You could spend a lifetime in Europe’s oldest city and still not see everything it has to offer. Settled over 3,500 years ago, Athens is like a mythological crossroads of the past and present, where modern buildings share the skyline with spectacular ruins like the Parthenon. To see a veritable “greatest hits” line-up, make your way to Vasilissis Amalias Street for the archaeological walk. Winding through the heart of the ancient city, the route leads to landmarks like the Temple of Olympian Zeus, Ancient Agora, Arch of Hadrian, and of course, the Acropolis.

This Greek seaside town is the gateway to the ruins of Olympia, where the ancient games began in 776 BC, and continued for over 1000 years, until they were outlawed as a pagan festival, after Rome officially adopted Christianity as the only legitimate imperial religion. The complex is made up of temples, workshops, and the training structures that have given us the word we still use today to describe such facilities – gymnasium. The games did not recommence until 1896, but their ancient roots are acknowledged when the modern Olympic flame is lit here every four years, before beginning its long journey to the host nation.

Siracusa is known for the archaeological and historical sights that define its grand past, as one of the major powers of the Mediterranean world in the 5th century BC. They include a Greek theater, still in use, where Aeschylus produced some of his plays; a dramatic necropolis with burial niches cut into the rock that include the tomb of Archimedes, famous mathematician, engineer, and inventor; and the Ear of Dionysus, a cave with amazing acoustical properties. The “modern” city was rebuilt in Sicilian Baroque style after the devastating earthquake of 1693.

Tiny Malta, smack dab in the middle of the Mediterranean and on everyone's route since ships began to ply the seas, is packed with history from top to bottom. Over time it was ruled by a variety of empires, all of which contributed to the look and culture of the islands. Valetta is living museum of baroque architecture, constructed by the Knights of St. John five centuries ago. Today the city is also a dynamic hub of cultural and commercial activity, its harbor now welcoming luxury yachts and cruise ships.

Few reminders still exist of Trapani’s ancient history, but from Phoenician days it was a trading port, well positioned for commerce with Africa, Naples, and the western Mediterranean. The Middle Ages is the era most evident in its old town, now a pedestrian zone. Aging palaces, some imposing and others in various stages of decay, cluster along a peninsula stretching into the bay. Worthy of note is the ominously named Chiesa del Purgatorio, home to wooden statues known as Misteri, that are paraded through the streets on Good Friday. Further out are saltpans, and plains punctuated by medieval windmills, home to some 170 species of birds.

Strategically located along historic sailing routes, Cartagena has been colonized by a veritable who’s who of Mediterranean superpowers over the millennia, resulting in a rich and multi-layered cultural heritage, and a history both glorious and turbulent. From atop a hill, Concepción Castle served as a fortress for Carthaginians, Romans, Visigoths, Arabs, and Castilians. The 13th century Old Cathedral stands on the remains of a Roman Theater just discovered in 1987. More recent architectural contributions include modernist designs of public buildings and private dwellings by pupils of the famous architect Antoni Gaudi.

Málaga is the lively capital of the Costa del Sol, famed for its beaches and mild climate, and gateway to Andalusia, with its Moorish architectural heritage. The city’s Alcazaba is a fine example, an 11th century citadel sitting in majestic splendor overlooking the African coast. It contains three magnificent palaces and graceful gardens with ornate fountains. In addition to their rich cultural heritage, Malagueños are also very proud of their most famous citizens – Picasso, for whom there is a museum commemorating his birth here, and actor Antonio Banderas, so far without a monument.

Tangier, a Moroccan port on the Strait of Gibraltar, has been a strategic gateway between Africa and Europe since Phoenician times. Its whitewashed hillside medina is home to the Dar el Makhzen, a palace of the sultans that's now a museum of Moroccan artifacts. The American Legation Museum, also in the medina, documents early diplomatic relations between the U.S. and Morocco in an 1821 Moorish-style former consulate.

Ponce de Leon never did find the Fountain of Youth, but he did find stumble upon this lovely island, which had to be a close second. Just move to the rhythm of the ever-present salsa beat and you’ll be in the spirit in no time (secret – it’s all in the hips). Old Town San Juan is still partially enclosed by the original fortress walls dating back to the early 1500s. Attractively restored buildings with filigree cast iron balconies line its narrow cobbled streets, and cafés in shaded squares provide an ideal spot to linger. Outside the city the island offers an appealing array of golf courses, rainforests, and beaches galore.

Propelled by Latin rhythms, with a bold style all its own, Miami is a spicy melting pot of cultures. Immerse yourself in the colorful Art Deco district, vibrant nightlife, and beaches for sun-worshipers and water sport enthusiasts alike. Put some money on the horses at Hialeah Park, one of racings oldest and most prominent tracks, right next to a lake full of pink flamingos. Go adventuring in the Everglades, looking for ‘gators and manatees, canoeing through mangrove tunnels, or paddling a sea kayak through the “10,000 islands”. Flashy and full of life, it’s a great place to play.