Italy: Tuscany – Cycling & Italian Culture Tour

Join CCSD  in Tuscany, Italy for the trip of a lifetime
Cycle some of the most beautiful roads in Europe in the hills around Florence and Siena, with first class support from CCSD.  Stay in our beautiful hotels , overlooking the City of Florence and just outside the walls of Siena.  After the day’s cycling prepare to be amazed by the historical wonders these fantastic cities have to offer, or simply relax and soak up the best of Italian culture with a gelato, espresso or a Chianti on the piazza. We also offer an full itinerary for non cyclists so you can enjoy the trip with a non cycling partner.

Spring 2016 (10 days, 9 nights).  $4,200*

*Based on double occupancy. Single occupancy $500 – $1000 (dependent on room type chosen – please contact us for details).   Price includes tours and trips for non cyclists or for cyclists choosing to take a day off the bike.


Starting in the Etruscan town of Fiesole, just outside Florence you’ll spend 4 nights at our wonderful hotel, in this historic walled town in the hills overlooking the city.  Cycle 30 – 50 miles each day on some of the most beautiful roads in Italy through the stunning Tuscan countryside to medieval towns and ancient hill top convents.  Take part in an Italian cooking class with our local chef Marcella, or relax with a glass of wine and enjoy the views.  For non cyclists or those with a love of history, Florence does not disappoint.  We arrange visits to the world famous Accademia gallery (home of works of art such as Michelangelo’s David); the Duomo, the Uffizi gallery or fully guided city tours if you want a day off the bike.

On day 5 you will travel the famous Chianti road by bike or CCSD vehicle, all stopping in Greve for a vineyard picnic lunch, before arriving at our next destination; the medieval walled city of Siena, the center of which is a UNESCO World Heritage site.  This ancient city sits among the rolling hills of Southern Tuscany and offers its visitors a variety of historical sites, bustling piazzas and cafés, in addition to beautiful countryside and enchanting hilltop towns to discover during the next 3 days.

For the last 2 days we return to Fiesole to allow you some time to relax and explore anything you missed in Florence at the start of the tour.



  • Accommodation in our 2 beautiful hotels in prime locations in Fiesole (Florence) and Siena
  • Daily substantial continental breakfasts
  • 5 group dinners with wine
  • Vineyard picnic lunch in Greve
  • Olive oil, vineyard tour and picnic lunch at Sagrona
  • Itinerary for non cycling partners including guided tours of the cities.  Our carefully planned itineraries make sure that cyclists and non cyclists can enjoy a trip together and meet up at key points during the day.
  • Snacks and light lunch items in the support vehicle
  • Participation in an Italian cooking class in Florence
  • CCSD guide to the region
  • CCSD language guide
  • All transfers between Florence airport and hotel
  • Luggage handling, bike box storage / transportation
  • Tourist taxes and fees
  • Assistance with bike assembly / packing
  • Bike rental arranged if necessary (rental extra charge)
  • Daily GPS files
  • Fully guided and supported rides with CCSD qualified coaches
  • CCSD support vehicle and mechanical support
  • All energy drink, light snacks on the road and sports nutrition
  • 25% discount code for CCSD coaching in advance of the trip


  • Airfare
  • Some evening dinners
  • Any lunches not highlighted in the itinerary (although light lunch items are usually in the support vehicle)
  • Bikes (rental bikes available for extra charge)
  • Personal services, including laundry, telephone, hotel minibar charges, etc.
  • Travel insurance (we strongly advise that all participants have travel insurance to cover the cost of unexpected cancellations.  Example)
  • Personal tips to guides, motor coach drivers or porters



Day 1, Fiesole, Tuscany
Arrive in Florence, Italy and arranged transfers to our hotel in the fantastic historic town of Fiesole, in the hills overlooking the City of Florence. We will take time to help you build and test bikes or rental bikes will be picked up and fitted. In the evening we all meet for pre dinner drinks before a trip briefing and group dinner at a local restaurant.

Day 2,  Fiesole and Monte Senario Convent
Ride 30 or 50 miles in the hills overlooking Florence, up to the ancient Monte Senario Convent then experience a true taste of Italy with a stop for lunch at a old local grocery store in Caselline, serving up hunks of bread, slabs of cheese and meats, accompanied by an espresso.  Non cyclists are also given the opportunity to visit the Monte Senario Convent and hike in the surrounding area, then join cyclists for lunch.

In the evening we meet for a group dinner where you sample 4 delicious courses of local cuisine with wine pairings.

Day 3, Hills of Florence and Cooking Class
A 40 – 55 mile ride to enjoy the breathtaking views of the rolling hills, farms, vineyards and olive groves around the North East of Florence.    Non cyclists have the chance to explore Florence and take part in a half day guided tour of the City, including visiting the church of Santa Maria Novella, the Basilica of Medicis, San Lorenzo, the famous market of San Lorenzo, the Cathedral, the Baptistery, the Giotto’s belltower, the Palazzo Vecchio, Piazza della Signoria and the Old Bridge: Ponte Vecchio.

In the afternoon we all head into Florence to learn the secrets to making traditional Italian gnocchi and other local dishes in our cooking class with chef Marcella Ansaldo.  After sampling our dishes Marcella recommends some of her favorite restaurants for dinner.

Day 4, San Godenzo and Borgo San Lorenzo
A 40 – 70-mile ride touching on the towns to the northeast of Florence. We stop briefly in the historic, Etruscan towns of Borgo San Lorenzo and San Godenzo to view some of the sacred buildings of great artistic interest dotted around, before heading to the ancient 13th century town of Dicomano.   A beautiful ride with stunning mountain views and quiet country roads.  For those wanting an easier day, a shorter cycling route is available and our CCSD vehicles will be out on the road to support you.

The itinerary for non cyclists will depend on the number signing up for the trip but may include private guided tours of the area, wine tasting or hiking in the nearby countryside, before meeting the cycling group in Dicomano for lunch.

Day 5,  Siena, Tuscany
Transfer from Florence to Siena, Tuscany.
A 60 mile scenic and challenging ride for cyclists, or a picturesque drive for non cyclists from Florence to Siena on the infamous Chianti road.  On the way we stop for a splendid picnic lunch at a vineyard with a panoramic terrace overlooking the Greve valley, then continue toward Siena through the towns of Panzano, Castellina and the hilltop town of Montifioralle. We cruise downhill to our hotel just outside the ancient city walls to finish an exciting day in the saddle by relaxing in the tranquil garden at our hotel before heading into Siena to a restaurant hidden in the winding cobbled streets of Siena.

Day 6, Siena or Strada Bianchi
For those wanting a well deserved rest there is the option to tour the historic, walled city of Siena with our local guide, a retired history teacher who was born and raised there. Afterwards, discover the local cuisine and wine or relax in the Piazza and watch the world go by.

If you really can’t stay away from the bike there is the option to ride the lightly traveled but infamous Strada Bianchi (white roads) of the well-known one-day professional cycling classic race, L’Eroica.

Day 7,  Monteriggioni and San Gimignano
A 30 – 60 mile ride into the Tuscan countryside northwest of Siena. Ride to the walled hilltop fortress towns of Monteriggioni and Colle di Val d’Elsa, then onto San Gimignano where you’ll have the opportunity to leave the bikes, wander the town and enjoy a leisurely lunch.  Non cyclists will also be taken to San Gimignano for a tour of the town, a perfect opportunity to meet during the day for a relaxed lunch.

In the evening we meet in the garden of our wonderful hotel, overlooking the Tuscan hills,  and as the sun sets we share food, wine and stories from the road.

Day 8, Vineyards, Olive Oil Tasting and Picnic
Return to the Florence area by bike, exploring new roads on the return journey, with a stop at a small family vineyard and olive oil producer to see them at work and taste their produce and enjoy a picnic lunch overlooking the olive groves.

In the evening we dine at a restaurant in the historic quarter of Florence before indulging in a chocolate lovers dream: a delicious dessert and wine bar, specializing in all things chocolate who serve their cappuccinos with edible chocolate spoons and have cakes designed by the world Champion of pastries.

Day 9, Fiesole, Tuscany
A final day in the Florence area.  Tours can be arranged to one of the world famous galleries such as the Uffizi, Accademia Gallery, or the Duomo if you wish.   You can simply relax and explore the city, or join us for a final ride in the Italian hills.


Day 10, Florence, Tuscany
After breakfast transfers are arranged to Florence International Airport for those returning home.

*Illustrative Itinerary. Full confirmed itinerary to be provided upon registration


Florence Airport (Peretola Airport)


Rides are designed to offer shorter and longer options of between 30 and 75 miles. Most days will involve climbing to some degree in the rolling hills around Florence and Siena. Structured training / professional coaching is available for those that want it during the tour and for those wanting a coaching package in advance of the trip CCSD can offer participants a 25% discount.  Coaching packages are HERE.


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