Available Months May to Oct
Nights Available 4 Nights
Tuscany Italy Rolling Hills, White Roads & La Dolce Vita, welcome to Tuscany!

Rolling Hills, White Roads & La Dolce Vita, welcome to Tuscany!

A long weekend in one of the great spots in the world for cycling. The riding is rolling and perfect for the end of the season and there is no better place to carb load. This Weekender is split across two locations - 2 nights in the walled town of Lucca and two in Chianti.

4 Nights Accommodation
Return Airport Transfers
All Breakfast & Dinners
Daily Guided Rides
Mechanical Support
Tuscany by Sportive Breaks
Routes Details
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Event Info

Ride Notes

Join us for four nights in cycling paradise. We spend two nights in beautiful Lucca and two nights in Chianti taking in stunning rolling terrain and the famous strade bianche. Discover why this region is a playground for pro cyclists and amateurs alike with mile upon mile of empty roads, amazing views and food that will make you put on weight no matter how hard you ride each day! Our social, small group weekenders to Tuscany include approx 100km per day with a couple of nice hills but ridden at a pace where we can chat with our fellow riders and soak up the atmosphere and beauty of this unforgettable place.

Real Rider Reviews

Stephen, Tour of Flanders, 2017: "Organisation was perfect and marshalling superb. Hotel was great, staff were brilliant - definitely the right move to stay in Oudernaarde and will go back. "

Ride Highlights

  • Ride the Strade Bianche

    We take in several sections of the famous white roads on the trip. The gravel is packed and well suited to normal road bikes.

  • Explore Lucca

    At the start & end of the trip we are in lovely Lucca, an old walled town close to Pisa.

  • Relax in Chianti

    In the middle of our Weekender we relax in Chianti, one of the world's most picturesque regions where the only thing to rival the quality of the food is the quality of the riding.

Trip Summary

  • 4 Night Breaks
  • Dates available: Wed to Sun in mid Oct
  • Total distance: Avg 100km per day
  • Total elevation: Avg 1,500m per day
  • £649 in twin room, £749 in single room
Routes Details

Route Overview

Our four night Tuscany Weekender includes three rides with two shorter optional rides on arrival & departure day. We start with a 110km ride on day two to Figline Valdarno in Chianti. This ride takes in some gravel sections that make Tuscany so famous. On day three we ride a 100km loop in Chianti following a route similar to the Strade Bianche / L'Eroica with a lunch stop in Siena before a final ride on day four of 120km back to Lucca. We have an optional 50km coffee spin on Wednesday & Sunday.

Climbs at Tuscany

Super Volpaia

Ride Distance 5.7km
Elevation Gain 7%
KOM  20min52

San Martino-Monte Luco

Ride Distance 9,4km
Elevation Gain 5%
KOM  24min37

Tuscany Cycling Itinerary

Our Tuscany Weekender runs Wednesday to Sunday in October. We arrive early on Wednesday in time to set bikes up and going for a quick spin from Lucca. On day two we ride to Chianti and spend two nights there before riding back to Lucca on Saturday for our last evening.


Day One Wednesday


Arrival day. Our main transfer leaves in Lucca at 1pm where our mechanic will be on hand to fit your rental bike or help build your own bike. We have an optional coffee spin leaving at 3pm to make sure the bikes and legs are working before the main start tomorrow.

Ride Distance 50 km.
Elevation Gain 800 m.

Day Two Thursday

Lucca - Figline Valdarno

Today we ride down from Lucca to our base in Chianti. The ride goes through Quarrata, home to many pro cyclists. The terrain is rolling pretty much all day so our avg speed will be between 22-25km/h. We leave at 9.30am and aim to be finish by 4pm with a lunch stop on the way.

Ride Distance 125 km.
Elevation Gain 2250 m.

Day Three Friday

Figline Valdarno

A stunning day riding in Chianti. Today's route follows some of the best sections of the Strade Bianche route and we get lunch in stunning Siena. We leave a bit later at 10am today and aim to finish by 4pm.

Ride Distance 110 km.
Elevation Gain 1850 m.

Day Four Saturday

Figline Valdarno - Lucca

The final big ride of the weekend. We head north in a different direction home taking a stop in Vinci before getting back to Lucca for 4pm where we will have a couple of beers & one final, amazing Tuscan dinner!

Ride Distance 120 km.
Elevation Gain 2050 m.

Day Five Sunday


Departure day. If you want to fly back early we will transfer you to Pisa, for everyone else we will have one last 45km coffee spin in the morning before packing bikes and heading back to Pisa for 3.30pm.

Ride Distance 45 km.
Elevation Gain 650 m.

Airport Transfers

Airport collections are from Pisa (PSA) and the drive to Lucca takes around 30 minutes. If you cannot find flights to match our times please get in touch and we should be able to collect you for no extra cost.


We will meet you in arrivals and give you a number to call if you are delayed.

Arrival Airport
Transfer Times
Pisa (PSA)
12.30pm (arrive before 12pm)


We leave Lucca to get to Pisa with plenty of time for you to check in with your bike, grab a last minute gift and have a stress free return flight.

Departure Airport
Transfer Times
Pisa (PSA)
Depart after 6pm (transfer arrives at Pisa at 3.30pm)
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Ride Tuscany's best routes. Four night packages with three main rides and two coffee spins. Two nights in the old walled town of Lucca & two nights in the heart of Chianti in Figline Valdarno. Packages include return airport transfers, 4 nights accommodation, all breakfast & dinners and ride support. Our group size is 8-14 and we have two road guides & a mechanic in our support van.

Date Hotel Name Room Type Price  

May to Oct

4 nights

Single Room £749
Twin Room £649
  • 4 Nights Accommodation in 4* & 3* hotels
  • Return airport transfers from Pisa
  • All breakfast & dinners
  • Daily Guided Rides
  • Mechanical support, feed stops & ride nutrition
  • Lunches
  • Drinks with dinner