Under Sail from the Riviera to Sicily

United with France only since 1860, Nice has its own history and atmosphere, which dates back 230,000 years. It was on Colline du Château (now château-less) and at the Plage des Ponchettes, in front of the Old Town, that the Greeks established a market-port in 350 BC and named it Nikaia, which would become Marseilles' chief coastal rival. The Romans established themselves a little later on the hills of Cimiez (Cemenelum), already previously occupied by Ligurians and Celts, and quickly overshadowed the waterfront port. After falling to the Saracen invasions, Nice regained power as an independent state, becoming an important port in the early Middle Ages.So cocksure did it become that in 1388, Nice, along with the hill towns behind, effectively seceded from the county of Provence, under Louis d'Anjou, and allied itself with Savoie. Thus began its liaison with the House of Savoy, and through it with Piedmont and Sardinia, it was the Comté de Nice (Nice County). This relationship lasted some 500 years, tinting the culture, architecture, and dialect in rich Italian hues.By the 19th century Nice was flourishing commercially, locked in rivalry with the neighboring shipping port of Genoa. Another source of income: the dawning of tourism, as first the English, then the Russian nobility, discovered its extraordinary climate and superb waterfront position. A parade of fine stone mansions and hotels closed into a nearly solid wall of masonry, separated from the smooth-round rocks of the beach by what was originally named Camin deis Anglés (the English Way), which of course is now the famous Promenade des Anglais. This magnificent crescent, which is seeking UNESCO recognition, is one of the noblest in France. Many of Nice's most delightful attractions—the Cours Saleya market, the Old Town streets, the Hotel Negresco, and the Palais Masséna—are on or close to this 10-km (6-mile) waterfront, making it the first stop for most visitors, while the redevelopment of Nice's port, around the other side of the Colline du Château, makes it easier for amblers who want to take in the Genoese architecture or peruse the antiques at the Puces de Nice, now part of the Promenade des 100 Antiquaires, along Quai Papacino. Nice also has the distinction of the "Family Plus" label, with free strollers, play areas, and restaurants with child-friendly activities.

One of the most photographed villages along the coast, with a decidedly romantic and affluent aura, Portofino has long been a popular destination for the rich and famous. Once an ancient Roman colony and taken by the Republic of Genoa in 1229, it’s also been ruled by the French, English, Spanish, and Austrians, as well as by marauding bands of 16th-century pirates. Elite British tourists first flocked to the lush harbor in the mid-1800s. Some of Europe's wealthiest drop anchor in Portofino in summer, but they stay out of sight by day, appearing in the evening after buses and boats have carried off the day-trippers.There's not actually much to do in Portofino other than stroll around the wee harbor, see the castle, walk to Punta del Capo, browse at the pricey boutiques, and sip a coffee while people-watching. However, weaving through picture-perfect cliffside gardens and gazing at yachts framed by the sapphire Ligurian Sea and the cliffs of Santa Margherita can make for quite a relaxing afternoon. There are also several tame, photo-friendly hikes into the hills to nearby villages.Unless you're traveling on a deluxe budget, you may want to stay in Camogli or Santa Margherita Ligure rather than at one of Portofino's few very expensive hotels. Restaurants and cafés are good but also pricey (don't expect to have a beer here for much under €10).

The colorful facades and pedestrians-only calata (promenade) make Portovenere the quintessential Ligurian seaside village. As a UNESCO World Heritage Site, its harbor is lined with tall, thin "terratetto" houses that date from as far back as the 11th century and are connected in a wall-like formation to protect against attacks by the Pisans and local pirates. Its tiny, carruggi (alley-like passageways) lead to an array of charming shops, homes, and gardens and eventually to the village's impressive Castle Doria high on the olive tree covered hill. To the west standing guard over the Mediterranean is the picturesque medieval Chiesa di San Pietro, once the site of a temple to Venus (Venere in Italian), from which Portovenere gets its name. Nearby, in a rocky area leading to the sea, is Byron's Cave, a favorite spot that the poet loved to swim out into the sea from.

Elba is the Tuscan archipelago's largest island, but it resembles nearby verdant Corsica more than it does its rocky Italian sisters, thanks to a network of underground springs that keep it lush and green. It's this combination of semitropical vegetation and dramatic mountain scenery—unusual in the Mediterranean—that has made Elba so prized for so long, and the island's uniqueness continues to draw boatloads of visitors throughout the warm months. A car is very useful for getting around the island, but public buses stop at most towns several times a day; the tourist office has timetables.

At first glance, it's hard to imagine that this resort destination was one of the world's great naval powers, and a sturdy rival of Genoa and Pisa for control of the Mediterranean in the 11th and 12th centuries. Once the seat of the Amalfi Maritime Republic, the town is set in a verdant valley of the Lattari Mountains, with cream-colored and pastel-hued buildings tightly packing a gorge on the Bay of Salerno. The harbor, which once launched the greatest fleet in Italy, now bobs with ferries and blue-and-white fishing boats. The main street, lined with shops and pasticcerie, has replaced a raging mountain torrent, and terraced hills flaunt the green and gold of lemon groves. Bearing testimony to its great trade with Tunis, Tripoli, and Algiers, Amalfi remains honeycombed with Arab-Sicilian cloisters and covered passages. In a way Amalfi has become great again, showing off its medieval glory days with sea pageants, convents-turned-hotels, ancient paper mills, covered streets, and its glimmering cathedral.

The largest and most developed of the Aeolians, Lipari welcomes you with distinctive pastel-color houses. Fields of spiky agaves dot the northernmost tip of the island, Acquacalda, indented with pumice and obsidian quarries. In the west is San Calogero, where you can explore hot springs and mud baths. From the red-lava base of the island rises a plateau crowned with a 16th-century castle and a 17th-century cathedral.

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).