22-Day Mediterranean Mosaic: Turkey, Greece, Italy & Spain

Istanbul exudes a fascinating mix of Western and Eastern cultures. Its strategic locale led to its role as a significant center of trade—eventually becoming a cultural crossroads along the world-famous Silk Road. One of the city’s stunning centerpieces is Hagia Sophia, founded as a basilica, converted to a mosque, then a museum; it is now a mosque again and features exquisite mosaics and frescoes. The city’s Grand Bazaar offers a rich taste of Turkish culture, from a vast selection of carpets and fabric to luscious dates and the local sweet favorite, Turkish Delight.

Çanakkale was an object of desire dating back to the ancient Greeks. Today, the nearby ruins of Troy, once a powerhouse of Asia Minor, provide a glimpse of the region’s former glory. The remarkably preserved structures of this UNESCO World Heritage Site offer hints of life here in the days of Alexander the Great and the later Roman Emperor Augustus. But it is the fabled Trojan Horse that is most prominent here. In Homer’s Iliad, the wooden steed gave ancient Greeks entry to the city during the Trojan War, and its legend is still very much alive today.

Nestled ideally between the gentle lapping waves of the Pagasetic Gulf and Mount Pelion, Volos is a Greek seaside town worth visiting. The town enjoys a near mythic status as being home of Jason and his Argonauts, and that, along with its reputation for being ‘Land of the Centaurs’ should go some way to illustrating the degree of ancient history to be found in Volos. The city was severely damaged in an earthquake in 1955 which regrettably means that much of the 19th-century architecture has been lost or damaged. A few traces do remain however, fine examples of neo-classical architecture that are hidden away around the town. If you want your history a little older than that, the superb archaeology museum will both surprise and delight you. Not only will you find objects from the Ancient Greek era but recent excavations have unearthed artefacts from the first Neolithic settlements of Dimini and Sesklo. The city itself is flat and easy to negotiate on foot. Or better still, make like the locals and hire a bike to cycle the city. For those feeling a little more adventurous, the 8-mile cycle up Mont Pelion rewards the sporty cycler with traditional stone tavernas and breathtaking views of the region. If relaxing closer to home is more your glass of ouzo, make for Palia, the old part of Volos, famous for having some of the finest cuisine on the mainland. Head into the narrow alleys, order a tsipouradika (a combination of traditional spirit served with local mezze) and enjoy.

For better or worse, it can be difficult to reach Patmos—for many travelers, this lack of access is definitely for the better, since the island retains the air of an unspoiled retreat. Rocky and barren, the small, 34-square-km (21-square-mi) island lies beyond the islands of Kalymnos and Leros, northwest of Kos. Here on a hillside is the Monastery of the Apocalypse, which enshrines the cave where St. John received the Revelation in AD 95. Scattered evidence of Mycenaean presence remains on Patmos, and walls of the classical period indicate the existence of a town near Skala. Most of the island's approximately 2,800 people live in three villages: Skala, medieval Chora, and the small rural settlement of Kambos. The island is popular among the faithful making pilgrimages to the monastery as well as with vacationing Athenians and a newly growing community of international trendsetters—designers, artists, poets, and “taste gurus” (to quote Vogue’s July 2011 write-up of the island)—who have bought homes in Chora. These stylemeisters followed in the footsteps of Alexandrian John Stefanidis and the English artist Teddy Millington-Drake who, in the early ’60s, set about creating what eventually became hailed as one of the most gorgeous island homes in the world. The word soon spread thanks to their many guests (who included Jacqueline Kennedy Onassis) but, happily, administrators have carefully contained development, and as a result, Patmos retains its charm and natural beauty—even in the busy month of August.

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.

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.

Embark your ship and settle into your stateroom. Athens has been called the “birthplace of democracy.” Its legacy looms large from atop Acropolis Hill, the pinnacle of ancient Greece. This open air museum is an astonishing repository of once-mighty structures. From its colonnaded Parthenon—built more than 2,600 years ago—revered Greek philosophers like Plato and Aristotle formulated new ideas of government and debated its role in civic life to captivated audiences. Remnants of spiritual life are also here in the several temples to Athena and Zeus.

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.

Trapani, the most important town on Sicily’s west coast, lies below the headland of Mount Erice and offers stunning views of the Egadi Islands on a clear day. Trapani’s Old District occupies a scimitarshaped promontory between the open sea on the north and the salt marshes to the south. The ancient industry of extracting salt from the marshes has recently been revived, and it is documented in the Museo delle Saline. In addition to the salt marshes,Trapani’s other interesting environs include the beautiful little hill town of Erice, the promontory of Capo San Vito stretching north beyond the splendid headland of Monte Cofano, the lovely island of Motya and the town of Marsala. Trips farther afield will take you to the magnificent site of Segesta or the Egadi Islands, reached by boat or hydrofoil from Trapani Port.

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.

A tourist-friendly town of about 45,000 inhabitants with a distinctly Spanish flavor, Alghero is also known as "Barcelonetta" (little Barcelona). Rich wrought-iron scrollwork decorates balconies and screened windows; a Spanish motif appears in stone portals and bell towers. The town was built and inhabited in the 14th century by the Aragonese and Catalans, who constructed seaside ramparts and sturdy towers encompassing an inviting nucleus of narrow, winding streets with whitewashed palazzi. The native language spoken here is a version of Catalan, not Italian, although you probably have to attend one of the Masses conducted in Algherese (or listen in on stories swapped by older fishermen) to hear it. Besides its historic architectural gems such as the Alghero Cathedral and Palazzo d'Albis, the fortified city is well worth a visit to simply stroll and discover local culture on narrow cobblestone streets. The city also has a reputation to serve great food at reasonable prices.

The capital of Menorca since 1721, Mahon has a impressive natural deep water harbour, which is one of the largest in the world. This, coupled with its strategic location, has made it a stronghold for many nations throughout history. Mahon has an abundance of historical buildings, the oldest being the Arch of Saint Roc which is all that remains of the wall that once encircled the whole town. The island was occupied by the British during the 18th century and Lord Nelson is thought to have stayed there. Indeed, San Antoni Mansion, located on the north side of the harbour, houses a collection of Nelson memorabilia. The legacy of colonial rule can be seen in the muted Georgian style of some of the buildings, but Mahon still boasts attractive examples of neo-Classical, Baroque and Romanesque architecture. With narrow streets to explore, pleasant shaded squares and welcoming pavement cafés, there is something for everyone to enjoy. Please be aware that most shops in town close for a siesta between 1330 and 1730.

Embark your ship and settle into your stateroom. The vibrant city of Barcelona, with its lively culture and inviting outdoor spaces, preserves a rich history. Picturesque medieval lanes wind through the oldest part of the city, the Gothic Quarter, where remnants of the city’s Roman wall were uncovered. Its treasures include the neo-Gothic Barcelona Cathedral, the medieval Jewish district of El Call and the Romanesque Church of Santa Maria del Pi. In the evenings, diners relax in the Royal Plaza at restaurants along the elegant square’s perimeter.

Valencia, Spain's third-largest municipality, is a proud city with a thriving nightlife and restaurant scene, quality museums, and spectacular contemporary architecture, juxtaposed with a thoroughly charming historic quarter, making it a popular destination year in year out. During the Civil War, it was the last seat of the Republican Loyalist government (1935–36), holding out against Franco’s National forces until the country fell to 40 years of dictatorship. Today it represents the essence of contemporary Spain—daring design and architecture along with experimental cuisine—but remains deeply conservative and proud of its traditions. Though it faces the Mediterranean, Valencia's history and geography have been defined most significantly by the River Turia and the fertile huerta that surrounds it.The city has been fiercely contested ever since it was founded by the Greeks. El Cid captured Valencia from the Moors in 1094 and won his strangest victory here in 1099: he died in the battle, but his corpse was strapped into his saddle and so frightened the besieging Moors that it caused their complete defeat. In 1102 his widow, Jimena, was forced to return the city to Moorish rule; Jaume I finally drove them out in 1238. Modern Valencia was best known for its frequent disastrous floods until the River Turia was diverted to the south in the late 1950s. Since then the city has been on a steady course of urban beautification. The lovely bridges that once spanned the Turia look equally graceful spanning a wandering municipal park, and the spectacularly futuristic Ciutat de les Arts i les Ciències (City of Arts and Sciences), most of it designed by Valencia-born architect Santiago Calatrava, has at last created an exciting architectural link between this river town and the Mediterranean. If you're in Valencia, an excursion to Albufera Nature Park is a worthwhile day trip.

A Mediterranean city and naval station located in the Region of Murcia, southeastern Spain, Cartagena’s sheltered bay has attracted sailors for centuries. The Carthaginians founded the city in 223BC and named it Cartago Nova; it later became a prosperous Roman colony, and a Byzantine trading centre. The city has been the main Spanish Mediterranean naval base since the reign of King Philip II, and is still surrounded by walls built during this period. Cartagena’s importance grew with the arrival of the Spanish Bourbons in the 18th century, when the Navidad Fortress was constructed to protect the harbour. In recent years, traces of the city’s fascinating past have been brought to light: a well-preserved Roman Theatre was discovered in 1988, and this has now been restored and opened to the public. During your free time, you may like to take a mini-cruise around Cartagena's historic harbour: these operate several times a day, take approximately 40 minutes and do not need to be booked in advance. Full details will be available at the port.

Motril is located in the Spanish region of Andalucia on the Costa Tropical. It is the biggest town on the Costa with a thriving commercial, fishing and leisure port. An hour and a half's drive east of Malaga and within easy reach of the magnificent Sierra Nevada mountain range, Motril makes an ideal base for exploring the many delights of the Andalucian coastline and its hinterland. Halfway between the resorts of Malaga to the west and Almeria to the east, nestling in the foothills of the Sierra Lujar mountains, Motril is at the heart of one of the most fertile and productive agricultural areas of Spain. The Costa Tropical takes its name from its sub-tropical climate which enables the cultivation of exotic fruits and crops such as sugar cane, oranges, lemons, apples, avocadoes, mangoes and bananas. One of the sights of Motril is the 17th-century church of Nuestra Señora de la Cabeza, dedicated to the town's patron saint.

The autonomous city of Melilla is a Spanish enclave located on the Mediterranean Rif coast of North Africa, bordering Morocco. Its chequered past embraced periods of Phoenician, Punic, Roman and Byzantine rule before it was conquered by Spain in 1497. The latter part of the 19th century and the first quarter of the 20th century saw hostilities between Rif berbers and the Spanish, with the latter finally reinstating their control in 1927. The city was used by General Franco as one of the staging points for the rebellion of 1936. As part of the Spanish protectorate, Melilla developed the architectural style of 'Modernisme', the Catalan version of Art Nouveau, and boasts the second most important concentration of Modernist works in Spain, after Barcelona.

Believed to be the oldest town on the Iberian Peninsula, the Andalusian port of Cádiz enjoys a stunning location at the edge of a six-mile promontory. The town itself, with 3,000 years of history, is characterised by pretty white houses with balconies often adorned with colourful flowers. As you wander around be sure to take a stroll through the sizeable Plaza de Espãna, with its large monument dedicated to the first Spanish constitution, which was signed here in 1812. Cádiz has two pleasant seafront promenades which boast fine views of the Atlantic Ocean, and has a lovely park, the Parque Genoves, located close to the sea with an open-air theatre and attractive palm garden. Also notable is the neo-Classical cathedral, capped by a golden dome.

Lively, commercial Oporto is the second largest city in Portugal after Lisbon. Also called Porto for short, the word easily brings to mind the city's most famous product - port wine. Oporto's strategic location on the north bank of the Douro River has accounted for the town's importance since ancient times. The Romans built a fort here where their trading route crossed the Douro, and the Moors brought their own culture to the area. Oporto profited from provisioning crusaders en route to the Holy Land and enjoyed the riches from Portuguese maritime discoveries during the 15th and 16th centuries. Later, port wine trade with Britain compensated for the loss of the spice trade and the end of gold and gem shipments from Brazil. In the 19th century, the city went through a period of new prosperity with the rise of industries. In its wake followed the building of workers' quarters and opulent residences. Since the declaration of Oporto as a World Heritage Site by UNESCO, the city aims to build up a cultural reference that will provide it with a new image, based on deep historical roots. Among the attractions that make Oporto such an interesting place are its graceful bridges spanning the Douro River, a picturesque riverfront quarter and, most notable, its world-famous port wine lodges. Although Oporto is a bustling centre and home to many different businesses, the source of its greatest fame is the rich, sweet fortified red wine we know as port.

Lisbon has inspired explorers for centuries with its stunning setting at the Tagus River’s mouth. Its labyrinthine streets carry echoes of 16th-century navigators who sailed on the winds of the Age of Discovery. The city prospered greatly from its trade. And today’s streets are lined with the legacies of wealthy builders, including the Jerónimos Monastery and Belém Tower, stunning works that introduced Manueline architecture. Savoring local cuisine and port wine are favorite pastimes here. On any evening, the strains of fadospill from clubs in the historic Alfama District.