Independent arrival Florence and check into the four-star Hotel Dei Medici or similar. Dinner is on your own this evening. Overnight Florence. If you wish to arrive earlier, please let us know and we will book you the extra nights. We do not charge for this service. Hotel included.

Pick up at the Hotel Orto Dei Medici and short transfer to the Villa Agape. A short hike to Abbazzia San Miniato al Monte for a visit of this exquisite basilica and monastery. One of Italy’s most beautiful medieval buildings. We will finish the morning with an urban hike (paved lanes, sidewalks, roads) through the historic Pian Di Giuliari district, a plateau that is dotted with Renaissance villas, and Galileo Galilei’s observatory and home. A 40-minute transfer brings us to la Cantinetta di Rignana, a classic trattoria set amongst the rolling hills not far from Panzano in Chianti. After lunch, a short transfer Fattoria Le Fonti, a beautiful small winery on the edge of Panzano in Chianti. Here we are welcomed by my friend Guido, who together with his wife Vicky own and run the winery. A brief visit of the winery is followed by a tasting of their Chianti Classico, Chianti Classico Riserva and “super Tuscan” wines. If it is a nice day, the tasting will include a magnificent view out over the vineyards onto the Villa Vignamaggio, where Da Vinci painted the Mona Lisa. Afterward, a twenty-minute drive brings us to Radda in Chianti where we check into the Relais Fattoria Vignale, an 118^th-centurymanor house that is now a four-star hotel with magnificent views over the Chianti hills. A two-minute walk into the village for dinner t trattoria Da Giovannino. The Hike: Very easy hiking on gently rolling terrain and on paved surfaces. Morning distance: 5.5 kms. Hike time. 1.5 hours plus time for explanations of the history. Overnight Radda in Chianti at the four-star Relais Fattoria Vignale.  Transfer, winery visit and tasting and dinner included. Lunch not included.

After breakfast a private transfer to the Castello di Brolio. Our morning hike takes us under the massive walls of the castle, through their vineyards and olive groves to the castle itself, whose gray stone walls have stood for 900 years. Visit the park and gardens of the castle and the small but fascinating museum that is dedicated to Baron Benito Ricasoli, who was Italy’s first Prime Minister and who established the recipe for Chianti Classico wines. Lunch at a local trattoria followed by a visit of Ceramica Rampini’s workshop and store. Rampini produces hand-painted majolica ceramics using traditional techniques which feature Renaissance-era designs as well as contemporary motifs to decorate dinner sets, jugs, and vases. The Hike:  1 hour in the morning, relatively flat but sometimes rolling. Optional afternoon hike: 6 km (4 mi) loop over rolling, hilly terrain. Overnight Radda in Chianti.  Hotel, breakfast, and dinner included.

Our morning hike starts directly from the hotel and leads up into the Chianti hills to the tiny hamlet of Bricciano, where we will meet Rory O’Kelly for a visit of his cantina. Yesterday we visited one of the largest producers in Chianti, today we visit one of the smallest! Rory’s South African father established this small boutique winery in the 1990s and Rory is continuing his father’s passion for the winery. He is intent on making world-class wine and the result is very persuasive. After the visit, we have a short hike to a private home where we have lunch. The afternoon hike takes us to the Castello di Meleto, a 13th century fortress that evolved over time into a Baroque summer residence. From here you have a short van transfer back to Radda. Dinner tonight is al fresco at Ristorante Le Panzanelle. The Hike:  1.5 hrs in the morning, 2.5 hrs in the afternoon through rolling terrain. Overnight Radda in Chianti.  Hotel, breakfast, lunch, dinner and tasting included.

Today we have a scenic 40-minute van transfer to Siena, one of Italy’s most beautiful and historic cities. We have a guided visit with Rita, our favorite city guide. Only a native of this Gothic city can explain the furor and passion that surround the famous bareback Palio horserace, which is run around the city’s 12th century Piazza del Campo twice a year. You will have free time to explore the exquisite historic center and admire its Gothic architecture. Of course, you might get side-tracked by the shops and cafés along the Banchi di Sopra, Siena’s main pedestrian shopping street. Enjoy lunch in Siena and then meet up again before a scenic drive through the Crete Senese to Pienza. Our hotel for the next two nights is the lovely four-star Relais il Chiostro, a former Franciscan Convent dating back to the 13th century, located in an enviable position, in the center of the magnificent hamlet of Pienza, in the heart of the Val d’Orcia. The Hike:  Urban hiking in Siena. Overnight in Pienza.  Hotel, breakfast and dinner included. Lunch not included

After breakfast we have a short transfer towards Montalcino to begin our hike to the 13^th century Abbey of Sant’Antimo. The hike takes us through Brunello vineyards, verdant woods, and rustic farming villages before we arrive at the abbey. Sant’Antimo is one of the most important and famous examples of Romanesque architecture in Italy. After lunch at the trattoria in Castelnuovo dell’Abate we have a short drive to “Uccelliera,” one of Brunello’s premier small wineries, for a truly unique and insightful tasting in their cantina. We start in the cellar and taste directly from the barrels the still unblended Sangiovese wines from two different vineyards. Here we taste the difference that terroir makes to a wine, and also age and even the type of oak barrel that is used. We then move to the tasting room to taste a flight of their Brunellos. Return to Pienza for free time to explore the town’s shops, cafés, and wine bars. Tonight’s dinner is at our favourite trattoria in Pienza, which also happens to have a superb wine list with many old vintages cellared to perfection. The Hike:  2.5 hrs in the morning, through rolling terrain, mostly downhill. Overnight Pienza. Breakfast, dinner, Brunello winery visit and tasting  and hotel included.

Transfer to Arezzo train station for trains after 10:30 a.m. to Florence and Rome. Drive time is 1 hour. Transfer included.

Please note: Some details of the itinerary may change according to the departure date of your tour. Whenever we run a tour we make new discoveries. Sometimes they are good discoveries, like a wonderful new trattoria, and sometimes they are bad, like a trail has been washed away. The result is that we sometimes change our itinerary to improve it by adding new wonderful elements to the tour or by removing something that does not work anymore. Rest assured, our goal is to always provide you with the best possible experience. We will advise you of any changes to the original itinerary prior to departure.