The Chianti region, world famous for its wine and its landscape, is a land of ancient traditions.
Etruscans first settled in this area where they started the wine-making activity continued by the Romans. In the Middle Ages this area was disputed between the cities of Florence and Siena. Villages and convents, fortresses and castles were built during that period and many of them later were converted in manor houses and country residences. During this period the original landscapes, including vast forests of chestnuts and oaks, were transformed and adapted for the cultivation of vines and olive trees. The activities related to these cultivation gradually assumed a major economic importance and established the international reputation of Chianti region. You explore this region having the possibility to experience at its best the local way of life and the breathtaking landscapes of this corner of Tuscany walking along some of the most scenic paths and staying in the handpicked accommodation we have carefully chosen for you close to some of the best highlights of the area.
  • ACTIVITY: Self-guided walking tour
  • NAME: Chianti Wine Trails
  • DURATION: 6 days/5 nights
  • GRADE: Easy to moderate
  • 2024 PRICES: Starting from Euro 1190.00 per person sharing twin/double room

    INQUIRY - Chianti Wine Trails

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    Arrival on your own in Florence. Our accommodation is centrally located and it is a wonderful base for exploring, at your own pace, the capital of the Renaissance, world known for its important cultural, architectural and artistic heritage. We are going to provide accurate pre-departure information about how to reach by local transportation the city of Florence. (Extra nights and Private transfer from Florence airport or train station on request).
    Overnight: Hotel*** in Florence
    Walking – easy to moderate min 2h,30min, max 4h,30 min.
    After breakfast a private transfer brings you to the starting point of the walk in the Chianti area. Starting from Greve in Chianti you walk along one of the most charming Tuscan landscape and you may choose between two different options depending on your level of fitness. A longer option includes the Verrazzano castle, where in 1485 Giovanni da Verrazzano was born, the explorer who discovered the Hudson bay (the current New York), a big statue dedicated to him stands in the middle of the main square. The shorter option includes a part of the longest one: it’s a pleasant and panoramic walk to join the medieval castle of Montefioralle passing by the St. Cresci Parish Church. Montefioralle is considered one of the most beautiful villages in Italy, and probably one of the most ancient castle in Chianti… it is still today enclosed within its original medieval walls! Nearby the hamlet you can enjoy a wine testing sitting in front of hectares of splendid vineyards. Your walk ends after a pleasant descent in Greve.
    Overnight: Hotel***in Greve in Chianti
    Meals: Breakfast & wine tasting
    Walking – easy to moderate 4 hours.
    Toscana comes from the latin Tuscia that means “lands of the Etruscans”: and today you walk just in middle of the Etruscan road networks. A big road was built crossing the Greve river to join the territories from Volterra through the Chianti region. In the Middle Ages this main roadway was dotted with castles, one of the most famed of them was the fortress of Uzzano, renowned for having provided the family name of the celebrated Niccolò di Giovanni da Uzzano, who, at beginning of the 15th century, vainly opposed the unstoppable power of Cosimo de’ Medici in Florence. You breath history in every corner… walking along these valleys also means to observe the changes brought about in agriculture during the centuries: the sharecropping has given way to intensive agriculture but the beauty and the perfection of the landscape is still intact.
    Overnight: Hotel***in Greve in Chianti
    Meal: Breakfast
    Walking – moderate 5 hours.
    Today with a private transfer you reach the starting point of your next walking experience: Panzano. From the market square of the village of Panzano you reach the Volpaia castle, built in the 11th century as a fortified village on border between Siena and Florence. Although only part of the original defensive walls and two of its six towers are still standing, the medieval layout and buildings within the village are still intact, making Volpaia certainly one of the best preserved villages of its period. One of most well-known families of the village were scientific instrument manufacturers. Their instruments are still displayed at the Science Museums in Florence and Greenwich, as well as the Adler Planetarium in Chicago and Palazzo Vecchio in Florence. Your walk ends in Radda in Chianti, your next destination.
    Overnight: Hotel***in Radda in Chianti
    Meal: Breakfast
    Walking – easy to moderate 4 hours.
    Today you walk along the Chianti Classico wine production area: surrounded by vineyards you enjoy a scenic walk starting from Gaiole in Chianti to Radda in Chianti, passing by a vast historical property including the Vistarenni villa, castles, parish churches, country houses and farms… In one day you cross most of the villages of the former “Chianti league”, the ancient consortium which has preserved the quality of the wine for centuries. You finish your walk arriving in the medieval village of Radda where you may get lost wandering around its medieval alleys or you may perhaps relax sipping a glass of wine while looking at the magnificent scenery of the vineyard covered hills surrounding the town.
    Overnight: Hotel***in Radda in Chianti
    Meals: Breakfast & wine tasting
    Your trip ends after breakfast (Private transfer on request to your next destination in Tuscany or to Florence airport or train station in Florence or Siena).
    • 1 nights Hotel *** in Florence
    • 2 nights Hotel *** in Greve in Chianti
    • 2 nights Hotel *** in Radda in Chianti
    • 5 breakfasts – 2 wine tastings
    • Luggage transfers on day 2 & day 4
    • Private transfers on day 2, day 4 & day 5
    • Detailed maps and route notes
    • Emergency phone number

    • Visas, Airfare & airport taxes
    • Travel Insurance (compulsory)
    • Drinks
    • Tourist taxes to be paid locally
    • Other meals not mentioned in the itinerary
    • Public transportation & entrance fees
    • Anything not mentioned in “inclusions”