• Dates: 05/05/2024 - 12/05/2024
  • Tour length: 8 Days, 7 Nights
  • Start / End: Pisa Airport
  • Terrain: Gravel and asphalt road mix. Rolling hills and steep climbs
  • Price Per Guest:


    $800 Single Occupancy Supplement

    10% Discount for returning guests

    Gravel bike rentals- contact Willie for pricing

    You also have the option to bring your own bike

    **Registration and $1,000 per person Deposit by February 1, 2024**



  • Non-Cycling Guest: $4,700
  • Book Now

The first 4 days of this tour will take us to the Val d’Orcia where we will ride the White Roads or Strade Bianche famous for the World Tour race Strade Bianche and L’Eroica. We will pedal near or through the famous hill towns of Montalcino, Pienza and San Quirco d’Orcia.

Our rides through the forests and rolling grasslands of this magical area, a UNESCO World Heritage site, will be an experience to be remembered. The challenge of riding on these gravel roads will be complimented with delicious meals and fine wines. The local cuisine will be paired with Vino Nobile di Montepulciano and Brunello di Montalcino wines.

Our accommodations will be at Villa Liberty, a historic Renaissance Villa in San Quirico d’Orcia, one of the most beautiful and charming medieval towns of the Orcia Valley located to the south of Siena.

On day five we will visit the beautiful medieval city of Siena and later that day transfer to Castello La Leccia.

Our rides will take us along the gravel roads of the Chianti region with vineyards of the Sangiovese grapes that are used to make the Chianti Classico and Chianti riserva wines. These beautiful roads are also used in the Strade Bianche race and L’Eroica dotted by medieval castles in a stunning countryside.

We will enjoy the hospitality at Castello la Leccia, intimate hideway in Tuscany. A wine retreat, between Siena and Florence. A luxury vineyard accomodation in Castellina in Chianti designed to benefit your mind and body. The castle from the year 1077 is totally new renovated.

Castello La Leccia includes twelve elegant bedrooms in the castle in three different categories, ranging 21 to 55 m² in size, and five bedrooms in our dependence which all enjoy splendid views over the surrounding countryside. Elegantly furnished, the rooms have been designed to render your stay intimate and comfortable. Wooden floors, beamed ceilings, pastel colors, precious fabrics and furniture designed by a Florentine artisan chosen exclusively for these rooms, create a warm and sophisticated atmosphere.

All in all, this will be a fantastic experience!

Food & Wine

Tuscany, like all the regions for Italy, is known for its exquisite food and wine. Below are some examples of the foods and wines we will enjoy on the tour.

FOOD: Olive Oil, Pecorino Cheese, Pici Pasta, Black and White Truffles, Cinghiale (wild boar), Cinta Sinese Pork, Seafood, Rabbit, Chianina Beef, Organic Produce, Salumi

WINE: Vino Nobile di Montalcino, Brunello di Montalcino, Chianti, Rosso di Montalcino, Sangiovese, Morellino di Scansano, Super Tuscans, Vernaccia, Chardonnay, Sauvignon Blanc, Vin Santo


Marco Saligari

Marco Saligari

Former Professional Cyclist

Marco has an impressive resume including stage victories in the 1992, 1993, and 1994 Giro d’Italia and overall winner of the 1993 Tour de Suisse. He has also been Directeur Sportif of Team Landbouwkrediet-Colnago and Team Crelan-Euphony from 2002 to 2013. Marco has been a race commentator of the Giro d’Italia for Gazzetta Dello Sport Radio, Eurosport Television, and has had his own show, The Coach, on the Bike Channel. Marco is currently a commentator for the Italian network RAI Sports for several races including the Giro d’Italia, Tour de France and Strade Bianche to name a few. He was part of the RAI 2020 Tokyo Olympics commentary team for the cycling events.  He is affectionately know as Il Commissario. In addition to all of his accomplishments in the world of professional cycling, Marco is a great guy with a beautiful family. We are honored to collaborate with Marco. He brings a slice of cycling history to share with our guests.

Marco is married to Lela and they have two children, Martina and Giacomo.


Daniele Righi

Daniele Righi

Cycling Guide

Daniele started bicycle racing at 8 years old and turned professional at age 24. He competed in the Junior category for various teams and secured several victories. His professional cycling career started with Alexia and after 3 years he participated in his first Giro d’Italia where his teammate Paolo Savoldelli won the tour. For the next 10 years, he rode with Lampre and was part of the team that participated in Michele Scarponi’s victory of the 2011 Giro d’Italia.

He has always played a support role for Lampre and participated in five Giro d’Italia, five Tour de France, four La Vuelta a Espana, Tour of Flanders, Amstel Gold, Coppi e Bartali, and the Tour of Poland. In the 2004 Giro d’Italia, he won the Piaggio Trophy for the most miles cycled by any participant that year. Literally, he has cycled almost all over the world in most of the races of the World Tour. In 2013, he retired from Lampre as a rider and subsequently was a Director Sportive with with UAE Team Emirates.

Daniele is married to Francesca and they have two children, Chiara and Alessandro.


Willie Joffroy

Willie Joffroy

Founder & President

I combine nearly 30 years of experience in international logistics planning with a quarter-century of cycling experience in Italy. My expertise allows Willie’s World Cycling to offer some of the finest cycling tour experiences in Italy. From the choice of simple elegance and intimacy in accommodations, to the delectable regional cuisine of carefully chosen local chefs, (we) my wife Margarita and I impart international style and pay careful attention to detail.

I accompany every Willie’s World Cycling tour, sharing the extensive knowledge I have gleaned from 25 years of cycling in Italy. This storehouse of information includes: Italy’s premier cycling regions, scenic wine-growing regions and small wineries, unique and private accommodations, and fine regional cuisine.

Prior to establishing Willie’s World Cycling, I spent 29 years in cross-border logistics services along the U.S.-Mexico border. Throughout my business career, I have focused on providing my clients with the very best in professional and personalized service. I have instilled this commitment to the client into the values of Willie’s World Cycling.

I have been an avid cyclist for more than 35 years and regularly start my day cycling up and down Mount Lemmon, a 6,800-foot climb from my home in Tucson, Arizona. Fluent in English, Spanish, and Italian, I have a great passion for the cycling, food, and wine unique to Italy, and take great pleasure in sharing that passion. I am a believer in the health benefits that flow from regular exercise such as cycling, fresh and wholesome local food, and fine wine. A consummate host, I make certain that each of my cycling tours inspires treasured memories.




  • Day 1:

    Sunday, May 5,
    Benvenuti in Italia! We will pick you up at 9:00am at Pisa Airport and transfer to our hotel. After check in we will enjoy a light lunch and put our cycling kits on after lunch. Final adjustments to the bikes and do a short shakedown ride from San Quirico d'Orcia to Pienza and loop back to San Quirico d'Orcia. Distance 25.77km and 438m elevation gain. Dinner in San Quirico d'Orcia.

  • Day 2:

    Monday, May 6,
    After breakfast we will ride from San Quirico d'Orcio to Buonconvento, Torrenieri and back to San Quirico d'Orcia. Distance 70.33 km and 1,285m elevation gain. Lunch on the road and dinner in San Quirico d'Orcia.

  • Day 3:

    Tuesday, May 7,
    After breakfast we will ride from San Quirico d'Orcia to Celamonti, Pienza and back to San Quirico d'Orcia. Lunch in San Quirico d'Orcia. After lunch we will visit Ciacci Piccolomini d'Aragona winery followed by dinner in Montalcino.

  • Day 4:

    Wednesday, May 8,
    After breakfast we will ride from San Quirico d'Orcia to Castelnuovo dell'Abbate, Sant'Angelo in Colle, Poggio Antico, Castiglion del Bosco,Torrenieri and back to San Quirico d'Orcia. Distance 72.66km and 1,583m elevation gain. Lunch on the road and dinner in San Quirico d'Orcia.

  • Day 5:

    Thursday, May 9,
    After breakfast we will visit the historic city of Siena. After lunch we will transfer to Castello La Leccia. Dinner will be at Castello La Leccia.

  • Day 6:

    Friday, May 10,
    After breakfast we will ride from La Leccia - Quercegrossa - Vagliagli - Castello Brolio - Pianella - Vagliagli - Castellina in Chianti - La Leccia. Distance 69.95km and 1,429m elevation gain. Lunch on the road and dinner at a restaurant.

  • Day 7:

    Saturday, May 11,
    After breakfast we will ride from La Leccia - Castellina in Chianti - Radda in Chianti - Volpaia - Panzano in Chianti - La Piazza - Madonna di Pietracupa - Castellina in Chianti - La Leccia. Distance 56.23 km and 1,367 elevation gain Lunch on the road and dinner at a restaurant.

  • Day 8:

    Sunday, May 12,
    After breakfast transfer to Pisa Airport. Please schedule return flight after May 12, 2024. If you need special arrangements please advise us in advance.


  • Included:
    4 to 5 cycling guides and van support
    Lodging 7 nights
    All breakfasts
    All lunches
    All dinners
    Wine pairings with dinners
    Wine tastings as part of the tour
    Cooking Class for non-cyclists if requested at least 6 weeks before the tour
    Cycling kit (jersey and shorts)
    Energy bars and water on bike rides
    Cycling guide, driver, and mechanic services
    Tips for cycling guides

    Not included:
    Gravel Bike Rentals- contact Willie for pricing
    Non-tour hotels
    Any rental car or train service you may use outside of tour activities.
    Any purchases of a personal nature including bar and hotel mini-bar.
    Any incidental expenses associated with non-cycling activities, such as cost of guide, museum entry fees, spa services, archaeological site entry fees, etc.
    Laundry service at hotel
    Post ride massage if available

    Please see instructions below for payment by check. Please contact us for Wire Transfer instructions & ZELLE account notification . We do not accept payment by PayPal.
    Credit card payments will have an additional 3% fee for USA transactions and a 4.5% fee for international transactions.

    Payment Instructions:

    Willie’s World Cycling prefers payment by check payable to:

    Willie’s World Cycling LLC

    4231 E. Pontatoc Canyon Dr.

    Tucson, Arizona 85718

    A *non-refundable deposit is required in the amount of $1,000 with the balance to be paid in full 60 days before the start date of the tour unless otherwise noted. Tour prices are based on double occupancy per cyclist or non-cyclist. A single occupancy supplement may apply to those traveling alone and requesting their own room. Please make checks payable to Willie’s World Cycling or pay via wire transfer. If your party includes a non-cyclist, please notify us when you register and submit your deposit so we can begin planning stimulating and rewarding activities while cyclists are on the road.

    Our prices are in U.S. Dollars and are based on exchange rates in effect at the time of publication. While we make every effort to avoid adding surcharges, Willie’s World Cycling reserves the right to do so should the U.S. Dollar lose substantial value against the Euro.

    After your deposit is received, you will be sent more information regarding the sizing for your bicycle, liability waiver, and general information that will be helpful for your visit to Italy.

    We recommend obtaining travel or trip cancellation insurance. Please speak to your travel agent for further assistance.

    Willie’s World Cycling reserves the right to cancel any tour prior to departure for any reason. We will refund any payment received by Willie’s World Cycling which will constitute full settlement.

    Although we make every effort to contract the very best in outside services, we do not guarantee services provided by third parties.

    Please make sure you have a valid passport.

    We count on our clients to ensure they are healthy and adequately fit for this tour. This tour is rated Activity Level C Challenging.

    *Cancellation Policy:
    Deposits are non-refundable if a guest cancels. If the guest signs up for a tour during the year of the cancelled tour or the following year then the deposit will be credited to the tour. After 1 full year the deposit is forfeited to Willie's World Cycling. Final payments are not refundable. Exceptions to this policy will be considered in cases of illness or family emergency

    45 Days or less: Cancellation charge of 100% of the total cost of the tour

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