Monte Carlo to Barcelona

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.

Established as the island's capital in 1722, when the British began their nearly 80-year occupation, Mahón still bears the stamp of its former rulers. The streets nearest the port are lined with four-story Georgian townhouses; the Mahónese drink gin and admire Chippendale furniture; English is widely spoken. The city is quiet for much of the year, but between June and September the waterfront pubs and restaurants swell with foreigners.

Málaga is one of southern Spain’s most welcoming and happening cities, and it more than justifies a visit. Visitor figures have soared since the Museo Picasso opened in 2003 and a new cruise-ship terminal opened in 2011, and much of the city has had a well-earned face-lift, with many of its historic buildings restored or undergoing restoration. The area between the river and the port is being spruced up and transformed into the Málaga Arte Urbano Soho (MAUS Art District), and in 2015 three new art museums opened, underlining the city's aim to become one of southern Europe's centers for art. Alongside all this rejuvenation, some great shops, and lively bars and restaurants have sprung up all over the center.True, the approach from the airport certainly isn’t that pretty, and you'll be greeted by huge 1970s high-rises that march determinedly toward Torremolinos. But don’t give up: in its center and eastern suburbs, this city of about 550,000 people is a pleasant port, with ancient streets and lovely villas amid exotic foliage. Blessed with a subtropical climate, it's covered in lush vegetation and averages some 324 days of sunshine a year.Central Málaga lies between the Guadalmedina River and the port, and the city’s main attractions are all here. The Centro de Arte Contemporáneo sits next to the river; to the east lies the MAUS district, slowly being hoisted from its former seedy red-light reputation to a vibrant cultural hub with galleries and up-and-coming restaurants. Around La Alameda boulevard, with its giant weeping fig trees, is old-town Málaga: elegant squares, pedestrian shopping streets such as Calle Marqués de Larios, and the major monuments, which are often tucked away in labyrinthine alleys.Eastern Málaga starts with the pleasant suburbs of El Palo and Pedregalejo, once traditional fishing villages. Here you can eat fresh fish in the numerous chiringuitos and stroll Pedregalejo's seafront promenade or the tree-lined streets of El Limonar. A few blocks inland is Málaga's bullring, La Malagueta, built in 1874, and continuing west, Muelle Uno (port-front commercial center), whose striking glass cube is now home to the Centre Pompidou. It's great for a drink and for soaking up views of the old quarter.

With the Atlantic Ocean on three sides, Cádiz is a bustling town that's been shaped by a variety of cultures, and has the varied architecture to prove it. Founded as Gadir by Phoenician traders in 1100 BC, Cádiz claims to be the oldest continuously inhabited city in the Western world. Hannibal lived in Cádiz for a time, Julius Caesar first held public office here, and Columbus set out from here on his second voyage, after which the city became the home base of the Spanish fleet. In the 18th century, when the Guadalquivir silted up, Cádiz monopolized New World trade and became the wealthiest port in Western Europe. Most of its buildings—including the cathedral, built in part with wealth generated by gold and silver from the New World—date from this period. The old city is African in appearance and immensely intriguing—a cluster of narrow streets opening onto charming small squares.

The Rock of today is a bizarre anomaly of Moorish, Spanish, and—especially—British influences. There are double-decker buses, "bobbies" in helmets, and red mailboxes. Millions of pounds have been spent in developing its tourist potential, and a steady flow of expat Brits comes here from Spain to shop at Morrisons supermarket and High Street shops. This tiny British colony—nicknamed "Gib" or simply "the Rock"—whose impressive silhouette dominates the strait between Spain and Morocco, was one of the two Pillars of Hercules in ancient times, marking the western limits of the known world and commanding the narrow pathway between the Mediterranean Sea and the Atlantic Ocean. The Moors, headed by Tariq ibn Ziyad, seized the peninsula in 711, preliminary to the conquest of Spain. The Spaniards recaptured Tariq's Rock in 1462. The English, heading an Anglo-Dutch fleet in the War of the Spanish Succession, gained control in 1704, and, after several years of local skirmishes, Gibraltar was finally ceded to Great Britain in 1713 by the Treaty of Utrecht. Spain has been trying to get it back ever since. In 1779 a combined French and Spanish force laid siege to the Rock for three years to no avail. During the Napoléonic Wars, Gibraltar served as Admiral Horatio Nelson's base for the decisive naval Battle of Trafalgar, and during the two world wars, it served the Allies well as a naval and air base. In 1967 Franco closed the land border with Spain to strengthen his claims over the colony, and it remained closed until 1985. Britain and Spain have been talking about joint Anglo-Spanish sovereignty, much to the ire of the majority of Gibraltarians, who remain fiercely patriotic to the Crown. There are likely few places in the world that you enter by walking or driving across an airport runway, but that's what happens in Gibraltar.

Don’t be put off by Cartagena’s outskirts, which house chemical plants and mining machinery; plunge straight into the Old Town near the port instead. Old Town is steeped in history and bustling with life. The Roman ruins here are among some of the best in the country and Cartagena’s tapas are justly famed. Holy Week processions are as moving as those in Seville and Málaga, and music fans will enjoy the Mar de Músicas international music festival in July and the Jazz Festival in November. Flamenco aficionados shouldn’t miss the Festival del Cante de las Minas in August, an annual flamenco contest plus concerts held in La Unión, 16 km (10 miles) to the east of the city (www.fundacioncantedelasminas.org).

If you look north of the cathedral (La Seu, or the seat of the bishopric, to Mallorcans) on a map of the city of Palma, you can see around the Plaça Santa Eulàlia a jumble of tiny streets that made up the earliest settlement. Farther out, a ring of wide boulevards traces the fortifications built by the Moors to defend the larger city that emerged by the 12th century. The zigzags mark the bastions that jutted out at regular intervals. By the end of the 19th century, most of the walls had been demolished; the only place where you can still see the massive defenses is at Ses Voltes, along the seafront west of the cathedral.A torrent (streambed) used to run through the middle of the old city, dry for most of the year but often a raging flood in the rainy season. In the 17th century it was diverted to the east, along the moat that ran outside the city walls. Two of Palma's main arteries, La Rambla and the Passeig d'es Born, now follow the stream's natural course. The traditional evening paseo (promenade) takes place on the Born.If you come to Palma by car, park in the garage beneath the Parc de la Mar (the ramp is just off the highway from the airport, as you reach the cathedral) and stroll along the park. Beside it run the huge bastions guarding the Almudaina Palace; the cathedral, golden and massive, rises beyond. Where you exit the garage, there's a ceramic mural by the late Catalan artist and Mallorca resident Joan Miró, facing the cathedral across the pool that runs the length of the park.If you begin early enough, a walk along the ramparts at Ses Voltes from the mirador beside the cathedral is spectacular. The first rays of the sun turn the upper pinnacles of La Seu bright gold and then begin to work their way down the sandstone walls. From the Parc de la Mar, follow Avinguda Antoni Maura past the steps to the palace. Just below the Plaça de la Reina, where the Passeig d'es Born begins, turn left on Carrer de la Boteria into the Plaça de la Llotja (if the Llotja itself is open, don't miss a chance to visit—it's the Mediterranean's finest Gothic-style civic building). From there stroll through the Plaça Drassana to the Museu d'Es Baluard, at the end of Carrer Sant Pere. Retrace your steps to Avinguda Antoni Maura. Walk up the Passeig d'es Born to Plaça Joan Carles I, then right on Avenida de La Unió.

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.

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.