Tough Choices in Siena

Begin your day people-watching as you have breakfast in the animated Caffè Garibaldi di Romano Gennaro. Try Gennaro's panini, pies, or pastries with a delicious Italian coffee on the side.
And excellent news: it's before 11 am, so you can order a cappuccino without any judgment from the locals!
Caffè Garibaldi di Romano Gennaro is open every day except on Tuesday, from 6 am to 12 am.

Legend has it that the son of Remus established Siena, and the sign of the wolf feeding the twins Romulus and Remus is as common in Siena as it is in Rome. Actually, the city most likely has Etruscan origins, even though it became a legitimate town when the Romans founded here a military colony named Sena Julia.
In 1348, a plague outbreak killed two-thirds of Siena's residents, ushering in an era of decline. This resulted in the city being given over to Cosimo I de' Medici, who prohibited the residents from operating banks, significantly limiting the city's influence.
The centuries-long economic crisis that followed the Medici takeover turned out to be a blessing in disguise since the lack of funding meant that Siena saw relatively little reconstruction or new buildings. As the living embodiment of a medieval city, the historic center was included in the UNESCO World Heritage List.
Siena has also kept a festival alive since the Middle Ages. At the beginning of July and in mid-August, part of Siena's contrade or town districts fight for the Palio, a silk banner. Late in the afternoon, locals in historical costumes wearing banners take part in a parade around Piazza del Campo. Then the Palio race takes place, and bareback riders on their horses speed three times through the temporary track. After that, the locals retreat in song on the narrow streets of Siena. Learn more about the Siena Palio here.

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The rivalry between Siena and Florence continues to this day, and involvement is not confined to residents; most travelers acquire a strong preference for one town over the other. I wonder which city will have stolen your heart by the end of this visit.

The Pubblico Palace still serves as the Sienese town hall and it also houses the Museo Civico.
The most renowned museum of Siena is housed in chambers lavishly frescoed by Sienese school artists.
Inside, you will see several outstanding pieces of art, including Simone Martini's Maestà (Virgin Mary in Majesty), in the Sala del Mappamondo (Hall of the World Map). It is Martini's earliest known work and depicts the Virgin Mary beneath a canopy surrounded by saints and angels.
Another interesting thing to see is Lorenzetti's Allegory and Effects of Good and Bad Government, a series of frescoes that provide a unique viewpoint on the medieval city and rural life.
Museo Civico is open every day between 10 am and 7 pm. Tickets can be bought on the spot and include access to Torre del Mangia.

Climb the 388 steps of the thin 14th-century Tower of Mangia for a different perspective over Siena and the Tuscan countryside. Make sure you get a good look at the shell-shaped Piazza del Campo and the beautifully preserved streets below.
Torre del Mangia is open daily, between 10 am and 6.15 pm.

Enjoy lunch outside at this osteria with authentic Tuscan cuisine. No matter what you choose, the food will be excellent - you're at yet another Michelin guide restaurant. As for the wine, you might want to try a young local Chianti Colli Senesi, from vineyards growing on Siena's hills.
Osteria Le Logge is open every day except Sunday from 12 to 2.45 pm, then from 7 to 10.45 pm.

Arriving on Via dei Pellegrini, you will reach the impressive Baptistry of San Giovanni. Inside, you can admire works by Florentine artists such as Ghiberti and Donatello, as well as local artist Jacopo della Quercia.
Battistero di San Giovanni Battista is open every day from 10.30 am to 7 pm. Visit included with Duomo ticket.

As you exit the Bapistry, go up the white marble steps to the Duomo di Siena.
Siena's cathedral was initially intended to be larger than St Peter's Basilica from Vatican City. Despite not succeeding in that performance, it's still a masterpiece of Tuscan Gothic architecture.
Its beautiful façade in red, green, and white marble is a spectacular work of art planned by Giovanni Pisano. And, inside, you'll uncover an impressive collection of Medieval and Renaissance artwork, including several statues by Michelangelo, Donatello, and Gian Lorenzo Bernini, and paintings by Pinturicchio.
Duomo di Siena is open daily from 10.30 am to 5 pm. Tickets can be bought on the spot.

Raised a magnificent game of one-upmanship between opposing aristocratic families in the 12th and 13th centuries, San Gimignano is dubbed Medieval Manhattan thanks to its tall towers that form one of Italy's most beautiful skylines.
If you're here on the second weekend of June, you can enjoy the San Gimignano Medieval Festival. Discover here all the annual events in San Gimignano.

In Piazza del Duomo, you will find the Duomo Collegiata di Santa Maria Assunta and the Palazzo Comunale, Pinacoteca and Torre Grosa.
The interior of this Romanesque basilica is lavishly adorned, with Old Testament cycles in the left nave and New Testament cycles on the right, a beautiful Saint Sebastian by Benozzo Gozzoli, and horrific portrayals of the Seven Deadly Sins.
Domenico Ghirlandaio, Michelangelo's master, presents the narrative of Santa Fina in a series of remarkable frescoes.
The Duomo is open every day from 10 am to 7.30 pm, with the last entry at 7 pm. Tickets can be bought on the spot.

The Pinacoteca houses numerous magnificent masterpieces, including Maestà by Lippo Memmi, works by Gozzoli, and an altarpiece depicting San Gimignano holding the town in his grip. A profane series of murals depicting the initiation is love was designed to turn away medieval eyes.
After visiting the town's art collection, you should climb up the Torre Grossa, the highest tower in San Gimignano. Going up the 218 steps will bring you to a beautiful panorama.
Palazzo Comunale is open daily, from 10 am to 7.30 pm. Tickets can be bought on the spot.

Enjoy an authentic meal at Perucà, a restaurant with a special atmosphere. The food is to die for because the owner knows and loves local food and wines. Try the fagottini del contadino (ravioli served with pecorino cheese, pears, and saffron cream) or ask for a recommendation from the menu.
Perucà is open every day except Thursday from 12 to 2.30 pm, then from 7 to 9.30 pm.

It was a full day, so walk to La Locanda di Quercecchio to get some rest. Luckily, it's located in the center of San Gimignano, so you're not far!