirmed in advance).
Fully sated, you'll depart for the beautiful medieval town of Cortona, that was already a very important village during the Etruscan period between the 8th and 7th Century BC. Enjoy a walking tour of town with an English speaking guide for approximately 2hrs, taking in the Romanic Church of St Christopher, the Town Hall Square with the Town Hall building as well as a stroll down the main street surrounded by beautiful medieval palaces from where you can admire beautiful panoramas.
From Cortona, the final stop and todays destination will be Castiglion del Bosco, approximately a 2hrs30minute drive away.
There are two restaurants and a cozy bar at the Castiglion del Bosco property which showcase the talented chefs' seasonal and regional cuisine using the finest local ingredients, complemented by an extensive list of Castiglion del Bosco and regional wines. The traditional Osteria offers a casual ambience for an informal lunch or dinner, while the fine dining restaurant, Ristorante Campo Del Drago, presents an elegant setting for a sumptuous Tuscan dining experience.
Accommodation: Castiglion Del Bosco (5*) As a protected nature preserve within the Val d’Orcia Parco Naturale, Castiglion del Bosco (5*) boasts spectacular natural beauty. Nearly three quarters of the Estate is blanketed in forest — home to boar, deer, fox, porcupines, badgers, hawks and pheasants. Staying at Castiglion del Bosco is a rare opportunity to enjoy Tuscany the way it is meant to be experienced—on a magnificent country Estate nestled among rolling hills, sweeping vineyards, centuries-old farmhouses and treasures of antiquity, while indulging in the fruits of the land in the form of fresh regional cuisine and delectable wines. At the heart of the estate, Il Borgo was where the estate's business was managed, and was the focus of the farm community's village life. Today its historic buildings have been transformed into 23 luxurious Suites that exude Tuscan class and culture. Castiglion del Bosco's 4,500 acres also play host to a number of stunningly located farmhouses – and nine of these have been restored to become sumptuous yet authentic villas offering unparalleled facilities and amenities. Inspired by the colors, textures and majesty of the Val d'Orcia, Il Borgo Suites are a haven for relaxation and quiet contemplation, a unique vantage point from which to revel in the myriad pleasures of the Tuscan lifestyle. The Suites have been lovingly restored, retaining the architectural details of the storied Estate, and blending the finest antiques with custom pieces created by local artisans. Ranging in size from 750 to 2,500 square feet (50 square metres to 220 square metres), the expansive Suites offer lovely master bedrooms, airy bathrooms with sensual soaking tubs, inviting sitting rooms warmed by the Tuscan sun and private terraces with panoramic views of the countryside. State-of-the-art conveniences, including LCD TVs, Wi-Fi high-speed Internet access and iPod stations, add a modern touch to each historic residence.