Duration: ~9 hours 
Season: All year round

From: starting from € 160 per guest

Up to 6 guests

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Your Exclusive Journey Through Tuscany

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Monteriggioni: the castle that even scared Dante

Monteriggioni is small, sure, but it's got a colossal ego: its circular walls with 14 towers were so imposing in the Middle Ages that Dante name-checks them in the Inferno, comparing them to the giants surrounding the ninth circle. Not a bad calling card. Today the village is a perfect stone circle poking up between the Sienese hills like a giant sandwich dropped on the lawn — and the moment you walk through the main gate, you land in a little square so tidy and picture-perfect it looks like a film set (and it has been, more than once). Fun fact: the walls are so well preserved you can still walk along the top of them, feeling half medieval guard, half tourist with a camera.

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Siena: the city that risks it all in 90 seconds

Siena is elegant, Gothic, and has a heart that beats hard twice a year: the Palio. Ten horses, ten jockeys, one and a half laps around Piazza del Campo, and in just about ninety seconds it's decided which neighborhood ("contrada") gets bragging rights for the next 12 months. Locals don't joke around about this — some of them think about it 365 days a year. Race aside, Piazza del Campo itself is a spectacle — shell-shaped, gently sloped, perfect for sitting down with a gelato and watching the sunset. And the Torre del Mangia towering over the square is named after a bell-ringer so notoriously gluttonous he earned a nickname that's stuck in history books ever since. Fun fact: the Duomo's floor is so precious and intricate that for most of the year it's kept covered to protect it — a museum that occasionally hides itself.

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San Gimignano: Italy's first skyscraper skyline (well, 72 of them)

San Gimignano is known as "the Medieval Manhattan," and that's not just a tourist brochure exaggeration: in the 13th century, the city's noble families competed by building ever-taller towers, a stone ego contest to flex power and wealth. Over 70 went up, and 14 survive today, still dominating the skyline and visible from miles away across the vineyards. Wander the cobblestone streets and you'll almost inevitably end up at an award-winning gelato shop (literally — world championship-winning) — so it's scientifically impossible to visit San Gimignano without eating gelato. Fun fact: the local white wine, Vernaccia di San Gimignano, is so ancient it gets a mention in the Divine Comedy — apparently Dante cared more about the wine than the towers.