We don’t know about you, but we’re ditching the Gran Fondo New York for the real thing in Italy this year, l’Eroica in Tuscany.
But you’ll have to move fast: registration for the October 5, 2014 event held in the Chianti wine region of Italy opens on Feb. 1, and slots are sure to be move quickly. (Women of all ages, and men over 60 register on March 15).
The event was started 17 years ago by Giancarlo Brocci, and has since grown to 5,500 participants–its limit.
This ride will offer you more than the usual ride to Nyack and Bear Mountain that you certainly can and have done yourself many times over until you’re dead in the head.
Offering 38, 75, 135 and 209 Km length routes that touch on the historical town of Sienna, you’ll pay only 45 Euros (about $65) for your ride compared to the enormous prices of U.S. gran condos (New York’s is now $269 plus fees), and you’ll get a tour of Italy’s Tuscany region too.
What’s more this ride can only be done on a bicycle that predates 1987. No clipless pedals allowed either, and gear switchers must be of down-tube variety.
Though it may be a challenge to find such a bicycle, some are available for rental through the local l’Eroica bike shop, Bottega de l’Eroica. (Or you can call Steve Klein–he has a collection of 26 bicycles in his New York apartment, many of them predating 1987. But don’t expect to get him by email, or Facebook. He’s pretty much old school all the way.)
Many riders can be seen in full retro garb made of wool rather than polyester, and officials rules state 
that you can use helmets dating from that time period and earlier, which includes the completely useless but oh so fun leather hairnets, or no helmet at all.
This seriously retro ride is no joke, and will test the best legs–steel bikes only with minor exceptions (see their site.)
What’s more, cycle cross bicycles are not allowed, this despite the fact that much of the roads are not paved, but of the trickier white gravel 
type, and riders are advised to carry full puncture kits. 
Significant climbing challenges abound, so it would not be a bad idea to come a few days early to practice. The entire route is now permanently marked so you won’t lose your way.
But you’ll be rewarded for all your hard work by rest stops loaded with real Italian food and Chianti wine from the region, not the factory-made crap that you’re used to.
That includes prosciutto, Italian cheeses, fruit tarts, wheat bread, salads and soup (see photo.)
Two thousand five hundred (2,500) places are reserved for men under the age of 60, 1,000 of those places to be won in the lottery which opens Feb. 1.
The remainder of spaces for men under 60 are obtained by paying a little more, but the difference in the entry fee is given to 
charity, and those fees range from 100 Euros (register by May) to 200 Euros, (register by Sept.
15.) Still, with the exception of the highest charity fee, the cost of attending this event is lower or the same as the New York Gran Fondo.
For women of all ages, and men over 60, registration doesn’t start until March 15.
The organizers also include special travel packages available through their site for various kinds of hotel, bed and breakfast, and other accommodations that range in price from 280 Euros and up for the three-day period (the Saturday before the ride, through the Monday after the ride.) That means your hotel can be about $93 a night, so you might as well extend the vacation and make it longer.
Or you can rent Sting and Trudie Styler’s guest houses on their estate Il Palagio, for $5,320 per week for up to 30 people.
Other estates and high end stays abound, including Castel Monastero, a former monastery that has been converted into a hydrotherapy spa and hotel where rooms start at $590.
The organizers also hold a running race on Nov. 2, and participants who are truly blessed, inspired, or both, can register for both events and qualify for prizes awarded for winning both events.
