December 31st 2025
Siena, Italy
Traveler: Evan Markley
Destination: Siena, Italy
On a chilly December day in Atlanta, Evan looks back fondly on a sunny September trip he took to Siena. He reflects on the various aspects of this medieval Italian city that may or may not compel someone to follow in his footsteps and pay a visit to this storied town.
I want to warn people: Siena might not be for you. Anyone thinking about traveling to Siena should thoroughly review the following items before booking their trip. Don’t be an unaware traveler; know what to expect. Here is a comprehensive list of why you might not want to visit this Tuscan hill city.
Don’t visit Siena if you don’t like sweeping vistas:
Siena as seen from the foot of the Basilica di San Domenico. The Torre del Mangia which sits on the main square – Piazza del Campo - is at center left, with the Duomo di Siena to its right.
View from the medieval city wall near Porta San Marco.
Peering out a window in Il Chiostro del Carmine hotel.
View from Via di Fontanella in the Contrada dell’Onda featuring a Tuscan moon and the neighborhood’s baptismal fountain (more on this later).
Don’t visit Siena if you don’t like narrow streets:
I wouldn’t touch the Grinch with a thirty-nine-and-a-half foot pole, but I could touch a building from across the street with a ten-and-a-half foot pole in most of Siena.
Left: A narrow street with a view of the unfinished addition to the Duomo di Siena; Center: A narrow street with a view of the Basilica di San Domenico; Right: A narrow street with a view of the Torre del Mangia
A narrow street in the Contrada dell’Oca. Siena is divided into seventeen contrade (neighborhoods) which compete twice a year in the Palio, a bareback horse race held in the Campo. Several Oca flags hang proudly over this street indicating that this contrada was the most recent winner of the Palio.
Don’t visit Siena if you don’t like hilly streets:
San Francisco? Never heard of it. Unless you mean the man from Assisi, then he’s about an hour and a half away.
Don’t forget your parking brake!
Sometimes the hills take the form of stairs. Undecided on whether this makes traversing them any easier…
A typical table set-up for dining in the streets of Siena.
Don’t visit Siena if you don’t like curvy streets:
Just look at those curves!
Don’t visit Siena if you don’t like secret tunnels:
Are these tunnels actually secret? Maybe. Do these passages appear on the Marauder’s Map? Probably.
I only got scared a couple times when I walked through the dark ones.
Don’t visit Siena if you don’t like arches:
Several arches can be found throughout the city spanning over narrow streets.
The Loggia della Mercanzia, just behind the Campo.
The unfinished addition to the Duomo di Siena. This addition was initiated in 1339 but was halted in 1348 because of the Black Death.
The backs of these buildings, which face the Duomo on the opposite side, feature some beautiful multi-story arched windows.
Don’t visit Siena if you don’t like towers:
Left: The tower of San Niccolò al Carmine church; Right: The tower of the Basilica di San Domenico at right and the tower of the Duomo di Siena in the background
The Torre del Mangia, as seen from the Piazza del Mercato, just south of the Campo.
The Torre del Mangia and Palazzo Pubblico, as seen from the center of the Campo on a moonlit night.
Don’t visit Siena if you don’t like highly stylized water drains:
This ornate water drain, known as the Gavinone, sits at the low point of the Campo, in front of the Palazzo Pubblico.
The Gavinone was installed in 1349 when the Campo was first paved in brick and travertine.
Don’t visit Siena if you don’t like animals:
Siena’s contrade are each represented by an animal which feature prominently in the flags, architectural embellishments, and a specific baptismal fountain within each contrada. Here is the fountain of Tartuca, ‘the tortoise.’
The fountain of Onda, ‘the wave,’ commonly represented with a dolphin.
The fountain of Selva, which means ‘forest,’ but is also represented with a rhinoceros (hey, I didn’t make the rules).
The statue at the fountain of Torre, ‘the tower,’ which is often depicted as a tower on the back of an elephant. If you don’t like towers and don’t like animals, you should definitely steer clear of this place.
A keystone featuring an eagle and a stag at Palazzo de’ Vecchi. This building sits in the Leocorno (unicorn) contrada so this is most likely a heraldic symbol of the de’ Vecchi family.
A dashing fellow who has caught himself some tasty dinner, featured in a service station on the road to Siena.
Don’t visit Siena if you don’t like painted facades:
Loving the two-tone here!
I appreciate that this building has its date of ‘1893’ painted on it not once, but twice (just in case you missed one).
Don’t visit Siena if you don’t like medieval churches:
Left: Interior of the Basilica di San Domenico; Right: The baroque chapel of Saint Catherine of Siena in the nave of San Domenico. This chapel features a reliquary housing Saint Catherine’s head which can be seen at center.
The rear façade of the Duomo di Siena.
The Chiesa di San Giuseppe, the oratory of the Onda contrada.
Left: The rear façade of the small Chiesa di Santa Maria delle Nevi; Right: The Chiesa di San Giorgio, which was originally built in 1081, but remodeled to its current appearance in 1731.
Don’t visit Siena if you don’t like walls with vines and a single streetlamp:
Get a load of this wall. Beautiful. More of this please.
Don’t visit Siena if you don’t like operable shutters:
Left: Some classic operable shutters with some nice filled-in windows to boot; Right: More classic operable shutters, but this building also has me scratching my head about what happened to the lower pediment.
This façade is featuring an intriguing ‘one shutter open, one shutter closed’ window.
The matching louvered arches above the shutters are a lovely added touch on this building.
The building at right features some unique half-Bahama-style shutters I have never seen before.
Pocketing shutters in a stucco wall. Now I have seen it all.
Don’t visit Siena if you don’t like unique doors and doorways:
Left: A lovely little doorway featuring the Siena coat of arms above; Right: A double door with wooden clavos-like knobs and intricately carved panels.
Beautiful brickwork at this door surround, I especially enjoy the round-bellied brackets on either side.
Another wonderful composition of brickwork. I love how the vertical piers and cornice at the door stand upright and reach out from the adjacent battered wall.
Never seen anything like this. Loving everything about it.
Extremely high contender for the best hidden garage door I have come across. Bravo.
Don’t visit Siena if you don’t like votive shrines in the sides of buildings:
These small shrines, often called ‘Madonnelle’ when featuring Saint Mary, are said to have been originally built to bring protection to the streets or corners they watch over. They vary in size and detail and can be found on almost every street and alley in Siena.
Don’t visit Siena if you don’t like buildings at forks in the road:
The Capella della Madonna del Rosario, a deconsecrated chapel in the Chiocciola (snail) contrada, which is now used as a stable during the Palio.
A building at the intersection of Via del Paradiso and Via della Sapienza featuring a Madonnella above its souvenir shop.
The Chiesa di San Gaetano di Thiene, the oratory of the Nicchio (shell) contrada.
Don’t visit Siena if you don’t like night lights and night life:
The curving façade on the north side of the Campo, where the ristoranti and caffè commonly stay open past midnight.
Piazza Salimbeni, which is home the world’s oldest bank, Banca Monte dei Paschi di Siena.
Left: The Chiesa di San Cristoforo in Piazza Tolomei, setting up for an outdoor concert; Right: Philadelphia Bar. How could I not mention Philadelphia Bar.
Don’t visit Siena if you don’t like sunsets:
A view from Via di Salicotto in the Torre contrada.
A view of San Domenico from Via Diacceto in the Selva contrada.
The Duomo di Siena, in all its splendor.
That’s all from me. If you don’t like any of the above things, you might want to reconsider that spring break trip to Siena this year. If you do like all these things, then it’s time to get booking, my friend! What are you still doing reading this blog post? Get yourself a ticket and go see it for yourself! Then after you do, you can help warn all the people who don’t know just what they’re getting into when they start considering a trip to this slice of Heaven in the Tuscan hills.
