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This Tuscan hill town will transport you back to the Middle Ages. Siena's grand cathedral, built in the 1200s, has treasured artworks and marvelous marble floors. The Piazza del Campo, the main town square, is a UNESCO World Heritage Site. It's also home to the Palio, perhaps the most infamous horserace in the world. No goofy hats and mint juleps here—this is a medieval tradition involving bareback riders racing on cobblestones (so as you might imagine, it's quite dangerous). Siena is an easy daytrip by train from Florence, just 43 miles away.
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    *Prices are based on 1-21 day travel. These are the best fares found by travelers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.