21-Day Adriatic & Western Mediterranean: Italy & Spain

Up until the end of World War I, Trieste was the only port of the vast Austro-Hungarian Empire and therefore a major industrial and financial center. In the early years of the 20th century, Trieste and its surroundings also became famous by their association with some of the most important names of Italian literature, such as Italo Svevo, and English and German letters. James Joyce drew inspiration from the city's multiethnic population, and Rainer Maria Rilke was inspired by the seacoast west of the city. Although it has lost its importance as a port and a center of finance, it has never fully lost its roll as an intellectual center. The streets hold a mix of monumental, neoclassical, and art-nouveau architecture built by the Austrians during Trieste's days of glory, granting an air of melancholy stateliness to a city that lives as much in the past as the present.

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.

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

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 Prčanj in one direction around the bay, or Perast and the Roman mosaics of Risan in the other direction.

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.

Home to the Museo Regionale of Messina, known for featuring two of Caravaggio's paintings, the city is also famous for having been the capital of the ancient kingdom of Sicily.

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.

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.

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.

As you sail into Malaga you will notice what an idyllic setting the city enjoys on the famous Costa del Sol. To the east of this provincial capital, the coast along the region of La Axarqua is scattered with villages, farmland and sleepy fishing hamlets - the epitome of traditional rural Spain. To the west stretches a continuous city where the razzmatazz and bustle creates a colourful contrast that is easily recognisable as the Costa del Sol. Surrounding the region, the Penibéetica Mountains provide an attractive backdrop overlooking the lower terraced slopes which yield olives and almonds. This spectacular mountain chain shelters the province from cold northerly winds, giving it a reputation as a therapeutic and exotic place in which to escape from cold northern climes. Malaga is also the gateway to many of Andalusia's enchanting historic villages, towns and cities.

Tangier can trace its origins back to the Phoenicians and ancient Greeks. It was named after Tinge, the mother of Hercules’ son, and its beginnings are embedded in mythology. It was subsequently a Roman province, and after Vandal and Byzantine influences, was occupied by the Arabs with Spain, Portugal, France and England also playing a part in the city’s history. With such a diverse past it is perhaps not surprising that Tangier is such an individual city. Overlooking the Straits of Gibraltar, the city lies on a bay between two promontories. With its old Kasbah, panoramic views, elegant buildings, squares and places of interest, there is much to discover in both the new and old parts of the city.

Known in Sardinia as Casteddu, the island's capital has steep streets and impressive Italianate architecture, from modern to medieval. This city of nearly 160,000 people is characterized by a busy commercial center and waterfront with broad avenues and arched arcades, as well as by the typically narrow streets of the old hilltop citadel (called, simply, “Castello”). The Museo Archeologico makes a good starting point to a visit. The imposing Bastione di Saint Remy and Mercato di San Benedetto (one of the best fish markets in Italy) are both musts.

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.

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.

Considered Corsica’s primary commercial and cultural hub, the largest city and regional capital of Ajaccio is situated on the west coast of the island, approximately 644 km (400 miles) southeast of Marseille, France. Founded in 1492, vestiges of ancient Corsica in this ville impériale revolve around the city’s most famous son, Napoléon Bonaparte, whose family home—now the national museum Maison Bonaparte—pays tribute to the emperor’s historical influence.Remnants from what was originally a 12th-century Genoese colony are still visible around the Old Town near the imposing citadel and watchtower. Perfect for exploring, the luminous seaside city surrounded by snowcapped mountains and pretty beaches offers numerous sites, eateries, side streets, and a popular harbor, where sailboats and fishing vessels moor in the picturesque Tino Rossi port lined with well-established restaurants and cafés serving fresh local fare.

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.

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.