Livorno to Monte-Carlo

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.

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).

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.