This hamlet high above the countryside's rolling hills has everything you'd expect from a mountain village in Tuscany: well-preserved medieval architecture, a central piazza, cute shops, and small restaurants where extended families gather for big meals. Massa Marittima's cathedral of St. Cerbone and the Palazzo del Podesta's archaeological museum are must-sees, but the tunnels beneath the historical town center are also impressive. At the Mining Museum (Museo della Miniera), you can explore areas where miners dug out travertine stone to build the village in the Middle Ages. Other travertine passageways that tap into natural springs are adorned with frescos in the Medieval Water Collection Gallery (Fonti dell'Abbondanza).
If You Go: Take a Monteregio Wine Trail tour starting from the palazzo that was once the government mint. Excursion company Tour of Italy, a father-and-son team, runs Tuscany tours and genealogy tours that put you in touch with long-lost relatives.
Getting There: Massa Marittima is 75 miles, or about a two-hour drive, southwest of Florence. On the coast 12 miles away, Follonica is the nearest train station to Massa Marittima.