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Nothing can surpass the exquisite beauty of the countryside of Tuscany-it is breathtaking. If you meander into the hill towns any time of the year, all your senses are rewarded with the splendors that this enchanting area of Italy has to offer. Almost every hillock is crowned with a picture-perfect walled town; fields are brilliant with vibrant red poppies; vineyards in all their glory and promise lace the fields; olive trees dress the hillsides in a frock of dusky gray-green; pine forests unexpectedly appear to highlight the landscape. As if these attributes were not enough, tucked into the colorful villages is a treasure-trove of some of the finest small hotels and bed and breakfasts in Italy. If this is still not sufficient to tempt you away from the normal tourist route, remember that the food and wines are unsurpassed.

If you are planning to include Florence on your trip to Italy, slip away into the countryside and treat yourself to Tuscany. You will be well rewarded with a wealth of memories that will linger long after you return home. The following itinerary suggests two stops-one in Chianti Classico wine region and the other in Southern Tuscany.

A convenient place to begin your journey is in Florence, Tuscany's jewel. Magnificent art is not confined to the city limits of Florence and you will see impressive cathedrals and museums hosting spellbinding works of art throughout Tuscany. See the Italian Highlights by Train & Boat-or Car itinerary for sightseeing suggestions for Florence.

Pacing: To explore the hill towns of Tuscany you need at least a week (in addition to the time you allocate to Florence). We recommend a minimum of four nights in the heart of Tuscany's Classico Wine Region, which stretches from Florence south to Siena. This will give the minimum time needed to enjoy the tranquil beauty of the hill towns and to sample the delicious Chianti wines. The second suggested stop is southern Tuscany where we suggest three nights to explore the stunning small towns that dot the hillsides, visit breathtaking monasteries, and taste more of Italy's superb wines: Vino Nobile, grown near Montepulciano, and Brunello, grown near Montacino.

Tuscany is laced with narrow roads that twist through the picturesque countryside. Take a detailed map so that if you get lost, you can find your way home, but part of the joy of Tuscany is to be unstructured. Enjoy the freedom to discover your own perfect village, your own charming restaurant, and your own favorite wine. Although in your wanderings you are sure to find some very special places that we have missed, we share below some of the towns we find irresistible and vineyards that are especially fun to visit.


This idyllic area lives up to every dream of Tuscany-hills crowned by picture-perfect villages, medieval walled towns, straight rows of towering cypresses, romantic villas, ancient stone farmhouses, vast fields of brilliant poppies, forests of pine trees, vineyards stretching to the horizon. Instead of moving about, packing and unpacking, choose a place to stay anywhere within the area and use it us your hub for exploring this utterly beguiling region of Italy. Below we give suggestions for towns to visit and some of our favorite wineries.


Monteriggioni: If you are looking for a town that is truly storybook-perfect, none can surpass the tiny, magical hamlet of Monteriggioni. It is such a gem that it is hard to believe it is real and not a creation by Disney! You can spot it from afar, nestled on the top of a small hill, with 14 towers punctuating the perfectly preserved enclosing walls. No cars are allowed here, so you have to park in the designated area below the walls before walking up to the town, which is composed almost entirely of a main square with small streets radiating from it. On the square you find a Romanesque church, restaurants, boutiques, and shops selling olive oil, cheeses, and wine. It takes only a few minutes to stroll from one end of the town to the other but I assure you, you will be enchanted. As a bonus, Monteriggioni produces its own fine wine, Castello di Monteriggioni.

Passignano in Chianti: Passignano in Chianti is rarely on a tourist route, but we can't help mentioning this tiny hamlet that exudes such a tranquil beauty. For sightseeing, there really isn't much to see except the Badia a Passignano Abbey, founded by Benedictine monks in the 11th century. The abbey is set in a pocket of lush landscape and dominates the village, which is no more than a cluster of houses and a restaurant. However, as you drive into the valley, approaching from the west, the abbey with its towering ring of cypresses has such an idyllic setting that it is one of our favorites-a photographer's delight. The abbey can be visited on Sundays at 3 pm; tours leave from the church (please check to verify the abbey is open the Sunday you want to visit). Fine wines, produced by the abbey's vineyards, can be purchased at the Osteria, tel: (055) 80 71 278.

Radda: Located in the very heart of the Chianti wine region, Radda makes a good base of operations. However, not only is the town very conveniently located for sightseeing, it is also extremely quaint and some of its walls are still intact. It was in Radda in 1924 that 33 producers gathered to create a consortium to protect a very special blend of wine that was known as Chianti Classico. Only vintners who maintain the standards of the consortium are allowed to proudly display its symbol of the black rooster.

San Gimignano: During your exploration of Tuscany, one town you must not miss is San Gimignano. What is so dramatic about San Gimignano is that at one time the walls of the town were punctuated by 72 towers. During the Middle Ages it was a status symbol for noble families to build their own personal towers for their protection-the higher the tower, the greater the image of wealth and importance. It is amazing that 14 of the original towers are still standing. They make a striking silhouette, soaring like skyscrapers, and on a clear day you can see them on the horizon from far away. San Gimignano is truly a jewel-plan to spend at least a day here. There are many shops and marvelous restaurants tucked along the maze of streets. On Fridays there are walking tours with English-speaking guides that leave from the Porta San Giovanni at 11 am (best check with the tourist office to be sure the time and day haven't changed). One of our favorite restaurants in San Gimignano is the delightful Ristorante Dorando, which has great food served in cozy rooms with coved ceilings that create the ambiance of an old wine cellar. Located on Vicolo del Oro 2, a small side street just off Piazza Duomo, tel: (0577) 94 18 62. Another favorite, Ristorante II Pino, offers mouthwatering homemade pastas-some of the best we have ever eaten. Located on Via Collolese, 8-10, just down the street from L'Antico Pozzo, tel: (0577) 94 04 15.

Siena: This is an entrancing walled hill town that deserves many hours to savor its rich delights-you should allow yourself at least one full day here. The ramparts are perfectly preserved with a series of massive gates guarding a meticulously maintained medieval stronghold. Drive as close as you can to the main square, park your car, and set out to explore on foot. You cannot drive into the center of the city, but there are designated parking areas (marked by "P") near each of the gates. One of the most convenient is the parking at the Porta Romana. Once you leave your car, strike off for the giant Piazzo del Campo. This central piazza is immense and, instead of being square, is fan-shaped and slopes downward like a bowl. Eleven streets surrounding the square converge into it like spokes of a massive wheel. Like the Spanish Steps in Rome, the Piazza del Campo is a favorite for tourists who linger here just enjoying the medieval ambiance. It is in this gigantic piazza that the colorful Palio delle Contrade (dating back to the 11th century) takes place twice a year, on July 2 and August 16. The horse race is only a part of a colorful spectacle of medieval costumes, impressive banners, and parades, and the festivities extend beyond the actual date of the races. Monopolizing one side of the Piazza del Campo is the 13th-century Gothic Palazzo Pubblico (Town Hall) whose graceful arches are embellished with Siena's coat of arms. The Palazzo Pubblico is open as a museum where you can stroll through the governor's living quarters.

Although Siena looks like a large city, it is easily negotiable on foot and most of the museums are in one small area. After visiting the Piazza del Campo, most of the other major places of interest are just a few minutes' walk away, clustered about the Piazza del Duomo. There are excellent tourist signs that will guide you along the maze of narrow streets to all the museums.

You absolutely must not miss Siena's 12th-century Duomo, facing the Piazza del Duomo. This is one of Italy's most astounding cathedrals. Not only is its exterior breathtaking, but once you enter, you will be overwhelmed by its dramatic black-and-white, zebra-striped marble columns. Don't miss the intricately carved, 13th-century panels depicting the life of Christ on the octagonal pulpit. Also, be sure to see the Piccolomini Library. You need to buy a ticket to enter, but it is well worth it. This relatively small room is totally frescoed with gorgeous murals in still-vibrant colors portraying the life of Pope Pius II. The cathedral also has 59 fabulous inlaid-marble mosaic panels on the floor depicting religious scenes. However, some of the most precious of these are covered to protect them and are on display only from the end of August to the first of October.

After visiting the Duomo, the following museums are just steps away. One of our favorites is the Ospedale di Santa Maria della Scala, located across from the entrance to the Duomo. At first glance, it is difficult to truly appreciate its wealth of things to see. The museum goes on and on-it is enormous. Just when you think you have finished, a discreet sign will lead you ever downwards to a lower level and a stunning array of artifacts. The building, dating back to the 800s, was originally constructed as a hospital. Be sure not to miss the former infirmary with its lushly colored frescoes by the master Domenico di Bartolo depicting scenes of patients being treated by their doctors. Another nearby museum is the Baptistry, a small museum that, as its name implies, houses the baptismal font for the Duomo. In addition to its beautifully frescoed walls and vaulted ceiling, of prime interest is the 15th-century baptismal font, which is adorned by religious scenes cast in bronze by some of Italy's most famous Renaissance masters, including one panel by Donatello. The Museo dell’Opera Metropolitana is worth a visit if for no other reason than to see the sublime Maestá by Duccio, painted in 1311. The central scene of the Virgin Mary is truly awesome. For art lovers, the Museo Civico must not be missed. Here you will see stunning masterpieces by Ambrogio Lorenzetti, Spinello Aretino, and Simone Martini. It is overwhelming to ponder how Italy could have produced so many geniuses.

NOTE: There is a comprehensive ticket valid for three days that allows you entrance into many of Siena's prime sightseeing attractions-this is a bargain compared to buying individual tickets. When you buy your ticket for the first museum ask about it and which museums it includes.

Volterra: Just a short drive from San Gimignano, Volterra is a delightful, non-touristy town enclosed by still-intact, 12th-century walls. Like so many of the cities founded by the Etruscans, Volterra is built upon the flat top of a steep hill. As you drive toward the city, the landscape becomes increasingly barren, since the soil is not conducive to growing grapes or olive trees. Instead, alabaster is king here and objects made of alabaster are sold in all of the shops. Not to be missed is the alabaster museum called Museo Etrusco Guarnacci, which has a fabulous collection of works of art, including sculptures and beautiful vases, displayed with great taste in a series of interlinking rooms that show the art to perfection. There is an adjacent shop selling many alabaster items. The whole town is a jewel whose charm is best experienced by strolling through the narrow cobbled streets. Its main square, Piazza dei Priori, the heart of the town, is surrounded by fine examples of beautifully preserved medieval buildings and with its towers, splendid town hall (the oldest in Tuscany), and Romanesque church, it is considered by some to be one of the finest squares in Tuscany. Stroll to visit one of the main gates, the Porta all’Arco, the origins of which date back to the 7th century B.C. During World War II, the loyal citizens of Volterra buried the stones of the gate to keep the Nazis from blowing it up.


The production of wine plays an enormous role throughout Tuscany, and between Florence and Siena (where Chianti Classico is produced) you are constantly reminded of this as you pass through vast rolling hills splendidly adorned with neatly tended vineyards. The Chianti Classico area covers over 172,000 acres, with Siena and Florence being the two "capitals" of the region. Included in the area are the towns of Castellina, Gaiole, Greve, Radda, and some of Barberino Val d'Elsa, Castelnuovo Berardenga, Poggibonsi, San Casciano Val di Pesa, and Tavarnelle Val di Pesa. Even if you are not a wine connoisseur, it would be a pity not to make at least one winery stop both for the fun of observing the production process and for an understanding of the industry that is so central to the soul and character of Tuscany. Many of the wineries also have gift shops and sell marvelous olive oils and cheeses in addition to wine.

As you meander through the countryside you see signs with Chianti Classico's black rooster symbol and you can buy directly from the producer where you see Vendita Diretta. In some cases there are also tours of the winery (these are sometimes free, but sometimes there is a charge). A Cantina sign means that the winery has a shop where wine is sold and can usually be sampled. One of the delights of touring the back roads of Tuscany is just to stop on whim. When you spot a Vendita Diretta, drive in, introduce yourself, and sample some wines. You might well discover one that will become one of your favorites.

Some of our favorite wineries to visit are listed below:

Castello di Brolio: If you visit only one winery, Castello di Brolio should be it since this is not only one of the oldest wineries the world, but also where Chianti wine was "born." Although the production of wine in Tuscany dates back to Etruscan times, the enormously wealthy Ricasoli family, owners of the Castello di Brolio since 1167, are responsible for the special blending of grapes we now consider "Chianti Classico." At one time the extremely powerful Ricasoli family owned most of the land and castles lying between Florence and Siena. The remote family castle, Castello di Brolio, had largely been abandoned when Bettino Ricasoli decided to move into it (so the story goes) after becoming jealous at a winter ball in Florence when his young bride danced a bit too closely to one of her young admirers. Thinking it best to take his wife away from temptation, he rebuilt the huge, remote, crenellated castle, replanted the vineyards, and experimented with the blending of grapes, coming up with the original formula that forms the basis of what is known today as Chianti Classico. The fortified castle tops a high, forested hill. You leave your car in the designated parking area and climb for about 20 minutes up a path or on the road through a parklike forest to the castle gates. Open daily from 9 am to noon and 3 pm to sunset. The castle is located about 10 kilometers south of Gaiole. Tel: (0577) 73 02 20, www.ricasoli.it.

Castello d’Albola: The Castello d'Albola, a spectacular property just a short drive north of Radda on a gentle hill laced with grapes, is owned by the Zonin family, who have restored the entire medieval complex beautifully. This is an intimate, extremely pretty place to taste wines and take a tour. What we particularly like about the Castello d'Albola is that it is in such a beautiful setting and offers delightfully informal, friendly, free tours. Drive up the hill to the castle, leave your car in the parking area, and walk into an inner castle courtyard, off which you find the winetasting room and cantina. Before or after winetasting, your hostess leads you on a short, professional tour showing you how fine wines are produced. The owner has other enormous estates as well as the Castello d'Albola and is one of the largest producers of wine in the world. Tours start at noon, 2 pm, and 5 pm daily. The cantina is open for complimentary wine tasting daily, April to October from 10 am to 6:30 pm (9 am to 5 pm November to March). Tel: (0577) 73 80 19, www.albola.it.

Castello di Volpaia: The 12th-century Castello di Volpaia, located on a narrow lane about 7 kilometers north of Radda, is one of our favorite places for winetasting. Plan to spend a day on this outing, with ample time to meander through the countryside en route, tour the winery, taste the superb wines, and enjoy a wonderful lunch at the winery's excellent restaurant, La Bottega. Although the winery is called Castello it really isn't located inside a castle at all, but rather in various medieval stone houses in a picture-perfect village wrapped by vineyards where you find a small church, a cluster of houses, La Bottega Ristorante, and the winetasting room. You need to preplan this wine tour and also make reservations for lunch since both are very popular and usually booked far in advance. There is a fee for the tour based on the number of people in the group. Tel: (0577) 73 80 66, www.volpaia.com.

Castello di Meleto: Another favorite destination for wine- tasting is the beautiful Castello di Meleto, which has an idyllic setting in the gentle hills near the town of Gaiole. Just across from the dramatic castle you find a pretty winetasting room and gift shop where fine wines and olive oils produced on the estate can be purchased. On request, tastings of olive oil and aromatic vinegars can be arranged. What makes this a very special experience is that there is an added bonus: not only can you sample wines, but you can also visit the beautiful interior of the castle. In addition to splendidly frescoed rooms, the castle has one exceptionally intriguing feature-a whimsical private theater complete with its original stage settings. Call ahead, tel: (0577) 73 80 66, to find out the time and cost of the guided tours of the cellars and castle. The Castello di Meleto also offers bed & breakfast accommodation.


The area of Tuscany that lies south/southeast of Siena is famous for its superb wines. A great bonus is that these vineyards are in one of Italy's most picturesque regions, filled with quaint villages and amazing abbeys, thus making your adventures even more enchanting. Whereas Chianti Classico wine is renowned in the area between Florence and Siena, the vineyards farther south also produce some of the mostly highly regarded wines in the world, the most famous of these being Vino Nobile, grown near Montepulciano, and Brunello, grown near Montacino. There are many wineries open to the public where wine can be tasted and purchased. Many winetastings are free, although some wineries charge a minimal fee. As you drive through the countryside look for signs reading Cantina (wine shop) or Vendita Diretta (direct sales).


We suggest a loop that covers some of our favorite wineries, medieval towns, and picturesque abbeys. It would be impossible to squeeze everything in this itinerary into one day unless you rush madly from place to place. Therefore, if your time is limited, don't stop at each place suggested but just choose a few of the sightseeing suggestions below that most appeal to you. But better yet, take several days and follow the itinerary in its entirety, covering a small section each day at a leisurely pace.

This loop begins in Montepulciano, a rare jewel of a walled hill town that not only oozes charm in its narrow, cobbled streets but is also center stage for the delicious Vino Nobile di Montepulciano. This wealthy town was home to many aristocrats who built magnificent palaces here. The heart of the city is the Piazza Grande where you find the dramatic 13th-century Palazzo Comunale accented by a stone tower. Also facing the square is the picturesque Palazzo Contucci, fronted by a charming Renaissance well decorated with the Medici coat of arms and highlighted by two stone lions. Leading off the Pizza Grande are small streets that crisscross the town, connected by staircases.

A masterpiece you absolutely must not miss when visiting Montepulciano is the Temple of San Biagio, a stunning church located on the west edge of town. You can walk from town, but it is a long way down the hill and then back up again, so you might want to drive, especially in hot weather. Made of creamy travertine, the church's façade is extremely picturesque and its elegant interior is equally lovely-nothing cluttered or dark but rather light and airy, with fine marble pastel-colored walls.

Within Montepulciano there are many boutiques, restaurants, and cantinas selling wine. Our favorite wine shop here is an extremely special one, the very old Cantina del Redi, located just down the street from the Piazza Grande with its entrance next to the Palazzo Ricco. Once you enter, an ancient staircase leads ever deeper into the hillside, passing rooms filled with huge wooden casks of wine. When you finally reach the lowest level, you wind your way through more casks until you arrive at the cantina where you can sample and purchase wine. When finished, you discover that you have descended quite a way down the hillside and the main entrance to the winery faces onto a lower terrace.

Another of our favorite wineries, Dei, is just a few kilometers outside Montepulciano's city walls. What is especially fun about this winery is that it is family-owned and managed by the lovely daughter, Maria Caterina Dei, who still lives in the beautiful family villa on the property. Maria Caterina is passionate about wine and with great professionalism can explain about the production of the Dei wines, which have won many awards. Before taking over the family's vineyards, the multi-talented Maria Caterina trained in music and the theater, and sometimes she entertains the guests during wine tours. There is a fee for tours, depending upon what is requested. Lunches and winetasting can be prearranged. Call in advance for tours: Dei, Villa Martiena, Montepulciano, tel: (0578) 71 68 78, www.cantinedei.com.

Leaving Montepulciano, take the S146 west toward Pienza. After driving about 3 kilometers, take a small road on the left marked to Monticchiello. You soon arrive at a sweet, tiny, charming walled town whose allure is its unpretentious, non-touristy ambiance. Park your car in the designated area outside the main gate. As you enter through the gate, you will see on your left La Porta, a charming restaurant with an outside terrace sitting on the town walls-a great place to stop for lunch. As you stroll through Monticchiello (it won't take you long), take a look inside the 13th-century church where you will see a beautiful altarpiece by Pietro Lorenzetti.

From Monticchiello, continue on the back road to Pienza. This is one of our favorite walled hill towns in Tuscany, a real gem that mustn't be missed. The town is perched on the top of a hill and is pedestrian-only so you need to park your car outside the walls. It is no wonder that the town is so perfect even though so tiny: it was here in the 15th century that Pope Pius II hired a famous architect, Bernardo Rossellino, to totally redesign the town where he was born, making it into a masterpiece. You will find many restaurants if you are inclined to dine.

Leaving Pienza, take S146 west to San Quirico d’Orcia, a very attractive small medieval town with a lovely Romanesque church. If you stop to see the town, you must not miss its lovely garden, called Horti Leonini. An entrance about a block from the main square leads into a tranquil Renaissance garden, originally designed as a beautiful resting place for the pilgrims who stopped here on the road to Rome. This cool oasis with clipped box hedges and shade trees makes an interesting stop. If you are hungry, the Osteria del Leone makes a good choice for lunch.

From San Quirico d'Orcia, head south on S2 for about 6 kilometers and watch for a small road to the right leading to Bagno Vignoni. This is a most unusual, very small town, known for the curative value of its hot sulphur springs. In the center of town, you find what would have been the town square made into a huge sulphur bath built by the Medicis. The pool is surrounded by picturesque medieval buildings that complete the interesting scene.

Leaving Bagno Vignoni, don't continue on the S2, but take S323 directly south for 12 kilometers and then turn right following signs to Montalcino. In a few minutes you come to Castelnuovo dell'Abate where, just a few minutes outside town, you will find the superb Romanesque Abbey Sant’Antimo, whose origins date back to the 9th century when it was founded as a Benedictine monastery. The abbey-a simple, pastel-pinkish stone church serenely set amongst fields of olive trees-makes a beautiful picture. Try to arrive at 11 am or 2:45 pm when the Benedictine monks, clad in long, pure-white robes, gather at the altar to chant their prayers in Latin. This is a haunting, beautiful experience. The singing lasts only a short time, and the times might vary from the ones we mention above, so to confirm the schedule call, tel: (0577) 83 56 59.

Leaving Castelnuovo dell'Abate, drive north on the road for Montalcino. In a few minutes you will see a sign to the Fattoria dei Barbi. Turn right and follow a small road up the hill to the Barbi winery, an excellent winery to visit. It is extremely pretty with many gardens and a charming cantina where you can sample the vineyard's fine wines and purchase wine and other gift items. Its restaurant serves wonderful meals made with only the freshest products, accompanied, of course, by their own wines. Tours of the cellar are available Monday to Friday with tours led at  12 noon and 3:00pm. The cost of the tour is €5.00 per person. www.fattoriadeibarbi.it.

After your visit to the Fattoria dei Barbi, continue north for 5 kilometers to Montalcino, which is world famous, along with Montepulciano, for its superb wine, Brunello di Montalcino. There are many places in town where wine can be tasted and purchased. In addition to wine, the town is famous for its fine honey, which can be purchased in many of the shops. Montalcino is fun for wandering-it is not large and you can in no time at all cover the area within the walls by foot. On the east edge of town is an imposing 14th century fortress.

From Montalcino, head south on the road to Grosetto for a little over 3 kilometers to another of our favorite wineries, Poggio Antico. Excellent tours are offered and, of course, you can also sample the superb wines. These tours are very popular so you should reserve in advance at tel: (0577) 84 80 44, www.poggioantico.com. For dining, the winery's Ristorante Poggio Antico serves outstanding Tuscany cuisine. Reservations for the restaurant are also highly recommended-tel: (0577) 84 92 00, email: rist.poggio.antico@libero.it.

After visiting Poggio Antico, retrace your way north to Montalcino and continue on for 9 kilometers to where the road intersects with the S2. Turn left here, going north toward Siena. In 10 kilometers, turn right on S451 and continue for another 10 kilometers to the Abbazia di Monte Oliveto Maggiore. Founded in the early 14th century by wealthy merchants from Siena as a Benedictine retreat, this fascinating abbey is well worth a detour. Be prepared to walk since you must park your car and follow a long path through the forest to the abbey's entrance, which is through a gatehouse crowned by a beautiful della Robbia terracotta. Once through the gate, you continue through the woodlands to the huge brick complex. After visiting the church, it seems you could wander forever through the various hallways. Before you get too distracted, however, ask directions to the cloister because you don't want to miss this marvel. Here you find 36 frescoes depicting scenes of the life of St. Benedict, some painted by Luca Signorelli, others by Antonio Bazzi.

In the region around the abbey you will come across an entirely different type of landscape, called the crete. Here, tucked among the green rolling hills, you unexpectedly come across bleak, canyon-like craters, caused by erosion. These are especially out of character as the surrounding scenery is so soft and gentle.

From Abbazia di Monte Oliveto Maggiore, weave your way through the small back roads to Montepulciano. Follow signs to San Giovanni d'Asso, then Montisi, then Madongino, then Montefollonico. Take time to stop in Montefollonico because this is another "sleeper"-a quaint, small, medieval walled town that is fun to explore. For the gourmet, there is a superb restaurant on the edge of town called La Chiusa.

From Montefollonico, go south on S327. When you come to the S146, turn left to complete your loop back to Montepulciano.

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A Karen Brown Recommended Hotel / Inn Marignolle Relais & Charme
Florence, Tuscany, Italy
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Tuscany, Italy
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Umbria, Italy
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Tuscany, Italy
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Umbria, Italy
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Tuscany, Italy

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[ icon ] Tenuta di Canonica
Todi, Umbria, Italy
Italian Cuisine
[ icon ] Fornace di Meleto
Gaiole in Chianti, Tuscany, Italy
Italian Cuisine
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Castelnuovo Berardenga, Tuscany, Italy
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Montepulciano, Tuscany, Italy
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