Extremadura

Monastery

Guadalupe's renowned, Unesco World Heritage–listed monastery is located, according to legend, on the spot where, in the early 14th century, a shepherd received a vision of the Virgin Mary. A sumptuous church-monastery was built on the site, drawing pilgrims from across the world ever since. Now cared for by nine Franciscan monks, it remains one of Spain's most important pilgrimage sites, especially for South American and Filipino Catholics. The building is an architectural delight, crammed with historical riches.

Ruins

Mérida's most spectacular Roman monument, and the only one to once again fulfil its original function – by hosting performances during the Festival Internacional de Teatro Clásico in summer – the Teatro Romano is the city's indisputable highlight. It was built around 15 BCE to seat 6000 spectators. The adjoining (slightly less-dazzling) Anfiteatro opened in 8 BCE for gladiatorial contests and held 14,000; the gladiator-versus-lion fresco in the Museo Nacional de Arte Romano was taken from here.

Square

Trujillo's main square is one of Spain's most spectacular plazas, surrounded by baroque and Renaissance stone buildings sporting intricately carved facades, topped with a skyline of towers, turrets, cupolas, crenellations and nesting storks.

Monastery

In a lovely shady setting 1.5km northwest of Cuacos de Yuste, this monastery is where Carlos I of Spain (Charles I; also known as Carlos V of Austria) came in 1557 to prepare for death after abdicating his emperorship over much of Western and Central Europe. It's a soulful, evocative place amid the forested hills, and a tranquil counterpoint to the grandeur of so many formerly royal buildings elsewhere in Spain.

Village

About 25km west of Hervás, the ghost village of Granadilla is a beguiling reminder of how Extremadura's villages must have looked before modernisation. Founded by the Moors in the 9th century but abandoned in the 1960s when the nearby dam was built, Granadilla's traditional architecture has been painstakingly restored since the 1980s as part of a government educational project. Enter through the narrow Puerta de Villa, overlooked by the sturdy 15th-century castle, which you can climb for brilliant panoramas.

Church

This 13th-century church is a stunner. It has a mainly Gothic nave and two towers that you can climb for fabulous views across Trujillo, the castle and the sprawling countryside. The church's magnificent altarpiece includes 25 brilliantly coloured 15th-century paintings by Spanish artist Fernando Gallego in the Hispano-Flemish style, depicting scenes from the lives of Mary and Christ. The 124-step Torre Julia is a Romanesque stunner, while the 106-step Torre Nueva has some interesting architectural notes on the first landing.

Cathedral

Plasencia’s magnificent cathedral is two-in-one. The 16th-century Catedral Nueva is a Gothic-Renaissance blend with a handsome plateresque facade, a soaring 17th-century retablo (altarpiece) and intricate walnut-carved choir stalls featuring seats dedicated to the Reyes Católicos (Catholic Monarchs). Within the Romanesque Catedral Vieja are 13th-century cloisters surrounding a fountain and lemon trees. The octagonal Capilla de San Pablo has a dramatic 1569 Caravaggio painting of John the Baptist, a religious museum and an arched Romanesque doorway.

Historic Building

The sumptuous home of Cáceres' prominent Golfín family has been beautifully restored. Built piecemeal between the 14th and 20th centuries, it's crammed with historical treasures: original 17th-century tapestries and armoury murals, a 19th-century bust of Alfonso XII, and a signed 1485 troops request from the Reyes Católicos (Catholic Monarchs) to their Golfín stewards. But it's the detailed, theatrical tours (Spanish, English, French or Portuguese), through four richly decorated lounges, an extravagant chapel and fascinating documents room, that stand out.

Bridge

Don't miss the extraordinarily powerful spectacle of the Puente Romano spanning the Río Guadiana. At 792m in length with 60 granite arches, it's one of the longest bridges built by the Romans. It was constructed in 25 BCE when Emerita Augusta (modern-day Mérida) was founded, and then partly restored in the 17th century. The 20th-century Puente Lusitania, a sleek suspension bridge designed by Santiago Calatrava, mirrors it to the northwest. The best Roman bridge views are from the Alcazaba's southwestern ramparts.