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In Siena, you’ll find all the classic architecture, amazing wine, delicious food, and medieval history that Italy is known for, but without the tourist hordes that descend on the big cities. In town, roam the streets around the piazza checking out the museums (most are free, and never have lines), shops, and cafes. Climb the medieval bell tower (the second highest in Italy) for a breathtaking view. The town’s center is so old and historic (part of it still has medieval walls) that it’s a UNESCO World Heritage Site, and yet, most attractions still remain free and un-crowded.
Venture into the three rolling hills that surround Siena, and check out the farms and vineyards. Be sure to stop and sample the wine at the Castel di Pugna, famous for its Chianti.
Where is it? In Italy, less than 40 miles south of Tuscany.
Where to stay? At Quattro Torra Residenza d’Epoca, a converted castle that’s now a homey B&B. Rates start around $190 per night.
What else should I know? The Palio Horse Race, held in Siena in the summer, attracts huge crowds.
Who’s it for? Wine-lovers, those who want to see the non-crowded side of Italy, and history buffs.