Timeless Tuscany
Classic
From the Pisan Hills to the Umbrian border: Through Chianti, Crete Senesi, Val d’Orcia and Maremma.
Over 15 years ago I said “yes” to racing for a small Lucca-based cycling team. I discovered the spellbinding beauty of the Tuscan countryside and an infinite selection of roads. A whimsical decision turned to an obsessive pursuit of deep subject matter expertise. 150,000 kilometers and an established vocation later, I present you with my version of how you ought to pedal la Toscana.
Duration
Group Limit
8 days / 7 nights
Up to 12 guests
Start Location
Finish Location
Palaia
Città della Pieve
Total Distance
Total Elevation
570 km
11,550 meters
What Past Guests Say
"It was a trip of a lifetime."
Stephanie and Klaus
The Land of Cycling Greats
Our 570-kilometer route traverses the heart and fringe of central and southern Tuscany, with the Cima Coppi at 940 meters. Following the tire tracks of pro cycling legends, from Gino Bartoli to Strade Bianche victors, you’ll be in the presence of a long-standing cycling legacy and its associated greatness. It’s here, immersed in Toscana’s iconic landscapes and painting-like vistas, that evoke a sense of wonder and bring you home to your happy place.
Heartfelt Smiles and Warm Welcomes
Life is good here in Tuscany: The food is the best and the people are wonderful. Think of hours pedaling winding country roads, post-ride gelatos in nearby piazzas and leisurely afternoons sipping Campari Spritz.
It’s the land of space, silence, time and freedom — to think, to let your mind wander and to dream. It’s the place to let the unbound natural beauty lift you up and take you to another realm.
The Gift of Good Company
We always encourage solo missions and quests inward, yet often our greatest learnings are in the company of others: old and new friends. So how about you come along and sink deeper in love with Tuscany and deeper in love with life?
Day to Day Itinerary
Trip Inclusions
We design our trips to unfold like a symphony where everything is handled confidently by our kindhearted and knowledgeable team. As a small Tuscan-based company with fewer than 150 guests annually, we consider you family, not a reservation number.
- Accommodations at three- and four-star hotels
- One wine-tasting and one group aperitivo
- Two expert on-road guides
- Top-level mechanic and daily bike maintenance
- Ride food and en route lunches provided by our performance chef
- Support vehicle stocked with ride food, water and spare parts
- Daily dinners with drinks
- Bi-weekly laundry service for cycling clothing
- Ride With GPS event access and detailed routing
- Daily luggage transfer
- Vetted and scouted trip design
- Airfare
- Bike rental
- GPS navigation device
- Trip cancellation and travel protection
- Gratuities for the trip team (see FAQ)
- Beverages ordered beyond normal amounts
- Credit card processing fees (see FAQ)
- Transfers to and from the trip start and finish
Arrival & Departure Suggestions
Where to Arrive
Florence Amerigo Vespucci (FLR), Pisa (PSA) and Rome Fiumicino (FCO) are the nearest international airports. Let us know of your travel plans and we’ll gladly point you to public transit options. Our team is available upon request for pick-ups from the Pontedera-Casciana Terme train station, an easy connection from Florence and Pisa.
Importante: We suggest arriving in Italy at least a day before the trip starts to adjust to the time zone and minimize the risk of missing the start due to flight-related delays.
Where to Depart
Drop-offs to the Chiusi-Chianciano Terme train station are available upon request. From there, trains connect to Florence Amerigo Vespucci and Rome Fiumicino airports.
Questions? Be Our Guest!
Dates & Availability
2025 Dates
Price
June 7 - 14
€4495
Guaranteed departure.
Single Supplement
€510
A Single Supplement is applied to secure a private room.
What Past Guests Say
"Alison's knowledge of the best routes is astonishing."
Bernadette