Included: An experienced, local gravel cycling guide with extensive knowledge of the area 4-day Strade Bianche bike tour in Tuscany (4 days of riding) Accommodation for 3 nights at partner accommodations along the route (double occupancy) One or more video calls with your guide before the trip to go through the mandatory gear list Add-ons (can be arranged at an additional cost, leave a note at checkout if interested): Gravel bike rental Bikepacking bag rental Luggage transport between accommodations Not included: Transportation to Italy Meals Anything not mentioned in the ‘Included’ section above Insurance — recommended, available at checkout Guide gratuities — optional

How fit do I need to be?

In order to join this Strade Bianche bike tour, good fitness is required as well as some previous gravel riding experience . The most you’ll cycle within a day is up to 67 km (42 mi) , over a mix of asphalt and unpaved Tuscan white roads. You don’t need to be training constantly, but this isn’t the trip for a first time on gravel. The days roll along with regular climbs, and the Crete Senesi stage packs in the most climbing of the four. Luggage transport is available as an optional extra, so you can ride light if you’d rather not carry your bags on the bike. Want to see what else is there in the area? Discover our collection of Tuscany bike tours !

What do I need to bring?

Bike and riding gear: Gravel bike (a mountain bike works too), in good working order Bikepacking bags, unless luggage transport is arranged Helmet Cycling gloves Front and rear lights Repair kit: spare tubes or tubeless plugs, tire levers, multitool, mini pump Two water bottles or a hydration bladder Bike computer or phone mount with the GPS track loaded (optional) Clothing: Cycling shorts or bib shorts and jerseys for each riding day Light insulating layer for cool mornings and descents Waterproof rain jacket Cycling shoes suitable for gravel, plus light shoes for the evenings Casual change of clothes for the accommodations Sunglasses Other: Toiletries, including sunscreen, hand sanitizer, and lip balm Phone, charger, and power bank Snacks and energy food for the longer stages ID, cash, and cards Camera (optional but recommended) Your guide will set up one or more video calls before departure to go through the mandatory gear with you, so you’ll know exactly what to pack. Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

What type of bike is needed?

A gravel bike is recommended for this Strade Bianche bike tour, though the route also works well on a mountain bike . You’ll ride a mix of 113 km (70 mi) of asphalt and 132 km (82 mi) of unpaved roads , including the classic Tuscan white roads and the clay soil of the Crete Senesi. If you’d rather not travel with your own bike, gravel bikes and bikepacking bags can be rented at an additional cost. Leave a note at checkout if interested.

Do I need to carry my luggage on the bike?

That’s up to you. Luggage transport is available as an optional extra on request , so you can ride light and find your bags waiting at the next accommodation. Otherwise, you’ll carry what you need in bikepacking bags on the bike.

Group sizes and age requirements

Group sizes and pricing: The maximum group size is set at 8 participants . Strade Bianche bike tours can be arranged for larger groups — contact us to make arrangements. Min. age requirements: If you are older than 18 , you’re good to go. Minors younger than 18 may be permitted to join the Strade Bianche bike tour on a case-by-case basis, but must be in the presence of a parent or legal guardian. If your group has participants under the age of 18, contact us prior to booking to make arrangements.

Getting there and meeting location

The starting point of your Strade Bianche bike tour is Florence , and the ride finishes in Siena . To get there, most people fly into Florence Airport (FLR) . From there, you can take a shuttle service, public transport, or rent a car to reach Florence.

Safety measures and insurance

We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout. Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.

Tuscany | Italy

Strade Bianche Bikepacking: 4-Day Gravel Ride From Florence to Siena

Name: Strade Bianche Bike Tour: Florence to Siena
Brand: 57hours
Availability: InStock

4 days | Moderate

From $2,935 ()

Book a call

Strade bianche are Tuscany’s white gravel roads: dusty, winding, and loved by cyclists ever since L’Eroica and the Strade Bianche pro race made them famous. Over four days, we follow them from Florence to Siena with our bags strapped to our bikes. We climb through Chianti vineyards and olive groves, roll past sleepy hilltop villages, and cross the bare clay hills of the Crete Senesi. The pace leaves room for the good stuff: an espresso in a village square, a long look over cypress-lined ridges, a glass of Chianti once the riding’s done. We ride in a small group of up to eight with a guide who knows every turn, so the only things to think about are the next climb and the next coffee. On the last day, we roll into Siena, right where the pros finish their race.

Matteo

International Mountain Leader & MTB Instructor

Adventure Highlights

Ride the real strade bianche: 245 km (153 mi) of Tuscan white gravel and Crete Senesi clay, the roads that made Eroica famous
Florence to Siena on two wheels: Four days linking Chianti's vineyards, the quiet hills around Murlo, and Castelnuovo Berardenga
Everything planned for you: Your guide plans the route and checks your gear on video calls before the trip, and a gravel bike, bikepacking bags, and luggage transport can all be arranged on request

Duration

4 days

Season

March through June, September through October

Group size

Up to 8 people

The adventure, day by day

Download itineraries

Four days of point-to-point gravel riding, starting in Florence and finishing under the walls of Siena. We ease in on secondary roads with the dirt sections building gradually, then climb into Chianti for our first night in Gaiole. Day two is shorter and rolling, dropping towards Murlo, before the biggest day: the Crete Senesi, with long climbs, open clay ridges, and the most elevation gain of the trip. The last stage mixes surfaces again on the approach to Siena. Nights are in partner accommodations along the route, and the group stays small, with a maximum of eight riders.

Day 1: Approach to Chianti — Florence to Gaiole in Chianti

Approach to Chianti: Florence to Gaiole in Chianti — Cycling in Tuscany

We roll out of Florence on quiet secondary roads, easing into the first dirt sections so everyone can get a feel for the bike and the surface. The gradient picks up as we cross into Chianti, where the climbs come at a steady rhythm rather than all at once. Vineyards and olive groves line the hills for most of the afternoon, and the white roads start to show their character. We finish the day in Gaiole in Chianti, a small village that has become something of a home base for gravel riders in this part of Tuscany.

Distance: 64 km (40 mi)
Accommodation: Partner accommodation in Gaiole in Chianti

Day 2: Southern Chianti — Gaiole to Pianella to Vescovado

Southern Chianti: Gaiole to Pianella to Vescovado — Cycling in Tuscany

A shorter stage today, which gives the legs a bit of a break after the Chianti climbs. We link secondary roads with compact dirt sections through Pianella and head into the less built-up corners of southern Chianti. The profile stays undulating, so there’s rarely a long flat stretch, but nothing here is brutal either. Later in the day the terrain opens up and we drop gradually towards the Murlo area, finishing in Vescovado. Plenty of time to clean up, eat well, and talk through the route ahead.

Distance: 55 km (34 mi)
Accommodation: Partner accommodation in Vescovado

Day 3: Crete Senesi — Vescovado to Buonconvento

Crete Senesi: Vescovado to Buonconvento — Cycling in Tuscany

Today is the big one, with the most climbing of the whole ride. We leave Vescovado and head into the Crete Senesi, where the white roads cut across clay hills and the gradients last a little longer than we’d like. Exposed ridges alternate with quieter valley sections, almost all of it on gravel, so we pace ourselves, spin easy on the steeper pitches, and take the time to look around. The colours out here are what people picture when they think of Tuscany. We roll into Buonconvento at the end of the stage, legs tired in the best way, and settle in for the night.

Distance: 67 km (42 mi)
Accommodation: Partner accommodation in Buonconvento

Day 4: Approach to Siena — Buonconvento to Castelnuovo Berardenga to Siena

Approach to Siena: Buonconvento to Castelnuovo Berardenga to Siena — Cycling in Tuscany

The final stage mixes asphalt and gravel with steady, regular climbs, nothing brutal, just enough to remind us we’ve been riding for four days. We pass through Castelnuovo Berardenga and then work our way closer to Siena, the hills gradually giving way as the city comes into view. Arriving in Siena by bike after all those white roads is a proper way to finish, and there’s time for a coffee and a few last photos before we say goodbye.

Distance: 59 km (37 mi)

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Lodging

Partner accommodations along the route

Each night we stop at partner accommodations spread along the way between Florence and Siena, in and around villages like Gaiole in Chianti, Vescovado, and Buonconvento. They’re simple, comfortable places chosen because they sit right on the route, so once the bikes are parked, the day is properly over. Expect a hot shower, a real bed, and somewhere to sit outside with the Chianti hills going quiet in the evening. Since we ride point to point, every night brings a different corner of Tuscany, and you’ll never have to think about where the day ends.

Adventure, packed to go

Strade Bianche Bikepacking: 4-Day Gravel Ride From Florence to Siena

Adventure Brochure

Adventure brochure

Download to share and explore full itineraries, key info, FAQs, and guide details.

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Meet your guide

Seasoned pros, local legends, and passionate adventurers—your trip is in the best hands.

5.00

Matteo

International Mountain Leader & MTB Instructor

Matteo is a certified International Mountain Leader and mountain bike instructor who left a corporate career at 27 to pursue exploration full-time. His mountaineering, climbing, and ski touring background has taken him on expeditions to Denali, Nepal, and Pakistan, and a serious paragliding accident shaped a guiding philosophy built on rigorous method, respect, and self-awareness. He has also completed extensive self-supported overland journeys—crossing Iceland, cycling from Iran through Central Asia, riding the Pan-American Highway from Bogotá to Ushuaia, and finishing a five-month Silk Road expedition from Beijing to Venice in 2025. He brings that direct field experience to every trip he leads, offering routes born from his own explorations rather than standard itineraries.

Things to know

Included:
- - An experienced, local gravel cycling guide with extensive knowledge of the area
  - 4-day Strade Bianche bike tour in Tuscany (4 days of riding)
  - Accommodation for 3 nights at partner accommodations along the route (double occupancy)
  - One or more video calls with your guide before the trip to go through the mandatory gear list
Add-ons (can be arranged at an additional cost, leave a note at checkout if interested):
- - Gravel bike rental
  - Bikepacking bag rental
  - Luggage transport between accommodations
Not included:
- - Transportation to Italy
  - Meals
  - Anything not mentioned in the ‘Included’ section above
  - Insurance — recommended, available at checkout
  - Guide gratuities — optional
In order to join this Strade Bianche bike tour, good fitness is required as well as some previous gravel riding experience. The most you’ll cycle within a day is up to 67 km (42 mi), over a mix of asphalt and unpaved Tuscan white roads.

You don’t need to be training constantly, but this isn’t the trip for a first time on gravel. The days roll along with regular climbs, and the Crete Senesi stage packs in the most climbing of the four. Luggage transport is available as an optional extra, so you can ride light if you’d rather not carry your bags on the bike.

Want to see what else is there in the area? Discover our collection of Tuscany bike tours!
Bike and riding gear:
- - Gravel bike (a mountain bike works too), in good working order
  - Bikepacking bags, unless luggage transport is arranged
  - Helmet
  - Cycling gloves
  - Front and rear lights
  - Repair kit: spare tubes or tubeless plugs, tire levers, multitool, mini pump
  - Two water bottles or a hydration bladder
  - Bike computer or phone mount with the GPS track loaded (optional)
Clothing:
- - Cycling shorts or bib shorts and jerseys for each riding day
  - Light insulating layer for cool mornings and descents
  - Waterproof rain jacket
  - Cycling shoes suitable for gravel, plus light shoes for the evenings
  - Casual change of clothes for the accommodations
  - Sunglasses
Other:
- - Toiletries, including sunscreen, hand sanitizer, and lip balm
  - Phone, charger, and power bank
  - Snacks and energy food for the longer stages
  - ID, cash, and cards
  - Camera (optional but recommended)
Your guide will set up one or more video calls before departure to go through the mandatory gear with you, so you’ll know exactly what to pack.

Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

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A gravel bike is recommended for this Strade Bianche bike tour, though the route also works well on a mountain bike. You’ll ride a mix of 113 km (70 mi) of asphalt and 132 km (82 mi) of unpaved roads, including the classic Tuscan white roads and the clay soil of the Crete Senesi.

If you’d rather not travel with your own bike, gravel bikes and bikepacking bags can be rented at an additional cost. Leave a note at checkout if interested.
That’s up to you. Luggage transport is available as an optional extra on request, so you can ride light and find your bags waiting at the next accommodation. Otherwise, you’ll carry what you need in bikepacking bags on the bike.
Group sizes and pricing:
- - The maximum group size is set at 8 participants.
  - Strade Bianche bike tours can be arranged for larger groups — contact us to make arrangements.
Min. age requirements:
- - If you are older than 18, you’re good to go.
  - Minors younger than 18 may be permitted to join the Strade Bianche bike tour on a case-by-case basis, but must be in the presence of a parent or legal guardian.
  - If your group has participants under the age of 18, contact us prior to booking to make arrangements.
The starting point of your Strade Bianche bike tour is Florence, and the ride finishes in Siena. To get there, most people fly into Florence Airport (FLR). From there, you can take a shuttle service, public transport, or rent a car to reach Florence.
We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.

Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.
Secure your spot with a 30% deposit upon booking! The remaining 70% of the trip price must be paid 90 days prior to departure at the latest. If booking within 90 days of departure, the full amount is required at the time of booking.
- If canceled within 48 hours of booking, a full refund will be issued.
- If canceled 90 or more days before departure, a 70% refund of the total trip price will be issued.
- If canceled within 89 days of departure, no refund will be issued.
- Booking fees are non-refundable after a 48 hours grace period.

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