Before Madrid was decreed the capital of Spain in 1561, the Spanish monarchs ruled from Toledo, known as the “City of Three Cultures” for its history as a melting pot of Jewish, Islamic, and Christian traditions. In fact, Toledo is home to Spain’s most precious vestige of Jewish history, the Synagogue of El Tránsito, whose florid stucco artistry is as spell-bindingly articulate as the Alhambra’s. Toledo’s other architectural opus—and top attraction—is the Catedral Primada de Santa María, a massive Gothic temple that houses centuries of priceless treasures such as the Monstrance of Arfe, a 10-foot-tall gold vessel studded with jewels.
Insider Tip: Since there’s so much history to digest in Toledo, optimize your time by hiring one of the city’s official local guides (Diego Esteban Sánchez is excellent), whose ear-to-the-ground knowledge and special access to cultural sites justify the investment.
Where to Eat: Toledo may have retained its medieval character through the centuries, but the city’s culinary scene is anything but antiquated. A case in point, Locum’s palate-thrilling cuisine is delightfully anachronistic, with modern Spanish tasting menus served in a 17th-century townhouse built around an indoor patio.
One of the most impressive Roman works of civil engineering to survive today, the Aqueduct of Segovia has stood for 2,000 years. Its longevity is particularly staggering, considering that it spans nine miles at a near-perfect 1% gradient—and that mortar is entirely absent from the construction. While the aqueduct may be Segovia’s star attraction, it’s worth wending your way through the narrow streets of the Judería (old Jewish quarter) to the Alcázar, whose turrets and battlements helped inspire Walt Disney’s Cinderella Castle.
Insider Tip: Climb the spiral staircase within the Alcázar’s Tower of Juan II to the top for the 360-degree views of the city, surrounding countryside, and Sierra Guadarrama mountain range.
Where to Eat: Ask any Spaniard what to eat in Segovia, and the unanimous response will be cochinillo asado, roast suckling pig so tender that it’s customarily carved using the dull edge of a plate. Most Segovianos agree that Restaurante José María’s rendition, with smoky notes from a wood-fire oven, is the city’s best.
Said to be the oldest city in Western Europe, Cádiz is also the continent’s southernmost capital. Sure, there are Roman ruins to uncover and pleasant parks to stroll, but Cádiz’s unspoiled beaches are what make this city stand out from its Costa del Sol neighbors. For tranquility and white sand, head to Playa de Levante, which doubles as a nature reserve. If beachside restaurants and busy boardwalks are more your speed, make camp at Playa Vistahermosa.
Insider Tip: Take a quick jaunt north of Cádiz to sip your way through the bodegas of the famous “Sherry Triangle” cities: Jerez, Puerto de Santa María, and Sanlúcar de Barrameda.
Where to Eat: Surrounded by water on three sides, it’s no wonder Cádiz is synonymous with pescaíto frito, a catch-all genre of seafood served crisp and hot from the fryer with plenty of fresh lemon. At Freiduría Las Flores, one of the city’s most legendary seafood houses, opt for the tortillitas de camarón, thin, crisp parsley-flecked shrimp fritters, or the cazón en adobo, succulent nuggets of garlic- and cumin-marinated shark.
Cáceres may not draw crowds, but this medieval city in Extremadura is one of Spain’s best-kept secrets. The entire Casco Antiguo (walled city)—with its crenellated archways, Golden Age palaces, and 30 Islamic towers—has been declared a UNESCO World Heritage Site. The city is sleepy enough for a weekend of uninterrupted relaxation, but there are more than enough spirited tapas bars and tabernas in and around the Plaza Mayor to keep visitors entertained.
Insider Tip: The yemas, sticky, cinnamon-scented egg-yolk confections sold by the nuns at Convento de San Pablo, make wonderful souvenirs.
Where to Eat: In Cáceres, one restaurant steals the show: Atrio. Chef Toño Pérez has single-handedly brought culinary renown to the city with his Michelin-starred cuisine, which hinges on regional ingredients like nutty ibérico pork and pungent torta del Casar cheese.
Oviedo is the capital of Asturias, the misty green province famous for its mountainous interior (serious climbers rave about Picos de Europa) and scenic coastline along the Cantabrian Sea. Like other ancient cities around the country, Oviedo features an Old Town with a majestic cathedral and a number of lovely plazas. But it’s worth getting out of the city center, if only to witness a sunset from Santa María del Naranco, a pre-Romanesque edifice remarkable for its slender contours and detailed archways, completed in 848.
Insider Tip: Oviedo is an ideal home base for an Asturian adventure. Take a meandering drive along the ocean, stopping in Cudillero, a colorful village built onto a hillside, and Cabo Peñas, whose cliffside walk offers unparalleled views of the coast.
Where to Eat: The beverage of choice in Asturias is sidra made with apples grown in the surrounding countryside. Stroll down Calle Gascona, the “cider street,” and you’ll see locals pouring the culo (Asturian slang for the last sip in the glass, said to taste bitter) right into the gutters. Take a table at the unpretentious sidrería El Rincón de Gascona, and dig into one of the region’s other delicacies, cachopo, a hefty breaded cutlet filled with bacon and cheese.
The quietest and least developed island in the Balearic archipelago, Menorca is a slice of paradise (think turquoise waters, abundant wildlife, and seldom-trodden trails) whose unadulterated natural beauty is becoming harder and harder to find among Mediterranean islands. Beaches—called calas in Menorca—abound, but for prime surfing amid craggy cliffs, look no farther than Cap de Cavalleria. For sunbathing and lapping waves, on the other hand, Playa de Son Bou offers gorgeous scenery without the crowds of Playa Santo Tomás and Cala Galdana.
Insider Tip: Spend a day or two in the northerly fishing village of Fornells, whose whitewashed houses encircle a palm tree–lined marina. In its calm waters, you can windsurf, kayak, and dive by day; after the sun goes down, make your way to any of its seafood restaurants to taste the daily catch.
Where to Eat: Panadería la Mejor in the village of Mahón, which has earned international acclaim for its eponymous cheese, has been satisfying sweet tooths since 1850 with its dinner plate–sized ensaimadas. It gets its signature flake from ibérico pork lard, which serves as a subtle savory counterpoint to its sugar-coated exterior.