adventure
Tuscany Traverse
Traverse Tuscany with ease and childlike wonder.
From Lucca to the Argentario Coast, through the Pisan Hills, Chianti, Crete Senesi, Val d’Orcia and Maremma, let life's greatest simplicities wash over you. Enjoy the rhythm of Tuscany done-for-you and elevated from start to finish. Yet, not without a satisfying sense of accomplishment, too.
duration
group limit
8 days / 7 nights
Up to 12 guests
start location
finish location
Lucca
Porto Santo Stefano
total distance
total elevation
585 km
10,445 meters
what guests say
"It was a trip of a lifetime."
Stephanie and Klaus
The Land of Cycling Greats
Our 585-kilometer route traverses the heart and fringe of central and southern Tuscany, with the Cima Coppi at 940 meters. Following in the tire tracks of legends — from Gino Bartali to Strade Bianche victors — you’ll ride through landscapes mingled with eons of cycling heritage. It’s here, immersed in Toscana’s iconic 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 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 and take you to another realm.
The Gift of Good Company
We encourage solo missions and quests inward, yet our greatest learnings often come 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. From the moment you arrive, our kindhearted, knowledgeable team takes care of everything. As a small Lucca-based company with fewer than 150 guests annually, we consider you family, not a reservation number.
- Accommodations at three- and four-star boutique hotels
- One wine tasting, a guided city tour of Sorano, and an 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
- 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 your travel plans and we’ll gladly point you to public transit options or help arrange a private driver.
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 Orbetello-Monte Argentario train station are available upon request. From there, trains connect to Rome Fiumicino and Pisa airports. Alternatively, we’ll have a limited number of spots in our vehicles for transfers back to Lucca.
Questions? Be Our Guest!
Dates & Availability
2027 dates
price
Private Only
€4495
Single Supplement
€550
A Single Supplement is applied to secure a private room.
Notes from Lucca Cycling Club Founder & Trip Designer, Alison Testroete
Over 15 years ago, I said “yes” to racing for a small Lucca-based pro cycling team. I discovered the spellbinding beauty of the Tuscan countryside and an infinite selection of roads. A whimsical decision turned into an obsessive pursuit of subject-matter expertise. 150,000 kilometers accrued (and counting) and an established vocation later, here’s my take on how you ought to pedal and enjoy la Toscana.
The route blends famous-not-too-miss sights with under-the-radar roads you’ll only find through deep work and focused exploration. The outcome is a unique, magical way to explore one of Italy's most popular regions. We’ve done our job when you return with a renewed lightness of being worth sharing with your closest friends and family.
what guests say
"Alison's knowledge of the best routes is astonishing."
Bernadette