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 and is responsible for the 2,500-acre estate of the Castello di Brolio. Five hundred of those acres regularly produce wines of exceptional quality, scoring consistently above 90 points in Wine Spectator magazine. Massi’s other passion is cooking, and we're lucky to be invited into his home for a fabulous home-cooked lunch.  Afterwards, visit the cellars and enjoy a tasting with Massi as your guide. A short van transfer then takes you to your hotel in Gaiole in Chianti, the four-star Castello di Spaltenna. (or similar). Keen walkers can do a late afternoon walk up to the medieval hamlet of Vertine, otherwise just relax until we meet at 7 p.m. for aperitivo, the Italian version of cocktail hour. Dinner tonight is in the village square.

The Walk:  1 hour in the morning, relatively flat but sometimes rolling. Optional afternoon walk: 6 km (4 mi) loop over rolling, hilly terrain. Overnight Gaiole in Chianti or Radda in Chianti. 

Hotel, breakfast, lunch and dinner included.

Our morning walk 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 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 hrs in the afternoon through rolling terrain. Overnight in Gaiole in Chianti or Radda in Chianti. 

Hotel, breakfast, lunch 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 to the workshop and showroom of Rampini ceramics, arguably the finest producer of hand-painted ceramics in Italy. Our friend Pino will explain how traditional majolica ceramics are made, and of course the showroom will be open should you want to pick up a few pieces to take home. 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 or Radda in Chianti. 
The Walk:  Urban walking in Siena. Overnight in Gaiole in Chianti or Radda 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 yesterday 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 arrive in Montalcino in late afternoon so you will have time to explore this beautiful hilltop town, renowned for its Brunello wine. Our hotel for the next two nights is centrally located at the entrance to the medieval walls of the town.  It has a charming, old-world feel, being a renovated and re-purposed 18^th century olive press. Risrorante Boccon di Vino welcomes us for dinner tonight. Besides its fantastic cuisine, the view from the terrace over the expanse of the valley below is breathtakingly beautiful.
The Walk:  1.5 hrs in the morning, 1 hour in the afternoon through rolling terrain. Overnight Montalcino. 

Breakfast, lunch, dinner and hotel included.

After breakfast we leave Montalcino on foot for our walk to the 13^th century 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. 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 San Giovese 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 Montalcino for free time to relax by the pool and take in the sweeping views of the countryside or explore the town’s shops, cafés, and wine bars. Tonight’s dinner is at our favourite trattoria in Montalcino, which also happens to have a superb wine list with many old vintages cellared to perfection.
The Walk:  2.5 hrs in the morning, through rolling terrain, mostly downhill. Overnight Montalcino.

Breakfast, lunch, and hotel included.

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