Win a Dream Cycling Vacation in Italy

07.6.2009 | 9:57 am

200907052349.jpgA Note to Team Fatty-San Jose Members: One of you is about to win a pair of Sidi shoes. Which kind? Any kind you want. That includes the $500 Ergo 2 road shoes or the Dragon 2 MTB shoes (a pair of which I both own and love). Mmmm. Handmade Italian cycling shoes. Smells like love.

How do you win, might you ask? Well, you have to be a member of Team Fatty San Jose, first of all. (If you want to join as a virtual team member and start getting people to donate right now, that’s totally cool with me.)

Second, you’ve got to raise money in your personal LiveStrong Challenge between now and this Wednesday at Midnight.

The more you raise between now and Wednesday, the better your chances of winning shoes that will make all of your riding friends’ jaws drop with a combination of lust and envy. And the best part is, you’ll have won these shoes by doing something really, really good.

That’s all there is to it. Now get out there and hit up your friends, family, neighbors, and coworkers. Tell them you want an early (late?) birthday present, and that present is a donation to your LiveStrong Challenge page. You don’t have to tell them what’s in it for you. That can be our secret.

Huge thanks goes out to Veltec Sports and Sidi for providing this very sexy prize.

Win a Dream Cycling Vacation to Italy200907082324.jpg

Dorothy Gibson takes the fight against cancer very personally. She should. She lost her mother and her father to it. Her two brothers are both survivors.

She also loves riding her bike.

And so, after coming home from a once-in-a-lifetime self-guided cycling tour through the heart of Tuscany, Italy with her friends, Dorothy didn’t just put the memories away. She looked for a way to share the experience, while helping Team Fatty with our LiveStrong Challenge.

And that, combined with the generosity of several Fat Cyclist readers who have volunteered their frequent flier miles, is how we have arrived at this contest.

Win the Terre di Siena Self-Guided Bike Tour With Cicloposse.

I’ll get to Dorothy’s story of her tour in a moment, but first, here are the details of how to enter:

  1. Go to Dorothy’s LiveStrong Challenge page and donate any multiple of $5.00. You’ll automatically be assigned a random number for every $5 you donate.
  2. Deadline for donations is Wednesday, July 8, at Midnight Mountain Daylight Time. That’s just three days, folks. Don’t put off your donation.
  3. Cross your fingers and hope you win, because this looks pretty darned incredible.

What You Get

If you win, you get the Cicloposse Terre di Siene Self-Guided Bike Tour for two, plus roundtrip airfare for two to Italy. Of course, you’re going to need to bring some money for handling buying stuff along the way.

Cicloposse supplies the bikes, pedals, and helmets, as well as pumps, spare tube, patch kits. You could also ship or take your own bike if you prefer. Dorothy and her crew went with a compromise route of bringing their own pedals, saddles, and helmets. Which seems like a good call.

Now, you may wonder, what does “self-guided” mean? Here’s how Dorothy describes it, at least in context of this trip. Self-Guided means you:

  • have your luggage in the lobby at the appointed time for transport to the next location
  • enjoy a leisurely breakfast at the hotel
  • carry your raingear, money, passports, snacks, tubes, tools, etc, to take care of yourself on the way (no sag wagon)–just like your regular road rides
  • follow the detailed map and route descriptions, odometer, and road signs (good map reading skills a plus, but Cicloposse makes this very easy)
  • ride as fast, or slow, as you’d like
  • stop when you’d like, eat when and where you’d (they have fabulous suggestions)
  • call the hot line number if in need of emergency support
  • arrive at your next hotel with your bags already there

I don’t know about you, but this sounds pretty much perfect to me. And from the way Dorothy describes them, Marco and Guilianna Mulas — the owners of Cicloposse — take great care of you and are excited to help out with the fight against cancer, too.

And now, to whet your appetite for this trip, here’s Dorothy’s story, along with a few photos.

Dorothy’s Terre di Siene Trip

We are tough, independent women…and are passionate cyclists. We’d also like to think that we ride too fast to be with an organized group, but, truth be told, we really just wanted to stop for gelato, pastries, or chocolate anytime we wanted. Terre di Siene was perfect for us!

We met Marco and Guilianna Mulas in the courtyard of our hotel, Relais il Chiostro (The Cloister), for our bike fitting and orientation on Day 1. This fabulous hotel is a renovated 15th century convent, adjacent to the church in the town square in the heart of Pienza.


A few streets away is “Via del Bacio,” or “Street of the Kiss” (just one street up from the “Via dell Amore”). We were only slightly disappointed to find neither there, and loved exploring this Renaissance town.


After and unbelievable breakfast the next morning, we started out into the Tuscan countryside, a patchwork of vineyards, fields, and orchards, punctuated by cypress trees. We circled back to Pienza the first day… our destination the summit in the distance.

Joy is reaching the town limits of Pienza.


They actually like cyclists here! We found the hospitality of motorists strangely refreshing.

That evening we dined in what is now one of my most favorite restaurant in the Northern Hemisphere. We were delighted we listened to Marco and Guinliana’s recommendations here–this is their hometown; they know what they are talking about.

The climb into Montepulchiano burned most of those calories…


Montalchino’s medieval fortress is impressive. We loved exploring the many castles along the way.


The ride into Siena was one of our favorites of this trip. We encountered some wet conditions that day, but loved the climb through quiet olive groves to Monte Oliveto Maggiore (Mount of Olives) to the Benedictine Abbey there. Here Joy and I were dropped hard, and were grateful to each have our own sets of maps and detailed instructions! It was blissful to arrive at our Siena hotel (another cloister/convent) to have our luggage ready and awaiting us, and to be clean and dry for our evenings out.

Siena was amazing. The heart of Tuscany.


We fell in love with this town, and came back again after our cycling was finished…one day here is just not enough! The Duomo is one of the most magnificent cathedrals in all of Italy, and not to be missed.

The Chianti wine region offers more splendid landscapes. Those that imbibe in the fine wines of the region may take a little more time on this leg than others.

Last, but certainly not least, was San Gimignano. Castles, towers, fountains, vineyards, art. How soon can I go back?

This trip was a dream… incredible cycling, scenery, history, art, food, and friends. It was educational, too.

A few of take home gems:

200907052336.jpg1. Gelato, enjoyed anywhere in Italy, is the best recovery food. Ever. We kept a commitment to have at least one gelato a day.

2. Climb any turret, tower, or Duomo you may come to in Italy. The views are spectacular, and may burn enough calories to have another gelato. Maybe.

3. You can never have too much memory for your camera.

4. Learning a little Italian can be very helpful.

5. Cinque Terre is a trip extension that is a “must do.” If, I mean when, I return there… I will mountain bike, as well as hike that.

So, Once Again, What’s The URL to Enter this Contest?

With those pictures and that story, I don’t feel like I need to give you a hard sell on entering this contest. You’re fighting cancer. You’re having the vacation of your life. Seriously, what could be better? Nothing comes to mind. Click here to donate and enter now.


  1. Comment by Katie | 07.6.2009 | 10:19 am

    I may have peed a little when I saw this contest. Just a little.

    Quick question, though– is there a specific time frame in which we need to cash in on the prize?

  2. Comment by Big Boned | 07.6.2009 | 10:30 am

    No great wisdom or insight here, but this blog has created an amazing group of “friends”.

  3. Comment by Linda | 07.6.2009 | 11:48 am

    Hey Elden, I think Bobke needs to shave his head again. It’s not quite as long as last year but hey, I’m just sayin’.

  4. Comment by James Todd | 07.6.2009 | 11:49 am

    WIN Susan!!!
    Reference ID: 93487216
    Participant Credited: Dorothy Gibson

  5. Comment by Angie G | 07.6.2009 | 12:06 pm

    What great incentive. Awesome prize Dorothy! Pick me :-)

    I am also having my last raffle. Not as awesome a prize as Dorothy’s.

    For every $5 you donate to my page you get a raffle ticket for a half a case of Roederer Estate Sparkling Wine, 4 champagne flutes and a chill bucket. The raffle will end at midnight on Wednesday 7/8.

    Roederer Estate is the american branch of the Louis Roederer Champagne House. One the finest Champagne houses in France. Established in 1776, Louis Roederer champagne has been served by the White House, dignitaries and Kings and Queens through out the world. Known as one of the finest champagnes, Roederer Estate continues this tradition.

    Good Luck! Any questions email me at

  6. Comment by Clydesteve | 07.6.2009 | 12:15 pm


    Even if I were a cool Californian, I would lose my cool over this contest.

  7. Comment by Philly Jen | 07.6.2009 | 12:44 pm

    I must take issue with the following assertion:

    “Gelato, enjoyed anywhere in Italy, is the best recovery food. Ever.”

    Freshly made gelato is the best recovery food no matter where you eat it.

    The fact that it magically contains no calories if you eat it while on vacation should not tip the scales in favor of the Italians.

    To wit: if Jan Ullrich had subsisted on a diet of delicious Philadelphia gelato during his off-season, he would have been as svelte as a supermodel every spring.

    I’m just sayin’…

  8. Comment by Cyclin' Missy | 07.6.2009 | 12:54 pm

    That is a seriously amazing prize! Maybe the best vacation ever. WIN SUSAN!

  9. Comment by Jabber Jaws | 07.6.2009 | 2:26 pm

    Please pick me, please pick me – I would totally learn to bike if I won. Don’t hate me for that either. I would write WIN SUSAN on something all along the way. Fun times!!

  10. Comment by stuckinmypedals | 07.6.2009 | 2:32 pm

    It is my birthday and donations to my ride are exactly what I asked for. The shoes would just make it that much better.

  11. Comment by Kyle | 07.6.2009 | 2:57 pm

    BEst prize ever!

    I need to think up a prize so my $ raised total can no longer be embarassing…

  12. Comment by KanyonKris | 07.6.2009 | 5:06 pm

    Very cool prizes.

    I hope I win the Italy cycling vacation. It would be an incredible 20th wedding anniversary for us. And if I don’t win cancer gets another kick in the shins.

  13. Comment by Kathleen@ForgingAhead | 07.6.2009 | 9:17 pm

    This prize is made of awesome! Fatty, how do you do it? One amazing thing after another. You’re a superhero, aren’t you?

    And mad props to the FC folks who kicked in their frequent flyer miles!

  14. Comment by David in Sydney | 07.6.2009 | 9:22 pm

    Off topic a bit, but I just saw that Jill Homer has finished the Tour Divide in 24 days and 7 hours, over 4 days in front of the previous womens record.

    Well done Jill.

  15. Comment by buckythedonkey | 07.7.2009 | 3:10 am

    What an extraordinary prize. That is a beautiful part of Italy. Get spending!

    A big hand to Jill the Giant too! ;-)


  16. Comment by Tejvan Pettinger | 07.7.2009 | 5:49 am

    Good post. I’ve enjoyed cycling in Italy in the past, they tend to be more considerate to cyclists than here in England

  17. Comment by Jeff L. | 07.7.2009 | 5:07 pm

    Nice. I’m down for $25. If you pick my ticket, I’ll take Fatty along as my guest….well, actually, my wife might have something to say about that. You guys can arm wrestle for it.


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