The second-largest city in Yucatán State, picturesque Valladolid (pronounced vye-ah-do-leed) is seeing a big boom in popularity among travelers en route to or from Chichén Itzá. (It’s a far closer base for exploring the ruins than either Mérida or Cancún.) Francisco de Montejo founded Valladolid in 1543 on the site of the Mayan town of Sisal. The city suffered during the Caste War of the Yucatán—when the Maya in revolt killed nearly all Spanish residents—and again during the Mexican Revolution.
Despite its turbulent history, Valladolid's downtown contains many colonial and 19th-century structures. For a taste of local life, check out the Sunday morning demonstrations of Yucatecan folk dancing in the main square; you can return at 8 pm, when the city's orchestra plays elegant, stylized danzón—waltzlike music to which expressionless couples swirl (think tango: no smiling allowed).
If you need help getting oriented, Valladolid's phenomenal municipal tourist office is open daily on the southeast corner of the square. You can also look for the bilingual tourist police dressed in spiffy white polo shirts and navy-blue baseball caps and trousers.