A SERIOUS SPIN: Gray & Co. offers extremely high-end bespoke trips in Argentina, with smooth pavement and stunning red-rock landscapes.

The highest of the high-end bike tour outfitters, Gray & Co. takes a different tact with its operations and philosophy, offering only completely custom bespoke trips, with no catalogs or scheduled departures. Its clientele includes A-list international entertainers, CEOs of Forbes 400 and Fortune 1000 companies, and at least one frequent repeat cycling billionaire. Since its customers have done most of the obvious destinations, the focus is on finding the best-quality riding in terms of roads and scenery in less explored areas from South Africa to New Zealand to Canada and Europe. But founder Cari Gray loves South America and frequently takes clients to Chile and Argentina. She is especially enamored with the Argentine wine country around Mendoza in the west and the Valle Calchaqui in the northwest, noting that, “The smooth pavement and ever-evolving, stunning red rock landscapes of the Quebrada de las Conchas valley between Salta and Cafayate make it one of the best roadbike rides in South America — if not the world.” Gray & Co. trips operate on a “no margin for error” philosophy that puts guest satisfaction above all else, with an unusually high guide- and driver-to-client ratio, dedicated mechanics, premium carbon bikes, and a truly white-glove touch. Custom itineraries start around $1,500 per person per day. grayandco.ca 

A SERIOUS SPIN: Trek Travel boasts a 3,600-mile once-in-a-lifetime dream ride from Portland, Oregon, to Portland, Maine.
For the most avid cyclists, even a week in Tuscany or Burgundy, while great, is not enough. The dream trip for these hammerheads is the width and breadth of the USA, a once-in-a-lifetime ride. While just about every top luxury tour operator, including Trek Travel, covers the classic destinations above, only Trek specializes in this epic journey from Portland, Oregon, to Portland, Maine — 3,600 miles in 45 days of 36 to 125 miles, with 15 rides over the century mark. Once a year they lead a group across the Rockies, across the Adirondacks, and everywhere in between, on a fully supported ride that is a relative bargain on a daily basis at $17,000 per person for the trip. Wisconsin-based Trek Bicycles launched Trek Travel, and while spun off in 2006, they retain a strategic partnership, so guests ride high-end Trek road bikes with state-of-the-art Shimano Ultegra Di2 electric shifting and optional carbon racing wheelsets. trektravel.com 

California’s famed wine country is consistently at the top of any U.S. cycling dream-trip list, with great weather, beautiful roads, and endless vineyards, plus fantastic food and luxury lodging. Backroads is still run by its hands-on founder from 30 years ago, Tom Hale, and individual trip planners average 17 years of experience. The largest top-quality outfitter, Backroads has cycling, hiking, and multi-sports trips across the globe, but the Berkeley-based company has an especially long history in California. As its name suggests, the wine country trip takes back roads through the less trafficked areas of  Pope Valley, Oakville, and coastal western Sonoma up to Bodega Bay. Participants visit famed wineries such as Frog’s Leap, Silver Oak, and PlumpJack; dine at Michelin-starred Santé and Dry Creek Kitchen; and stay in deluxe style at the Fairmont Sonoma Mission Inn and Spa and Hotel Healdsburg. For 2014, Backroads replaced its bike fleet with Shimano Ultegra-equipped custom titanium models, shaving a whopping two pounds off their predecessors, with optional upgrades to pro-level Specialized S Works models. backroads.com