Toledo

The ancient city of Toledo is surrounded by the sweeping plains of Castilla-La Mancha and perched above the Tagus River, so it certainly makes a striking impression. Dominated by the 4-towered 11th-century Alcazar fortress, the city's old town is a labyrinth of winding cobbled streets, where mosques, synagogues, and Gothic churches co-exist – remnants of the Middle Ages when it was dubbed the 'city of 3 cultures'.

Beyond picturesque architecture, Toledo has many trappings: Here, you can see the works of artist El Greco, dine on authentic Spanish fare and sangria, and hunt for handmade trinkets crafted by the city's skilled artisans.