Small town Sienna

For a long time Italy wasn't a country, it was a bunch of cities that fought with each for power and influence. Sienna and Florence were two of the top contenders, and their rulers tried to out-do each other for centuries.

Like the modern day sponsors of Burj Dubai, or the Three Gorges Dam, or the Maglev Train in Shanghai, or the Space Race, huge public works that creates lots of buzz around your city-state were the way to go.  Look!  We're so rich and powerful that we have the biggest, most bad-ass cathedral in the world!  Thank you, peasants of yesteryear, for paying the taxes and providing the labor that lets us ooh and aah at the cathedrals your rulers built.  

Florence gets all the attention these days, but Sienna is the way better place to spend an afternoon.  Sure, you can't check the box on seeing Michelangelo's David or some other famous works of art, but it's way less crowded, way more charming, and the gelato is pretty damn good.

Are you into freaskish Saintly treasures?  That's another good reason to come to Sienna.  The patron Saint of Sienna, St. Catherine, is sort of celebrity in Catholic circles and her mummified head and thumb are still on display at one of the cathedrals.  It's easy to miss until your guidebook says (3): Mummified head of so and so and you're like no way!  It's really there!  I'm not sure I could spend a whole Mass with her eerily staring at me from her glass jar.

For a taste of small-town Italian life, find one of the little hole-in-the-wall trattorias and let the family in charge pick a plate of Italian cold cuts and some appetizers.  Then, wash it down with a glass (or a couple) of the house wine while you watch the locals come and go, shoot the breeze with the owners and each other, and live the small town life.  It's pretty damn charming.  Even if you love being anonymous in a huge, bustling city like New York, there's something about that small town intimacy that hits at a place really deep in our soul, where we wish we had that local bar where everyone knows everyone else (or... maybe that's just me.)

Also, in my purely personal and highly amateur opinion, Sienna won the Cathedral wars.  Sure, Florence's has more square footage, but the inside of Sienna's is breathtakingly over the top.  Their medieval square also has a nice slant to it, is located right outside the entrance to the town hall, and has a bunch of great gelato joints.  Even giving Florence some points of shopping and great art, I think Sienna squeaks by with the win.

Charming Sienna, city on a hill.

Less charming and way more creepy - the mummified head of St. Catherine of Sienna.

Her thumb

Back to charming - a little trattoria in the medieval center.

Family pride

The steep streets of Sienna

Another example of out-of-control Church architecture.

Sculptures of popes heads line the main chamber - all of them.

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The outside - looks a lot like the cathedral in Florence, doesn't it?

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The other, less fancy, church, just outside of the city walls.

The picture-perfect drive home.

Tuscan villages.