Start by asking yourself these questions: Where in Italy do I want to ride? During what season? In what type of terrain? What distance, pace and level of difficulty am I comfortable with? How much am I willing to spend?
Make an honest assessment of your riding skills and endurance. Most trips cater to the out-of-shape tourist (hence the full-time van support); this means a lot of waiting around. If you're a strong rider, a more challenging tour operator such as La Corsa Tours would be a better match.
Cruise the Web. Type "Italian bicycle vacation" in a search engine and spend a few hours shopping for the tour outfits that best suit your requirements.
Call and ask these questions: What's the typical riding day like in terms of duration and difficulty? What are the accommodations? How much experience does the tour leader have? Is transportation from the airport provided? What's the leader-to-client ratio? What's not covered (for example, meals, bikes and helmets)? Is there a maximum number of people? Will the trip be canceled if not enough riders sign up? Will there be van support? Are marked maps and written route instructions included? How many days do riders actually ride?
Budget in tips for your guides along with other trip expenses. Ten percent is standard; 15 percent will reward superior service.
Pedala forte, mangia bene. (Ride hard, eat well.)
