FAQs
Toscana
Via I Maggio, 27
Pienza (SI)
Website

ABSTRACT

Cicloposse Bike Tour was founded in 1994 in the heart of Tuscany by a passionate cycling couple. Based in the charming hill town of Pienza, our dream has always been to share the beauty of this corner of Tuscany with cycling enthusiasts from around the globe. We specialise in crafting unforgettable memories and once-in-a-lifetime journeys on two wheels.

Our range of biking holidays caters to every preference, from fully guided escorted tours to self-guided adventures, and even short cycling experiences or bike rental services. Our guided tours can be personalised for private groups, while our self-guided tours offer flexibility and customization.
As proud owners of our own fleet of bikes, we maintain strict quality control to ensure that every rider enjoys a great experience. Our collection includes carbon frame road bikes & gravel bikes, powerful e-bikes, and lightweight hybrid bikes.
We have personally selected the best regions and routes for cycling exploration, showcasing scenic and peaceful roads, rich history and art, exquisite food and wine, and charming accommodations.

Our signature trips include the ultimate Cycling & Cooking Adventure, an immersive experience focused on food & wine. Guests stay at a Tuscan charming villa where they can enjoy cooking lessons and discover local cuisine.
At Cicloposse Bike Tour, we are dedicated to provide unparalleled cycling experiences that immerse our guests in the essence of Tuscany’s cultural and natural treasures.

TOURS

The Bella Italia collection features SELF-GUIDED bike tours with overnight stays in 3-4 star accommodations, baggage transfers and several signature experiences designed to engage you with the local culture. All tours are fully customizable with the option to add a guide, van support, or additional experiences; upgrade accommodations; or extend your stay.

Tuscany
 Short Escape Tuscany
Explore Tuscany’s scenic hills, hill towns, vineyards, and olive groves on this 5-day bike tour. Enjoy rigorous rides, local wines, art, and relaxing Tuscan retreats….
Tuscany
“Under the Tuscan Sun” from Cortona to Siena
Cycle from Cortona to Siena through Tuscany’s stunning landscapes, medieval villages, and historic vineyards for an unforgettable journey through Italy’s heart….
Tuscany
Tuscany Wine & Gravel Bike Tour
Get ready to immerse yourself in the essence of Tuscany on our ultimate Wine Gravel Tuscany Tour….

FEED

Dan G.
One of the greatest trips my wife and I have ever taken. We loved the area of Italy we were in, the wine experiences, the cooking and dining. But most of all we loved the family that operated the company. It’s very small and “grassroots” feeling, like you’re getting the true local experience as opposed to something you’d get with a big tour company. I’d highly recommend this biking / cooking experience!
2024
Ruth B.
This local company knows all the routes, period hotels, and local restaurants. The equipment and logistics are superb and well orchestrated. They are very responsive before and during the trip. This is our 2nd time touring with Cicloposse. We came back because the first time was a great experience. The gravel tour following l'Eroica is very special.
2024
K Jospe
Everything was beautifully organised! I loved the special attention to the descriptions in the booklets, the variety in the rides. I was thrilled with the bicycle (e-bike) provided and appreciated the concern to match bicycles and needs, including options for those wanting to do longer rides. The hotel accommodations were incredible — far surpassed anything I might have imagined, as were the meals. I think all of our group appreciated the care to recommend restaurants offering local specialties. What a treat to discover places in Umbria we did not know, although we have been to Umbria and Tuscany several times. I am left with a wonderful sense of getting to know something “real” about Italy — not just a “tourist version”.
2024
Patricia R.
We chose CicloPosse’s Southern Tuscany tour for our first e-bike trip and we loved it! This trip featured 2 or 3 nights in each town. We loved the hotels and the routes were beautiful. There were many cyclists and walkers on the routes and at the hotels . We were two couples in our 60’s and we felt so young with our extra power up the hills. We did the trip in early June, a gorgeous time of year. Everyone at CicloPosse was friendly and accommodating. We asked for old school turn by turn directions and found them flawless. We give this company and area 5 stars!!
2024
Carolyn H.
This was a fabulous experience in every sense - majestic 13th century towns, incredible vistas, wonderful caring guides, amazing farmhouse accommodation, a world class chef, a genuine family with local knowledge and a generous spirit wanting you to feel and live the Tuscan way. We felt like we had the privilege to be brought into their world and didn’t want to leave. The cycling was outstanding and cooking lessons encouraging and informative - I highly recommend you do this!
2024