Civitavecchia to Monte Carlo

For centuries, Rome ruled much of Europe, building a vast empire from the power of emperors. More than 2,500 years of history live in the city’s streets. Ancient structures recall those heady days when the cheers of 80,000 spectators roared from the Colosseum, citizens mingled in the Forum and senators asked the gods for guidance at the Pantheon. Along with the Vatican and St. Peter’s Basilica, this rich pocket of Italy is one of the world’s greatest repositories of history and civilization.

A summer escape for Rome's historic elite, the stacked waterfront of Porto Santo Stefano is a secluded taste of idyllic southern Tuscany. Physically closer to Rome than Florence, the city is strung to Italy's western coast by two sandy harnesses and sits on the unique peninsula of Monte Argentario - which was once an island. Flamboyant pink flamingos and herons stroll through the encased lagoon, while Porto Santo Stefano's waterfront hums with clinking cafes and strolling visitors. The luxury yachts in the harbor show that Porto Santo Stefano has lost none of its luxury appeals, and with beaches, wild hikes, and waterfront beauty, it continues to lure visitors to this secluded escape. Known for its fishing and cuisine - which is based on heavy use of the Tyrrhenian Sea's juicy bounty. Stroll to Piazza dei Rioni for a dripping lemon gelato, or wander the streets noticing the lingering World War II damage - the city was heavily bombed during the conflict. Fortunately, the historic, star-shaped, Spanish fort was spared, and it still watches out resolutely over the waters. Built during the Napoleonic Wars, it fortified the exposed town against pirate raids and offers beautiful views over the old town's terracotta roofs. Rugged coastline falls to secluded beaches, with a wilder, unkempt charm. Sail the coves - seeing cascading olive groves - or island hop to Giglio and Giannuti, which lie 12 miles from shore, and can be seen from the monastery-topped Argentario Mountain. On the other side of the promontory, you'll find Porto Ercole - where the lifeless body of the Old Master, Caravaggio, was discovered.

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.

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).

Home to France’s principal naval base, aircraft carriers, and naval shipyards, Toulon stands apart from the glitzy allure of the rest of the Cote d’Azur. At first glance, its own genuine charms can appear guarded by this military presence but seeking them out is part of the fun. For a city that’s all about the sea, there’s no better place to start than the harbor. With yachts and fishing boats providing an animated backdrop, there are plenty of good restaurants to eat in. It’s also where to find the highly recommended French naval museum, which traces Toulon’s long and often dramatic maritime history. Above the town rises Mont Faron, nearly 600 meters high, offering an overview and is the place for some great photos of this southern French city and turquoise bay below. A cable car takes the effort out of the climb, and nearby is the newly renovated Mémorial du Débarquement et de la Libération de Provence. It tells the moving story of the Allied landings that took place here in 1944. Sea salt breezes mingle with the perfume of lavender and herbs from the marketplaces in the recently restored Old Town. It’s a maze of narrow alleyways that open onto delightful squares like Cours Lafayette. Within easy walking distance of the city center lies the small fishing port Mourillon, with its haut bourgeoise architecture, traditional French market, and sandy beaches. Follow the locals to the wild, secluded beach of Anse de Magaudis it is definitely one of the most beautiful places in Toulon.

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.