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The bordering countries of Azerbaijan, Armenia, and Georgia—known together as the region of Transcaucasia—can seem worlds apart. Each country’s language shares no roots with the others, and while most Azerbaijanis practice Islam, Georgia and Armenia are predominantly Christian. A trip through the region with outfitter Caucasus Travel takes you to Azerbaijan’s 8th-century mosques, Armenia’s Eastern Orthodox monasteries, chic Rustaveli Avenue inTbilisi, Georgia, and Dilijan, a mountain resort town that has been called “the Armenian Switzerland.” Caucasus Travel employs only local guides, and their 14-day trip ends with a celebratory toast in Georgia, the birthplace of winemaking. From $3,900.

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