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 perfectly located hotels right in the heart of the cultural centers of the cities and after the day’s cycling prepare to be amazed by the historical wonders they 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 itinerary for non cyclists so you can enjoy the trip with a non cycling partner.

Next CCSD trip in 2015.  Please email us if you would like a custom version of this trip for you and a group of friends.


Starting in Florence, the birthplace of the Renaissance, you’ll spend 4 nights at our wonderful hotel, moments from the Ponte Vecchio and right in the heart of the historical center of this magnificent city.  Cycle 30 – 50 miles each day on some of the most beautiful roads in Italy, many of which will be the routes later in the year for the World Road Championships.  Cycle 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 in the tower top bar with its 360 degree view of Florence.  For non cyclists or those with a love of history, Florence does not disappoint.  We arrange visits to the world famous Accademia gallery (home 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 Florence to allow you some time to relax and explore anything you missed out on at the start of the tour.



  • Accommodation in our beautiful hotels in prime locations in 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 planning for non cycling partners – all location have an abundance of non cycling activities which we organize for you, tailored to your interests.
  • 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
  • Formal group lunches
  • Bikes (rental bikes available for extra charge)
  • Personal services, including laundry, telephone, hotel minibar charges, etc.
  • Travel insurance
  • Personal tips to guides, motor coach drivers or porters


Day 1, Florence, Tuscany
Arrive in Florence, Italy and arranged transfers to our hotel right in the center 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 dinner at a local restaurant.

Day 2,  Florence, Tuscany
A 35-mile ride to Fiesole, the nearby hillside town with a magnificent view of Florence. Stop for coffee with the locals at the café on the piazza then continue on to the ancient Monte Senario Convent. 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 Fiesole for walking tour of the town.

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

Day 3, Florence, Tuscany
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.

In the afternoon we 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, Florence, Tuscany
A 40 – 70-mile ride touching on the towns of the San Godenzo northeast of Florence. We stop briefly in the historic, Etruscan town of Borgo San Lorenzo 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.  For the non cyclists there are so many activities we can’t possibly list them, but rest assured we will arrange something perfect for you which matches your interests or hobbies.

In the evening you’re free to explore as you wish but we will let you into our secret: the location of the best gelato in the whole of Florence!

Day 5,  Siena, Tuscany
Transfer from Florence to Siena, Tuscany.
A 55 mile scenic and challenging ride 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, Tuscany
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,  Siena, Tuscany
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, Florence, Tuscany
Return to Florence 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, Florence, Tuscany
A final day in Florence.  Tours can be arranged to one of the world famous galleries such as the Uffizi, Accademia Gallery, or the Duomo if you wish.   Or you can simply relax and explore the city as you wish.

In the evening we meet for our final group dinner at a wonderful restaurant to enjoy a sumptuous 4 course meal with wine pairings.

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, Tuscany, Italy 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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