Tuscany is famed as one of the most picturesque regions of Italy, renowned for its rolling green countryside, world-class wines and historic landmarks like the Leaning Tower of Pisa and the Ponte Vecchio of Florence. Native Toscani believe that their state is the cultural, architectural and culinary capital of Italy. They also take credit for the modern Italian language.

Tuscany is also home to some of the most stunning small towns, each with its individual charm, character and postcard-worthy views. Often surrounded by heavy fortified walls with fortresses and towers, these cities are a legacy of the Middle Ages and a testament to the wealth and prestige that the area enjoyed during the medieval period.

Outside the cities, are magnificent medieval castles, over 150 in Tuscany alone. While some of these architectural masterpieces are well preserved, others lie in ruins and are mere fragments of their former self. They were once the bastions of power for feudal warlords and ruling families that dominated the political and social landscape of what was then a collection of city-states.

If you are looking for an escape from some of the more tourist infested towns of Florence, Pisa and Siena, you may want to take a journey back in time to the countryside of Tuscany with its commanding castles, fortresses, watch-towers, and walled cities. Fortunately many of the most picturesque towns are located within the Chianti region so you can combine you love of history and architecture with indulgence in wines that have grown in this region for centuries. All are located within an hour's drive of Florence so we recommend hiring a car for a few days to experience the beauty that is rural Tuscany. Once you get off the main highways (autostrade) with their racing Ferraris and total disregard for speed limits, you will discover more tranquil and relaxing driving conditions.

Located on the road between Florence and Siena, some 10 miles outside Florence, and on the northern edge of the Chianti region is San Casciano Val di Pesa -- a long name for a town with a long history dating back to the Roman era. In the13th century, the city, best known for its wine production came under the rule of Florence. In the 14th century, following several attacks by rival states, the massive fortified walls were constructed, most of which are intact today. From the city walls, the view of the surrounding vineyards is breathtaking. Just outside of San Cascino is the Castello Bibbione, an imposing14th century castle that was once the hunting lodge of the Prince himself, Niccolò Machiavelli.

Less than 20 miles west of San Casciano is the pretty hillside town of Certaldo, another walled city with superb views, some historic tourism attractions and next to no tourists. It is here that the author of The Decameron, Giovanni Boccaccio was born and later interred. Rare copies of his book are housed at a library/museum in the walled upper city (Certaldo Alto) and there is also a museum of Etruscan and Roman artifacts located within the impressive 14th century Palazzo Pretorio. The walled city is a labyrinth of small cobblestone streets with shops and restaurants.

Another eight miles south is the quintessential walled city of Tuscany, San Gimignano. Here, unfortunately, you will come face to face with tour buses, but you can avoid the crowds by visiting early in the morning or late in the afternoon, when most groups have disappeared. The city of towers is a glowing tribute to the architects and craftsmen of the Middle Ages. Today, 13 original towers still stand, although in its heyday, the towers numbered more than 70. San Gimignano is lined with palaces and churches, quaint shops and expensive restaurants to satisfy your hunger for Tuscan fare.

Volterra, a city over 3000 years old, is highly under-rated as a tourist destination. It possesses incredible charm and beauty with so few tourists, that you'll wonder why it hasn't been over-run with tour buses by now. The city is built atop a large hill, some 1500 ft above sea level and is surrounded by picturesque green valleys. Impressive medieval walls and ramparts encircle the city, with fortifications in excellent condition. You can stay in one of a hotels converted from monasteries and convents, or a hotel that is built into the city wall ( to enjoy the same view as visitors did hundreds of years ago. The main attraction, besides the quaint Tuscan town environment is the abundance of Etruscan tombs, located just outside the city. The Etruscans were the first inhabitants of the area (from the 12th to the 4th centuries BC) and they buried their dead in unique decorated vaulted tombs. Within the city area are a 14th century fortress, an Etruscan gate (Porta all'Arco) an Etruscan museum and a well-preserved Roman theatre and bath complex. The fact that cars must park outside the city walls helps to ensure that the city remains decongested and peaceful. If you happen to be visiting during September, on the first Sunday of the month, the Astiludio, a colorful and historic flag throwing competition takes place in Volterra.

It is quite refreshing to note that the town of Barga, in the Garfagnana region of Tuscany is rarely featured in Italian travel guides (Frommer's aside). This 12th century walled city may boast small tourist numbers but it is a great example of Medieval Tuscany with a maze of small piazzas, shops and galleries located on narrow streets, which criss-cross the hillside before reaching the main piazza at the top, with its grand cathedral (duomo) built in the 9th century.

When to Go and How to Get There

September is a great month to visit Italy -- the climate is sunny and mild and the peak tourist season has ended so hotel prices start coming down. Go-Today (tel. 800/277-3235; has a super cheap fly/drive package deal that gives you the freedom to explore the beauty of Tuscany or other parts of Italy at your own pace. For $649 plus taxes, Go-Today gives you round-trip airfare to Rome from New York, seven-day Hertz car rental, local taxes (rental fees and/or surcharges may be extra), unlimited mileage and collision damage waiver. Add $30 from Boston or Philadelphia, $140 from Chicago or Miami and $239 from Los Angeles or San Francisco. Valid for departures from September 1 to 30, 2005 (October departures are $20 less). Their five-day self-guided "Biking Italy: Treasures of Tuscany Mini Break" starts at Montepulciano and ends in San Gimignano. The $1049 per person price includes four-nights accommodation (Montepulciano, Montalcino, Siena and San Gimignano), breakfast daily, bicycle and equipment, luggage transfers, a local contact for questions, detailed route notes and map. Or go the extra mile with two extra nights and end up in Florence for another $340 on the "Treasure of Tuscany Bike Tour". Bookings must be completed by June 5, 2005 for travel until October 31, 2005.

Cheap Flights ( has a selection of discount airfares to Rome, starting at a low $349 round-trip direct from New York on United Airlines during June. Alternatively you can fly for as low as $330 with one stop from October 27 to December 15, 2005. You can also fly to Florence or Pisa, but these are regional airports that are serviced by smaller aircrafts with less regular flights, for often-higher prices.

Accommodation in the Chianti region comes in all forms -- from hostels and budget bed and breakfasts to lavish private villas with swimming pools and grounds. If you're looking for a central location at reasonable prices the Antica Pieve Bed and Breakfast (tel. 39/055-8076314; is an ideal spot. Prices range from $57 to $77 per person, depending on the season and although breakfast is included, they can also arrange a traditional Tuscan dinner. The swimming pool is a welcome addition on hot summer afternoons. An intimate hotel with only six rooms, it is located half way between Florence and Siena on the ancient Cassia Roman road in Tavarnelle val di Pesa.

For other accommodation options, visit,, and, which all provide a booking service and/or links to hotels, villas, farmhouses and bed and breakfasts in various price ranges within the Chianti area.

For maps and information highlighting the castles of Tuscany, visit For more information about traveling in Tuscany visit

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