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.

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.

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.

Between the Mediterranean Sea and Mount Etna lies the beautiful city of Catania, where it’s “if it ain’t Baroque don’t fix it” architecture has earned it UNESCO World Heritage status. Along with flamboyantly designed buildings, Catania is home to many ancient sites, like the Odeon and Amphitheatre—unearthed from under Mount Etna’s lava that covered the city at least seven times. These ruins can be viewed in the archaeological park, in the compact (AKA great for walking) city center.

Rome has something special to offer to all visitors, no matter their interests and tastes. Whether you daydream about fighting with gladiators in the Coliseum, debating with togaed senators in the Forum, tossing a coin in a fabled fountain, or being awestruck by the magnificence of St Peter’s Basilica and Michelangelo’s masterpieces, Rome seems to live up to its sobriquet – the Eternal City. When you need sustenance, today’s Rome will provide delizioso pasta e vino. Or perhaps you draw strength from a little retail therapy – the Italians are also renowned for their sense of style.

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.

Not your typical tourist site, this town entices you to stroll along the vegetable stands, head into the markets and wander into almost any welcoming cafe. And if that's not enough, visit the Bardo Museum and its stunning selection of mosaics.

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.

In AD 711 Moors from North Africa conquered most of the Iberian Peninsula, and retained portions of it for 800 years. Granada was the last stronghold, and a symbol of economic, cultural, and artistic prosperity until it too was overcome in 1492. The city’s glory is embodied in the magnificent Alhambra, a compound of palaces and gardens that is a masterpiece of Moorish style. It appears that a primary goal of the architects was to cover every single inch with decoration. As Islam bans the representation of figures of any kind, the decorative elements are made up of complex, detailed, and intertwining geometric and floral images, and Arabic script.

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.

This stunning harbor, filled with pleasure boats and encircled by emerald hills dotted with pastel houses, was once the center of a bustling pirate culture, as swashbuckling knaves such as Blackbeard and Drake traded stolen wares in the port of Charlotte Amalie. Today many of their old warehouses have been converted to shops and malls, where you may spend your pieces of eight on an array of treasures those buccaneers could never have imagined. Not a shopper? Hit the water without walking the plank when you pilot your own zodiac, or an underwater motor scooter.

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.