Monte Carlo to Fusina

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.

Days at sea are the perfect opportunity to relax, unwind, and catch up with what you've been meaning to do. So whether that is going to the gym, visiting the spa, whale-watching, catching up on your reading, or simply topping up your tan, these blue sea days are the perfect balance to busy days spent exploring shoreside.

Malta's capital, the minicity of Valletta, has ornate palaces and museums protected by massive fortifications of honey-color limestone. Houses along the narrow streets have overhanging wooden balconies for people-watching from indoors. Generations ago they gave housebound women a window on the world of the street. The main entrance to town is through the City Gate (where all bus routes end), which leads onto Triq Repubblika (Republic Street), the spine of the grid-pattern city and the main shopping street. Triq Mercante (Merchant Street) parallels Repubblika to the east and is also good for strolling. From these two streets, cross streets descend toward the water; some are stepped. Valletta's compactness makes it ideal to explore on foot. City Gate and the upper part of Valletta are experiencing vast redevelopment that includes a new Parliament Building and open-air performance venue. The complex, completed mid-2013, has numerous pedestrian detours in place along with building noise and dust. Before setting out along Republic Street, stop at the tourist information office on Merchant Street for maps and brochures.

The medieval cliff-hanging town of Taormina is overrun with tourists, yet its natural beauty is still hard to dispute. The view of the sea and Mt. Etna from its jagged cactus-covered cliffs is as close to perfection as a panorama can get—especially on clear days, when the snowcapped volcano's white puffs of smoke rise against the blue sky. Writers have extolled Taormina's beauty almost since it was founded in the 6th century BC by Greeks from nearby Naxos; Goethe and D. H. Lawrence were among its well-known enthusiasts. The town's boutique-lined main streets get old pretty quickly, but the many hiking paths that wind through the beautiful hills surrounding Taormina promise a timeless alternative. A trip up to stunning Castelmola (whether on foot or by car) should also be on your itinerary.

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.

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 Ploče 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

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).

Dalmatia's capital for more than 1,000 years, Zadar is all too often passed over by travelers on their way to Split or Dubrovnik. What they miss out on is a city of more than 73,000 that is remarkably lovely and lively despite—and, in some measure, because of—its tumultuous history. The Old Town, separated from the rest of the city on a peninsula some 4 km (2½ miles) long and just 1,640 feet wide, is bustling and beautiful: the marble pedestrian streets are replete with Roman ruins, medieval churches, palaces, museums, archives, and libraries. Parts of the new town are comparatively dreary, a testament to what a world war followed by decades of communism, not to mention a civil war, can do to the architecture of a city that is 3,000 years old. A settlement had already existed on the site of the present-day city for some 2,000 years when Rome finally conquered Zadar in the 1st century BC; the foundations of the forum can be seen today. Before the Romans came the Liburnians had made it a key center for trade with the Greeks and Romans for 800 years. In the 3rd century BC the Romans began to seriously pester the Liburnians, but required two centuries to bring the area under their control. During the Byzantine era, Zadar became the capital of Dalmatia, and this period saw the construction of its most famous church, the 9th-century St. Donat's Basilica. It remained the region's foremost city through the ensuing centuries. The city then experienced successive onslaughts and occupations—both long and short—by the Osogoths, the Croatian-Hungarian kings, the Venetians, the Turks, the Habsburgs, the French, the Habsburgs again, and finally the Italians before becoming part of Yugoslavia and, in 1991, the independent republic of Croatia. Zadar was for centuries an Italian-speaking city, and Italian is still spoken widely, especially by older people. Indeed, it was ceded to Italy in 1921 under the Treaty of Rapallo (and reverted to its Italian name of Zara). Its occupation by the Germans from 1943 led to intense bombing by the Allies during World War II, which left most of the city in ruins. Zadar became part of Tito's Yugoslavia in 1947, prompting many Italian residents to leave. Zadar's most recent ravages occurred during a three-month siege by Serb forces and months more of bombardment during the Croatian-Serbian war between 1991 and 1995. But you'd be hard-pressed to find outward signs of this today in what is a city to behold. There are helpful interpretive signs in English all around the Old Town, so you certainly won't feel lost when trying to make sense of the wide variety of architectural sites you might otherwise pass by with only a cursory look.

Chioggia is a charming fishing community located at the southern end of the Venetian Lagoon and steeped in age-old seafaring traditions. Its combination of canals, bridges and fishing boats have lent it the nickname “Little Venice.” Lined with shops, bars and restaurants, the main pedestrian street of Corso del Popolo exudes a lively atmosphere amid the aroma of delicious fresh seafood dishes. Chioggia shares a long history of cultural and economic ties with Venice, dating back to the Middle Ages, and is a scenic journey by water taxi from the capital of the Veneto region.