Siena and Assisi: Italy's Grand Hill Towns

In red-bricked Siena, we tour the town's innovative medieval hospital, lavish cathedral, and a bakery that makes panforte (like fruitcake, only delicious). Exploring the Chianti region, we sip Brunello di Montalcino — with its makers. Spending the night at a farmhouse, we meet the family and its sheep, learn of the Slow Food movement, and enjoy a homegrown dinner. In Assisi, we follow the footsteps of St. Francis, from his humble chapel to the Giotto-frescoed basilica that holds his tomb.

Travel Details

Il Palio

In the Palio, the feisty spirit of Siena's 17 contrade (neighborhoods) lives on. Contrada pride is evident any time of year in the parades and colorful neighborhood banners, lamps, and wall plaques. (If you hear distant drumming, run to it for some medieval action, often featuring flag-throwers.) But contrada passion is most visible twice a year — on July 2 and August 16 — when they have their world-famous horse race, the Palio di Siena.

Santa Maria della Scala

This museum (opposite the Duomo entrance) was used as a hospital until the 1980s. Its labyrinthine 12th-century cellars — carved out of volcanic tuff and finished with brick — go down several floors. They once stored supplies for the medieval hospital upstairs. Today the hospital and its cellars are filled with museum exhibits, including these main attractions: the fancy frescoed hall (Pellegrinaio Hall, ground floor), most of the original Fountain of Joy (from which the replica in Il Campo was modeled), St. Catherine's Oratory chapel (first basement), and the Etruscan collection in the Archaeological Museum (second basement).

Albergo Bernini

Albergo Bernini makes you part of a Sienese family in a modest, clean home with 10 traditional rooms. Giovanni, charming wife Daniela, and their daughters welcome you to their spectacular view terrace for breakfast and picnic lunches and dinners.

Tours by Roberto: Tuscany Minibus and Siena Walking Tours

Roberto Bechi offers off-the-beaten-path minibus tours of the surrounding countryside (up to eight passengers, convenient pickup at hotel) and also arranges Siena city walks. Regardless of the size of your group, they charge per person, so these minibus tours are very economical. The first participants to book choose an itinerary — then others can join until the van fills. Roberto’s passions are Sienese culture, Tuscan history, and local cuisine.

Basilica of St Francis

The Basilica de San Francesco is one of the artistic and religious highlights of Europe. In 1226, St. Francis was buried (with the outcasts he had stood by) outside of his town on the "Hill of the Damned" — now called the "Hill of Paradise." The basilica is frescoed from top to bottom by the leading artists of the day: Cimabue, Giotto, Simone Martini, and Pietro Lorenzetti. A 13th-century historian wrote, "No more exquisite monument to the Lord has been built." There are three parts to the church: the upper basilica, the lower basilica, and the saint's tomb (below the lower basilica). Free entry, modest dress is required to enter the church — no sleeveless tops or shorts for men, women, or children.


See the Travel Details above for recommendations highlighted in bold, excerpted from Rick’s guidebooks.

Hi, I'm Rick Steves back with more of the best of Europe. This time we explore Italy's two greatest hill towns: Siena and Assisi plus the countryside in between. If you fall in love with Italy, good chance it'll be right here.

While the big cities of Italy have their great sights, in many ways the heart of this country is the region of Tuscany. It's here where the rustic soul and rural mystique of Italy combine to seduce speedy travelers into tossing their itineraries and settling in.

In Siena we'll climb the highest tower, savor local cuisine, and get to know a family. And then, for a taste of Tuscany, we'll explore tiny hill towns, sleep rustic but classy in a country farm, and sample some great wine. In Assisi we'll join pilgrims at the Basilica of St. Francis.

Italy packs 55 million people into an area about the size of Arizona. We'll start in Siena and visit highlights of Tuscany before finishing in Assisi.

Siena seems to be every Italy connoisseur's favorite town. In the 1300s, Siena was a major military power in a class with Florence, Venice, and Genoa. With a population of 60,000, it was one of Europe's largest cities. But weakened by a disastrous plague and conquered by her bitter rival, Florence, Siena has been a backwater for five centuries.

Siena's loss became our sightseeing gain, as its political and economic irrelevance preserved its purely Gothic identity. Siena's great central piazza — Il Campo — is like a people-friendly stage set. Its gently tilted floor fans out from the tower. Sprawling before the city hall backdrop, it offers the perfect invitation to loiter. The Sienese lounge comfortably on this square, as if it's their community living room.

Twice each summer, Siena holds the Palio, a wild bareback horse race around this square. Neighborhoods compete, hurling themselves with medieval abandon into a festival that climaxes in this ninety-second romp. It's standing room only as 60,000 people — mostly locals — pack this square.

But today, it's quiet. And at the Fountain of Joy, pigeons politely wait their turn to slurp a drink.

While most Italian cities have a church on their main square, Siena gathers around its city hall. It was an autonomous republic, and this was its "declaration of independence"...the tallest secular medieval tower in Italy.

Three hundred steps take you 100 yards high. The reward: one of Italy's finest views. The dominant color...Siena.

Inside the City Hall, in the "room of peace" — the town council met under instructive frescoes showing the effects of good and bad government. Bad government — a dictatorship counseled by greed and tyranny — brings a dreary city without spirit...and violence in the streets.

But a good government — with wise and virtuous council — results in a utopian republic where the shopping's brisk, professors teach attentive students, construction is booming, and women dance freely in the streets.

The message: a community ruled by a just government enjoys peace, prosperity...and a great neighborhood in which to raise your kids.

In the nearby hospital of Santa Maria della Scala, a series of idealized frescos illustrates how far secular society had come in Siena by the 1440s. The city ran this hospital in a way that seemed to take over the church's traditional social role. It took in orphans and raised them — from wet nurse through homework — to a civil wedding. And this wedding is not arranged — as this man would have liked — it's based on love.

Sienese society provided welfare — bread to needy people — through this hospital rather than the church. Note the loaves are cleverly stamped — to prevent resale. The hospital was run by doctors and secular nurses. In a slap to church authorities, the well-fed monk looks bored as he hardly hears a dying patient's confession.

We're staying at Albergo Bernini in the old town center — with the magic of Siena right out our window. The rooms are homey and comfortable, breakfast on the terrace comes with a spectacular view, and a friendly family member at the desk is always ready to help you with travel questions.

And, in a little family-run place like this, serendipity is almost a certainty and you feel like part of a Sienese family.

Siena's Duomo, or cathedral, is as over-the-top as Gothic gets. The striped pajama facade is piled with statues and ornamentation; its interior is decorated from top to bottom. The heads of 172 popes peer down on all those who enter.

The church is filled with great art. Nicola Pisano's wonderful pulpit was carved out of marble in 1268. It's crowded with delicate Gothic storytelling — scenes from the life of Christ and the last judgment.

This tomb — dedicated to a Sienese pope — includes a minor Michelangelo. But the most exciting statuary hides here — in a side chapel — where you'll understand why Lorenzo Bernini is considered the greatest Baroque sculptor. Mary Magdalene is in spiritual ecstasy. And St. Jerome caresses the crucifix like a violinist lost in beautiful music.

Next door, the Cathedral Museum holds many of the church's most precious originals. Duccio's Enthroned Virgin — painted for the cathedral's high altar — is the most captivating piece of art in all Siena. It's from around 1300, long before the Renaissance, when the artist's mission was to tell a Bible story, emphasizing easy-to-read symbolism and serene beauty over realism.

The flip side of this two-sided altarpiece has 26 panels — the artistic equivalent of pages. It shows scenes from the Passion of Christ — the last days that led up to his crucifixion. In this panel, Jesus washes the feet of the apostles. And here, Judas kisses Jesus, identifying him to his Roman captors.

And the cathedral museum comes with a surprise — a commanding view. From this hilltop, Siena unfolds in all directions.

Consider this: When Florence began building its grand cathedral, the rival republic of Siena responded with a plan to build the biggest church in all Christendom. Its existing cathedral would be used only as a transept or wing off the new nave or main building. I'm sitting atop what would have been the front of the new church.

These towering marble arches hint at the immensity of the project.

But these arches were as far as Siena got before construction problems and a plague scuttled the project. Were it completed, this square would have been the nave.

Hiding behind all these great sights are intriguing back streets. Here you'll get away from the crowds and find yourself all alone with the medieval magic of Siena — steep lanes and mysterious byways that have changed little over the centuries.

And all over town, shops tempt you with Sienese specialties — gourmet pasta, vintage Chianti, wild boar proscuitto, extra virgin olive oil, and panforte. Siena's claim to caloric fame, panforte is a chewy local delicacy that impresses even fruitcake haters.

When I'm in town with tour groups, I team up with my Sienese friend and tour guide Roberto Bechi. To Roberto, Siena is the fountainhead of all civilization.

Roberto's taking us to his cousin's bakery for a peek at how the panforte's actually made...a recipe that can be traced back to the 13th century.

Roberto asks his cousin about the ingredients (in Italian).

Antonio explains that traditional panforte consists of nuts, honey, flour, vanilla and an interesting variety of dried fruit. And his employees might have to sign a non-disclosure agreement when it comes to Antonio's mix of spices.

This medieval concoction is all mixed together and turned into dense wheels of Sienese delight.

No look at Tuscany is complete without getting out of its cities. Many travelers come here to the Chianti region — with its rolling hills and vineyards — to enjoy a slower, richer lifestyle. Its fortified farmhouses are reminiscent of medieval days, when this was part of the Florence/Siena battlefield. Today they're peaceful...growing ever more graceful with age.

Vertine is typical of Chianti's fortified villages. While tourists pack the famous places, little off beat gems like this — even in peak season — remain sleepy.

Towns like this originated as communities of farmers banded together on easily defensible hilltops overlooking their farmland

In rural Tuscany, traditional farming is kept alive by farmers like Franco Cucini. While his swans think this pool's made for them, it's actually a reservoir used to power Franco's flourmill.

The mill — with working parts that have changed little over the ages — has been grinding corn and wheat since the 17th century. Until the 1960s, neighboring farmers brought their grain here to be ground. While locals know stone-ground flour is tastiest, mills like these are a tough fit in our fast-paced world.

South of Chianti country is a region called the Crete [Senesi]. It features clay hills — the topsoil washed away by ages of rain — and delicate lanes of cypress. The dramatic beauty of the countryside changes with the seasons. And the terrain is dotted by rustic yet noble farmhouses — many of which rent rooms to tourists.

Small farms are struggling to survive here, as in America. All over Europe, farms rent rooms to travelers — now harvesting their rural charm as well as produce to help make ends meet. Here in Italy, farmhouse B&Bs are called agriturismos.

We're staying in the 13th-century home and farm of Sylvia Gori. And she's happy to show us around.

As her family has for centuries, Sylvia lives in the manor house — and, after a look at the living room, it's clear: the rural nobility of Italy survives.

Roberto: This is the fireplace where you can still cook. It's for polenta.

Upstairs is the vast billiards room. For generations, evenings ended here. Musty portraits are reminders of the family's long and noble lineage.

The farm is strictly organic. These pigs are a rare breed, brought back from the edge of extinction by people who care about traditional agriculture. And gazing at these huggable sheep, you can almost taste the pecorino cheese.

And cheese is an important part of this farm's economy. Walls are stacked with rounds of pecorino, made from the unpasturized — and therefore tastier — milk of the farm's sheep. Traditional organic methods are labor intensive...but connoisseurs of good living here know it's worth the trouble and expense.

The farm also produces top grade prosciutto. The hams are not cooked, but cured in salt. After hanging in a cool room for several weeks, each one is given a spicy coat of pepper. The slow curing process — here they're checking the progress with a horse-bone needle — takes over a year.

The tradition of making these foods is as timeless as the Tuscan countryside.

Sylvia — happy to share the fruits of her labor — invites us for dinner. While this prosciutto and pecorino cheese is sold all over Italy with the family's label, it's particularly tasty when eaten right here. It's a classic Tuscan table: Simplicity, a sense of harmony, and no hurry...enjoyed with a great glass of Chianti.

Sylvia rents out a few rooms to travelers. As is typical of agriturismos, the furnishings are rustic but comfy and the well-equipped kitchen is ideal for anyone settling into Tuscany.

And, if you're really on vacation, this is a good place to be. Distances are short in Tuscany and, while public transportation is meager, those with a car can enjoy fascinating days exploring from a rural homebase like this.

We're heading south to Montalcino — home of the much-loved wine: Brunello di Montalcino.

Typical of the region's hill towns, Montalcino sprawls under its castle with characteristic stepped lanes, peaceful piazzas, and shops selling local this case the area's famous wine.

We're here in September, the grapes are at their peak, and it's harvest time. All around, small family vineyards are busy making the renowned Brunello di Montalcino. The Cencioni family is giving us a look at their operation. This clever machine sends grapes one way and the stems this way.

While the emphasis on quality feels old fashioned, all the latest machinery is employed as they produce 70,000 bottles a year. It's a labor-intensive industry...but right now the grapes are doing all the work as they ferment in these huge oak barrels.

As they share their Brunello, father and son Cencioni seem to understand the happiness their work brings to wine lovers all over the world.

If anything characterizes the Tuscan lifestyle, it's a knack for taking time to savor simple, uncluttered quality — whether it's wine, food, art, or friendships like Roberto's.

Assisi — home of St. Francis and a place where simple living is nothing new — sits on a hill just outside of Tuscany in neighboring Umbria.

Around the year 1200, Francis, a simple friar from Assisi, challenged the decadence of church government and society in general with a powerful message of nonmaterialism and simplicity. His "slow down and smell God's roses" lifestyle drew a huge following and his teachings were gradually embraced by the Church.

The story of St. Francis starts here, below Assisi, in the church of Santa Maria degli Angeli. St Mary of the Angels is actually a church within a church. When the pope gave Francis his blessing, he also gave him this fixer-upper chapel. This is the actual chapel that Francis and his first followers rebuilt. Stepping inside, pilgrims remember it was here, in 1208, that Francis established the Franciscan Order.

A visit to Assisi shows Francis' message of love and care for creation has a broad and timeless appeal. And even non-religious travelers become pilgrims of a sort as they explore the town and remember Italy's patron saint

Any pilgrimage site will be commercialized, and Assisi — which cashes in on the legacy of St. Francis — is no exception. In summer the town overflows with Francis fans and an flood of Franciscan knickknacks.

But, those able to see beyond the tacky friar mementos can actually have a meaningful experience. Most visitors are day-trippers. To enjoy a peaceful Assisi, spend the night. See it early or late and wander the back lanes.

As you explore, look up. Assisi has a balcony garden competition each summer. Medieval Assisi was defended by a fortress that provided townsfolk a refuge in times of attack. Doorways with pointed arches indicate that the buildings date from the 12th through the 14th century. The vaults that turn lanes into tunnels are reminders of medieval urban expansion. While the population grew, people wanted to live safely within Assisi's fortified walls, so Assisi became more dense. Medieval Assisi had five times the population density of the town today.

The town's welcoming Main Square is an inviting place to relax. As in many old European towns, today traffic is limited to taxis and buses.

Assisi has long been a spiritual center. Two-thousand years ago, this Temple of Minerva was a centerpiece of Roman Assisi.

The main drag leads from the town center to the basilica, which holds the much-venerated body of St. Francis.

Francis was a big deal even in his own day — he was made a saint within a few years of his death. Assisi became a busy pilgrimage center, and this street was a booming thoroughfare. This hospice — built in 1237 — gave pilgrims a place to rest, and on their way to the basilica, pilgrims would have stopped at this fountain for a drink.

The Basilica of St Francis was built between 1228 and 1253 over the remains of the beloved saint. For the last 750 years it's been one of the most visited pilgrimage sites in all of Christendom. The tomb lies on the lowest level of the Basilica. Its humble elegance and beauty befits the saint who preached simplicity and poverty. His body became one of the most important relics anywhere.

To medieval Christians, holy relics gave you power — they got your prayers answered, helped you win wars and, ultimately, helped get you to heaven.

The basilica rises in two levels above the tomb. It's one of the artistic highlights of medieval Europe and a theological work of genius. With its fine art, it still functions as a splendid classroom. It was frescoed from top to bottom by leading artists of the 13th century.

Here in the lower Basilica, Cimabue painted what is considered the earliest and most accurate portrayal of St. Francis.

This fresco by Giotto, a follower of Saint Francis himself, was the most powerful storyteller of his day.

In the 13th century, Giotto's art was radical — unprecedented in its realism... believable homespun scenes, landscapes, trees...real people. For the first time, holy people are expressing emotion: One angel turns her head sadly at the sight of Jesus, and another is in such anguish she scratches her hands down her cheeks, drawing blood. Mary, until this fresco always portrayed in control, has fainted in despair. The Franciscan monks, with their goal of bringing God to the people, found a natural partner in Europe's first modern painter, Giotto.

The upper basilica, built shortly after the lower, was the first Gothic church in Italy. It's brighter and nearly wallpapered by Giotto and his assistants. The nave shows 28 scenes from the life of St. Francis.

The 13th century was a troubled time. Franciscan friars, actually known as the "Jugglers of God," were a joyful part of the community. In a land torn by fighting, Francis promoted peace. He also challenged the excesses of the church and made its message more accessible to common people.

Francis' message of non-materialism rattled the wealthy and powerful. Here Giotto shows a nearly naked Francis — the rich kid tossing his fancy clothes to his father — befuddling high society by trading a life of power and luxury for one of simplicity and poverty.

But ultimately, even the pope recognized that Francis could restore a church and society in need of reform.

Perhaps the most endearing scene shows Francis preaching to the birds. But Francis was more than a nature lover. The various birds represent the diverse flock of humanity and nature, all created and loved by God and worthy of each other's love.

Travel far from home can help you better understand what home is all about. Whether wandering through ancient olive groves, climbing medieval towers, or dining slow in a Tuscan villa — travel teaches, and rewards.

I like to reflect on these ideas in a place like this — enjoying the same birdsong and vast Tuscan and Umbrian views St. Francis enjoyed 800 years ago. Thanks for joining us. I'm Rick Steves. Until next time, keep on travelin'. Ciao.