170 - 400+kms   ❖   3,600m - 7,500+m   ❖   5 Nights/6 Days   ❖   From 2589€ pp

The price includes your choice of a Carbon Fibre racing frame or an E-Bike. 

Tuscany is an amazing region to visit and your time spent here goes by far too fast. This is exactly the reason why you should slow down and cycle in Bella Toscana with TTT! You will see, smell and feel Tuscany better than anyone stuffed inside a tour bus or a rental car. We have noticed the admiring looks for almost two decades.

We love our first two nights in "unknown" Certaldo, our very own hill-top "Borgo." First noted in 1164 but the village is much older and beautifully restored. Even the Michelin Guide gives it a miss. The Certaldo Loop ride is an easy pedal to San Gimignano (or further) then roll downhill on a great Tuscan road back to your Medieval village, which is up, of course. But in this neck of the woods, all the good things are up.

Then we must talk about the amazing food. Every meal seems better than the last. And our favourite topic; Gelato! Over the years we have found some of the best “hidden” Gelaterias in Tuscany.

We have been riding in Tuscany four or more weeks a year since ’98 so we know it very well and we actually love to vacation here too. This trip can be modified to include a stay in Siena if you wish.

Gallery here.

Ride Difficulty 6/10: Moderate to challenging (dependant on your fitness and your climbing ability), because nothing is flat in Tuscany. All rides are in the hills and if you take on the extensions you will add more climbs. Extremely rewarding rides and you will want to come back and ride another week. A TTT promise, “every day here has the WOW factor!” 


Optional:  You can (and should) arrive a day early in Pontedera, which is located on the main line between Pisa and Firenze (Florence). This will give you time to relax before the ride which starts tomorrow morning. Ask us, we can include this.

Day 1: We ride form Pontedera to Certaldo Alto via Paláia and Gambassi Terme. This can be a big(ish) day for some, but we have our secret weapon, Erika, our support vehicle. Two nights in Certaldo. 30 - 70+ kms 

Day 2: A beautiful 28km loop ride from your very own hill-top town to another; San Gimignano. Or you can add on a longer and hillier ride to Volterra or Cásole d’Elsa. Fantastic rolling Tuscan countryside with postcard views all around you and rarely a car. Truly an exceptional day. 28 - 100kms

Day 3: Today we leave Certaldo and ride to Castellina in Chianti and then on to Radda, where you spend two nights. We pass through Poggibonsi then up a stunning road through a nature preserve. Nearing Castellina we have lunch in one of our all-time favourite restaurants in Italy. We have eaten at Roberto’s Osteria every single trip since ’98! Try the Carciofi Romamana and the Pici con Sugo di Cinghale.   40 - 75+kms

Day 4: Rolling or hilly loop rides from Radda to Castello Brolio and Gaiole. Lots of choice and tremendous riding and views. Hang out at the best Gelateria in the region. Or you can just sample Chianti by the pool. Tough choices. 0 - 100+kms

Brolio is really worth a visit. It's been in the same family (Ricasoli) since 1141. One of the owners, Bettino Ricasoli, developed the wine in the mid 19th C. that we know today as Chianti.

Day 5: We leave Radda and ride to Greve in Chianti which is all of 21 kms away. But we have other plans … the long and hilly ride option allows you to pass by the regions best Gelateria three times! 21 - 100+kms

Day 6: Departure day. Pedal your way to Figline Valdarno in our car-free, secret valley, then yet another superb downhill! Our trip ends in Figline where you can catch a train to Firenze, Rome or you can stay with us and ride for another week. The riding is that good! 45 - 85kms