Call it unfair, but there's something unbeatable about the dolce vita wattage of this country's legendary playgrounds.

By Alexander Lobrano, Town & Country 
Taormina
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in this epicenter of tourism in Sicily, and, as Hemingway put it, “so 
pretty that it hurts to look at it.” Both are, we feel, risks worth 
taking. “Here the past is so much stronger than the present that one 
seems remote like the immortals, looking back at the world from their 
otherworld,” D.H. Lawrence wrote in 1920. That tension between past and 
present is why Taormina has drawn writers, artists, and aesthetes for 
centuries. Every evening at dusk, countless starlings add a thin black 
veil to the melon-colored skies over the third-century BC Greco-Roman 
theater that sits atop the cliff on which modern Taormina rests. 
Hundreds of feet below, the Mediterranean turns indigo with the fading 
light. Mount Etna in the distance adds even more drama. 

Stay 
The elegant yet animated Grand Hotel Timeo has a beautiful pool, and there’s a beach at its sister property, the Villa Sant’Andrea. Hotel Villa Ducale attracts a crowd of chic Italian regulars. 
Eat 
Sicily has some of the best food in the country. Locals recommend Casa GioLi or La Capinera for spaghetti with grouper, mint, lemon, and toasted pine nuts, as well as other inventive dishes. 
Shop 
Do not miss the trompe l’oeil marzipan fruits, a Sicilian specialty, at La Bottega del Buongustaio. 
In the know 

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Portofino 
Why
 mess with perfection? That sentiment is probably why so little of 
consequence changes in this almost unbearably pretty port, with colorful
 houses set on lushly wooded hills overlooking a small blue bay. Think 
of it as a lively Latin Nantucket, or Camden, Maine, where life revolves
 around boating (although in Portofino the lobster is usually served 
atop spaghetti). Grandees have been coming here since the Romans, with 
their unerring nose for real estate, founded it, from the lords of Genoa
 and Milan to today’s fashion elite. (Giorgio Armani and Domenico Dolce 
and Stefano Gabbana own villas here.) 

Stay 
The peaches-and-cream Hotel Splendido,
 with wisteria trellises on a hillside overlooking the port, evokes the 
era of the Grand Tour and still can’t be beat. (Dick proposed to Liz 
here.) If you plan to arrive by yacht or want to be in the thick of the 
action, check out its sister hotel, the Splendido Mare—it’s right on the waterfront.
Eat 
Though hardly undiscovered, Da Puny sends out very good Ligurian specialties including pappardelle in pesto corto. Taverna del Marinaio has excellent seafood salad and sea bream with green sauce. 
Shop 
Nearby Chiavari has a wonderful antiques market on the second Sunday of every month. 
In the Know 
A day out on a luxury charter is de rigueur—the best view of Portofino and of this whole gorgeous coastline is from the sea.
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Capri
If
 there’s one place to go during shoulder season (May–June and 
September), Capri is it. Though this shockingly beautiful little 
limestone shard in the Bay of Naples exceeds all expectations—as it has 
since the days of Caesar Augustus—and draws a nonstop pageant of 
bold-faced names, the crowds are of another order. The best sightseeing 
is done from a sunbed at the Fontelina Beach Club or a table at Capri 
town’s Gran Caffe.

Stay 
J.K. Place Capri, with interiors by Michele Bonan, is perfect for hip couples. Capri Tiberio Palace is within walking distance of everything. 
Eat 
Dine outdoors in a fragrant lemon grove at Da Paolino—don’t miss the mozzarella grilled between lemon leaves. La Capannina is a tad touristy but makes delicious local specialties like linguine with scorpion fish.
Shop 
Il
 Laboratorio, for the ultimate trousers and Capri pants, which frequent 
visitor Jackie O, of course, showed the world how to wear (fitted, with a
 big belt). 
In the Know 
Take a day trip to the quiet island of Procida to see what Capri was like before it became so famous.
Amalfi Coast
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 of what makes this 25-mile lemon blossom–scented stretch of coastline 
so appealing is the slight, constant frisson of danger. There’s the 
switchback road, the infinity pools. Plus the eternal question: How do 
you choose your spot? Our suggestions: Base yourself in Amalfi (with its
 grand 11th-century cathedral), Conca dei Marini (an overlooked gem), or
 Ravello (a haven in the sky). Visit Positano as a daytrip—there are too
 many crowds and tour buses for more than that—and, unless you happen to
 be energized by white-knuckle drives, use boat service whenever 
possible to get around. 
Stay 
In Amalfi, the Hotel Santa Caterina, an Italian Art Nouveau beauty with charming service; in Conca dei Marini, the cliffside 17th-century Monastero Santa Rosa; in Ravello, the serene Hotel Caruso, with its spectacular infinity pool. 
Eat 
Perhaps the best dining on the whole coast is at Lo Scoglio da Tommaso, a simple restaurant in Marina del Cantone,
 whose mostly Italian clientele come by boat for sublime dishes like 
fresh sea urchins and marinated anchovies. Also for seafood lovers, Acqua Pazza, in Cetara.

Shop
Stock up on summer shifts and accessories at Positano's Antonello della Mura, the chicest clothing shop on the coast.
In the Know 
The outstanding Ravello Festival of music usually runs from July through September.
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