We pick you up from Florence at 9:30 a.m. for a private transfer to the Castello di Brolio. Our morning walk 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 Ricasoli family private museum, then begin a short walk to a very special lunch with our friend Massimiliano Biagi. “Massi” is the manager at the famous Barone Ricasoli vineyards. He is responsible for the 2,500-acre estate of the Castello di Brolio, 500 acres of which are vineyards which regularly produce wines of exceptional quality, scoring consistent 90 plus points from Wine Spectator magazine. Massi’s other passion is cooking, and we're lucky enough to be invited into his home for lunch, and what a lunch!  Afterwards we visit the cellars and enjoy a tasting with Massi. A short van transfer then takes you to your hotel in Gaiole in Chianti, the four-star Castello di Spaltenna. Keen walkers can do a late afternoon walk up to the medieval hamlet of Vertine, otherwise relax until we meet at 7 p.m. for an aperitivo. Dinner tonight is in the village square at Trattoria Sfizio. Here the Bianchi family makes simple but tasty Tuscan dishes including excellent truffle ravioli or tagliatelle with porcini mushrooms. The walk:  1 hour in the morning, relatively flat, but rolling. Optional afternoon walk: 6 km loop over rolling, hilly terrain. Overnight Gaiole in Chianti. Hotel, breakfast and dinner included.

Our morning starts directly from the hotel and leads us up into the Chianti hills to the tiny hamlet of Bricciano, where we will meet Peter 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! Peter, originally from South Africa, has been living in Chianti for twenty years and his hobby and passion is his wine. He is intent on making world-class wine and the result is very persuasive! After the visit we have a short walk to a private home where we have lunch. The afternoon walk 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 Gaiole. Dinner tonight is al fresco at Ristorante Le Contrade. The walk:  1.5 hrs in the morning, 2.5 hours in the afternoon through rolling terrain. Overnight in Gaiole in Chianti. Hotel, breakfast and dinner 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 for a transfer to Castellina in Chianti, where we will stop at what we consider to be the best gelateria in Tuscany. We then carry on the workshop and showroom of Rampini ceramics, arguably the finest producer of hand-painted ceramics in Italy. The head designer will take time to explain how traditional majolica ceramics are made. For those who are interested there is also the showroom to explore! If you've got energy to burn, return to your hotel on foot (1.5 hours), otherwise return by van. Dinner tonight under a canopy of sycamore trees at Osteria Il Ponte. Overnight Gaiole in Chianti. Hotel, breakfast and dinner included.

Today we transfer from the Chianti region southwards to the hilltop town of Montepulciano and the region known as the Val d’Orcia (Valley of the Orcia River). It’s a beautiful drive, and we stop on the way for a pretty morning walk through the estate of the historic Villa Arceno to the charming village of San Gusmé, where we can enjoy a mid-morning cappuccino.  A short drive takes us into the stark and gorgeous clay hills of the Crete Senesi, where we will stop for lunch in the walled village of Asciano. After lunch we have a beautiful walk to the village of Petroio, where we visit a producer of terra-cotta. This is quite different from the ceramics that we saw at Rampini’s, since here they produce the huge planters and olive oil urns that have been used for centuries by the great “fattoria” and villas of Tuscany. We will arrive in Montepulciano in late afternoon so you will have time to explore this beautiful hilltop town, renowned for its Vino Nobile wine. Our hotel for the next three nights is centrally located within the medieval walls of the town.  It has a charming, old world feel. Tonight’s dinner is at the best restaurant in Montepulciano – which also happens to have a superb wine list and a selection of amazingly good grappa!  Overnight Montepulciano. Breakfast, dinner and hotel included.

A 25-minute van transfer brings us to Montalcino, a small village famous for its powerful “Brunello di Montalcino” wine. We stop in the village for a coffee break and purchase our picnic lunch before we begin our walk to the Abbey of Sant’Antimo. The walk 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. Then take a late afternoon walk to the small town of Castelnuovo dell’Abate where we will have the chance to visit the cellars of a local winery and taste a variety of aged Brunello wines. Or if you prefer, we can arrange a visit and tasting at Casanova di Neri, whose wines have won perfect 100 scores from Wine Spectator as well as “Wine of the year.” You decide! We then transfer by van back to Montepulciano.  Dinner tonight is at the Café Poliziano, the second-best restaurant in Montepulciano! Overnight Montepulciano. Breakfast, dinner and hotel included.

A pleasant morning walk takes us past the imposing villa and fortress of Massaini. Then we continue to Castelmuzio for lunch followed by a visit of a very small olive oil producer who has won the top prizes at both Italian and international olive oil fairs and competitions. Here you will be schooled in the art of distinguishing characteristics of different kinds of olive oils.  After your education (and indoctrination!) about the merits of Tuscany’s olive oil, we can enjoy a short walk from the village of Castelmuzio to the monastery of Sant’Anna where “The English Patient” was filmed, or you can choose to return to Montepulciano. One last delicious meal awaits us at one of our favorite restaurants, the “Osteria Acquacheta.” Overnight Montepulciano.  Breakfast, dinner and hotel included.

The trip ends with a van transfer to the Chiusi train station after breakfast on Saturday. We arrive around 10:00 a.m. to make connections to Florence. There are later trains for Rome, or other destinations.