WELCOME TO ITALY: Tuscany is perhaps the most desirable cycling destination on the planet. Ciclismo Classico offers everything from an advanced coast-to-coast Ride Across Italy to the Tuscan Fantasy itinerary, which is aimed at families and includes pizza making and olive oil tastings.

Tuscany offers the arts of Florence; the magnificent walled towns of Sienna, San Gimignano, and Monteriggioni; the famed Chianti vineyards; and fantastic dishes like legendary bistecca alla Fiorentina. Couple that with the Italian passion for cycling and drivers’ willingness — or insistence — on sharing the road, and Tuscany is perhaps the single most desirable cycling destination on earth. While Ciclismo Classico has trips across Europe and Asia, it has always focused on Italy, where its tours first started more than two decades ago. After graduating from Cornell University, founder Lauren Hefferon moved to Florence to study fine arts, fell in love with Italian cycling, and rode more than 35,000 miles before launching the company to share her passion. Hefferon still guides tours herself and employs fellow guides who are experts in local cuisine, language, history, and customs. Ciclismo Classico uses only four- and five-star lodgings, and includes a bike jersey in the package. In keeping with the company’s roots, it provides high-end 30-speed Bianchi road bikes with Campagnolo components, the classic Italian ride. The Tuscan Fantasy itinerary is aimed at families and includes everything from pizza making to olive oil tastings. Ciclismo also offers Tuscany on its private and custom trips and as part of its more advanced coast-to-coast Ride Across Italy. ciclismoclassico.com   

An offshoot of the popular outdoor-gear retailer REI, this company has been leading a wide variety of active travel trips worldwide for more than a quarter of a century, and for a pure cycling destination, emphatically recommends the South Island of New Zealand. Its classic South Island cycling trip runs 11 days and takes guests from the Southern Alps to the Pacific, including one of the world’s most renowned rides, the Central Otago Rail Trail. All the epic beauty that makes New Zealand a dream destination is on display, from rugged mountains to verdant pastures to volcanic landforms and sandy beaches. Lucky participants ride by the nation’s highest peak, Mount Cook, and through the famous wine country — with stops for tasting, of course. The penultimate day traverses New Zealand’s highest paved road before dropping into Queenstown. REI has more of a cultural and experiential focus, with less emphasis on luxury and more on accommodations and cuisine that showcase local authenticity. REI also boasts a company stewardship policy that ensures a commitment to sustainability and environmental responsibility on every trip. rei.com/adventures

OUTDOOR FUN: DuVine's classic Spanish itinerary winds through miles of spectacular rolling Basque countryside.
Like other top companies, DuVine Cycling & Adventure Company sprang from its founder’s passion for cycling and travel. In this case, global two-wheeled explorer Andy Levine founded DuVine nearly two decades ago. While the company hits all the right points with top-notch guides and accommodations, it really stands out for its love of wine, right down to its name, and when you combine this with one of the greatest cycling nations in the world, where top pros like Miguel Indurain have long chosen to train, you get incredible weather plus rides through some of the world’s finest wine country. DuVine has more inclusive pricing than its competitors, in large part so that wine is complimentary at every lunch and dinner, along with après vélo cocktails, a jersey, and even a t-shirt emblazoned with the company motto, “Bike. Eat. Drink. Sleep.” DuVine also offers a series of very high performance trips along the routes of top races such as the Tour de France and Tour of California, but on this classic Spanish itinerary the living is much easier, with six days of tapas, fine wines, medieval towns, vineyards, flamenco shows, and 23 to 29 daily miles of fun, including the rolling Basque countryside. Lodging includes the plush Hotel Marques de Riscal, designed by Frank Gehry and home to a Caudalie Vinothérapie spa. duvine.com