
Do you have a love affair with Italy? Maybe you’ve traveled there for a vacation or for other reasons but you never got to do any kind of cycling. And why wouldn’t want to do that? Italy is one of the epicenters of European cycling and plays host to one of the most renowned stage races on the earth: the Giro d’Italia.
Maybe it’s not Italy you’re interested in, though, but Morocco, the United States, or some other European country? And maybe it’s not cycling you’re interested in at all but walking or hiking trips and tours. Maybe it’s a multisport vacation with your family that involves cycling, kayaking, and snorkeling? While Ciclismo Classico sees itself as primarily a bicycle travel company, it will help you design the type of active vacation you’ve always wanted to take.
Who is Ciclismo Classico?

The company was founded in 1989 by Lauren Hefferon and is based in Arlington, Massachusetts. She caught the cycling bug while an anthropology student at Cornell University in upstate New York. She taught cycling skills to college freshmen in addition to doing her own riding.
From there, Hefferon knew her future was to work in the cycling industry, so she went to Italy and rode through the country to rediscover her own Italian roots. This trip gave her the inspiration to develop the first woman-owned bicycle travel company.
Years later, that vision of adventure and fun continues. In fact, Hefferon sees Ciclismo Classico’s primary mission as this: “Life should be active, fun, delicious, educational, flowing, strengthening, energizing, and deeply connected with beautiful places and their people.”
The Ciclismo Classico Experience and Difference

With mostly an exclusive focus on Italy and the opportunity to explore its cities, towns, culture, history, and people, Ciclismo Classico hopes its guests will discover the rich beauty of life that can only be experienced by bike. The company wants to bring its guests back to that level of excitement first felt when they started cycling.
If that feeling and passion can’t be rediscovered in Italy, then the company hopes it can be found in one of the other 12 countries in which it offers trips. As pointed out on Ciclismo Classico’s website, “we have created, curated and perfected unique, one-of-a-kind itineraries that combine gorgeous roads, fascinating culture, succulent specialties and a steady diet of learning opportunities led by extraordinary tour guides. That’s how we earned our reputation as the bicycle tour pioneers.”
Ciclismo Classico Destinations

One of the biggest challenges a bicycle travel company faces (or any travel company for that matter) is finding a way to differentiate itself from other companies that offer similar things. Ciclismo Classico, for instance, prides itself on trips that explore every region of Italy and make cultural immersion, wine, food, and history a focus.
The company offers its guests lots of choices for destinations. The hope is that if a guest likes a trip, they’ll come back for another to a different region of Italy or choose another European destination. But clearly, it has enough staff to cover trips to most areas, including the United States and Canada.
- Italy (full coverage)
- France
- Spain
- Austria
- Belgium
- Croatia
- Czech Republic
- England
- Germany
- Ireland
- Morocco
- United States (mostly northeast destinations) and Canada.
What’s Included in a Ciclismo Classico Booking and Tour

Since Ciclismo Classico is a larger bicycle travel company with offices in the United States (Massachusetts where the company is based) and Italy, it covers a lot of bases. In addition to the things most bicycle travel companies offer guests, such as accommodations, breakfast, dinners (most), lunches (some), snacks and drinks, and luggage handling, it offers things other companies don’t.
In essence, each guest is treated not only to an exceptional cycling adventure but also to the amenities of an outstanding vacation. Even travelers on a basic European trip won’t get the level of access or cultural immersion that guests on a Ciclismo Classico trip experience. They certainly would have to go to great lengths to find the things included in one of the company’s trips.
Cycling Amenities
- Experienced and bilingual (native and local) guides
- Local guides for walks, educational talks, etc.
- Shuttles
- Tips/ gratuities
- Office staff to help with trip planning
- Pre-departure package
- Meeting for arriving and departing
- Detailed maps/ routing options
- Garmin GPS
- Additional routes for cyclists who feel the need for more miles
- 3 cycling clinics and expert coaching
- A large stable of rental bikes: La Classica Ribelle carbon road bike with SRAM electronic shifting and disc brakes. The company also offers Hybrids, Tandems, and E-bikes.
Vacation/ Tour Amenities
- Wine/ food tastings
- Cooking demonstrations
- Language lessons
- Museum visits
- Interaction with locals at festivals and special events
- Cycling Jersey
- Group transfers
An example of an Italian Tour with Ciclismo Classico

The company offers so many diverse choices for trips and tours that it is hard to choose just one as an example. However, since Italy is the jewel in its crown of locations, I’ve chosen to mention the company’s Puglia trips. It turns out Ciclismo Classico offers three cycling trips and one hiking/ walking trip.
The company’s trips are designed for all levels of ability from advanced to beginner. Its La Bella Puglia trip is for 9 days/ 8 nights and is $6,554. On this trip, cyclists can expect 30-mile days with gently rolling terrain and a combined elevation of almost 14,000 feet. Click the link to read more about this trip.
Last Thoughts

Ciclismo Classico looks like an excellent bicycle travel company that offers lots of choices and variations. Their trips almost seem like two trips in one: a cycling holiday mixed with unique access to locals, food, wine, and museums that many European tourists just don’t get to experience.
So, if you’re looking for a luxurious cycling trip/ vacation, Ciclismo Classico is a great company with which to plan your dream trip.

