Lucca—Pienza Timeless Tuscany | Lucca Cycling Club

Lucca—Pienza Timeless Tuscany

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From the Adriatic Coast to the Tyrrhenian Sea: Through Abruzzo, Le Marche, Umbria and Tuscany.

After pro cycling, I moved from Canada to central Italy — I was looking for empty roads with the wind in my face and the sun on my back. Silence and traffic-free tarmac created space for what could and might be. I designed this trip so you, too, might quiet your mind and fill your cup with never-ending terra incognita.

Duration

Group Limit

9 days / 8 nights

Up to 12 guests

Start Location

Finish Location

San Vito Chietino

Cala Piccola

Total Distance

Total Elevation

1050 km

21,850 meters

What Guests Say

"I’ve ridden 20+ trips over the years and this one is among the best."

Male cyclist Mike

"I ride the trainer year-round so when Mike calls, I can say “yes” to trips like these."

Male cyclist Ray

“The 156 kilometers from Norcia to Fabriano is one of my top five rides of all time."

Male cyclist Jorg

Mountainous and Meandering Terrain

The idea behind this rigorous, bicoastal traverse was to showcase Italy’s central regions to those passionate about cycling and il Bel Paese. We wanted our guests to experience at least a full day in Abruzzo, Le Marche, Umbria and Tuscany rather than merely pass by. The result is an eight-day dedication to the bike across three National Parks, five regions and the width of Italy.

A Club for the Quirky

You’re scrolling the Lucca Cycling Club site, where we call our members Club Insiders and where participation is not only encouraged but endorsed. We believe there’s no shame in chamois time and that routes should be designed for bikes (not cars). We consider low-hanging fruit a bore, rules a suggestion and stagnation a tragedy.

If you’re interested in becoming a participating member, we welcome you with ciao socks and unlimited cappuccini.

Apennine Peaks and Hilltop Towns

From the highest Apennine peaks to vineyards, olive groves, and cypress trees, here’s a week worth training for. We’ve plotted a thousand kilometers of rugged terrain between the Adriatic and Tyrrhenian seas — call your coach, buy that new bike and let’s pedal the days away.

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 Italian-based company with fewer than 150 guests per year, we consider you family, not a reservation number.

  • Accommodations at three-, four- and five-star hotels
  • 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

Rome Fiumicino Airport (FCO) is the nearest international airport and reasonably accessible to the start and finish of the trip. There are train connections from Rome to Pescara yet the bus is the most direct. Let us know of your travel plans and we’ll gladly point you in the right direction. Our team is available upon request for pick-ups from Pescara.

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.

Questions? Ask Away!

Dates & Availability

2025 Dates
Price

June 22 - 30

€4495

September 7 - 15

€4495

Single Supplement

€780

A Single Supplement is applied to secure a private room.

What Guests Say

"Tours through the Dolomites or Tuscany are a dime a dozen, whereas C2C felt special."

Male cyclist Chris

"Every member of your team was warm, welcoming, accommodating and personable."

Male cyclist Dave

"I was blown away by the attentiveness of your team."

Female cyclist Val

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