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Self-Guided Gravel Bike Tour in Tuscany
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Accommodation options

Price is based on twin-share rooms. Choose how many members of your group would like to stay in single occupancy rooms during the trip.

Bike rental

Bike rentals are available for an additional fee. Price is per person and for the whole trip.

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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
Self-Guided Gravel Bike Tour in Tuscany
Itinerary
Self-Guided Gravel Bike Tour in Tuscany
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  • The gravel roads of Tuscany and its pristine bucolic landscapes are the perfect setting for a serene self-guided bike journey. Spend a week cycling along beautiful roads and hamlets of Chianti and Siena provinces, and soak in everything Italian along the way. The beloved Italian cuisine is always a good idea, but make sure to also taste espresso, gelatos, and delicious red wines. You’ll ride on both gravel and asphalt roads, your luggage will be transferred between accommodations, and you’ll stay at fantastic villas and hotels.

    • Make your way to Pienza, a wonderful renaissance town in Tuscany. Pienza is a remarkable example of renaissance architecture and it’s truly a treat to just stroll around its cobblestone streets. After a bike fitting, go for a short bike ride to Bagno Vignoni, a thermal spa town dating back to Roman times, and Madonna di Vita Leta chapel.

      Accommodation: Hotel Rutiliano or Piccolo Hotel La Valle
      Distance: 25 km / 15 miles
      Elevation: +558 m / +1,830 ft | -565 m / -1,854 ft
      Terrain: 12 km (7.5 miles) asphalt, 13 km (8 miles) gravel

      Pienza in Tuscany

    • Today’s tour starts with a circular ride from Pienza. Red poppies blossom and overflow the verdant wheat fields of Tuscany in spring, and nowhere is it more brilliant than the hills of Val d’Orcia, a UNESCO World Heritage Site.

      Pedaling through corridors of cypress trees, follow the gravel tracks off the beaten path through a timeless slice of Tuscany and enjoy an espresso at La Foce, overlooking the roads you just conquered. By lunchtime, arrive to Montepulciano, the jewel of southern Tuscany, full of renaissance palaces. After relaxing a while, return to Pienza with a stop in Monticchiello, the quintessential Tuscan hill town.

      Accommodation: Hotel Rutiliano or Piccolo Hotel La Valle
      Distance: 51 km / 31.5 miles
      Elevation: +872 m / +2,860 ft | -875 m / -2,870 ft
      Terrain: 17 km (10.5 miles) asphalt, 34 km (21 miles) gravel

      Cycling quiet roads of Tuscany

    • To get to Montalcino, you’ll pedal along sections of the Eroica route called Lucignano d’asso and Pieve a Salti. After 6 km on a paved road, take the white road toward Cosona and reach the hamlet of Lucignano—perfect for an espresso stop. After a brief paved road section, start the Pieve a Salti section on a gravel road. Enjoy 9 km up and down through the bucolic scenery!

      Arrive in Buonconvento by lunch time. The last push of the day is reaching the famed town of Montalcino—this will be a 10-kilometer climb on both paved roads and gravel though vineyards. Once there, it’s warmly recommended that you visit the fortress and admire the valley you’ve just biked through. Make sure to treat yourself to a glass of Brunello at dinner!

      Accommodation: Hotel Il Giglio or Vecchia Oliveira in Montalcino
      Distance: 41 km / 25 miles
      Elevation: +855 m / +2,805 ft | -807 m / -2,647 ft
      Terrain: 17 km (10.5 miles) asphalt, 24 km (15 miles) gravel

      Montalcino town in Tuscany

    • Today you’ll get to pedal along one of the most beautiful gravel sections of L’Eroica—a route and a yearly event that celebrates the golden age of cycling with thousands of cyclists. From the heart of Brunello di Montalcino, Tuscany’s most beloved wine region, you’ll ride to the top of Passo del Lume, starting the Castiglion del Bosco section (the biggest Brunello winery & farm).

      Once in Bibbiano, cycle through another section called La Piana and reach Murlo after 30 km. Rest, have a cup of coffee, and tour the village. Get back on the road and get ready for another legendary Eroica section to Radi, with some steep but short ups and downs. Reach Ville di Corson and have a well deserved lunch. From there, you have 12 km left on a paved road to Siena.

      Accommodation: Villa STR in Siena
      Distance: 58.5 km / 36 miles
      Elevation: +1,015 m / +3,330 ft | -1,229 m / -4,032 ft
      Terrain: 32 km (20 miles) asphalt, 24 km (15 miles) gravel

      Murlo in Tuscany

    • After a gourmet breakfast, head out into the magical Chianti. Exit from Siena via the Eroica gravel section of Pieve a Bozzone, Vico d’Arbia, making your way through wheat fields before reaching vineyards.

      After 15 km, reach Pianella—take a long glorious section to Canonica A Cerreto, Vagliagli, through Chianti classico vineyards. You’ll pass by castles and old hilltop hamlets! Reach Radda in Chianti for lunch time after a 38-kilometer ride mostly on gravel roads. After getting some rest, hop back on your bike and finish the last 8 km to Gaiole following the Eroica route.

      Accommodation: Hotel Castello Spaltenna
      Distance: 48.5 km / 30 miles
      Elevation: +923 m / +3,028 ft | -874 m / -2,867 ft
      Terrain: 12 km (7.5 miles) asphalt, 34 km (21 miles) gravel

      Gaiole, Chianti in Tuscany

    • Today is reserved for exploring all the villages around Chianti and the hamlet of Chianti Senese. Departing from Gaiole, reach Castello di Brolio after 10 km and stop at the Agribar cafe—it’s a must where everyone seems to meet! Continue riding along the gravel section of Eroica and then along secondary roads to Castelnuovo Berardenga.

      Have some lunch and get back on the saddle to explore other small villages—San Gusmé and Villa a Sesta, then back to Brolio. There are two options for returning to Gaiole, one downhill and flat (somewhat easier) or a challenging uphill to Castagnoli and downhill to Castello di Meleto.

      Accommodation: Hotel Castello Spaltenna
      Distance: 55 km / 34 miles
      Elevation: +1,013 m / +3,324 ft | -1,013 m / -3,324 ft
      Terrain: 44 km (27 miles) asphalt, 10 km (6 miles) gravel

      Brolio castle, Italy

    • To end your trip, you have an optional short ride to Badia a Coltibuono—a 21-km loop on paved road. Come back to Gaiole where you’ll leave your bikes if you rented them. This marks the end of your self-guided journey through Tuscany!

      Distance: 21 km / 13 miles (optional)
      Elevation: +395 m / +1,295 ft | -420 m / -1,378 ft

      Badia a Coltibuono

    • Please note that accommodations are subject to availability and it may not be possible to book the exact accommodations listed day-by-day in the itinerary (in case there is a detailed list).
      Also note that your chosen dates for the tour are not guaranteed until confirmed by the guide. If the guide is unable to secure your preferred dates/accommodation, you’ll get a full refund!

    • Included:

        • 7-day self guided gravel bike tour in Tuscany
        • Accommodation for 6 nights in excellent hotels (double occupancy)
        • Six breakfasts (special dietary requirements can be accommodated)
        • All baggage transfers
        • RideWithGPS App: tracks, route notes, off-line navigation
        • Maps with elevation gain
        • Trip notes: sightseeing, restaurant, and shopping suggestions
        • Bike delivery at Pienza hotel & bike fitting
        • Pick-up of bikes and gear in Gaiole
        • Keepsake water bottle
        • Sales taxes

      Add-ons (available to add at checkout):

        • Bike rental (choice of gravel bike, e-bike, or e-gravel bike)
        • Single occupancy room

      Not included:

        • Transportation to Italy
        • City taxes — each village/town charges a day tax (0,70 to 3 EUR per person, per night)
        • Lunches and dinners (though you’ll get the best local recommendations)
        • Insurance — recommended, available to add at checkout

    • This self-guided gravel bike tour in Tuscany is rated to be moderate to challenging. Exact daily distances and elevation gains are listed in the itinerary, but in general, prepare for your trip with regular conditioning at least two months in advance.

      While this is a self-guided tour and you can pedal at your own pace, you’ll make the most of this adventure if you’re fit enough to cover daily itineraries without struggling too much. You’ll cycle on gently rolling terrain, there will be some hills and climbs, both on asphalt and gravel. You can make it easier for yourself by renting an e-bike with your guides.

      Keep in mind that you’ll cover between 25 and 58 km (15.5-36 miles) daily and that you’ll have to reach your booked accommodations for the night.

      Want to see what else is there in the area? Discover more Tuscany bike tours here!

    • This is a list of clothing & footwear we recommend you bring:

        • Cycling shorts (padded shorts recommended, try them out before the tour)
        • Riding jerseys
        • T-shirts and/or casual shirts (quick-dry)
        • Bathing suit
        • Bike socks and/or sports socks (quick-dry)
        • Dress or casual socks
        • Windbreaker or cool-weather jacket (rainproof and breathable)
        • Light rain jacket or poncho (cheap version is fine—insurance on sunny days!)
        • Bike shoes
        • Riding gloves
        • Underwear (quick-dry)
        • Sweater or fleece
        • Slacks or light jeans (quick-dry, wrinkle resistant)
        • Belt
        • Comfortable walking shoes
        • Sandals

      Miscellaneous

        • Passport, wallet and ID
        • Waterproof, zip-lock type plastic bag for your valuables
        • Health insurance card
        • Travel insurance card
        • Cash, credit cards and/or travel cheques
        • Electronic chargers (for camera, MP3 player, e-reader, cell phone)
        • Adaptors or convertors

      First aid kit

        • Insect repellent
        • Antiseptic cream or antibiotic ointment
        • Antihistamine tablets for hay fever
        • Sunscreen and total bloc
        • Throat lozenges or hard sweets
        • Painkillers
        • Band-aids and ‘Second Skin’ for blisters
        • Rehydration salts
        • Multi-vitamins

      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!

    • Yes! If you’d like to skip the hassle of bringing a bike for your Tuscany Maremma bike tour, your guides offer bike rental. You can add a bike to your booking at checkout—either a gravel bike, an e-bike, or an e-gravel bike.

    • Self-guided tours are perfect for those who enjoy exploring on their own terms—at their own pace, and with the company they choose. By joining this self-guided Tuscany Maremma bike tour, we take care of:

        • Accommodation for 6 nights in excellent hotels, villas, and castles (double occupancy)
        • Six breakfasts (special dietary requirements can be accommodated)
        • One gourmet dinner
        • All baggage transfers
        • RideWithGPS App: tracks, route notes, off-line navigation
        • Maps with elevation gain
        • Trip notes: sightseeing, restaurant, and shopping suggestions
        • Bike delivery at Pienza hotel & bike fitting
        • Pick-up of bikes and gear in Gaiole
        • Keepsake water bottle
        • Sales taxes

      Rather than joining a guided group, you’ll navigate the tour yourself, using resources provided by the tour operator. For a hassle-free journey with everything arranged for you in advance, there’s no better option!

      As a self-guided tour is built around your preferred travel dates, your guide will take care of arranging accommodations and details after you book. Note that exact accommodations and dates might shift slightly, so don’t make any travel arrangements until the details of your adventure are confirmed.

    • Group sizes and pricing

        • It takes a minimum of 2 people for this self-guided gravel bike tour in Tuscany to operate.
        • The maximum group size is set at 16 people.

      Gravel bike tours in Tuscany 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 older than 16 may be permitted to join the gravel bike tour in Tuscany on a case-by-case basis, but must be in the presence of a parent or legal guardian.

      If your group has hikers under the age of 18, contact us prior to booking to make arrangements.

    • The price for this Tuscany bike tour is based on twin-share rooms, but a single occupancy room can be arranged at an additional fee. You can add it to your booking at checkout.

    • The starting point of your gravel bike tour in Tuscany is Pienza. To get there, the nearest airports are Rome Fiumicino (FCO) and Florence Airport (FLR). It’s up to you whether you’d like to rent a car to reach Pienza, the starting point of your tour, or you’d like to use public transport. Driving with a car takes between 1.5-2.5 hours to Pienza, depending on where you land.

      For the public transport option, after landing you have to reach Chiusi. The easiest option would probably be to take the train. Once in Chiusi, you can take a bus or a taxi to Pienza, the starting point of your gravel bike tour in Tuscany.

    • 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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