24 September – 1 October 2027
Deposit €299
Bring a non-cycling companion for €1299
To stay for a shorter or longer amount of time, please contact us
From coast to coast through the heart of Italy: this road bike tour takes you on a truly unique ride, from the blue waters of the Tyrrhenian Sea to the golden shores of the Adriatic.
You’ll pedal through some of Italy’s most breathtaking and diverse landscapes—rolling hills covered in vineyards, the dramatic climbs of the Apennine Mountains, and quiet, winding roads leading to hidden medieval villages untouched by time.
Each day offers new scenery, new flavors, and new challenges to enjoy. In just 6 unforgettable riding days, you’ll cross three iconic regions—Tuscany, Umbria, and Marche—each rich with history, culture, and culinary traditions.
Along the way, you’ll experience warm hospitality, local wines, authentic cuisine, and stays in charming, cyclist-friendly accommodations.
This is more than a cycling tour—it’s a deep dive into the soul of Italy, seen from the saddle. Whether you’re chasing performance or just the perfect cappuccino stop with a view, this journey delivers it all.
Airport Transfers:
Inbound
25/09
14:30 pm from PSA (Pisa Airport)
START & FINISH LOCATION: Viareggio to San Benedetto Del Tronto
DAYS RIDING: 6 days
TOTAL DISTANCE 450 km approx
GROUP SIZE: 7 to 14 max (there will be two groups each day based on the fitness level)
LEVEL Intermediate & Expert
LONGEST DAY: Day 5 – Pienza to Marina di Grosseto
On today’s route we by stunning medieval town of San Giminiano and Monteriggioni.
The route is up and down through medieval villages, and stunning contryside, where everywhere you look, is a postcard!
We finish off the day in the famous Piazza Del Campo in Siena.
We have selected the best locations and hotels with bike facilities to ensure that our customers have the best experience possible
There are many options available, depending on your measures and budget we work with you to find the best bike for you. From standard mechanical groupset and alloy wheels to electric shifting and carbon wheels.
Road E-bikes are also available.
START & FRAMESET: Guerciotti, Wilier, De Rosa, Bianchi, Ktm
GRUPPO: Sram Rival/Force AXS, Shimano 105, Ultegra, Durace Di2 and Mechnical
PEDALS: Bring your own
SADDLE: Selle Itala
WHEELSET: Alloy, Carbon
Professionals, with many years of experience.
Founder & Head Coach
Since founding Cigala Cycling Tours in 2015, Matteo has been leading over 10 tours per year. A former pro and current amateur racer, Matteo is the 2022 European Champion Gran Fondo.
Tour Guide Leader
A former pro cyclist, Amedeo is a cycling tour guide for a decade. It is one of the most experience guides that you will ever find, counting almost over 1000 days on tours.
Finally, Amedeo is a qualified massage therapist.
Tour Guide, Nutritionist, Massage Therapist & Yoga Teacher
You’re welcome to bring your own bike, or rent one for the week. After booking, you will receive a form to fill out via email. You can let us know there and in the case you want to rent, you will see an option to fill up details for your measurements.
This trip is best suited to Intermediate and Expert riders. The route features rolling terrain with several challenging climbs each day, so a good level of fitness and previous cycling experience are required.
Yes every day a support vehicle will be following the group. The vehicle will carry suitcaseses from point A to B as well as food and snack for each ride.
Yes, a single room supplement is available.
You don’t need to ride every day. If you feel tired just let your guide know and you can just go in the van.
The climbs on the Italy’s Coast to Coast are not the Alps or the Dolomites. Generally anything from 3-6km in length and 5-8% avg gradient.
If you want to enjoy the trip without feeling too tired each day, is a good idea to put some training for it and arrive with some good level of preparatio. If you’d like a structured plan built around this trip, visit our cycling coaching page and Matteo can help you put together a plan based on your current level and the time you have before you travel.
Beyond your usual riding kit, bring layers and some rain gear, just in case. You can leave it in the van each day and you might don’t need it, but best to have it. Our full guide to packing for a European cycling holiday covers everything else you’ll need for the week.
