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Available Months 18th - 22nd Sept
Nights Available 4 Nights
Tuscany Gravel Weekender Italy Adventure on the white roads of Siena & Chianti

Adventure on the white roads of Siena & Chianti

4 nights in the heart of Tuscany exploring the iconic white roads around Siena & Chianti. Famous in cycling for l'Eroica & Strade Bianche, this is one of the capitals of the gravel riding world.

4 Nights in 4* Hotel
Return Transfers from Pisa
Daily guided rides
Mechanical support
Optional Extras Bikes Available To Rent
Tuscany Gravel Weekender by Sportive Breaks
Routes Details
Book Now
Event Info

Ride Notes

For centuries the Kingdoms of Siena and Florence fought over the rich Chianti region and its easy to see why. A more scenic and rich area of countryside is hard to find and luckily for us the beautiful ‘strada bianche’ roads haven't all be paved over, their namesake race has swiftly established itself as one of the most exciting in the race calendar and day 3 of our trip will see us take on the race route including many challenging white gravel sections and also enjoy a slap up Tuscan feast halfway round. This is the race route as it should be enjoyed, in the warmer months with time to stop, take pictures and enjoy the view.

Real Rider Reviews

Mark, Sportive Breaks Rider, 2017: "Sportive Breaks' attention to detail and communication are spot on! Will be back next year. "

Ride Highlights

  • Ride the route of the famous Strada Bianche

    Probably Italy’s most exciting one day race (though Milan San Remo and the Giro Lombardia should never be missed) Strada Bianche is by far the youngest of the spring classics at just over 10 years it was swiftly added to the world tour and has swiftly become a fan favourite. We will ride the full gran fondo route.

  • Experience historic Siena

    Siena is likely Italy's loveliest medieval city, its heart is its central piazza known as Il Campo, known worldwide for the famous Palio run, a horse race run around the piazza two times every summer. Set atop a steep hill expect steep streets and some or Europes most stunning architecture, the gelato is world class too!

  • Tuscan Feasting

    Pasta and pizza have long been perfect cycling fuel, the jury is out on wild boar and chianti red wine but they are traditional. You wont go hungry here in Tuscany.

Meet the Team

Taylor Gunman

Tour Leader

Happiest on gravel, these are the tours Taylor most looks forward of the year. A former pro rider, Taylor is one of our lead guides who spends his year running trips in Morocco, Mallorca, Italy and our gravel tours. He is knowledgeable about all things bike and super friendly. You are in safe hands!

Adam Wolley


Another keen gravel rider, Adam is our head mechanic on this tour. He can match anyone in an eating contest and knows a thing or two about bikes. He will be on hand to build and pack bikes and will have the bike stand up every day to work on anything needed.

Trip Summary

  • 5 day / 4 night break
  • Small group, max size 14
  • Date available: September 18th to 22nd
  • Suitable for experienced and new gravel riders
  • Prices from £699pp
Routes Details

Route Overview

This long Tuscan weekend consists of 4 stages. We will ride on and off the beautiful and quiet white roads between castles and scenic towns between ice cream stops.
Our rides are:
Arrival Day: A short 40km ride to get used to the surface
Stage One: Ice cream at the castle – The castle town of Monteriggioni will be the destination for today’s ride through the hills.
Stage Two: Chainti classico – Fridays route has us tour the Chainti region, expect vinyards castles and stories of old from our local guide.
Stage Three: The big day – today we take on the route of the punishing Strada Bianche sportive, 140km of hills, white roads and stunning vistas. Unlike the sportive in March its likely to be much warmer and we stop for coffee and a slap up lunch.

Climbs at Tuscany Gravel Weekender

Tuscany Gravel Weekender Cycling Itinerary

Our four night break starts on Wednesday and the main rides are Thursday, Friday and Saturday. We stay just 10 minutes out from the city centre for all four nights .


Day One Wednesday 18th Sept

Arrival Day

Arrival day. We depart Pisa Airport at 11am getting to our Hotel at 1pm in time for lunch, bike building and an afternoon ride. The ride is a gentle 40km just to check bikes & legs and to give you a chance to get used the gravel. In the evening we have our welcome dinner where our guides will go over the rides in more detail.

Ride Distance 40 km.
Elevation Gain 450 m.

Day Two Thursday 19th Sept

Monteriggioni Loop

Heading north out of Siena, we head to the famed hilltop town of Monteriggioni and then head into the Chianti countryside. This part of the route is lumpy with some short gravel climbs before the terrain becomes more rolling as we head back home.

Ride Distance 99 km.
Elevation Gain 1700 m.

Day Three Friday 20th Sept

Chianti Classico

A tour of the most famous wine region in Italy by bike taking in the Castello di Brolio. We tackle some more testing white roads and visit the home of the Eroica vintage bike ride in Gaiole in Chianti before lunch by the little bridge. A vintage day out on the bike.

Ride Distance 95 km.
Elevation Gain 1600 m.

Day Four Saturday 21st Sept

Strade Bianche

Chicken or egg? The pro race stems in this case actually stems from the sportive set up in the late 90s L’Erioca which celebrates the golden age of cycling where amateurs ride old bikes in retro kit over the white Tuscan roads. This became so popular the pros wanted a race on the same terrain, and to come full circle there is now a sportive for the pro race which is based on a sportive. We ride the full route.

Ride Distance 123 km.
Elevation Gain 1750 m.

Day Five Sunday 22nd Sept

Departure Day

Our mechanics will pack your bikes up the night before so you can have a relaxed morning before the transfer leaves at 9.30am to get back to Pisa for 11am.

Airport Transfers

Our team will be in arrivals waiting for you. We run transfers on Wednesday and Sunday from Pisa to Siena.


The transfer from Pisa takes around 1.5 hour. We get into Siena around lunchtime where our mechanics will build your bikes ready for the first ride.

Arrival Airport
Transfer Times
Pisa (PSA)
Transfer leaves Pisa at 11:30, please book flights that arrive before 11am


We get back to Pisa for 11am in time for the early afternoon flights home.

Departure Airport
Transfer Times
Pisa (PSA)
Depart after 1pm (transfer arrives at 11am)


Executive Hotel Siena

Via Nazareno Orlandi, 32, 53100 Siena SI, Italy

    About the Hotel

    Hotel Executive is a modern 4-star hotel in a peaceful location just outside Siena. Good size rooms, a nice restaurant and friendly staff makes this an ideal base for our weekend.

    Book Now

    Four night packages with four fully supported rides to the best gravel roads around Siena. Twin package prices are for two people.

    Date Hotel Name Room Type Price  
    18 - 22nd Sep 2019 Executive Hotel Siena Single Room £799 Book Now
    Twin / Double Room £1399 Book Now

    Tuscany Gravel Weekender
    18th - 22nd Sept

    4 nights

    Single Room £799
    Twin Room £699
    • Return transfers from Pisa
    • 4 nights accommodation in 4* hotel
    • All breakfast & dinners
    • Full ride support with expert guides & mechanics
    • Flights
    • Lunches, drinks with dinner
    • Insurance