ITALY'S COAST TO COAST

25 September – 2 October

€1649 | £1449 | $1899*

Deposit €299

Bring a non-cycling companion for €699

To stay for a shorter or longer amount of time, please contact us

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AN INCREDIBLE CYCLING EXPERINCE

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.

What's included

  • 7 Nights in stunning typical Tuscan rural hotels
  • 6 Spectacular days of gravel cycling
  • 7 Buffet breakfast at the hotels
  • Airport transfers including bike and luggage transfers at the below details. Private transfers can be also organised at a supplement.
  • Ground transportation to evening restaurants
  • Every day guided cycling routes by our ex pro, experienced and friendly guides.
  • Every day full Pro Experience with van feeding zones with snack & water on route
  • Pro tips by our ex pro staffs
  • GPX files sent in advance

What's not included

  • Flights
  • Dinners – organised with a few great restaurants in the area
  • Single room limited availability at €60/night
  • Bike rental from €290 for 6 days depending on specs
  • Travel insurance
  • Massages
​Airport Transfers: Day 8 – San Pellegrino & Fedaia

Inbound
25/09

14:30 pm from PSA (Pisa Airport)

Outbound
02/10
10:30 am from Hotel to BLQ (Bologna Airport) / 3hrs transfer

TRIP AT GLANCE

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

PREVIOUS TRIPS GALLERY

DAY TO DAY BREAKDOWN

GPX files will be sent before the trip.

ARRIVAL DAY

After the airport pick up, we head straight to dinner in the town of Viareggio for our first Italian Meal.
After dinner, setting up the bikes for the next day, when the gravel adventure begins!

VIAREGGIO - PECCIOLI
85km | 700mt

Starting from the beautiful costal town of Viareggio, we soon head inland and make out first stop in Pisa, by the leaning tower.
After grabbing some lunch, the road starts to go up and down, we enter the Tuscan countryside and finish the day in the beautiful town of Peccioli where views of the rolling hills are spectaculars.

PECCIOLI - SIENA
65km | 1100mt

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.

SIENA - MONTEPULCIANO
70km | 1200mt

A word to describe today’s route is: magnificent.
Possible one of your most beautiful day ever on the bike.
You will be going through he most beautiful countryside that you can imagine, even more as you are getting close to Pienza and continuing on to Montepulciano where we you can sit back and relax with some good food and wine for dinner.

MONTEPULCIANO - ASSISI
86km | 730mt

Today’ we cross into Umbria few km after starting off from Montepulciano.
25km into the ride you will be riding on the side of the Lake Tresimeno.
You’ll ride past olive groves, sunflower fields, vineyards, and tranquil lakeside villages.
We finish today’s ride in Assisi (birthplace of St. Francis of Assisi, patron saint of Italy and founder of the Franciscan order) , a town that combines rich spiritual history with stunning medieval architecture and unforgettable views.

ASSISI - CAMERINO
66km | 950mt

You’ll start the day leaving Assisi, descending gently into the Umbrian valley before turning northeast toward the Apennine foothills. The route weaves through peaceful countryside, olive groves, and quiet hill towns, gradually gaining elevation as you approach the border between Umbria and Marche. Expect a series of rolling climbs and descents in the first half, followed by one or two longer climbs as you near Camerino. The final stretch into Camerino includes a steady uphill—a real finish-line feeling as you arrive in this hilltop gem.

CAMERINO - SAN BENEDETTO DEL TRONTO
111km | 200mt

The longest day, but also the easiest from an elevation point of view.

The ride from Camerino to San Benedetto del Tronto is a perfect final stage. It’s a classic “mountains to sea” experience—starting in the Apennines and descending through rolling hills and villages before finishing at the beach.

The final stretch is flatter and faster cruising into San Benedetto del Tronto, one of the most bike-friendly towns on the Adriatic coast.
Here we can celebrate the last night together and achieving the Coast to Coast!

LEAVING DAY

After a delicious breakfast. We set off in the van for the airport transfer to BLQ Airport (Bologna).
See you next time 🙂

ACCOMODATION

We have selected the best locations and hotels with bike facilities to ensure that our customers have the best experience possible

BIKE RENTAL

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

START & FFRAMESET ​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

DO YOU WANT TO CUSTOMISE YOUR TOUR?

Build your tour with us. Choose your dates, location, distances and much more.

MORE INFORMATION

YOUR TOUR GUIDE

Professionals, with many years of experience.

MATTEO CIGALA

Founder & Head Coach

Since founding Cigala Cycling Travel 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.

AMEDEO TABINI

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.

MARINE LENEHAN

Tour Guide, Nutritionist, Massage Therapist & Yoga Teacher

Current European Champion Gran Fondo Women, Marine has a vast knowledge in cycling as well as individuals wellness.
She is a qualified sports nutritionist, massage therapist & yoga teacher.

READ OUR TESTIMONIALS - WHAT PEOPLE SAY ABOUT CIGALA CYCLING TOURS

ITALY'S COAST TO COAST

25 September - 2 October 2026

BOOK NOW