Day 1 Piraeus, Greece

It's no wonder that all roads lead to the fascinating and maddening metropolis of Athens. Lift your eyes 200 feet above the city to the Parthenon, its honey-color marble columns rising from a massive limestone base, and you behold architectural perfection that has not been surpassed in 2,500 years. But, today, this shrine of classical form dominates a 21st-century boomtown. To experience Athens—Athína in Greek—fully is to understand the essence of Greece: ancient monuments surviving in a sea of cement, startling beauty amid the squalor, tradition juxtaposed with modernity. Locals depend on humor and flexibility to deal with the chaos; you should do the same. The rewards are immense. Although Athens covers a huge area, the major landmarks of the ancient Greek, Roman, and Byzantine periods are close to the modern city center. You can easily walk from the Acropolis to many other key sites, taking time to browse in shops and relax in cafés and tavernas along the way. From many quarters of the city you can glimpse "the glory that was Greece" in the form of the Acropolis looming above the horizon, but only by actually climbing that rocky precipice can you feel the impact of the ancient settlement. The Acropolis and Filopappou, two craggy hills sitting side by side; the ancient Agora (marketplace); and Kerameikos, the first cemetery, form the core of ancient and Roman Athens. Along the Unification of Archaeological Sites promenade, you can follow stone-paved, tree-lined walkways from site to site, undisturbed by traffic. Cars have also been banned or reduced in other streets in the historical center. In the National Archaeological Museum, vast numbers of artifacts illustrate the many millennia of Greek civilization; smaller museums such as the Goulandris Museum of Cycladic Art Museum and the Byzantine and Christian Museum illuminate the history of particular regions or periods. Athens may seem like one huge city, but it is really a conglomeration of neighborhoods with distinctive characters. The Eastern influences that prevailed during the 400-year rule of the Ottoman Empire are still evident in Monastiraki, the bazaar area near the foot of the Acropolis. On the northern slope of the Acropolis, stroll through Plaka (if possible by moonlight), an area of tranquil streets lined with renovated mansions, to get the flavor of the 19th-century's gracious lifestyle. The narrow lanes of Anafiotika, a section of Plaka, thread past tiny churches and small, color-washed houses with wooden upper stories, recalling a Cycladic island village. In this maze of winding streets, vestiges of the older city are everywhere: crumbling stairways lined with festive tavernas; dank cellars filled with wine vats; occasionally a court or diminutive garden, enclosed within high walls and filled with magnolia trees and the flaming trumpet-shaped flowers of hibiscus bushes. Formerly run-down old quarters, such as Thission, Gazi and Psirri, popular nightlife areas filled with bars and mezedopoleia (similar to tapas bars), are now in the process of gentrification, although they still retain much of their original charm, as does the colorful produce and meat market on Athinas. The area around Syntagma Square, the tourist hub, and Omonia Square, the commercial heart of the city about 1 km (½ mi) northwest, is distinctly European, having been designed by the court architects of King Otho, a Bavarian, in the 19th century. The chic shops and bistros of ritzy Kolonaki nestle at the foot of Mt. Lycabettus, Athens's highest hill (909 feet). Each of Athens's outlying suburbs has a distinctive character: in the north is wealthy, tree-lined Kifissia, once a summer resort for aristocratic Athenians, and in the south and southeast lie Glyfada, Voula, and Vouliagmeni, with their sandy beaches, seaside bars, and lively summer nightlife. Just beyond the city's southern fringes is Piraeus, a bustling port city of waterside fish tavernas and Saronic Gulf views.

Day 2 Milos, Greece

Milos or Melos is a volcanic Greek island in the Aegean Sea, just north of the Sea of Crete. Milos is the southwesternmost island in the Cyclades group. The Venus de Milo and the Asclepius of Milos were both found on the island, as were a Poseidon and an archaic Apollo now in Athens.

Day 3 Rhodes, Greece

Early travelers described Rhodes as a town of two parts: a castle or high town (Collachium) and a lower city. Today Rhodes town—sometimes referred to as Ródos town—is still a city of two parts: the Old Town, a UNESCO World Heritage site that incorporates the high town and lower city, and the modern metropolis, or New Town, spreading away from the walls that encircle the Old Town. The narrow streets of the Old Town are for the most part closed to cars and are lined with Orthodox and Catholic churches, Turkish houses (some of which follow the ancient orthogonal plan), and medieval public buildings with exterior staircases and facades elegantly constructed of well-cut limestone from Lindos. Careful reconstruction in recent years has enhanced the harmonious effect.

Day 4 Heraklion (Iraklion), Crete, Greece

Having been controlled by Arabic, Venetian and Ottoman empires over the years - it's no surprise that Heraklion is a diverse patchwork of exotic cultures and historical treasures. Celebrated as the birthplace of the Spanish Renaissance artist, El Greco, you can visit to explore the storied ruins of the Minoan empire's capital, and unearth the rich cultural treasures that Crete's bustling modern capital has to offer.

Day 6 Siracuse, Sicily, Italy

Siracusa, known to English speakers as Syracuse, is a wonder to behold. One of the great ancient capitals of Western civilization, the city was founded in 734 BC by Greek colonists from Corinth and soon grew to rival, and even surpass, Athens in splendor and power. It became the largest, wealthiest city-state in the West and a bulwark of Greek civilization. Although Siracusa lived under tyranny, rulers such as Dionysius filled their courts with Greeks of the highest cultural stature—among them the playwrights Aeschylus and Euripides, and the philosopher Plato. The Athenians, who didn't welcome Siracusa's rise, set out to conquer Sicily, but the natives outsmarted them in what was one of the greatest military campaigns in ancient history (413 BC). The city continued to prosper until it was conquered two centuries later by the Romans.Present-day Siracusa still has some of the finest examples of Baroque art and architecture; dramatic Greek and Roman ruins; and a Duomo that's the stuff of legend—a microcosm of the city's entire history in one building. The modern city also has a wonderful, lively, Baroque old town worthy of extensive exploration, as well as pleasant piazzas, outdoor cafés and bars, and a wide assortment of excellent seafood. There are essentially two areas to explore in Siracusa: the Parco Archeologico (Archaeological Zone), on the mainland; and the island of Ortygia, the ancient city first inhabited by the Greeks, which juts out into the Ionian Sea and is connected to the mainland by two small bridges. Ortygia is becoming increasingly popular with tourists, and is starting to lose its old-fashioned charm in favor of modern boutiques.Siracusa's old nucleus of Ortygia, a compact area, is a pleasure to amble around without getting unduly tired. In contrast, mainland Siracusa is a grid of wider avenues. At the northern end of Corso Gelone, above Viale Paolo Orsi, the orderly grid gives way to the ancient quarter of Neapolis, where the sprawling Parco Archeologico is accessible from Viale Teracati (an extension of Corso Gelone). East of Viale Teracati, about a 10-minute walk from the Parco Archeologico, the district of Tyche holds the archaeological museum and the church and catacombs of San Giovanni, both off Viale Teocrito (drive or take a taxi or city bus from Ortygia). Coming from the train station, it's a 15-minute trudge to Ortygia along Via Francesco Crispi and Corso Umberto. If you're not up for that, take one of the free electric buses leaving every 10 minutes from the bus station around the corner.

Day 7 Naples, Italy

Naples, in the Campania region, is Italy's third largest city. Its claim to fame is the spectacular location along one of the world's most splendid bays, backed by the perfect cone of Mount Vesuvius. In addition to its beautiful setting, Naples' surprises with other outstanding attractions such as the Royal Palace, San Carlos Opera House, the impressive National Archaeological Museum and the Castel Nuovo, dating from the 13th-century. The city's central area is best explored on foot. Chaotic traffic conditions make driving around the city a very frustrating experience. Naples provides a convenient starting point for trips to such favored destinations as Pompeii, Herculaneum and Mount Vesuvius. The Isle of Capri can be reached via a 45-minute hydrofoil service. The region of Campania was home to Greeks settlers some 300 years before Rome was founded. Pompeii, too, was a Greek town before being conquered by the Romans during the 5th century BC. It was under the Romans that Pompeii flourished and grew prosperous. When Mount Vesuvius erupted in 79 AD, the population of 20,000 was wiped out, but dozens of buildings were preserved under layers of cinder more than 20 feet deep. The most important finds from Pompeii are displayed in Naples' National Archaeological Museum. A visit here will no doubt enhance a visit to ancient Pompeii.

Day 8 Civitavecchia, Italy

Italy's vibrant capital lives in the present, but no other city on earth evokes its past so powerfully. For over 2,500 years, emperors, popes, artists, and common citizens have left their mark here. Archaeological remains from ancient Rome, art-stuffed churches, and the treasures of Vatican City vie for your attention, but Rome is also a wonderful place to practice the Italian-perfected il dolce far niente, the sweet art of idleness. Your most memorable experiences may include sitting at a caffè in the Campo de' Fiori or strolling in a beguiling piazza.

Day 9 Livorno, Italy

Livorno is a gritty city with a long and interesting history. In the early Middle Ages it alternately belonged to Pisa and Genoa. In 1421 Florence, seeking access to the sea, bought it. Cosimo I (1519–74) started construction of the harbor in 1571, putting Livorno on the map. After Ferdinando I de' Medici (1549–1609) proclaimed Livorno a free city, it became a haven for people suffering from religious persecution; Roman Catholics from England and Jews and Moors from Spain and Portugal, among others, settled here. The Quattro Mori (Four Moors), also known as the Monument to Ferdinando I, commemorates this. (The statue of Ferdinando I dates from 1595, the bronze Moors by Pietro Tacca from the 1620s.)In the following centuries, and particularly in the 18th, Livorno boomed as a port. In the 19th century the town drew a host of famous Britons passing through on their grand tours. Its prominence continued up to World War II, when it was heavily bombed. Much of the town's architecture, therefore, postdates the war, and it's somewhat difficult to imagine what it might have looked like before. Livorno has recovered from the war, however, as it's become a huge point of departure for container ships, as well as the only spot in Tuscany for cruise ships to dock for the day.Most of Livorno's artistic treasures date from the 17th century and aren't all that interesting unless you dote on obscure baroque artists. Livorno's most famous native artist, Amedeo Modigliani (1884–1920), was of much more recent vintage. Sadly, there's no notable work by him in his hometown.There may not be much in the way of art, but it's still worth strolling around the city. The Mercato Nuovo, which has been around since 1894, sells all sorts of fruits, vegetables, grains, meat, and fish. Outdoor markets nearby are also chock-full of local color. The presence of Camp Darby, an American military base just outside town, accounts for the availability of many American products.If you have time, Livorno is worth a stop for lunch or dinner at the very least.

Day 10 Marseille, France

Since being designated a European Capital of Culture for 2013, with an estimated €660 million of funding in the bargain, Marseille has been in the throes of an extraordinary transformation, with no fewer than five major new arts centers, a beautifully refurbished port, revitalized neighborhoods, and a slew of new shops and restaurants. Once the underdog, this time-burnished city is now welcoming an influx of weekend tourists who have colonized entire neighborhoods and transformed them into elegant pieds-à-terre (or should we say, mer). The second-largest city in France, Marseille is one of Europe's most vibrant destinations. Feisty and fond of broad gestures, it is also as complicated and as cosmopolitan now as it was when a band of Phoenician Greeks first sailed into the harbor that is today's Vieux Port in 600 BC. Legend has it that on that same day a local chieftain's daughter, Gyptis, needed to choose a husband, and her wandering eyes settled on the Greeks' handsome commander Protis. Her dowry brought land near the mouth of the Rhône, where the Greeks founded Massalia, the most important Continental shipping port in antiquity. The port flourished for some 500 years as a typical Greek city, enjoying the full flush of classical culture, its gods, its democratic political system, its sports and theater, and its naval prowess. Caesar changed all that, besieging the city in 49 BC and seizing most of its colonies. In 1214 Marseille was seized again, this time by Charles d'Anjou, and was later annexed to France by Henri IV in 1481, but it was not until Louis XIV took the throne that the biggest transformations of the port began; he pulled down the city walls in 1666 and expanded the port to the Rive Neuve (New Riverbank). The city was devastated by plague in 1720, losing more than half its population. By the time of the Revolution, Marseille was on the rebound once again, with industries of soap manufacturing and oil processing flourishing, encouraging a wave of immigration from Provence and Italy. With the opening of the Suez Canal in 1869, Marseille became the greatest boomtown in 19th-century Europe. With a large influx of immigrants from areas as exotic as Tangiers, the city quickly acquired the multicultural population it maintains to this day.

Day 11 Monaco, Monaco

The 202-hectare Principality of Monaco is located east of France's Mediterranean coast. Known for its royal family, especially Prince Albert of Monaco, its casinos and racetracks and for being a wealthy state with no applied taxes. Monaco is reachable by air through the French airport of Nice Côte d'Azur, located approximately 16 miles from the principality.