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Strade Bianche Bikepacking: 4-Day Gravel Ride From Florence to Siena
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Cancel within 48h of booking 100% refund
Cancel 90+ days before departure (Any or no reason) 70% refund
Full coverage details
Basic Standard terms Most popular Core protection Recommended Premium protection
Cancel within 48h of booking
100% refund 100% refund 100% refund
Cancel 90+ days before departure (Any or no reason)
70% refund 70% refund 75% refund
Cancel any time (Covered reason)
75% refund 100% refund
Cancel any time (Any or no reason)
75% refund
Cancel under 90 days (Any or no reason)
75% refund
Travel: canceled flights, lost baggage, delays
Up to $1,000 p.p. Up to $1,000 p.p.
Rescue, evacuation, and medical coverage
Up to $100,000 p.p. Up to $100,000 p.p.
Basic Standard terms
Cancel within 48h of booking
100% refund
Cancel 90+ days before departure (Any or no reason)
70% refund
Cancel any time (Covered reason)
Cancel any time (Any or no reason)
Cancel under 90 days (Any or no reason)
Travel: canceled flights, lost baggage, delays
Rescue, evacuation, and medical coverage
Most popular Core protection
Cancel within 48h of booking
100% refund
Cancel 90+ days before departure (Any or no reason)
70% refund
Cancel any time (Covered reason)
75% refund
Cancel any time (Any or no reason)
Cancel under 90 days (Any or no reason)
Travel: canceled flights, lost baggage, delays
Up to $1,000 p.p.
Rescue, evacuation, and medical coverage
Up to $100,000 p.p.
Recommended Premium protection
Cancel within 48h of booking
100% refund
Cancel 90+ days before departure (Any or no reason)
75% refund
Cancel any time (Covered reason)
100% refund
Cancel any time (Any or no reason)
75% refund
Cancel under 90 days (Any or no reason)
75% refund
Travel: canceled flights, lost baggage, delays
Up to $1,000 p.p.
Rescue, evacuation, and medical coverage
Up to $100,000 p.p.
Cancellation policy

The percentages in the table above are of the full trip price, not of what you’ve paid at the time of booking.

Cancellations made within 48 hours of booking receive a full refund on all plans, including booking fees and insurance. After the 48-hour window, your refund depends on your selected protection plan and when you cancel. Core and Premium plans extend your cancellation rights beyond the Standard policy:

  • With Core, a covered reason gets you 75% of your trip cost back — even the day before you go.
  • With Premium, a covered reason gets you 100% of your trip cost back — and any other reason gets you 75%, right up to the day you leave.
What counts as a covered reason
  • Sudden illness or injury — yours, a travel companion’s, or an immediate family member’s, confirmed by a doctor
  • Death of a traveler or an immediate family member
  • A natural disaster affecting your destination or your departure point
  • A government travel advisory against travel to your destination

Changing your mind isn’t a covered reason. Premium is the only plan that covers that. Documentation is required for all insurance claims.

Everything the travel insurance covers

Both plans include travel insurance through Redpoint Travel Protection. Core insures 75% of your trip cost; Premium insures 100%.

Maximum per person:

  • Trip cancellation — up to 100% of your trip cost
  • Cancel for any reason — up to 75% of your trip cost (Premium only)
  • Trip interruption — 150% of the trip cost limit
  • Trip delay — $200 a day, $1,000 max
  • Itinerary change — $250
  • Single occupancy supplement — up to 100% of trip cost
  • Missed connection — $1,000
  • Travel inconvenience — $250 each, $750 max
  • Pet return — $1,000 per pet
  • Baggage and personal effects — $2,500, max $300 an item
  • Baggage delay — $600, after 12 hours
  • Baggage delivery — $100 per trip
  • Emergency medical expenses — $100,000
  • Medical evacuation and repatriation — up to $1,000,000

These are maximums. What a claim actually pays depends on what you can document and on the policy’s exclusions — pre-existing conditions and undeclared activities among them. We’ll send the full policy wording with your confirmation.

Reserve deposit (30%) $0
Second Payment Amount: $0
Strade Bianche Bikepacking: 4-Day Gravel Ride From Florence to Siena
Itinerary
Strade Bianche Bikepacking: 4-Day Gravel Ride From Florence to Siena
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1 Person
  • Strade Bianche Bikepacking: 4-Day Gravel Ride From Florence to Siena
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  • 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.

    • 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

      Approach to Chianti: Florence to Gaiole in Chianti — 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

      Southern Chianti: Gaiole to Pianella to Vescovado — 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

      Crete Senesi: Vescovado to Buonconvento — 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)

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

    • 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.

      Got everything you need? Grab your gear through Active Junky and earn cash back on top outdoor brands — plus a $10 bonus on your first $25+ purchase. Shop now at Active Junky!

    • 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.

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