Civitavecchia (Rome) to Barcelona

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.

La Spezia is sometimes thought of as nothing but a large, industrialized naval port en route to the Cinque Terre and Portovenere, but it does possess some charm, and it gives you a look at a less tourist-focused part of the Riviera. Its palm-lined promenade, fertile citrus parks, renovated Liberty-style palazzos, and colorful balcony-lined streets make parts of La Spezia surprisingly beautiful. Monday through Saturday mornings, you can stroll through the fresh fish, produce, and local-cheese stalls at the outdoor market on Piazza Cavour, and on Friday take part in the busy flea market on Via Garibaldi. There's also Porto Mirabello, a newly built tourist port with a pool club, shops, and several restaurants that overlook the fleet of super-yachts.

Villefranche-Sur-Mer is located on the Côte d’Azur in Provence – known for its fields of lavender and warm weather – and is highly appreciated for its 14th Century architecture.

At first glance, it really doesn't look all that impressive. There's a pretty port with cafés charging €5 for a coffee and a picturesque old town in sugared-almond hues, but there are many prettier in the hills nearby. There are sandy beaches, rare enough on the Riviera, and old-fashioned squares with plane trees and pétanque players, but these are a dime a dozen throughout Provence. So what made St-Tropez an internationally known locale? Two words: Brigitte Bardot. When this pulpeuse (voluptuous) teenager showed up in St-Tropez on the arm of Roger Vadim in 1956 to film And God Created Woman, the heads of the world snapped around. Neither the gentle descriptions of writer Guy de Maupassant (1850–93), nor the watercolor tones of Impressionist Paul Signac (1863–1935), nor the stream of painters who followed (including Matisse and Bonnard) could focus the world's attention on this seaside hamlet as did this one sensual woman in a scarf, Ray-Bans, and capris. Vanity Fair ran a big article, "Saint Tropez Babylon," detailing the over-the-top petrodollar parties, megayachts, and Beyoncé–d paparazzi. But don't be turned off: the next year, Stewart, Tabori & Chang released an elegant coffee-table book, Houses of St-Tropez, packed with photos of supremely tasteful and pretty residences, many occupied by fashion designers, artists, and writers. Once a hangout for Colette, Anaïs Nin, and Françoise Sagan, the town still earns its old moniker, the "Montparnasse of the Mediterranean." Yet you might be surprised to find that this byword for billionaires is so small and insulated. The lack of train service, casinos, and chain hotels keeps it that way. Yet fame, in a sense, came too fast for St-Trop. Unlike the chic resorts farther east, it didn't have the decades-old reputation of the sort that would attract visitors all year around. For a good reason: its location on the south side of the gulf puts it at the mercy of the terrible mistral winter winds. So, in summer the crowds descend and the prices rise into the stratosphere. In July and August, you must be carefree about the sordid matter of cash. After all, at the most Dionysian nightclub in town, a glass of tap water goes for $37 and when the mojo really gets going, billionaires think nothing of "champagne-spraying" the partying crowds—think World Series celebrations but with $1,000 bottles of Roederer Cristal instead of Gatorade. Complaining about summer crowds, overpricing, and lack of customer service has become a tourist sport and yet this is what makes St-Tropez—described by the French daily newspaper Le Figaro as the place you can see "the greatest number of faces per square meter"—as intriguing as it is seductive.

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.

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.

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.