Sicily

Bike Italy's Spiciest Island.

Sicily     Photo: courtesy of De Agostini Picture Library

IT'S ONLY DAY THREE of our 220-mile cycling trip through Sicily, but I already get Don Corleone's attachment to this island punted into the sea by mainland Italy.

No wonder the mythical Mafia boss was so protective of his turf: While honor killings and extortion are more than just legend in some parts of Sicily, today I'm living la dolce vita. The largest island in the Mediterranean sprouts wild oregano, smells of citrus, and harbors some of the world's most important Greek and Roman ruins.

The 75-degree autumn sun beats down on our 17-person Ciclismo Classico peloton—a crew of 35-to-65-year-old American cycling fanatics—as we head from the Baroque southeastern seaside city of Siracusa and eventually out to the Aeolian Islands (the La Bella Sicilia trip starts at $4,695; ciclismoclassico.com). Our two Italian guides, Enrico Pizzorni and Paolo Nicolosi, have titanium lungs, a vast knowledge of Italian history and culture (e.g., never drink cappuccino after 10 A.M.), and a serious sense of humor.

"It's very hard to get in a fight with a Sicilian," rants Pizzorni, who is from Piedmont, as he and Nicolosi, a native Sicilian, get into a wildly gesticulating standoff over trip logistics and bicker like brothers. "They're always trying to get around things."

At the moment, Nicolosi, who's known throughout the island as "the King of Sicily," is hammering up a steady climb in his sleek Acqua & Sapone riding kit, with no hands, while belting out Italian arias a cappella. We Americans, on the other hand, sport Arrogant Bastard Ale jerseys and bonk—at least I did—on the 60-mile ride to the hilltop city of Ragusa, the centuries-old hideout where crusaders rested on their way to conquering Jerusalem.

After we settle into the Locanda Don Serafino boutique hotel, the hippest (and only) rehabbed 19th-century mansion I've ever slept in, we step into the street, which is crowded with jugglers, fire eaters, clowns, and street musicians who've turned this World Heritage site into a five-night bacchanalia—the annual Ibla Busker, a raucous street fair where performance artists from all over Europe test their best conceptual work and everyone drinks too many Negronis.

At dinner, after we've sampled a few bottles of local Cerasuolo Avide-Barroco frappato, Pizzorni tells us how to catch an octopus. "My grandfather taught me," he says. "The trick is to turn his head inside out and bite it on the brain."

I'm skeptical but slightly preoccupied by the edible sculpture of eggplant ricotta that's just been placed in front of me.

We eventually eat and cycle our way to the seaside city of Taormina, where Richard Burton and Elizabeth Taylor used to hide from the paparazzi, and hike to the sulfuric crater of active Mount Etna. Then we hydrofoil north to Lipari, the hub of the Aeolian Islands and the backdrop for the film Il Postino. We've cycled more than 200 miles, drunk too much Sicilian pinot, chardonnay, and Nero d'Avola, and eaten pizza with crust as thick as my skull. I haven't bitten an octopus on the brain. I'm saving that old fishing trick to make my living after I move to Lipari.

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