Lisbon, Portugal's Atlantic capital, is spread across seven hills. Start in Alfama, with its medieval streets leading to Castelo de São Jorge and sweeping city views. Head to Baixa for shopping, restaurants, and neoclassical architecture. In Belém, see two UNESCO sites: Belém Tower and Jerónimos Monastery. If time allows, visit nearby Sintra and Cascais, or continue to Fátima, where Virgin Mary apparitions were reported in 1917.

Santa Cruz de Tenerife, 130 miles from Africa, was founded in 1494 and became a key port on the Europe-Americas trade route. Its plazas, Baroque churches, historic buildings, Plaza de España, the modern Torres de Santa Cruz, and the Auditorio de Tenerife blend old and new. Calle de la Noria offers shopping and cuisine. Nearby are Anaga Rural Park, UNESCO-listed Teide National Park, and San Cristóbal de La Laguna. Tenerife is also known for beaches and mild weather.

Tortola is the heart of the British Virgin Islands' sailing culture. Long and narrow, it is the BVI's largest island, with secluded white-sand beaches, hidden coves, and natural anchorages. Road Town, in a horseshoe harbor, is the laid-back capital for commerce, seafood, and access to nearby islets, cays, reefs, and dive sites. Museums highlight local history, and Sage Mountain, the archipelago's highest point at 1,714 feet, offers the best views.

San Juan, Puerto Rico's capital, blends old and new. Founded in 1521, it was a key Spanish colonial port; El Morro still guards the harbor. Old San Juan, behind thick stone walls, keeps blue cobblestone streets, plazas, and colorful heritage buildings, and serves as the island's cultural hub. Nearby Santurce is the trendiest district, with shops, restaurants, and nightlife. Minutes away, Condado and Isla Verde offer iconic palm-lined Atlantic beaches.