Baracoa, which was founded in 1511 as the first Spanish settlement on the island, is at the eastern tip of Cuba 545 mi/875 km southeast of Havana—and it may (or may not) be the place where Columbus first landed in Cuba. Surrounded by lushly forested mountains and dramatic flat-topped formations, Baracoa was cut off from the rest of the island until the early 1960s.

It's a great place to escape for a couple of days. A fort from the 1700s that overlooks the town has been turned into Hotel El Castillo. Spend your time rambling through the somewhat tumbledown town, soaking up the unique atmosphere and meeting the intriguing local characters. Every Saturday, food stalls spring up along Calle Antonio Maceo and street musicians entertain the dancing crowd. Be sure to make time to tour the beautiful—and largely untouched—rain forests and rivers in the surrounding countryside.

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