Costa del Sol to the Canary Islands

Málaga is a port city on southern Spain’s Costa del Sol, known for its high-rise hotels and resorts jutting up from yellow-sand beaches. Looming over that modern skyline are the city’s 2 massive hilltop citadels, the Alcazaba and ruined Gibralfaro, remnants of Moorish rule. The city's soaring Renaissance cathedral is nicknamed La Manquita ("one-armed lady") because one of its towers was curiously left unbuilt.

Gibraltar is a British Overseas Territory and headland, on Spain's south coast. It’s dominated by the Rock of Gibraltar, a 426m-high limestone ridge. First settled by the Moors in the Middle Ages and later ruled by Spain, the outpost was ceded to the British in 1713. Layers of fortifications include the remains of a 14th-century Moorish Castle and the 18th century Great Siege Tunnels, which were expanded in WWII.

Tangier, a Moroccan port on the Strait of Gibraltar, has been a strategic gateway between Africa and Europe since Phoenician times. Its whitewashed hillside medina is home to the Dar el Makhzen, a palace of the sultans that's now a museum of Moroccan artifacts. The American Legation Museum, also in the medina, documents early diplomatic relations between the U.S. and Morocco in an 1821 Moorish-style former consulate

Funchal is the capital city of Portugal's Madeira archipelago. It's backed by hills, and known for its harbor, gardens and Madeira wine cellars. The centuries-old Funchal Cathedral, which mixes Gothic and Romanesque styles, is notable for its carved wooden ceiling. Fronting the harbor is the São Tiago Fortress, built in the 1600s. It now houses the Contemporary Art Museum, with a large collection of Portuguese works.

Funchal is the capital city of Portugal's Madeira archipelago. It's backed by hills, and known for its harbor, gardens and Madeira wine cellars. The centuries-old Funchal Cathedral, which mixes Gothic and Romanesque styles, is notable for its carved wooden ceiling. Fronting the harbor is the São Tiago Fortress, built in the 1600s. It now houses the Contemporary Art Museum, with a large collection of Portuguese works.

Funchal is the capital city of Portugal's Madeira archipelago. It's backed by hills, and known for its harbor, gardens and Madeira wine cellars. The centuries-old Funchal Cathedral, which mixes Gothic and Romanesque styles, is notable for its carved wooden ceiling. Fronting the harbor is the São Tiago Fortress, built in the 1600s. It now houses the Contemporary Art Museum, with a large collection of Portuguese works.

Santa Cruz de Tenerife is a port city on the island of Tenerife, in Spain’s Canary Islands. Well-preserved buildings in its old town include the colonial Church of the Immaculate Conception. The 1700s Palacio de Carta has baroque and neoclassical features. In the Old Civil Hospital, the Museum of Nature and Man has interactive displays on the islands. The city’s squares include the central Plaza de España.