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Bike Tour
ON DEMAND

Tuscany Gravel Ring

from €1.290

A five day, full-immersion ride through the varied Tuscan landscape.

Departing from Florence this bike tour takes in all the well-known parts of Tuscany: its famous strade bianche (or white roads), famous towns like Monteriggioni and San Gimignano, Tuscany’s most famous road in Bolgheri and introduces us to the lesser known parts of the region: the coast of Maremma and the town of Follonica, the pine forests surrounding Volterra and the Pesa river leading us back to Florence.

Available either as a fully supported Pro Tour or Self Guided, with or without bike rental.

Start
Florence
Finish
Florence
Duration
5 days
Distance
500km
Total ascent
7,150m
Terrain
80% unpaved
Difficulty
Intermediate
Price
From €1.290

The Tuscany Gravel Tour is 5 days and 4 nights, starting and finishing in Florence.


Day 1: Florence – Siena

Distance: 103km / Gain: 1.690m

Day 2: Siena – Ribolla
Distance: 102km / Gain: 1.690m

Day 3: Ribolla – Bolgheri
Distance: 106km / Gain: 1.070m

Day 4: Bolgheri – San Gimignano
Distance: 100km / Gain: 2.160m

Day 5: San Gimignano – Florence
Distance: 90km / Gain: 670m

Rolling Dreamers Photo

Day 1: Florence – Siena

From Florence, we immediately climb towards Impruneta; the home of terracotta and from there through the world-famous sloping vineyards of Chianti. There are four principle climbs on the first day and many more to come so pacing yourself is vital!

Today we get to experience Chianti Classico at its finest; the heartland of Tuscan wine and the Sangiovese grape. The rolling hills continue and once the battlements of Monteriggioni come into view, we are on the homeward stretch (for today at least) onwards to the first night in the Colli Senesi: the hills of Siena.

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Day 2: Siena – Ribolla

The area south of Siena is famous for its colour palette – fans of the film Gladiator will instantly recognise the meandering cypress-lined driveways. Signs point to the route of NovaEroica, the more modern version of the classic Eroica cycling event before the gravel climb that featured in the 2021 Giro d’Italia. Fortunately we aren’t on aero race bikes with skinny tires but the gradient is still a challenge.

Today is the day we get wider: the houses become more infrequent and soon there are no more vineyards just miles and miles of woodland. Into the trails and tracks of this hidden Tuscany we go, eventually emerging onto a road for a few kms on asphalt before dinner.

Rolling Dreamers Photo

Day 3: Ribolla – Bolgheri

The midpoint of our Tuscany Gravel bike tour is the day we hit the sea. Plenty of flat and mildly undulating kilometres await us before we arrive at the gravel path that skirts along the Mediterranean coast. With the sea breeze blowing alongside us, we can see the rocky cliffs of the southern Tuscan coast; a world away from the tourist hot spots of overcrowded beaches to the north.

This coastal cruise provides some recuperation before the one and only climb of the day. A not inconsequential 5km at 8.5% – rising to 16% or more in some sections! Once that is done, it’s on to Bolgheri where more good food and wine awaits (for those who partake).

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Day 4: Bolgheri – San Gimignano

A stage that begins with one of the most famous and photographed roads in Italy. But don’t spend too long on Instagram as there’s over 2000m of gain to conquer today. The day’s ride continues in photogenic fashion as we continue: wide open plains, gravel trails and forest roads.

The Castello Ginori, a castle and medieval borgo, or village, that traces its history back over one thousand years greets us at the top of a climb. From this landmark we head towards another: Volterra. Skirting around the hill on which the town sits, we proceed to San Gimignano.

Rolling Dreamers Photo

Day 5: San Gimignano – Florence

As the many towers of San Gimignano disappear behind us, familiar sights greet us on this last day as we roll into the colli Fiorentini – the Florentine hills. The shorter ride is welcome after the many kilometres travelled. There is one big climb to overcome before the valley of the river Pesa and those last few effortful kilometres toward the Cascine Park on the outskirts of Florence. We roll back into the city having seen and experienced the best that this region has to offer.

Tuscany Gravel Ring

Self Guided Tour

In the Self Guided version of our Tuscany Gravel bike tour you will independently carry out the trip together with your group while we take care of organising all the details for an unforgettable experience.


Starting price:

€1.290/person


What’s Included

  • GPX files with routes, maps and stage info
  • Accomodation with double room occupancy (3* or 4*)
  • Breakfast each day
  • Rolling Dreamers welcome pack
  • Extra goodies and lots of advice on unmissable views, places to eat and drink and hidden gems
  • 24H remote support

Optional Extras

  • Gravel bike rental €80 per bike per day
  • Single supplement €400 per person
  • Daily luggage service (from stage start to stage end each day) €1500
Tuscany Gravel Ring

Pro Service Tour

In the Pro Service version of our Tuscany Gravel bike tour you will be accompanied our expert guides whilst they take care of all the practical details so that you can enjoy a unique and memorable experience.


Starting price:

€2.390/person**


What’s Included

  • Professional bike guide
  • Support van with mechanic
  • Accomodation with double room occupancy (3* e 4*)
  • Breakfast each day
  • Dinner each day
  • Rolling Dreamers welcome pack
  • Fun, authentic views, unmissable places to eat and drink

Optional Extras

  • Gravel bike rental €80 per bike per day
  • Single supplement €400 per person

**The Pro tour is available for private groups of 8 or more participants starting from €2,390 per person. For groups smaller than 8 there will be a supplemental charge

Ready for your adventure?

Request a personalised quote

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  • Twin accommodation must be booked as a couple – for both twin and double.
  • Travel Insurance is not included.
  • For the Self Guided Tour there will be a dedicated member of the Rolling Dreamers staff available for remote assistance and 24H support. There will be no staff members traveling with the group.
  • The Self Guided Tour is available for private groups of 2 or more participants starting from €1.290 per person.
  • During the Pro Tour there will be a Rolling Dreamers bike guide for every 8 participants (example: for a group of 9 there would be 2 guides riding with the group).
  • The Pro tour is available for private groups of 4 or more participants starting from €2.390 per person.

*Please note that all measurements are approximate and the exact distances and duration of the tour will be confirmed upon booking.

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