Lisbon, Portugal's capital, is a beautiful city of seven hills, fado, pastel houses and azulejo tiles. Wander Alfama's steep cobbled streets, visit the Azulejo Museum, then head to São Jorge Castle or Miradouro da Graça for sweeping views over red rooftops, the Tagus and the suspension bridge. See Belém Tower and Jerónimos Monastery, and take a trip to nearby Sintra and Pena Palace. Finish with ginjinha and a pastel de nata.

Madeira is a lush, colorful island of dramatic cliffs, fertile mountains and sunny beaches. In Funchal, the laid-back capital, cobblestone old-town streets, painted doors, whitewashed buildings and iron balconies echo Lisbon. Taste Madeira wine, see Corpo Santo Chapel, and enjoy Parque de Santa Catarina, Madeira Botanical Garden, Palheiro Garden, and the views from Cap Girão, where cliffs drop to the blue sea.

Madeira is a lush, colorful island of dramatic cliffs, fertile mountains and sunny beaches. In Funchal, the laid-back capital, cobblestone old-town streets, painted doors, whitewashed buildings and iron balconies echo Lisbon. Taste Madeira wine, see Corpo Santo Chapel, and enjoy Parque de Santa Catarina, Madeira Botanical Garden, Palheiro Garden, and the views from Cap Girão, where cliffs drop to the blue sea.

Tangier, on Morocco's north coast by the Strait of Gibraltar, is a lively blend of cultures and a historic Phoenician trading town. Explore the bustling Medina, where hawkers, spices, dried fruit, and fabrics fill the narrow alleys; try fresh orange juice or mint tea. Nearby are the Caves of Hercules, and inland the Rif Mountains lead to blue-washed Chefchaouen, a stunning hillside town.

Malaga, on Spain's sunny Costa del Sol, blends beaches, history, and art. Visit La Malagueta beach, the old town, Moorish Alcazaba fortress, and the cathedral known as La Manquita. See the Picasso Museum and Pompidou Centre, plus street art in Soho. Nearby, explore Granada's Alhambra, Cordoba's La Mezquita, and Seville's cathedral for Andalucía's Moorish Golden Triangle.

Gibraltar is a unique British outpost on Spain's southern tip: a historic peninsula crowned by the iconic Rock of Gibraltar. It mixes red phone boxes, Union Jacks, fish and chips, and sunny Mediterranean views. From one moment you can see Africa across the strait; the next, cross the airport runway. The 400m Rock can be hiked or reached by cable car to see Barbary macaques, the Siege Tunnels, caves, and the Moorish castle. In town, Grand Casemates Square offers a lively, sunlit historic center.

Cádiz, Western Europe's oldest city, holds 3,000 years of history in cobbled streets and shaded plazas. Founded by Phoenicians c.1100 BC and later used by Columbus, it grew rich from New World trade. See the cathedral, with its twin towers, and Torre Tavira, the city's best watchtower. Relax on Playa Victoria, cross the modern Constitución de 1812 bridge, and sample tapas at the lively central market.

Porto is a steep, atmospheric Portuguese city of cobbled streets, stacked buildings, azulejo tiles, and strong wine culture. Explore historic Ribeira on the Douro, wander alleys lined with cafes, try pastel de nata, cross the Ponte de Dom Luis I, and visit Porto Cathedral for views and cloisters. Eat Francesinha or bacalhau, then head to the Douro Valley for vineyards and local wines.

Lisbon, Portugal's capital, is a beautiful city of seven hills, fado, pastel houses and azulejo tiles. Wander Alfama's steep cobbled streets, visit the Azulejo Museum, then head to São Jorge Castle or Miradouro da Graça for sweeping views over red rooftops, the Tagus and the suspension bridge. See Belém Tower and Jerónimos Monastery, and take a trip to nearby Sintra and Pena Palace. Finish with ginjinha and a pastel de nata.