For a certain sort of daydreaming, desk-bound cyclist, João Correia is the ultimate hero. A competitive rider as a young man, he'd given up the sport in his early 20s and settled into a comfortable career as an ad-sales executive in New York, his once-lithe frame bloated by frequent expense-account dinners. Five years ago, he started riding his bike to get back in shape, and not only lost 60 pounds but got so good he turned pro, riding for the Cervélo TestTeam at the top level of the sport. Imagine Keith Olbermann going to pitch for the Yankees, and you've got the idea.

Still, Correia didn't abandon all of life's pleasures after returning to biking. The love of food that once inflated him to 205 pounds inspired him two years ago to start a tour company that combines his two greatest passions: cycling and eating. A trip with InGamba will have you pedaling alongside Correia and his pro buddies – guys like former world champion Thor Hushovd, American racer Ted King, and Dutch Tour de France star Laurens ten Dam – during the day, and toasting with them at night over the best food Europe has to offer. And it's as important to keep up at those marathon meals as it is on the bike: Correia has been known to threaten to send people home if they aren't "pulling their weight" at the table.

Building an appetite shouldn't be a problem, however, as this high-intensity, eight-day tour of Correia's native Portugal – covering 50 to 100 miles a day – would have anyone, amateur or pro, eager to refuel as often as possible. Beginning in Lisbon, you'll head for the pilgrimage center of Fátima, before riding north into the rustic Douro wine valley, with its unique landscape of terraced hills. Here, you'll taste many (very many) of Portugal's wine varieties, from bold, full-bodied tintos (reds) to delicate, effervescent vinho verdes, many of which are still hard to find stateside. Then the route snakes into the mountains – and the riding gets hard.

Each night, you'll rest your weary bones in a different pousada – castles, monasteries, and mountain lodges converted to high-end hotels (at least one, the Pousada de Manteigas, has natural lagoons to cool off in) – and sample the country's signature dishes, from simply grilled chouriço and fresh seafood to every preparation of bacalhau imaginable. Along for the ride are a top-flight mechanic who'll keep your $10,000 Pinarello Dogma 2 in working order (no chance of blaming a "crappy bike" for your performance), and the inimitable Raul, a professional-grade soigneur (masseuse) who is especially skilled at reviving aching legs.

Through it all, you'll be buoyed by Correia's outsize personality – he still acts like the guy with the biggest expense account in the room – and camaraderie forged with the gregarious band of pro cyclists, who make the rides fast and the dinners hilarious, recounting off-the-record stories you won't read in any magazine.

"One thing that's important to me is to lift that velvet rope between the fans and the riders," says Correia. "You don't feel like you're just shaking a hand – you're connecting with somebody and getting to know them like a friend."

Getting There: InGamba's inaugural run of this itinerary is from September 8–16. Fly to Lisbon, InGamba will provide transfer to your hotel. The trip cost includes hotels and meals and finely tuned high-end rental bike. [$6,800; ingamba.pro]