hill towns of umbria and tuscany - detailed itinerary

  Orvieto Spoleto Assisi Siena San Gimignano Lucca

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Day 1 - Orvieto
Pick up your rental car in Rome this morning and leave the city on Via Cassia bound for the little town of Bagnoregio.

Find a place to park your car, then follow the signs to Civita, one of Umbria's hidden jewels. The tiny town – which is comprised of a church, a main square, and a few narrow alleyways – is reached by walking across a long donkey path spanning a deep gorge. The 180 degree views of the surrounding canyon are absolutely breathtaking. Bring lots of film.

There's one restaurant in town, Al Forno, and a wine cellar on the main street. Relax. And take in the sights and sounds of Italian village life as it has existed for centuries.

Return to Bagnoregio, which by comparison is bustling, and drive through rolling vineyards and olive groves to Orvieto.

Perched atop a massive plateau of volcanic tufa, Orvieto is one of the most dramatically situated towns in the region. The Etruscans appreciated the defensive advantages of such a location and founded a town here around 500 B.C.

Get settled into your hotel and then head for the Piazza Duomo. Orvieto has lots of day trippers from Rome, so if the crowds have thinned out already, visit the Cathedral. Otherwise, visit early the next morning before the tour busses arrive.

Orvieto's Cathedral, or Duomo, is one of the finest in Italy. Begun in 1288 to commemorate the Miracle of Bolsena, the church is a remarkably harmonious blending of Romanesque and Gothic – the work of 33 architects, 152 sculptors, 68 painters, and 90 mosaic artists.

The façade, which took 300 years to complete, is the undeniable highlight. The four enormous fluted columns were carved by Maitani, one of the church's original architects. The level of detail in the bas reliefs and sculptures is amazing. And the brilliant rose window dates from the 14th-century.

Be sure to notice the modern bronze portals created by Emilio Greco in 1970.

Inside the Duomo, there are two chapels you mustn't miss. The Cappella di San Brizio contains frescoes of the Last Judgement begun in 1447 by Fra Angelico and completed in 1503 by Luca Signorelli. The frescoes were recently restored at a cost of over $4 million.

The Cappella del Corporale has a jewel-encrusted silver shrine dating from 1338. This reliquary houses the altar cloth of the Miracle of Bolsena. There are also 14th-century frescoes by Ugolino di Prete in the chapel.

When you're ready for a breather, have a refreshing glass of Orvieto Classico at the wine cellar on Piazza del Duomo. Legend has it that Signorelli requested part of his compensation for painting the frescoes in the Duomo be paid in wine.

For dinner, try La Volpe e L'Uva, a popular trattoria on Via Ripa Corsica, or Le Grotte del Funaro which is located in a series of caves beneath the city. Though the restaurant offers a number of Umbrian specialties, it's hard to beat the pizza from the wood-burning oven.

Day 2 - Orvieto
After breakfast at your hotel, if it's Saturday, head to Piazza del Popla for the pottery market. If not, visit some of Orvieto's beautiful churches. San Lorenzo in Arari at the end of Via Scalza was built in the 13th century and has some frescoes depicting the martyrdom of St. Lawrence.

San Giovenale on Via Malabranca at the western edge of the city is almost completely covered in 15th- and 16th-century frescoes. This church was Orvieto's cathedral before the Duomo was built. Spectacular views of the valley below are an added bonus.

Those interested in ancient history should visit the Museo Archeologico Faina and Museo Civico. Located in the former Papal Palace on Piazza del Duomo, the museum contains Etruscan artifacts and Greek vases.

Also on the Piazza, the Museo dell' Opera del Duomo houses various treasures the Cathedral has acquired over the years as well as the original plans for the church.

The Etruscans carved nearly 1,200 wells and storage caverns from the tufa on which Orvieto is built. If you'd like to explore this side of Orvieto's history, take an Undergound Tour. They leave from in front of the Tourist Information Office at 11AM or 4PM.

Spelunkers will also enjoy Pozzo di San Patrizio (St. Patrick's well). Fearing having the city's water supply cut off during a siege, Pope Clement VII ordered the well built in 1527. Two never-touching, double helix staircases descend 200 feet into the well.

For another take on Etruscan life, you can visit the Necropolis del Crocifisso del Tufo. Dating from the 6th century BC, this burial ground has tombs made of tufa.

If shopping is on your agenda, the pedestrian-only Corso Cavour is a great place to start. Lace, woodwork, pottery, and food, are all top quality. If you enjoy the local white wines, stock up for the rest of your trip.

For dinner, consider trying one of the restaurants in the country hotels outside town, La Badia or Villa Ciconia.

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Day 3 - Spoleto
After breakfast, drive south along the Lake of Corbara until you see the turn off for Todi. Partially surrounded by Etruscan, Roman, and medieval walls, this lovely town is often called Umbria's prettiest.

Start your exploration at Piazza del Popolo, the town's main square built atop a Roman forum. The 12th-century Romanesque-Gothic Duomo and three beautiful palaces line the square. The Palazzo del Popolo, which dates from 1213, houses the Museo Etrusco-Romano.

A short stroll away on the Piazza della Republica, San Fortunato is a Gothic church completed in 1462. Inside, the choir and portrait of the Madonna and Child are worth a look.

If you'd like to get some exercise, a path to the right of the church leads to the ruins of La Rocca, a 14th-century castle. It's a steep climb, but you'll be rewarded with wonderful views of the surrounding valley.

The same path leads down the hill to Santa Maria della Consolazione. This domed Renaissance church is one of the finest in Italy and shouldn't be missed. Based on a Greek cross plan, the church took over 100 years to complete.

When it's time to eat, try Ristorante Umbria on Via San Bonaventure. It's been doing business here for over 40 years and the view from the terrace is great.

From Todi, it's a brief drive to Spoleto, your base for the next two nights. Enclosed by medieval walls, Spoleto is one of the most enchanting of the Umbrian hill towns. Today, it's best known for the Festival dei Due Mondi which brings world-class artists and performers here every June and July. But it's history is long and colorful.

If you plan to visit during the festival, be sure to make arrangements well in advance. And expect crowds.

After settling into your hotel, if you're ready to stretch your legs, walk to the Ponte delle Torre. This magnificent bridge with its ten Gothic arches was built in the 14th century atop a Roman aqueduct. At its highest point, the bridge is 262 ft. above the ravine below. If you're not troubled by heights, walk out on the span for incredible views and great photographs.

On the way back into town, you'll pass La Rocca, the fortress that dominates the city. Built in the 1360s to defend the bridge, the castle served as a high-security prison until recently.

Although there's no main piazza in Spoleto, you can find a place to park and enjoy a drink at Piazza della Liberta, Piazza del Marcato, or Piazza del Duomo.

When you're ready for dinner, there are several good choice: Il Pentagramma off the Piazza della Liberta, Il Panciolle on Via del Duomo, and Il Tartufo which specializes in truffles.

Day 4 - Spoleto
Start your day at the open-air market at Piazza del Mercato. It's open every morning but Sunday and it's great for picnic supplies if you want an al fresco lunch later.

At the narrow end of the Piazza, the Arco di Druso once marked the entrance to the Roman forum. It was built in the 1st century AD to honor the son of Tiberius.

Walk along Via Brignone across Piazza della Liberta to Via Sant'Agata. You can visit the Teatro Romano and the Museo Archeologico in any order you prefer. A combination ticket will admit you to both.

The Teatro Romano dates from the 1st century, but is very well-preserved. In fact, it's still used for performances. The Museo Archeologico is reached through the west portico. It contains the Spoleto Law tablets dating from 315 B.C. and other ancient artifacts.

Head back toward Il Duomo. Art lovers should stop by the Pinacoteca en route. This small gallery includes works from the 12th through the 18th centuries, including works by Perugino.

The 11th-century St. Eufemia is not far from here. The small church is noted for the gallery above the nave where women were seated. Attached to the church, the Museo Diocesano contains some important work by Bernini, Fra Filippo Lippi and Filipino Lippi.

Spoleto's fine Romanesque Cathedral, Il Duomo, was consecrated in 1198 and remodelled in the 1600s. The exterior features a mosaic by Solsterno dating from 1207 and a rose window. The real reason to visit is the interior frescoes by Fra Filippo Lippi. They were his last works and his son Filippino designed his tomb which is also here.

If you bought picnic supplies, the Church of San Salvatore is in a cool, quiet cypress grove. The church itself was one of the first Christian churches in Italy and after lunch, you can explore Spoleto's old cemetery, which is next to the church.

Shoppers will enjoy looking for pottery and other handicrafts along Via Fontesecca. And those who can't get enough churches should visit San Ponziano and San Gregorio.

As one of Umbria's loveliest towns, Spoleto was meant to be savored. So take time to just relax on the piazza of your choice with a gelato or glass of wine.

If you're in the mood for a little drive, head up to Monteluca, about five miles from Spoleto. The monastery here was frequented by St. Francis. The view from here at 2,500 feet, is well worth the drive.

For a memorable dinner in sophisticated surroundings, try the restaurant at the Hotel San Luca.

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Day 5 - Assisi
Sleep in and enjoy a leisurely breakfast this morning. Assisi is just 30 miles away so you can take your time hitting the road.

There are two ways to get to Assisi. You can take S53 and go via the village of Trevi, which enjoys a spectacular setting in the Vale of Spoleto. Trevi is a maze of winding cobblestones encircled by two sets of medieval walls. There are two small churches here with paintings by Perugino and Toberio d'Assisi, and the town's small Pinacoteca or art gallery has several Renaissance paintings.

The other route takes you through Bruna and Mercatello to Montefalco, which has more to offer but is still so small that a stroll from one end to the other takes about five minutes.

It's fine Museo Civico in the old Church of San Francesco contains a fresco by Benozzo Gozzoli that draws heavily on Giotto's frescoes in Assisi. Other worthwhile sights are the Gothic Church of Sant'Agostino, which contains three mummies, and the Church of Sant' Illuminata – just outside the city walls.

Those who plan to have lunch en route should visit Montefalco, if only to sample the local red wine, Sagrantino di Montefalco.

Like Orvieto, Assisi is a popular spot. But most visitors dash in, visit the Basilica, and then head out. To maximize your enjoyment, plan to visit the church when it is not open to tour groups – before 9AM or after 5PM. It is open from 6AM to 6PM daily. In this way, you'll have plenty of time to savor the Basilica's superb frescoes.

If you do plan to visit the churches this afternoon, please dress appropriately. Otherwise you will not be admitted.

Within the city walls, the town is closed to traffic. You'll need to park in one of the lots outside the walls and take a city bus to the center of town. This just adds to the appeal of Assisi, which is lovely, draped with geraniums and filled with narrow alleyways leading to sparkling fountains and small piazzas.

Born to wealth and privilege, Francis, who is now the patron Saint of Italy, embraced a life of poverty, humility, and simplicity that was a radical departure from Catholicism at that time. His reverence of nature, purity of spirit, and great compassion brought him many followers, then and now. Today, Franciscans are the largest Catholic order.

Francis asked to be buried among the sinners on the "hill of the damned." Two years after his death, the Basilica di San Francesco was built above his tomb as a tribute to his life of piety. The church contains some of the most magnificent art in the world and it is one of the most revered shrines in Christendom.

Begun in 1228, the Basilica was severely damaged in the 1997 earthquake. But restoration has been swift and extensive. And you'll likely be able to see most parts of the church. Luckily, even the heavily damaged upper basilica has been reopened.

The Basilica di San Francesco is actually two churches, one built atop the other. Start your tour in the lower basilica, the more somber of the two. In the first chapel on the left, you'll see the life of Saint Martin portrayed in frescoes by Simone Martini.

The third chapel on the right contains scenes from the life of Mary Magdalene. Their authorship is in dispute. Many believe Giotto painted these frescoes, others believe they are the work of one of his followers. The paintings behind the high altar showing Saint Francis embracing poverty, chastity, and obedience, have sparked a similar controversy.

The right transept contains frescoes of the Madonna and saints by Cimabue. And the right transept shows the Madonna, a crucifixion, and the Descent from the Cross by Pietro Lorenzetti.

The lowest level of the church contains the crypt of St. Francis. It was hidden from the public until 1818.

A stairway next to the altar takes you to the Chiostro di Morti or Cloister of the Dead, which leads to the Treasury and the Perkins Collection. The Treasury contains relics of St. Francis, including his grey sack cloth. The Perkins collections display Renaissance treasures from Tuscany, including paintings by Luca Signorelli and Fra Angelico.

Exit onto the courtyard and climb the stairs to the upper basilica. The light-filled, soaring Gothic space is brighter – literally and figuratively – than the lower church.

The frescoes that surround you are monumental in the history of art. Painted by Giotto when he was in his twenties, the 28 frescoes represent a departure from the flat, Byzantine style that was prevalent at the time. Giotto's figures have weight, depth, and emotion.

To see the frescoes in order, start at the altar and work your way clockwise around the church. You'll see scenes from St. Francis's life, including the lovely St. Francis Preaching to the Birds. Look for Cimabue's Crucifixion, also in the upper church.

If time permits, you may want to visit the Basilica della Santa Chiara (St. Clare). With St. Francis, Santa Chiara founded the Order of the Poor Clares. The painted, wooden crucifix behind the altar and the beautiful icons on both sides of the transept date from 1260 when the church was built. The crucifix spoke to St. Francis, causing his conversion.

Don't miss the view from the church. You'll look out over 700-year-old olive groves and the widest valley in Umbria.

Before the Basilica di San Francesco was built, the Duomo di San Rufino was the city's main church. In fact, St. Francis and St. Clare were baptized here.

When you run out of steam, walk up to Piazza del Comune, the town's main square. Enjoy the fountain, the main square, and a glass of red wine.

For dinner, try Ristorante Buca di San Francesco or the restaurant in the Hotel Umbra.

Day 6 - Assisi
If you saw the Basilica di San Francesco yesterday, you can have a leisurely breakfast at your hotel this morning.

There are several ways to enjoy the day, depending on your interests. For great photographs, hike up to Rocca Maggiore, the 14th-century castle that towers over Assisi. Inside, there's a rather gruesome torture museum.

If you'd like to picnic, hike up to Rocca Minore, the small castle, above Piazza Matteotti. You'll escape the crowds and have wonderful views.

The other pleasant picnic spot is good for walkers too, since it's about a two-and-a-half mile hike each way. Leave Assisi on Via Santuario di Carceri and walk through the woodlands on Mount Subasio. You'll be rewarded with fantastic panoramas as you hike through olive groves, broom, and cypress.

Your destination is Eremo delle Carceri, a 14th-century spiritual retreat built on the site where St. Francis would come for quiet contemplation. Originally a cave, the present Hermitage has been hollowed from the rock.

Behind it, there's a terrace with sweeping views and a 1,000-year-old live oak from which St. Francis sent the birds to the four corners of the Earth to spread the word of God.

Wine lovers should plan to visit Torgiano and the Cantina Lungarotti winery. Tours are by appointment on weekdays only. Best known for their Rubesco Lungarotti, they also produce San Giorgio, and chardonnay.

The Lungarotti family has also opened the world-class Museo del Vino. No oenophile should miss this marvelous collection of artifacts, documents, and vessels tracing the history of Umbrian viticulture. If you didn't tour the winery, you can taste and purchase Lungarotti's award-winning wines at the Osteria del Museo here.

In the town, the Lungarotti-owned Le Tre Vaselle hotel – set in a 17th-century country house – is a delightful spot for lunch.

Four miles south of Torgiano, Deruta has been known for its ceramics since the 16th century. Anyone interested in housewares should put this on their itinerary. The highly-glazed terra cotta ware comes in a variety of patterns, often in brilliant blues and yellows.

There are more than 100 ceramics shops here, as well as the Museo della Ceramica Umbra. And prices are much lower than at Williams Sonoma and other U.S. resellers. Most are around the town's main square, Piazza dei Consoli.

The Museo dell Ceramica is a good place to shop because it will give you a quick overview and tell you what to look for. Ubaldo Grazie, Maioliche Cintia, and Antonio Margaritelli are shops with good reputations.

For dinner in Assisi, try San Franceso near the Basilica or Medioevo.

If you're staying in town when you visit Siena, pack a small bag with just a few day's worth of clothes so you won't have to carry much when you walk to your hotel.

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Day 7 - Siena
Get an early start this morning for the drive to Siena. There are two good stops en route, depending on you interests. The total travel time between Assisi and Siena is about two and a half hours, so plan your day accordingly.

Art lovers – and chocoholics – should visit Perugia, Umbria's atmospheric capital.

Driving in the city is pointless. So park your car near the train station and take a city bus to the heart of the city, Piazza IV Novembre. With its sparkling 13th-century fountain sculpted by Niccola Pisano, the square is one of the loveliest in Italy.

The Duomo here is rather plain. But there's a nice Madonna by Luca Signorelli inside. Of more interest is the National Gallery of Umbria, located on the third floor of the Palazzo dei Priori, one of Italy's most impressive public buildings. Take time to explore the façade of this 13th-century palace before going inside. Note the griffin – the symbol of the city – and the lion, which signified allegiance to the Pope.

The gallery has a stellar collection of Umbrian art from the 13th to the 19th century. Highlights include work by Duccio, Fabiano, Fra Angelico, Pierro della Francesca, and Perugino, the city's native son.

Also part of the Palazzo complex, the Collegio del Cambio was once the city's commodities exchange. The Hall of the Audience here is covered with frescoes by Perugino and his students, including the 17-year-old Raphael.

The Sala die Notari, or Lawyer's Hall, is decorated with scenes from the Old Testament painted by Pietro Cavallini. The Chapel of S.J. Battista contains frescoes by Niccola di Paolo. And Sala di Udienza del Collegio della Mercanzia – the former merchant's guild hall – is decorated in the late Gothic style with exquisite paneling and inlaid wood.

Those interested in ancient history may want to visit the Museo Archeologico Nazionale, which contains Etruscan artifacts from all over the region.

Serious shoppers shouldn't leave Perugia without a stroll down Corso Vannucci, the city's main pedestrian boulevard. Pick up enough Perugina chocolates to last the rest of the trip.

If you'd rather be outdoors than in, drive to Lake Trasimeno, the largest lake on the Italian peninsula. Passignano sul Trasimeno is the main town on the north shore of the lake. You can rent boats or bikes here or take a short cruise to Isola Maggiore – one of the lake's two islands – where lace is made in the charming village.

You can cruise across the lake to Castiglione del Lago, where you can see the remains of a medieval castle or relax on the small, sandy beaches.

Walkers can hike from Passignano i Castel Rigone to the highest point in the area, Monte Castiglione, for sweeping views and great photographs.

As you leave Umbria and enter Tuscany, you'll pass lovely Cortona on the way to Siena, your base for the next three nights.

Siena has, thankfully, eliminated automobile traffic, so if you're staying in town, you'll need to head for the parking lot and then take a city bus or walk to your hotel. Chances are, it won't be far. And you'll be eternally grateful for this small inconvenience for the rest of your stay.

During the middle ages, Siena rivaled Florence in wealth and power. But Florence eventually prevailed, and the resulting downturn left Siena stuck in a time warp.

Today, Siena is the most perfectly preserved Gothic city in Italy. Wandering the narrow maze of streets radiating from the superb Piazza del Campo – surely Italy's loveliest – provides one of life's great travel experiences.

The town is still divided into 17 contrade, or neighborhoods, each with their own symbol, church, and museum. Look for plaques, flags, and carvings around town identifying which contrada you have entered.

Twice each year, on July 2 and August 16, ten of the contrada compete in a bare-back, horse race called the Palio. The event is filled with medieval pageantry and drama, but the no-holds-barred nature of the competition makes it a little brutal. If you'd like to experience the Palio, make your reservations well in advance and be prepared for crushing crowds.

The rest of the year, Siena is a pretty peaceful place.

Once you've settled into your hotel, head to Piazza del Campo for a glass of wine. This shell-shaped piazza is the perfect place to drink in the atmosphere of Siena. After the sightseers have left for the day, you'll have the city almost to yourself and you'll have no trouble getting your bearings for tomorrow.

When it's time for dinner, you won't have to venture far. Osteria le Logge on Via del Porrione has outdoor tables and great food. And Enoteca I Terzi on Via dei Termini has light meals and several hundred wines by the glass.

Be sure to try panforte – a swell combination of fruits, nuts, and honey – for dessert.

Day 8 - Siena
Depending on the day of the week, spend the day either exploring Siena or touring the wineries along La Chiantigiana. Many of the wineries can only be toured during the week, so make your plans accordingly. Most of Siena's attractions are open seven days a week.

Start your tour of Siena at the Museo Civico in the Piazza Publico or City Hall on Piazza del Campo. The Palazzo dates from 1288 and contains a Madonna by Simone Martini and Lorenzetti's Allegories of Good and Bad Government.

For breathtaking views, climb the 505 steps to the top of Torre di Mangia, the palazzo's bell tower. It's the second tallest medieval tower in Italy. Be sure to take lots of film.

Leave Piazza del Campo on Via Casato di Sotto until you come to the Palazzo Buonsignori on Via San Pietro. The palace contains the Pinacoteca Nazionale, Siena's art museum.

The Sienese School of painting was once as important as the Florentine School. Masterpieces by early Sienese painters from the 12th through the 16th century such as Duccio, Simone Martini, Pietro Lorenzetti, and Pietro la Domenico are exhibited.

After you've explored the gallery, walk down Via San Pietro to Piazza del Duomo. If it's time for lunch, Al Marsili, between the Duomo and Via Di Citta, offers a very civilized dining experience. If you'd like something more casual, you should be able to find Pizza Rustica whenever the mood strikes.

Siena's cathedral is one of the finest Gothic churches in Italy and a showcase of priceless sculpture. The façade, with its inlaid stripes of marble, was designed in part by Giovanni Pisano.

Inside, the inlaid marble floors, which took 200 years to complete, are absolutely wondrous. More than 40 artists created the 56 biblical and allegorical scenes that are depicted.

The 13th-century pulpit is the masterpiece of Niccola Pisano. Sculpture by Michelangelo of Saints Peter, Paul, Pius, and Gregory decorate the north aisle. In the south transept are Bernini's exquisite statues of Mary Magdalene and St. Jerome. And the left transept chapel houses Donatello's bronze of John the Baptist.

The Piccolimini Library inside the church contains some well-preserved frescoes by Pinturicchio and some illuminated sheet music.

Behind the cathedral, the Baptistery contains one of the finest baptismal fonts in existence. Italy's greatest sculptors – Jacopo della Quercia, Giovanni di Turino, Lorenzo Ghiberti, and Donatello – each contributed a bas relief panel.

In the 14th century, the Sienese had plans to expand their Duomo, using the existing church as the transept of the new church. The Black Death, which killed nearly half of the city's population, brought construction to a halt in 1348. All that remains of the expansion now forms one wall of the Museo dell'Opera del Duomo, the cathedral's art museum.

The ground floor displays many sculptures by Giovani Pisano, Jacopo della Quercia, and Donatello. The undisputed masterwork is upstairs. Duccio's huge Maesta shows the Madonna and Child enthroned on one side and the passion of Christ on the other.

Before leaving the building, follows the signs on the top floor saying, "panorama." The view is the perfect way to complete your visit.

By now, you should be ready to call it a day. Find whichever wine bar appealed to you when you passed it earlier in the day, and park for a while. Or if you're serious about wine, head for Enoteca Italica Permanente outside the entrance to Fortezza Medicea, the old fortress.

Run by the Italian government, the Enoteca offers fantastic wines by the glass or bottle and a series of sunny terraces for plopping.

If your hotel is in one of the villas outside the city, have dinner there this evening. If you're staying in town, try Da Guido on Vicolo Pier Pettinaio.

Day 9 - Siena
Today is a wonderful day for oenophiles. Although most of the wineries can be toured for free, you should phone ahead so you won't be disappointed or make a wasted trip.

With its thousands of acres of vineyards, 300-year-old farmhouses, and medieval castle ruins, the Chiantigianna, as the winding road through Tuscany's Chianti Classico district is called, is a must for wine lovers. And cooks – since many of the vineyards produce vinegar and olive oil too.

But even those with no particular interest in food or wine will enjoy touring this lovely area.

The district is only about 30 miles long, but since the road is twisty and you'll make frequent stops, you probably won't cover as much ground as you plan to.

It makes sense to visit the most distant winery you want to tour first and then work your way back to Siena. The main road from Florence to Siena is SS522 and most of the wineries will have "degustazione" signs leading the way from there. But a good map of the region is helpful.

A few words of caution. The roads leading to the wineries aren't the best. They're hilly, dusty, and narrow. The legal blood alcohol limit in Italy is 0.08% so appoint a designated driver or sample responsibly.

Castello di Tizzano is the farthest from Siena. To reach it, take SS522 past Spedaluzzo, but not as far as Strada in Chianti. Then follow the signs. The 11th-century castle is surrounded by vineyards and olive groves. Chianti Classico is produced here under the Gallo Nero label. Tastings are available in the 15th- and 16th-century cellars.

Heading back toward Siena, Fattorio Castello di Vicchiomaggio is outside the village of the same name. Seventy of the estate's 300 acres are vineyards producing a good Riserva, a very good Prima Vigna, a vin santo and grappa. There's a formal garden looking out over the Greve Valley.

Not far from Vicchiomaggio, Castello di Verrazzano is the birthplace of the immigrant for whom the Manhattan bridge is named. The center of this estate is its 10th-century tower and 15th- and 16th-century out buildings. Make reservations if you'd like to sample the estate's reds and whites in the old caves. Otherwise, you can purchase wines at their outlet in Greve on weekends.

If you visit only one winery, visit Castello di Uzzano, about a mile north of Greve. The castle was built in the 13th century for the bishop of Florence and it is the heart of the 700-acre estate. It's everything you imagine a Tuscan villa should be.

The castle is surrounded by six acres of well-tended gardens. For a real treat, the owners will prepare a picnic lunch for you to enjoy here. The estate produces Chianti Classico, a Riserva, a Sangiovese aged in French oak, honey, olive oil, jams, and preserves. Reservations are not required.

The main town in the area is Greve in Chianti. The town has a small square, a parish church, and a jillion wine shops.

Castello di Querceto produced reds, whites, and olive oil on the 125 acres surrounding its 11th-century castle. Fontodi has 155 acres surrounding an 18th-century stone house.

Garden lovers should not miss Vignamaggio, just south of Greve. This Renaissance villa was once the home of La Gioconda, the subject of the Mona Lisa. The gardens were featured in Kenneth Branagh's Much Ado About Nothing, and they are among the most beautiful in Tuscany. Be sure to phone ahead as tours are by reservation only.

The charming little town of Castellina in Chianti is certainly worth a brief visit. After your visit, leave SS522 in the direction of Radda in Chianti. Tenuta Badia a Coltibuono was founded by Vallombrosian monks in 770. Today, the estate has one of the best restaurants in the area. If you didn't picnic at Castello di Uzzano, have lunch here. Phone ahead for reservations.

If you want to know more about the wines of the region and their production, Agricoltori Chianti Geografico outside Gaiole in Chianti is a good stop. This cooperative represents about 200 wine growers.

Castello di Brolio was the home of the Barone Ricasole, unified Italy's second Prime Minister. An ardent winemaker, Ricasole dramatically improved the quality of wine produced in this area. Today, the Brolio Ricasole label is one of the most prestigious in Chianti. The winery is currently managed by the 32nd Barone Brolio.

A mile or so on SS484 toward Siena, Fattoria dei Pagliaresi has lovely gardens and a 300-year-old farmhouse where you can have lunch. The last winery before Siena is Fattoria della Aiola. The estate's 90 acres of vineyards produce Chianti, Sangoveses, grappa, and a sparkling wine. You can taste in the 15th-century cellar or in the garden.

If you return to Siena before 7PM, try to catch the evening passeggiata or promenade along Via Banchi di Sopra. The experience will create one more fond memory of your stay in this lovely city.

For dinner your last night here, splurge and go to the restaurant at Certosa di Maggiano. Set in a 13th-century monastery, the vaulted dining room is lovely and the food is excellent.

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Day 10 - San Gimignano
Sleep in and enjoy one last leisurely morning in Siena. Tonight, you'll overnight in San Gimignano, one of Italy's most picturesque towns. But chances are it will be swarmed with tourists until late afternoon. So take your time, and do a little last-minute shopping for wine and pastries.

The town of Monteriggioni makes an interesting stop en route to San Gimignano. Its location nine miles north of Siena made it an ideal fortress for protecting the city from Florentine attack.

Built around 1213, the wall which completely encircles the city and its 14 square towers are still intact. There's a large piazza, a Romanesque church and some crafts shops.

Have lunch at Il Pozzo on the piazza and try the local Castello di Monteriggioni wine. When you've BTDT (been there, done that) drive the 12 miles to San Gimignano.

Like Siena, the town is closed to automobile traffic, so you'll need to park outside the walls and walk in. It won't be far.

Largely unchanged since the 14th century – thanks, in part, to the plague of 1348 – San Gimignano has more surviving towers than any other city in Tuscany; 14 of the original 72 remain. In the middle ages, the towers were high-visibility status symbols erected by noble families to display their wealth and power.

Unlike Assisi with its Basilica or Siena with its Duomo, San Gimignano is its own highlight. There are sights to see here. But by in large, you can see them in a couple of hours, preferably late in the day after the tour groups have gone on to Florence or Pisa.

The Piazza della Cisterna is the main square in town, named for the 13th-century cistern at the center. It is connected to the Piazza del Duomo, where the Romanesque Duomo Collegiata o Basilica di Santa Maria Assunta dates from the 12th century. With its frescoes and gold-starred ceiling, the interior is more impressive than the exterior suggests.

Don't miss the Chapel of Santa Fina with frescoes by Domenico Ghirlandaio.

Also on the piazza, the Palazzo del Popolo, or town hall, houses the Museo Civico. The museum has a nice Maestra by Lippo Memmi and an Annunciation by Filippino Lippi. You can climb the tower for great views. But the views from the Rocca or castle behind the church are wonderful and less steep. Go at sunset.

Those interested in illuminated manuscripts and medieval tombstones should visit the Museo d'Arte Sacra on Piazza Luigi Pecori.

The Church of Sant'Agostino has a Rococo interior. The Coronation of the Virgin by Pollaiuolo dates from 1483 and there's a cycle of frescoes illustrating the life of St. Augustine by Benozzo Gozzoli.

Once you've seen everything on your list, just wander the winding medieval streets, soaking up the atmosphere.

If you'd like to try the local wine – Vernaccia – go to Da Gustavo on Via San Matteo or Bar Enoteca il Castello on Via de Castello. Both offer lots of wines by the glass.

When it's time for dinner, try Ristorante Bel Soggiono or Ristorante La Terrazze. Both feature produce from local farms, wild boar and charming ambience.

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Day 11 - Lucca
After breakfast at your hotel, drive to Lucca, which was founded as a Roman colony in 180BC. In fact, it was in Lucca that Caesar, Pompey, and Crassus agreed to rule Rome as a triumvirate in 56BC.

Depending on your plans the next two days, you might want to turn in your rental car when you arrive in Lucca.

At one time, Lucca was the de facto capital of Tuscany and at times, it was an independent principality, like Genoa. The city is surrounded by three sets of walls. The third, dating from the 17th century, are the best-preserved Renaissance ramparts in Europe.

Today, the city offers examples of architecture from Roman times up to the turn of the last century. It's an affluent, less touristy town that many travelers consider a favorite.

The best way to get oriented is to walk the city ramparts surrounding the old town. There are ten bastions in the massive walls, which are 40 ft. high and 115 ft. wide at the base. The most accessible is behind the tourist office on Piazzale Verdi. The loop is about 2 1/2 miles and the walls were converted into a park in the 19th century, so many trees shade the way.

The Duomo, or Cattedrale di San Martino, dates from 1060. The exuberant Pisan-Romanesque style is most evident in the façade, which is an idiosyncratic series of arched galleries with twisting columns. The Journey of the Magi and Deposition on the left portal were carved by Nicola Pisano.

Inside, there's a crucifix carved by Nicodemus from the Cedar of Lebanon, a portrait of the Madonna by Domenico Ghirlandaio, and a tomb sculpted by Jacopo della Quercia.

Begun in 1143 on the site of the Roman forum (foro), San Michele in Foro is another of Lucca's fine Pisan-Romanesque churches. The intricately-carved marble columns – each different – and inlaid marble make the exterior especially notable. Most of the figures are pagan. In fact, St. Michael is the only religious subject.

Filippino Lippi's Saints Sebastian, Jerome, Helen, and Roch is on the far wall of the right transept. And there's a nice terra cotta by Andrea della Robbia.

San Frediano's façade features a splendid 13th-century mosaic of The Ascension. Inside, there's a Romanesque font depicting scenes from the life of Christ and the story of Moses.

When it's time for lunch, try Tratorria da Leo near Piazza San Michele or Da Guillio in Pelleria.

Lucca's art gallery, the Pinoteca Nazionale, is not particularly compelling, although the 17th-century Palazzo Mansi in which it resides is lovely.

Of more interest is Museo Nazionale di Villa Guinigi which houses a nice collection of local Romanesque and Renaissance art, including works by Civitali, Jacopo dells Quercia, and Fra Bartolomeo.

The Torre dei Guinigi, part of the villa built in 1418 for one of Lucca's leading families, has a grove of oak trees growing at the top. The roots have infiltrated the room below and there's a splendid view from the top of the tower.

In Piazza del Mercato, the shape of the Anfiteatro Romano or Roman amphitheater is discernable among the medieval buildings built atop the original arches.

Opera buffs should visit Casa di Puccini. The great composer was born here in 1858 and today the house contains a music school and a small museum.

Garden lovers should visit Palazzo Pfanner. If you walked the city walls, you probably saw the palace. The formal 18th-century gardens lined with Baroque statues of Greek gods and goddesses are some of the loveliest in Tuscany.

Lucca offers some of the best shopping outside of Florence. On stylish Via Fillungo or Via del Battistero, you'll find everything from Luccan olive oil – which many Epicureans consider the best in the world – to beautiful home furnishings.

For dinner, you can't beat Buca di Sant'Antonio, Lucca's best-known restaurant, or Giglio on the piazza of the same name.

Day 12 - Lucca
Today is yours to explore as you please.

There are a number of interesting day trips from Lucca that offer another glimpse of Tuscany.

Sun worshippers should head for Forte di Marmi, the exclusive beach resort to which Tuscan and Milanese movers and shakers retreat to beat the heat of summer. There's a large, sandy beach and many gorgeous villas there.

Drive down the coast to Viareggio where there are lots of "Liberty" or art nouveau buildings from the 1920s. An avenue lined with lime trees connects Viareggio with Torre del Lago Puccini, the villa where the composer and his wife lived.

Those who enjoy gardens should visit Villa Reale in Marlia, just five miles north of Lucca. The villa was once the home of Napoleon's sister Elisa who bought the adjoining Villa Orsetti palace and gardens. Today, the gardens are highlighted by an open-air theater created with topiary and the Alley of the Camelias.

If you want to visit Pisa, consider turning in your rental car and taking the train. The trip takes less than half an hour and service is frequent.

Traffic – and parking – in Pisa are obstacles to enjoyment. And since you can easily reach everything you want to see on foot, it doesn't make sense to be encumbered by a car.

From the train station, it's about a ten-minute walk to the Campo dei Maracoli (Field of Miracles). Just follow the signs. Here, you'll find Pisa's most important sites: the Leaning Tower, the Duomo, and the Baptistery. The Tower is available to tour only by reservation, make them well in advance.

Take the requisite picture of the tower, then head into the cathedral to see the 14th-century pulpit carved by Giovanni Pisano.

Across from the Duomo, the Baptistry features a pulpit carved by Nicola Pisano, Giovanni's father. The circular building is known for its sound quality. If you're lucky, one of the doormen will sing so you can hear the remarkable acoustics.

For lunch, visit the market in Piazza Vettovaglie for picnic supplies. It's open daily until 1:30PM.

Pisa's Museo Nazionale di San Matteo is well worth a visit for art lovers. On the banks of the Arno River, the gallery contains Pisan and Florentine art from the 12th to the 17th century. There is work by Francesco Traini, Simone Martini, Andrea Pisano, Masaccio, Donatello, and Fra Angelico.

If you'd like to do a little shopping before returning to Lucca, Via Borgo Stretto has an arcade filled with interesting stores.

For your last night in Lucca, if you still have a car drive to Locanda l'Elisa for an elegant dinner in their conservatory dining room.

Day 13
Florence is just an hour away by train. If you are returning home, you can connect there to trains or flights to Rome. If you have more time, spend several days exploring Florence. Or venture on to Venice.