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Exploring the Tuscan Hills by Jason & Laura

Laura and Jason are a couple sharing their passion for cycling. They are a strong part of the London and Moloko cycling communities, with whom they regularly lead rides.


J & L have just come back from a three-month road cycling escape in Mallorca, Tuscany and Girona; a thrilling adventure that they're excited to share.


cyclists by the seaside

Their two weeks in the medieval city of San Gimignano (Italy) was one of the highlights of their trips: acres of vineyards, olive groves, quaint villages, lush green Tuscan hills...


Read all about it all and save their routes for your next travel to Italy!


Instagram: @laura.anne.fraser and @jasons_cyclingunboxed


San Gimignano - Volterra (Short Loop)

63 km | 39 mi from San Gimignano feat. Volterra.

Rating > Intermediate - Difficult

Terrain > Long rolling hills

Elevation Gain > 1,300 m | 4,265 ft


A route best started early in the morning to enjoy the quiet roads and take in the misty views over acres of vineyards. This ride has a collection of long rolling hills and you will enjoy smooth winding descents with gentle to moderate climbs through the green hills. After 25km starts a long scenic climb (6 km) into Volterra, the perfect town to reward yourself with a coffee and a gelato in the medieval centre (which is well worth a stop).



Next is an incredible descent out of Volterra, with beautiful far-reaching views of the Tuscan hills and a number of fun hairpin bends! Enjoy this 10 km thrill as it's shortly followed by one final long gradual climb. Then take in the views looking ahead at the towers of the medieval city of San Gimignano on the 6 km downhill approach before rolling your way back into town.


vineyards in a cycling trip in Tuscany



San Gimignano - Chianti Loop

90 km | 56 mi from San Gimignano feat. Radda in Chianti & Castellina in Chianti.

Rating > Difficult

Terrain > Rolling hills with sections of challenging gradients

Elevation Gain > 1,480 m | 4,860 ft


This route is the ultimate Tuscany experience with infinite vineyards views through the Chianti wine region, challenging climbs and spectacular scenery. Definitely my favourite ride of our Tuscany adventure!


The ride begins with a short climb from San Gimignano followed by an absolutely stunning descent to Certaldo where you can enjoy views of vineyards surrounding the marvellous medieval city of San Gimignano.



Enjoy the easy start of descending the windy quiet lanes across the valley before the climbing begins at 20 km. The first climb up to Tavarnelle Val di Pesa is punchy, with sections frequently kicking up to 16% (thankfully broken up with some easier inclines). We refuelled in the town square at the top of the climb before admiring the beautiful green rolling hills of Tuscany for the next 20 km. There are lots of small towns for a quick espresso stop if needed or a Coop after 35 km.


The most challenging climb of the route (and of our Tuscany trip!) comes after 49 km: the climb to Radda (Strada Comunale Fiorentia). It is a relentless climb, averaging 9.2% for 2 km including a 1.2 km section at 11.8%! There are easier roads you can take into Radda however if you love a challenge, this is definitely one to test yourself on.


cyclist in a village in Tuscany

Radda (51 km) is a beautiful hilltop town with panoramic views and is definitely worth a visit/ Its many cafes and restaurants will allow you to recover and refuel on cold drinks, bruschetta and pasta.


With most of the climbing done, the rest of the ride is the perfect opportunity to take in more of the beautiful Tuscan scenery as you go through Castellina in Chianti and down to Poggibonsi, saving just enough energy for the 3 km climb back up to San Gimignano.



San Gimignano Northern Loop

64 km | 40 mi from San Gimignano feat. flower lanes & rolling Tuscan hills.

Rating > Intermediate - Difficult

Terrain > Rolling hills with a long gentle climb

Elevation Gain > 1,020 m | 3,346 ft


It was a pleasure to explore a different side of Tuscany on this ride. More flower-lined country lanes surrounded by green fields rather than your traditional vineyards. In May, there were giant dandelion clocks (called “Jack Go To Bed At Noon”).


The route is a rolling with one of the most enjoyable descents of the trip after 10 km. It also features one long (12 km, 475m elevation) but gentle climb at 30 km from the town of Alberi to Marrado.



This map explores rural Tuscany, which mean you can benefit from quiet lanes and very few cars! With no particularly large towns on route for a coffee stop we took enough fuel for the full distance and saved our coffee stop for the end of the ride at San Gimignano. We highly recommend stopping for gelato at Gelateria Dondoli (world champion winning!) or the equally delicious Gelateria dell'Olmo (if the queues are not too long!).


View of Gimignano village in Tuscany cycling paradise


San Gimignano - Volterra (Big Loop)

112 km | 70 mi from San Gimignano feat. Casole d’Elsa, Volterra & Poggio Cornocchi.

Rating > Difficult

Terrain > Long rolling hills

Elevation Gain > 2,370 m | 7,776 ft


This route follows the same smooth winding descents and climbs as the Volterra ‘short loop’ for 15 km before heading to explore the rolling hills of the southern region. There are a number of picturesque and quaint hilltop towns on route, with scenic climbs followed by breathtaking descents.


views whilst cycling in Tuscany

Taking a different route into Volterra, the climb from Saline starts at 70 km and is challenging yet hugely enjoyable (8.5 km, 4.6%, 400m elevation gain). The climb has stunning views as it winds its way up to the high hilltop town of Volterra. This route would be best enjoyed on a weekday or early morning since it there was quite a lot of traffic on a Sunday. Volterra is the perfect place to stop for a coffee and a cake in the main square, we've been twice and it's one of our highlights in Tuscany.



Rolling hills take you to the final climb of the ride, up Poggi Cornocchi (8 km, 400 m elevation gain) which is a long gentle beautiful climb with, as always, views for days: one of Jason’s favourites in the area!



Komoot map of cycling in Tuscany


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