Day 1 Istanbul, Turkey

The only city in the world that can lay claim to straddling two continents, Istanbul—once known as Constantinople, capital of the Byzantine and then the Ottoman Empire—has for centuries been a bustling metropolis with one foot in Europe and the other in Asia. Istanbul embraces this enviable position with both a certain chaos and inventiveness, ever evolving as one of the world's most cosmopolitan crossroads. It's often said that Istanbul is the meeting point of East and West, but visitors to this city built over the former capital of two great empires are likely to be just as impressed by the juxtaposition of old and new. Office towers creep up behind historic palaces, women in chic designer outfits pass others wearing long skirts and head coverings, peddlers' pushcarts vie with battered old Fiats and shiny BMWs for dominance of the noisy, narrow streets, and the Grand Bazaar competes with modern shopping malls. At dawn, when the muezzin's call to prayer resounds from ancient minarets, there are inevitably a few hearty revelers still making their way home from nightclubs and bars. Most visitors to this sprawling city of more than 14 million will first set foot in the relatively compact Old City, where the legacy of the Byzantine and Ottoman empires can be seen in monumental works of architecture like the brilliant Aya Sofya and the beautifully proportioned mosques built by the great architect Sinan. Though it would be easy to spend days, if not weeks, exploring the wealth of attractions in the historical peninsula, visitors should make sure also to venture elsewhere in order to experience the vibrancy of contemporary Istanbul. With a lively nightlife propelled by its young population and an exciting arts scene that's increasingly on the international radar—thanks in part to its stint as the European Capital of Culture in 2010—Istanbul is truly a city that never sleeps. It's also a place where visitors will feel welcome: Istanbul may be on the Bosphorus, but at heart it's a Mediterranean city, whose friendly inhabitants are effusively social and eager to share what they love most about it.

Day 2 Istanbul, Turkey

The only city in the world that can lay claim to straddling two continents, Istanbul—once known as Constantinople, capital of the Byzantine and then the Ottoman Empire—has for centuries been a bustling metropolis with one foot in Europe and the other in Asia. Istanbul embraces this enviable position with both a certain chaos and inventiveness, ever evolving as one of the world's most cosmopolitan crossroads. It's often said that Istanbul is the meeting point of East and West, but visitors to this city built over the former capital of two great empires are likely to be just as impressed by the juxtaposition of old and new. Office towers creep up behind historic palaces, women in chic designer outfits pass others wearing long skirts and head coverings, peddlers' pushcarts vie with battered old Fiats and shiny BMWs for dominance of the noisy, narrow streets, and the Grand Bazaar competes with modern shopping malls. At dawn, when the muezzin's call to prayer resounds from ancient minarets, there are inevitably a few hearty revelers still making their way home from nightclubs and bars. Most visitors to this sprawling city of more than 14 million will first set foot in the relatively compact Old City, where the legacy of the Byzantine and Ottoman empires can be seen in monumental works of architecture like the brilliant Aya Sofya and the beautifully proportioned mosques built by the great architect Sinan. Though it would be easy to spend days, if not weeks, exploring the wealth of attractions in the historical peninsula, visitors should make sure also to venture elsewhere in order to experience the vibrancy of contemporary Istanbul. With a lively nightlife propelled by its young population and an exciting arts scene that's increasingly on the international radar—thanks in part to its stint as the European Capital of Culture in 2010—Istanbul is truly a city that never sleeps. It's also a place where visitors will feel welcome: Istanbul may be on the Bosphorus, but at heart it's a Mediterranean city, whose friendly inhabitants are effusively social and eager to share what they love most about it.

Day 4 Mykonos, Greece

Although the fishing boats still go out in good weather, Mykonos largely makes its living from tourism these days. The summer crowds have turned one of the poorest islands in Greece into one of the richest. Old Mykonians complain that their young, who have inherited stores where their grandfathers once sold eggs or wine, get so much rent that they have lost ambition, and in summer sit around pool bars at night with their friends, and hang out in Athens in winter when island life is less scintillating. Put firmly on the map by Jackie O in the 1960s, Mykonos town—called Hora by the locals—remains the Saint-Tropez of the Greek islands. The scenery is memorable, with its whitewashed streets, Little Venice, the Kato Myli ridge of windmills, and Kastro, the town's medieval quarter. Its cubical two- or three-story houses and churches, with their red or blue doors and domes and wooden balconies, have been long celebrated as some of the best examples of classic Cycladic architecture. Luckily, the Greek Archaeological Service decided to preserve the town, even when the Mykonians would have preferred to rebuild, and so the Old Town has been impressively preserved. Pink oleander, scarlet hibiscus, and trailing green pepper trees form a contrast amid the dazzling whiteness, whose frequent renewal with whitewash is required by law. Any visitor who has the pleasure of getting lost in its narrow streets (made all the narrower by the many outdoor stone staircases, which maximize housing space in the crowded village) will appreciate how its confusing layout was designed to foil pirates—if it was designed at all. After Mykonos fell under Turkish rule in 1537, the Ottomans allowed the islanders to arm their vessels against pirates, which had a contradictory effect: many of them found that raiding other islands was more profitable than tilling arid land. At the height of Aegean piracy, Mykonos was the principal headquarters of the corsair fleets—the place where pirates met their fellows, found willing women, and filled out their crews. Eventually the illicit activity evolved into a legitimate and thriving trade network. Morning on Mykonos town's main quay is busy with deliveries, visitors for the Delos boats, lazy breakfasters, and street cleaners dealing with the previous night's mess. In late morning the cruise-boat people arrive, and the shops are all open. In early afternoon, shaded outdoor tavernas are full of diners eating salads (Mykonos's produce is mostly imported); music is absent or kept low. In mid- and late afternoon, the town feels sleepy, since so many people are at the beach, on excursions, or sleeping in their air-conditioned rooms; even some tourist shops close for siesta. By sunset, people have come back from the beach, having taken their showers and rested. At night, the atmosphere in Mykonos ramps up. The cruise-boat people are mostly gone, coughing three-wheelers make no deliveries in the narrow streets, and everyone is dressed sexy for summer and starting to shimmy with the scene. Many shops stay open past midnight, the restaurants fill up, and the bars and discos make ice cubes as fast as they can. Ready to dive in? Begin your tour of Mykonos town (Hora) by starting out at its heart: Mando Mavrogenous Square.

Day 5 Santorini, Greece

Undoubtedly the most extraordinary island in the Aegean, crescent-shape Santorini remains a mandatory stop on the Cycladic tourist route—even if it's necessary to enjoy the sensational sunsets from Ia, the fascinating excavations, and the dazzling white towns with a million other travelers. Called Kállisti (the "Loveliest") when first settled, the island has now reverted to its subsequent name of Thira, after the 9th-century-BC Dorian colonizer Thiras. The place is better known, however, these days as Santorini, a name derived from its patroness, St. Irene of Thessaloniki, the Byzantine empress who restored icons to Orthodoxy and died in 802. You can fly conveniently to Santorini, but to enjoy a true Santorini rite of passage, opt instead for the boat trip here, which provides a spectacular introduction. After the boat sails between Sikinos and Ios, your deck-side perch approaches two close islands with a passage between them. The bigger one on the left is Santorini, and the smaller on the right is Thirassia. Passing between them, you see the village of Ia adorning Santorini's northernmost cliff like a white geometric beehive. You are in the caldera (volcanic crater), one of the world's truly breathtaking sights: a demilune of cliffs rising 1,100 feet, with the white clusters of the towns of Fira and Ia perched along the top. The bay, once the high center of the island, is 1,300 feet in some places, so deep that when boats dock in Santorini's shabby little port of Athinios, they do not drop anchor. The encircling cliffs are the ancient rim of a still-active volcano, and you are sailing east across its flooded caldera. On your right are the Burnt isles, the White isle, and other volcanic remnants, all lined up as if some outsize display in a geology museum. Hephaestus's subterranean fires smolder still—the volcano erupted in 198 BC, about 735, and there was an earthquake in 1956. Indeed, Santorini and its four neighboring islets are the fragmentary remains of a larger landmass that exploded about 1600 BC: the volcano's core blew sky high, and the sea rushed into the abyss to create the great bay, which measures 10 km by 7 km (6 mi by 4½ mi) and is 1,292 feet deep. The other pieces of the rim, which broke off in later eruptions, are Thirassia, where a few hundred people live, and deserted little Aspronissi ("White isle"). In the center of the bay, black and uninhabited, two cones, the Burnt Isles of Palea Kameni and Nea Kameni, appeared between 1573 and 1925. There has been too much speculation about the identification of Santorini with the mythical Atlantis, mentioned in Egyptian papyri and by Plato (who says it's in the Atlantic), but myths are hard to pin down. This is not true of old arguments about whether tidal waves from Santorini's cataclysmic explosion destroyed Minoan civilization on Crete, 113 km (70 mi) away. The latest carbon-dating evidence, which points to a few years before 1600 BC for the eruption, clearly indicates that the Minoans outlasted the eruption by a couple of hundred years, but most probably in a weakened state. In fact, the island still endures hardships: since antiquity, Santorini has depended on rain collected in cisterns for drinking and irrigating—the well water is often brackish—and the serious shortage is alleviated by the importation of water. However, the volcanic soil also yields riches: small, intense tomatoes with tough skins used for tomato paste (good restaurants here serve them); the famous Santorini fava beans, which have a light, fresh taste; barley; wheat; and white-skin eggplants.

Day 7 Corfu, Greece

Corfu town today is a vivid tapestry of cultures—a sophisticated weave, where charm, history, and natural beauty blend. Located about midway along the island's east coast, this spectacularly lively capital is the cultural heart of Corfu and has a remarkable historic center that UNESCO designated as a World Heritage Site in 2007. All ships and planes dock or land near Corfu town, which occupies a small peninsula jutting into the Ionian Sea.Whether arriving by ferry from mainland Greece or Italy, from another island, or directly by plane, catch your breath by first relaxing with a coffee or a gelato in Corfu town's shaded Liston Arcade, then stroll the narrow lanes of its pedestrians-only quarter. For an overview of the immediate area, and a quick tour of Mon Repos palace, hop on the little tourist train that runs from May to September. Corfu town has a different feel at night, so book a table at one of its famed tavernas to savor the island's unique cuisine.The best way to get around Corfu town is on foot. The town is small enough so that you can easily walk to every sight. There are local buses, but they do not thread their way into the streets (many now car-free) of the historic center. If you are arriving by ferry or plane, it's best to take a taxi to your hotel. Expect to pay about €10 from the airport or ferry terminal to a hotel in Corfu town. If there are no taxis waiting, you can call for one.

Day 8 Gallipoli, Italy

Kalè polis, meaning beautiful city, is the name ancient Greek mariners bestowed on Gallipoli, with good reason. Situated on a mound, the Old Town with its labyrinth of winding lanes, emerges from the Ionian Sea. It is connected to the mainland and modern Gallipoli via a 17th-century bridge. The area lies on the Salentina Peninsula in the extreme southeast end of Italy, commonly referred to as the heel of the boot. The Salento region was inhabited already in prehistoric times; later centuries were marked by Greek, Norman, Byzantine and Baroque cultures. It is a land of farms, castles, works of art, myths and legends. Many heroic battles were fought; fierce resistance was shown by Gallipoli's citizens against numerous invaders that included Romans, Vandals, Swabians, Venetians, French and lastly the English in 1809. In addition to its tumultuous history and natural beauty, the city's claim to fame rests in its art treasures, most notably, the Basilica of Sant'Agata with its majestic 17th-century façade. Inside, the church contains a rich and important art collection with numerous works by its great native son, Giovanni Andrea Coppola.

Day 9 Hvar Island, Croatia

The Croatian island of Hvar bills itself as the "sunniest island in the Adriatic." Not only does it have the figures to back up this claim—an annual average of 2,724 hours of sunshine—but it also makes visitors a sporting proposition, offering them a money-back guarantee if there are seven consecutive days of snow (snow has been known to fall here; the last time being February 2012).

Day 10 Pula, Croatia

Today an industrial port town and Istria's chief administrative center (pop. 58,000), as well as a major tourist destination, Pula became a Roman colony in the 1st century BC. This came about a century after the decisive defeat by the Romans, in 177 BC, of the nearby Histrian stronghold of Nesactium, prompting the Histrian king Epulon to plunge a sword into his chest lest he fall into the hands of the victors, who indeed conquered all of Istria. Remains from Pula's ancient past have survived up to the present day: as you drive in on the coastal route toward its choice setting on a bay near the southern tip of the Istrian peninsula, the monumental Roman amphitheater blocks out the sky on your left. Under Venetian rule (1331–1797), Pula was architecturally neglected, even substantially dismantled. Many structures from the Roman era were pulled down, and stones and columns were carted off across the sea to Italy to be used for new buildings there. Pula's second great period of development took place in the late 19th century, under the Habsburgs, when it served as the chief base for the Imperial Austro-Hungarian Navy. Today it's as much working city as tourist town, where Roman ruins and Austro-Hungarian architecture serve as backdrop for the bustle of everyday life amid a bit of communist-era soot and socialist realism, too. James Joyce lived here for a short time, in 1904–05, before fleeing what he dismissed as a cultural backwater for Trieste. What's more, there are some outstanding restaurants and a number of pleasant family-run hotels, not to mention the nearby resort area of Verudela, where seaside tourism thrives in all its soothing, sunny sameness.

Day 11 Fusina, Italy

Day 12 Dubrovnik, Croatia

Nothing can prepare you for your first sight of Dubrovnik. Lying 216 km (135 miles) southeast of Split and commanding a jaw-dropping coastal location, it is one of the world's most beautiful fortified cities. Its massive stone ramparts and fortress towers curve around a tiny harbor, enclosing graduated ridges of sun-bleached orange-tiled roofs, copper domes, and elegant bell towers. Your imagination will run wild picturing what it looked like seven centuries ago when the walls were built, without any suburbs or highways around it, just this magnificent stone city rising out of the sea.In the 7th century AD, residents of the Roman city Epidaurum (now Cavtat) fled the Avars and Slavs of the north and founded a new settlement on a small rocky island, which they named Laus, and later Ragusa. On the mainland hillside opposite the island, the Slav settlement called Dubrovnik grew up. In the 12th century the narrow channel separating the two settlements was filled in (now the main street through the Old Town, called Stradun), and Ragusa and Dubrovnik became one. The city was surrounded by defensive walls during the 13th century, and these were reinforced with towers and bastions in the late 15th century.From 1358 to 1808 the city thrived as a powerful and remarkably sophisticated independent republic, reaching its golden age during the 16th century. In 1667 many of its splendid Gothic and Renaissance buildings were destroyed by an earthquake. The defensive walls survived the disaster, and the city was rebuilt in baroque style.Dubrovnik lost its independence to Napoléon in 1808, and in 1815 passed to Austria-Hungary. During the 20th century, as part of Yugoslavia, the city became a popular tourist destination, and in 1979 it was listed as a UNESCO World Heritage Site. During the war for independence, it came under heavy siege. Thanks to careful restoration, few traces of damage remain; however, there are maps inside the Pile and Ploce Gates illustrating the points around the city where damage was done. It's only when you experience Dubrovnik yourself that you can understand what a treasure the world nearly lost

Day 13 Kotor, Montenegro

Backed by imposing mountains, tiny Kotor lies hidden from the open sea, tucked into the deepest channel of the Bokor Kotorska (Kotor Bay), which is Europe's most southerly fjord. To many, this town is more charming than its sister UNESCO World Heritage Site, Dubrovnik, retaining more authenticity, but with fewer tourists and spared the war damage and subsequent rebuilding which has given Dubrovnik something of a Disney feel.Kotor's medieval Stari Grad (Old Town) is enclosed within well-preserved defensive walls built between the 9th and 18th centuries and is presided over by a proud hilltop fortress. Within the walls, a labyrinth of winding cobbled streets leads through a series of splendid paved piazzas, rimmed by centuries-old stone buildings. The squares are now haunted by strains from buskers but although many now house trendy cafés and chic boutiques, directions are still given medieval-style by reference to the town's landmark churches.In the Middle Ages, as Serbia's chief port, Kotor was an important economic and cultural center with its own highly regarded schools of stonemasonry and iconography. From 1391 to 1420 it was an independent city-republic and later, it spent periods under Venetian, Austrian, and French rule, though it was undoubtedly the Venetians who left the strongest impression on the city's architecture. Since the breakup of Yugoslavia, some 70% of the stone buildings in the romantic Old Town have been snapped up by foreigners, mostly Brits and Russians. Porto Montenegro, a new marina designed to accommodate some of the world's largest super yachts, opened in nearby Tivat in 2011, and along the bay are other charming seaside villages, all with better views of the bay than the vista from Kotor itself where the waterside is congested with cruise ships and yachts. Try sleepy Muo or the settlement of Prcanj in one direction around the bay, or Perast and the Roman mosaics of Risan in the other direction.

Day 15 Sorrento, Italy

Sorrento may have become a jumping-off point for visitors to Pompeii, Capri, and Amalfi, but you can find countless reasons to love it for itself. The Sorrentine people are fair-minded and hardworking, bubbling with life and warmth. The tuff cliff on which the town rests is spread over the bay, absorbing sunlight, while orange and lemon trees waft their perfume in spring. Winding along a cliff above a small beach and two harbors, the town is split in two by a narrow ravine formed by a former mountain stream. To the east, dozens of hotels line busy Via Correale along the cliff—many have "grand" included in their names, and some indeed still are. To the west, however, is the historic sector, which still enchants. It's a relatively flat area, with winding, stone-paved lanes bordered by balconied buildings, some joined by medieval stone arches. The central piazza is named after the poet Torquato Tasso, born here in 1544. This part of town is a delightful place to walk through. Craftspeople are often at work in their stalls and shops and are happy to let you watch; in fact, that's the point. Music spots and bars cluster in the side streets near Piazza Tasso.

Day 16 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 17 Monte-Carlo, Monaco

On one of the best stretches of the Mediterranean, this classic luxury destination is one of the most sought-after addresses in the world. With all the high-rise towers you have to look hard to find the Belle Époque grace of yesteryear. But if you head to the town's great 1864 landmark Hôtel de Paris—still a veritable crossroads of the buffed and befurred Euro-gentry—or enjoy a grand bouffe at its famous Louis XV restaurant, or attend the opera, or visit the ballrooms of the casino, you may still be able to conjure up Monaco's elegant past. Prince Albert II, a political science graduate from Amherst College, traces his ancestry to Otto Canella, who was born in 1070. The Grimaldi dynasty began with Otto's great-great-great-grandson, Francesco Grimaldi, also known as Frank the Rogue. Expelled from Genoa, Frank and his cronies disguised themselves as monks and in 1297 seized the fortified medieval town known today as Le Rocher (the Rock). Except for a short break under Napoléon, the Grimaldis have been here ever since, which makes them the oldest reigning family in Europe. In the 1850s a Grimaldi named Charles III made a decision that turned the Rock into a giant blue chip. Needing revenue but not wanting to impose additional taxes on his subjects, he contracted with a company to open a gambling facility. The first spin of the roulette wheel was on December 14, 1856. There was no easy way to reach Monaco then—no carriage roads or railroads—so no one came. Between March 15 and March 20, 1857, one person entered the casino—and won two francs. In 1868, however, the railroad reached Monaco, and it was filled with Englishmen who came to escape the London fog. The effects were immediate. Profits were so great that Charles eventually abolished all direct taxes. Almost overnight, a threadbare principality became an elegant watering hole for European society. Dukes (and their mistresses) and duchesses (and their gigolos) danced and dined their way through a world of spinning roulette wheels and bubbling champagne—preening themselves for nights at the opera, where such artists as Vaslav Nijinsky, Sarah Bernhardt, and Enrico Caruso came to perform. Along with the tax system, its sensational position on a broad, steep peninsula that bulges into the Mediterranean—its harbor sparkling with luxury cruisers, its posh mansions angling awnings toward the nearly perpetual sun—continues to draw the rich and famous. One of the latest French celebrities to declare himself "Monégasque," thus giving up his French passport, is superchef Alain Ducasse, who said that he made the choice out of affection for Monaco rather than tax reasons. Pleasure boats vie with luxury cruisers in their brash beauty and Titanic scale, and teams of handsome young men—themselves dyed blond and tanned to match—scour and polish every gleaming surface. As you might expect, all this glitz doesn't come cheap. Eating is expensive, and even the most modest hotels cost more here than in nearby Nice or Menton. As for taxis, they don't even have meters so you are completely at the driver's mercy (with prices skyrocketing during events such as the Grand Prix). For the frugal, Monaco is the ultimate day-trip, although parking is as coveted as a room with a view. At the very least you can afford a coffee at Starbucks. The harbor district, known as La Condamine, connects the new quarter, officially known as Monte Carlo with Monaco-Ville (or Le Rocher), a medieval town on the Rock, topped by the palace, the cathedral, and the Oceanography Museum. Have no fear that you'll need to climb countless steps to get to Monaco-Ville, as there are plenty of elevators and escalators climbing the steep cliffs. But shuttling between the lovely casino grounds of Monte Carlo and Old Monaco, separated by a vast port, is a daunting proposition for ordinary mortals without wings, so hop on the No. 1 bus from Saint Roman, or No. 2 from the Jardin Exotique - Both stop at Place du Casino and come up to Monaco Ville.

Day 18 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 20 Barcelona, Spain

The infinite variety of street life, the nooks and crannies of the medieval Barri Gòtic, the ceramic tile and stained glass of Art Nouveau facades, the art and music, the throb of street life, the food (ah, the food!)—one way or another, Barcelona will find a way to get your full attention. The capital of Catalonia is a banquet for the senses, with its beguiling mix of ancient and modern architecture, tempting cafés and markets, and sun-drenched Mediterranean beaches. A stroll along La Rambla and through waterfront Barceloneta, as well as a tour of Gaudí's majestic Sagrada Famíliaand his other unique creations, are part of a visit to Spain's second-largest city. Modern art museums and chic shops call for attention, too. Barcelona's vibe stays lively well into the night, when you can linger over regional wine and cuisine at buzzing tapas bars.