Under Sail from Puglia to Sicily

Emblem of the Dalmatian coast, Dubrovnik is magnificently positioned on a rocky spur. History is sovereign here, in this ancient city, now a listed UNESCO World Heritage site. You will perhaps be surprised by the proportions of La Placa, the central drag through the city. The sheer width of it can be explained by the fact that it straddles a former lagoon. The elegant houses along La Placa are built in the legendary travertine stone. At Pile gate, you will be greeted by the statue of the patron saint of Dubrovnik, and you can admire the coastline as you walk along the ramparts. But what’s inside Fort Saint John, adjoining the outer walls? A maritime museum and an aquarium featuring rare fish from the Adriatic.

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

Perched on the Adriatic coast in Puglia, the charming small town of Monopoli blends history and authenticity. Protected by its fortified walls along the seafront and its castle, in the shade of the cathedral’s elegant bell tower, the town is bustling with fishermen who come to repair their nets or unload the day’s catch. But it is also the gateway to the village of Alberobello, a UNESCO World Heritage Site. Alberobello is famous worldwide for its traditional dry stone huts called trulli. These dwellings with whitewashed walls and conical, domed or pyramid-shaped roofs are built without any mortar, using a construction technique inherited from prehistoric times.

Located in the heel of Italy's boot, Monopoli is a Puglia port town that knows how to make a splash. In fact, the Greek words Monos and Polis mean ‘uniquely singular’ - and Monopoli's special blend of part historical, part functional is most definitely that. The city might lack some of the more aesthetic elements of its neighbors, but that only means good things for those who do discover it: far from the tourist route you'll be greeted with medieval churches and castles, white stone buildings (contrasting perfectly with the azure of the sea and sky) and authenticity in buckets. Founded by the Greeks in 500 BC, then taken over by the Romans (and beset by various invaders), Monopoli was - and still is - a thriving port town. Its position in Puglia between the seas made it strategic, while its placement on the Via Traiana (which led all the way to Rome) made it prosperous. The city came under Venetian control in 1484 and much of Monopoli's architecture can be attributed to this period. The charming Old Town is dominated by Castello Carlo V, built in 1552, while the still solid Baroque-Romanesque cathedral, built in 1693, is considered positively modern. Like most of Italy, the food here is as important as religion. As a port town, fish and seafood are deliciously fresh. Do not miss tasting scapece (small fish covered in flour, deep-fried, put in layers with breadcrumbs and saffron, then soaked with vinegar) for a tasty treat that you will find nowhere else in the country.

Located in the Apulia region, Otrante is the easternmost transalpine town. Behind its medieval ramparts, you will taste the sweetlife of Salento, the “heel on Italy’s boot”. Inhabited since Antiquity, Otrante has today become a very pleasant seaside town. Yet its history is still visible as you meander through the little streets of its old centre. With its magnificent 12th century ornamental mosaic tiling, the Cathedral is one of its most beautiful treasures. During a stroll along the ramparts, you can sit and relax at a café terrace.

Located right in the heel of the Italian boot, Otranto’s scenic landscape often plays the protagonist in displaying the beauty of Puglia, Italy’s easternmost region. Facing the Adriatic sea, the seducing weather and pristine waters have made it a popular destination where on a clear day, wanderers can see the coast of Albania. Like much of Italy, the city boasts a rich and mixed history. Once a Greek and Roman port, it was later occupied by the Byzantines, the Normans and the Spanish before the Ottoman invaded in during their Jihad to conquer Europe. Remains of forts are still visible and are a living testimonial of the town’s rich history along with Otranto’s cathedral, which still encloses today the relics of martyrs who refused to convert to Islam.

Gallipoli, which comes from the Greek kalle polis, meaning beautiful town, is very aptly named. Located on the heel of the boot, the town known as “the pearl of Puglia” has many attractions. The whiteness of its façades recalls its Greek origins while its architecture echoes its multiple influences. Its old town, perched on a limestone island, concentrates the cultural heritage of this city with a thousand faces, alternately a Roman colony, then Byzantine, the property of the Popes, Norman, under the rule of Taranto… By itself, it tells the story of the different civilisations of the Mediterranean Sea.

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.

Located on Sicily’s eastern coast, in the province of Messina, the seaside town of Taormina is Sicily’s Saint-Tropez, boasting heritage sites, secluded beaches and luxury shopping. You can visit its medieval centre, suspended 300 metres above sea level, where terraces offer a spectacular view of the Mediterranean Sea. Another vestige from its past are the ruins of the Greco-Roman theatre. This extremely well-preserved site attracts visitors who are fascinated by the natural beauty of the area which overlooks a turquoise bay.

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.

At the southern tip of the Italian boot, Reggio di Calabria guards the eastern shore of the Strait of Messina. From the lungomare, the sea front promenade, there are magnificent views over Sicily, a little over 3 km away, and Etna. Rebuilt after the 1908 earthquake, Reggio is set out in a grid pattern and has Art Nouveau and Belle Époque architecture that add to its charm. And the fragrance of bergamot, the citrus fruit that dominates the region’s confectionery and perfumery.

Palermo is the guardian of the Sicilian soul. Many have been attracted to this city, the largest capital of the Italian islands. Phoenicians, Carthaginians, Romans, Byzantines, Arabs, Normans... Palermo is a rich culmination of so many cultural influences as seen in the Moorish designs on the cathedral, and the Byzantine mosaics of the Palatine chapel, which is itself housed within the precincts of the Norman palace. You will fall under the spell of the palaces, baroque splendours that grace the town with their obsolete beauty. It is thrilling to stumble upon one of those fabulous markets, high in colour, and headily picturesque.

Once the intellectual capital of southern Europe, Palermo has always been at the crossroads of civilization. Favorably situated on a crescent-shaped bay at the foot of Monte Pellegrino, it has attracted almost every culture touching the Mediterranean world. To Palermo's credit, it has absorbed these diverse cultures into a unique personality that is at once Arab and Christian, Byzantine and Roman, Norman and Italian. The city's heritage encompasses all of Sicily's varied ages, but its distinctive aspect is its Arab-Norman identity, an improbable marriage that, mixed in with Byzantine and Jewish elements, created some resplendent works of art. No less noteworthy than the architecture is Palermo's chaotic vitality, on display at some of Italy's most vibrant outdoor markets, public squares, street bazaars, and food vendors, and above all in its grand climax of Italy's most spectacular passeggiata (the leisurely social stroll along the principal thoroughfare).