We transfer to a fattoria/winery that was once home to a 16th century bishop.  After a look about the grounds walk to a beautiful little hamlet dominated by a 13th century Abbey.  Pass by the many vineyards of the famous Chianti wineries, and for those that wish, we can stop in for a tasting.  Our loop back via a trail lined by oak and pine forest passes several abandoned stone farm houses en route to the estates vanishing edge pool where a crisp dry rose is waiting.

The following day a long ridge path allows us to enjoy the vast views for which the region acquires its fame. This gentle walk through serious wine country drops into a tiny hamlet of stone houses and vine-covered walkways.  After lunch we visit one of the medieval villages that formed the Chianti Alliance 500 years ago as well as the ancient Abbey of Coltibuono, where the art of wine, honey and olive oil production has been perfected for hundreds of years which we sample. Enjoy in a special sampling of these many products with an optional wine tasting. At the end of our day's walks an optional hands-on Tuscan cooking class, winery tour and tasting is offered at the fattoria we stay.

Lodgings: A very friendly & quiet farmstead/Villa within the Chianti Classico.

The soft colorful landscapes of fine lines formed by the numerous vineyards,gently rolling hills and fields of sunflowers are unforgettable within this idyllic route of the Chianti.  At the end of our path we stop at the important Etruscan tombs of 700 BC and following a tour of the grounds a grand gourmet picnic lunch, featuring many of the regions specialties, is fully appreciated.  After lunch, and before we leave the Chianti Classico region we enjoy a brief visit of the 3rd medieval village that formed the Chianti Alliance, Castellina in Chianti.

It’s not long before one begins to see the diversity Tuscany offers. Our afternoon walking-path follows an old farm road and soon displays an entirely different panorama than any we have witnessed thus far as rolling hills dotted with farmsteads of wheat, and sunflower unfold before us. This quiet approach to the northern gate of San Gimignano soon has everyone looking for their camera as the unforgettable sight of the "medieval skyscrapers" come into view. We arrive early enough that you can enjoy some shopping and a nice glass of the crisp white wine the region is famed. Before dinner an optional brief city tour is arranged that includes a visit of La Rocca for the perfect photo op.

Lodgings: Two days at a family run hotel in the historic center of San Gimignano.

From a tiny quaint village known for its production of the famed Vernaccia white wine we walk along a wooded path and into a peaceful nature reserve that was once an ancient Etruscan salt road that leads to a fascinating ruinous village and castle.  This long-forgotten site of Castelvecchio not only offers us splendid views, photo-ops & exploration, but has recently roused archaeological interest and allows us the chance to visit a site still being uncovered.

The afternoon offers us two great options.  We can either end our walk here to visit the significant Etruscan and medieval-town of Voltera, where the finest Etruscan museum is considered a “must see”. Or we continue walking from the fortress, in which case we’d follow a trail that is lined by poppy and sunflower fields along a quiet country road to Isola d’Abazzia (island abbey) which we will explore before walking up to the completely walled multi-towered medieval outpost, Monteriggione.

No soldier of rank lived within the walls, but it was the important fortress of Monteriggioni for the Sienese foot-soldier during their middle age battles with Florence.  Once Siena was conquered, the Florentines considered the fortress insignificant. We take time to explore the grounds that until 1960, when it was slowly brought back to life, was populated by fewer than 20 people.

For those interested in a Vernaccia wine tasting, both options allow for a return to the tiny hamlet we began our morning. Another wonderful dinner is planned in the old city.

Our exploration now takes us south of Siena to a region much less known to the tourists that visit Tuscany. We witness the strange landscape known as Crete, a bare, ash gray soil of deeply fissured hills and vast views then walk along the original stone path of medieval & ancient Rome.  These farm tracks within the rolling hills forested with black cypress & scrub oak and the "strada bianca", often seen as Mary’s pathway to heaven in medieval religious art are our primary walking routes.  Along the way we visit the Abbey of Monte Oliveto Maggiore. Here the significant frescoes of Sodoma & Signorelli are on displayed.

Our route eventually leads us to the cloister of Sant'Anna di Camperna—the location for the filming of the "English Patient" and then to Pienza for a cheese tasting. For those that express interest we make a detour to the nearby land of Brunello wines.  An extensive tasting of these wines, one of Italy's most prestigious, can be scheduled at the end of our day and if time allows we will visit the Abbey of Sant'Antimo where the Gregorian music in the background offers a mystical air to this magical place. 

Lodgings: A 4-star converted palace within the medieval gate of Pienza.

In the morning we transfer north to Siena, the ancient arch-rival of Florence, for a private tour of the regions most important town. We start from what many think is the most beautiful square in the world, and location of the renowned “Palio” horse race. We soon uncover its past and discover a medieval treasure with a unique and proud spirit. 

In the afternoon we have the option of extending our exploration of the city or doing a side-trip to the home of the original Chianti blend, Castle di Brolio. Here we enjoy a look around the castle grounds then enjoy a wonderful wine tasting. For those partaking in the 6-day package you will be transferred to the Siena train station or as pre-arranged.

Lodgings: In Siena, a 3-star hotel with old-world charm and modern conveniences. 

Transportation Logistics

The following is a list of train schedules for transportation to and from the tour start and end locations. Train departure times and tracks are subject to change, so verify before boarding.

Trains from Rome to Firenze/Florence (tour start): ~1.5 hour 
#9310 Roma Termini departs 9:00 AM, arrives in Firenze S. M. Novella 10:37 AM

From Pisa to Firenze/Florence: ~1 hour 
#3110 Pisa Centrale departs 10:27 AM, arrives Firenze S. M. Novella 12:45 PM

From Milan to Firenze/Florence: ~3.5 hour 
#9433 Milano Centrale departs 10:00 AM, arrives Firenze S. M. Novella 12:45 PM

From Chiusi (tour end) to Rome: ~1.5 hour (departs every half hour) 
#577 Chiusi-Chianciano Terme -09:35 AM, arrives Roma Termini 11:03 AM