Grand Iberian Odyssey: Madrid, Lisbon & Scenic Regional Escapes

Explore one of the world's premier art galleries housing masterpieces by Velázquez, Goya, and El Greco. Book skip-the-line tickets online in advance to avoid long morning lines.

Tour Western Europe's largest functioning royal residence. Walk through the opulent throne room and relax in the adjoining Sabatini Gardens.

Stroll through the vibrant kilometer-zero square of Madrid. Take a photo with the iconic statue of the Bear and the Strawberry Tree.

Unwind in Madrid's green lung. Rent a rowing boat on the central lake and visit the stunning glass Crystal Palace.

Walk along Madrid's bustling main avenue, filled with impressive early 20th-century architecture, theaters, and shopping boutiques.

A covered iron market featuring gourmet food stalls. Ideal for sampling artisan jamón ibérico, patatas bravas, fresh seafood, and Spanish wines.

Experience Madrid's lively bohemian nightlife in the Malasaña neighborhood. Enjoy drinks at retro bars or head up to rooftop lounges overlooking Gran Vía.

Indulge in a classic Madrid tradition: hot, crispy, golden churros paired with thick melted chocolate at the city's most historic chocolatería.

If visiting on a Sunday morning, wander through Spain's largest open-air flea market to browse vintage antiques, clothing, and unique souvenirs.

Take a 30-minute high-speed AVE train ride from Madrid to the UNESCO-listed medieval city of Toledo. Wander ancient cobblestone alleyways, gothic cathedrals, and old city gates.

Board the famous historic yellow tram as it rattles up the narrow, tiled streets of Lisbon's oldest neighborhood. The creator recommends hopping on early in the morning to beat the tourist crowds.

Climb up to this 11th-century hilltop fortress for sweeping 360-degree views over terracotta rooftops and the Tagus River.

Visit Lisbon's highest official viewpoint for panoramic sunset vistas overlooking the city skyline, Tagus River, and 25 de Abril Bridge.

Marvel at the intricate Manueline gothic architecture of this World Heritage landmark, built during Portugal's Age of Discovery.

Visit the 16th-century fortified tower situated along the Tagus riverbank that served as a ceremonial gateway to Lisbon.

Taste warm, freshly baked pastel de nata sprinkled with cinnamon and powdered sugar at the legendary bakery where monks originally crafted the recipe.

Spend an intimate evening in a dimly lit Alfama fado house, listening to soulful Portuguese vocalists and classical guitars.

Experience Lisbon's nightlife as the narrow cobblestone streets of Bairro Alto become an open-air street party, before heading down to Cais do Sodré's Pink Street.

Take a 40-minute train ride to Sintra to explore the colorful romanticist Pena Palace and the mysterious gardens and initiation well at Quinta da Regaleira.

Stand on the dramatic rugged cliffs at Continental Europe's westernmost point, overlooking the crashing Atlantic ocean waves.

Visit this famed coastal beach near Cascais, renowned for its dramatic wind-swept sand dunes, surfing waves, and fresh seafood restaurants.

Experience a day tour to the world-famous Douro Valley wine region. Sample fortified port wines and crisp Vinho Verde direct from century-old vineyard cellars.

Kayak into the breathtaking sea cave at Benagil along Portugal's southern Algarve coast to admire its natural skylit dome and secluded inner beach.