Rick Steves Calls This Historic Gem Italy's 'Ultimate Hill Town'

If you're visiting Italy, you might already have your destinations picked out. Perhaps your itinerary has items like eating gelato in front of the Colosseum in Rome, taking a picture on Florence's Ponte Vecchio, or exploring the ruins of Pompeii. Those are all worthy ideas, but if you're visiting this beautiful country, you cannot miss its glorious hill towns. One that you should put on your itinerary immediately is Siena in Tuscany, according to travel pro Rick Steves. On his website, Steves says, "Situated atop three hills, Siena qualifies as Italy's ultimate 'hill town.' Its thriving historic center, with movie-set-worthy lanes cascading every which way, offers Italy's best medieval city experience." Siena was one of the biggest cities in Europe in the 14th century, but things like the plague took away its prominence. Now, however, it's one of the loveliest places you can visit in Italy. 

The closest airport to Siena is the Florence Airport, Peretola, which is around 50 miles away. However, you can also fly into Perugia San Francesco d'Assisi – Umbria International Airport, which is 72 miles away, or Pisa International Airport, which is 74 miles away. From the Florence airport you can get to Siena by tram, bus, or train, in addition to driving. If you're going by train, the Trenitalia S.p.A. from Firenze S.M. Novella to Siena is between $12 and $15 at the time of this writing. However, Steves suggests renting a car while in Tuscany, as this allows you the freedom to enjoy the scenic drives in the region. Siena is busiest, he tells us, in April through June, and September through October. If you go off-season, keep in mind that some things may have short hours or be closed altogether. 

One reason Steves recommends Siena is that it's great for pedestrians. In fact, the whole center of town is off-limits to cars unless you're a resident or a taxi driver. Wander the narrow streets of town, or plop yourself right on the ground in the Piazza and do some people watching. In fact, Steves recommends enjoying a drink at one of the cafes around the square. While he generally says to walk a few blocks from a crowded tourist area for your meals, this is an exception. Grab something small with a glass of wine and relax. Make sure you stop by the lovely 15th-century Fountain of Joy in the Piazza, too, while you are there. 

Steves suggests enjoying a leisurely walk around the streets of Siena, simply taking it all in. He tells us, "While nearby Florence has the blockbuster museums, Siena has an easy-to-enjoy soul: Courtyards sport flower-decked wells, alleys dead-end at rooftop views, and today, even with all the tourists, a strong local spirit pervades." As you stroll, you'll see colorful flags hung all over. These represent the contrade, or neighborhoods of Siena, and there is friendly competition between them. On July 2 and August 16, the Palio, a bareback horse race, happens in the Piazza del Campo, while the contrades enthusiastically back their contestant. (If you've visiting during that time, Steves says to make sure you have reservations.) 

While Siena can be a day trip, you may want to stay overnight. If you do, you can enjoy one of Steves' favorite parts of the day, the aperitivo hour. He explains, "Bars tucked here and there attract an early crowd by serving a free buffet of food with the purchase of a drink. It's a light dinner obtained for the cost of a beverage."

While a simple walk through the city, stopping at shops and cafes is a glorious pastime on its own in Siena, there are some incredible sights to explore. If you've got the stamina, climb the Torre del Mangia right in the Piazza. Built in the early-to-mid 14th century, there are 400 steps to the top of the tower. It's pretty warm if you try it in the summer, but it's worth it for the spectacular city views. 

Another place Steves says is a must-see is the Cathedral of Siena, with its striped tower and incredible duomo. Inside you'll see mosaic floors that will blow your mind, and breathtaking art and sculpture, including works by Donatello, Michelangelo, and Bernini. When you visit, make sure you stop by the Piccolomini Library. The walls and ceiling are astonishing in their level of decoration, from the Pinturicchio frescoes that almost appear to be 3D to the gilding and arches and the statue of the Three Graces. The Duomo Museum is another stop you have to make. You can see the stained-glass rose window by Duccio di Buoninsegna, as well as his altarpiece showing the Madonna and Child Enthroned with Angels and Saints, the Treasury, and the Tapestry Room.

If your eyes can take in more beauty, hit the Santa Maria della Scala Museum, which is opposite the Cathedral. The frescoes alone are worth the stop. The 14th-century Baptistery of San Giovanni is another Steves recommendation, and is a sculpturally-gorgeous baptismal font that stands in the middle of domes and arches covered with riotous paintings, sculpture, and frescoes from Vecchietta. Finally, Siena is less than 50 miles from Florence, an idyllic city full of art and architecture that Steves calls Europe's "cultural capital." Just don't try to do them both in one day.