Tuscany and Chianti Wine Tour

Explore with the experts, uncovering the sensual wonders of Tuscany’s cities and wine regions: six days of indulgence and extravagance.

Wine tasting in Chianti, elegant whites that complement fresh pasta dishes. The reds of Montepulciano, rounded and robust as they roll around the tongue. Gorgeous little towns made of cobbles and piazzas, panoramas from an Italian fairytale, and churches that are more like Renaissance art galleries.

    Six days allows you to really indulge in Tuscany, a loop from Florence taking you to destinations like Siena, San Gimignano, Montalcino, Pienza and Montepulciano. Handcrafted for connoisseurs’ tastes, this example itinerary combines famous stops with cellars and villages that only the locals know about. You’ll explore and taste your way around the best of Tuscany.

    All our tours are individually customized to your interests. This day to day program was designed for previous guests of Italy Charme. While we loved guiding this private tour, it is purely an example of what can be possible and we will tailor your day to day program to your interests.

    Day 1: Arrival in Florence [dinner]

    Welcome to Italy! Upon your arrival in Florence airport, you will meet an English speaking assistant waiting for welcome you and transfer by private car to your hotel in Florence. Accommodation at Hotel centrally located and free time to rest or explore the city center on your own. A welcome dinner tonight will be served in a typical restaurant within walking distance from your hotel. Overnight in Florence.


    Day 2: Full Day Private tour in Chianti area with wine tasting and light lunch [breakfast, wine tasting and light lunch]

    Breakfast at hotel. Morning meeting with a private car and an English speaking assistant to enjoy a Full Day private tour around the wonderful Chianti area famous for its incredible views, intimate piazzas and wonderful restaurants and wineries. The Chianti wine region is a gorgeous part of Tuscany, and Castellina in Chianti is one of its most evocative medieval towns in the territory. During the tour you will stop in a local winery, to visit the cellar with the local and enjoy a wine tasting followed by a light lunch with typical salumi and cheese. At the end of this amazing day, you will come back to your hotel in Florence. Time at disposal to relax and dinner on your own. We could provide to suggest you a typical restaurant walking distant from your hotel. Overnight in Florence.


    Day 3: Full Day Private tour in Siena & San Gimignano [breakfast, wine tasting and light lunch]

    Breakfast in hotel. Morning meeting with your driver waiting for you in the lobby of the hotel and departure for a Full Day tour dedicated to visit the wonderful Tuscany towns of Siena and San Gimignano. First stop in Siena where you will meet an English speaking local guide for about 2 hours walking tour to admire the magnificent Cathedral and St Juan’s Baptistery. At the end visit the guide will walk with you till a typical Osteria in the historical city center, where you will have the chance to taste some glass of local wine tasting followed by a light lunch with typical products. Early afternoon continue to San Gimignano and meeting again with an English speaking local guide to walk about this hill small town famous for it’s medieval architecture, towers and white wine. This is a pretty unusual Tuscan town, where originally there were 76 towers built by rival families. Late afternoon transfer back to your hotel in Florence and balance of the day at disposal to relax. Overnight in Florence.


    Day 4: Full Day Private tour around Montalcino, Pienza and Montepulciano [breakfast, wines tasting and cheese tasting]

    Breakfast at hotel. Morning meeting with a private car and an English speaking assistant to enjoy a Full Day private tour dedicated to visit the villages of Montalcino, Montepulciano and Pienza famous over the world for their old tradition of food and wine. You will stop on the hill town of Montalcino, completely encircled by fortified walls, situated in the Val d’Orcia, not far from Mount Amiata. It is a special place to spend a day immersed in Tuscany’s history and countryside. Climbing to the top of the hill you will have stunning views over the valleys all around, characterized by vineyards, olive trees, fields and other little villages. Here you will taste the famous wine “Brunello di Montalcino” in a local cellar. Continue to Pienza, a charming village known as the “ideal city of the Renaissance” but better famous to be the city of Cacio cheese. The “Pecorino of Pienza” is a cheese made from sheep’s milk that of course you will taste in one of the local factory. The town streets are full of small charming shops selling a large quantity of various types of pecorino, from fresh to aged pecorino, that you can taste together with a number of other local products, such as fine wines, spices, handmade pasta and so on. The last stop before to come back in Florence at the end of this special day will be Montepulciano, a medieval wonderful town, full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners with splendid panorama all over the Val D’Orcia and Val di Chiana. A walk through Montepulciano is the best way to view the town and its beautiful landmarks as well as enjoy a tasting of their local famous Nobile wine. Late afternoon you will come back at your hotel in Florence. Time at disposal to relax and dinner on your own. Overnight in Florence.


    Day 5: An Half Day guided tour in Florence and Unforgettable special evening [breakfast, dinner]

    Breakfast in hotel. Morning at leisure for personal activities and maybe shopping in Florence. We would suggest you to not lose a walk to Ponte Vecchio, known for the many shops built on the bridge. Shops usually sell a wide assortment of jewelry and antiques. Lunch on your own and early afternoon meeting with an English speaking local guide in the lobby of your hotel to enjoy a walking guided tour around Piazza della Signoria, the main square of the city and to admire Ponte Vecchio, Pitti Palace, the Church of Santa Croce, the Cathedral with Brunelleschi’s Dome, and the adjacent Baptistery with its renowned “Gates of Paradise” doors. The visit also includes a stop to visit the Accademia of Art, where you can admire the David of Michelangelo. At the end of the tour time at leisure to relax before to enjoy an unforgettable Renaissance evening in the magnificent setting of the ancient halls of a noble residence in the historical city center. You’ll step into the atmosphere of a 15th century Florentine banquet, with the sound of a harp and flute, the sweet voice of a soprano,
and dances of the period. Waiters, musicians, dancers, and the jester – all in beautiful Renaissance costumes – invite you to be a part of the evening. And if you want, you can wear the traditional costumes and learn dance steps of the 1400’s! During the evening you will enjoy a welcome drink followed by a 3 courses menu.  Overnight at your hotel in Florence.


    Day 6: Flight Home

    Breakfast in hotel and private transfer to Florence airport on time to embark on your return flight.


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