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Escape the ordinary and embark on an MTB adventure along the sacred routes of Tuscany, where history, culture, and breathtaking landscapes converge to create an unforgettable experience. Tuscany’s long history of trade and agriculture has resulted in an extensive network of trails — from thrilling forest singletrack to scenic country lanes. Follow the legendary Via Francigena pilgrimage, picturesque Montagnola trails, and the exhilarating Eroica roads, discovering the essence of Tuscany in every pedal stroke. Immerse yourself in the Renaissance splendor of hilltop towns and pause to savor traditional delicacies paired with magnificent wines of the region.

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Adventure highlights

  • Taste Tuscan cuisine

    Pair traditional delicacies with the best wines of Chianti, Montepulciano and Montalcino

  • Enjoy the journey across Tuscany

    Ride down the Crete Senesi on a roller-coaster ridge ride and visit famous hilltop towns

  • Italian hospitality

    Stay in lovely Tuscan accommodation overlooking stunning landscapes

Itinerary

Explore famous sights of Tuscany on this 7-day mountain biking adventure. Make your way through woodlands, vineyards, hills and valleys along great tracks and routes that link famous hilltop towns such as San Gimignano, Siena and Pienza.

  • After arriving in Pisa, your guides will drive you through the beautiful Tuscan Landscape, arriving at the first accommodation set in the outskirts of the famous town—in the countryside of San Gimignano. You’ll stay in a stunning agriturismo, where your host will prepare your first Tuscan dinner. With a plunge in the pool overlooking the vineyards, your holiday can officially start!

    Driving: 90 minutes
    Meals: Dinner

    San Gimignano old town photographed from above during golden hour

  • Set off the day with a fun off-road section into the valley before looping back towards San Gimignano. Journey south following a mix of dirt roads and trails through woods, over hills and crossing streams, through a constantly changing rolling Tuscan landscape. Most climbs will be on farm or forest gravel routes, which lead onto sections through vineyards and fields, trails and paths used mostly by local people and farmers. Your destination for today is Strove, a small hamlet not far from Abbadia Isola and Monteriggioni. After stopping in the square for a well-deserved beer, reach your accommodation, where you can enjoy a dip in the pool before heading out for dinner.

    Distance: 22 miles / 35 km
    Ascent: 600 m
    Meals: Breakfast, lunch

    Two mountain bikers riding through Italian countryside

  • Your first stop for today is the quaint medieval hamlet of Monteriggioni, with time to explore the castle walls and narrow streets. Leaving the fortified village, you’ll continue with a steady off-road climb through the Montagnola range, an area well known for the Gran Fondo Sienese MTB race. Explore the network of dirt tracks leading into the hillside forests, looping on fun rolling singletracks towards little hamlets and twisting down over rolling fields. A final fun section of singletrack winding through forests will lead you to the outskirts of Siena. Spend some time wandering through the town and visit the Palio Square and Duomo, before heading out to dinner.

    Distance: 22 miles / 35 km
    Ascent: 750 m
    Meals: Breakfast, lunch  

    Drone view of Monteriggioni fort town in Tuscany, Italy

  • Leave Siena and continue your journey south on the Eroica route and into the Crete Senesi. Arriving near the ancient Etruscan hamlet of Murlo, enjoy a fun ride on narrow trails by the Crevole River and up a former mining railway track. Head to Buonconvento, where you’ll stop for a refreshing break and, if inclined, visit the fortified walls. Your accommodation is right in the center of town, so enjoy some downtime and join the locals for aperitivo!

    Distance: 28 miles / 45 km
    Ascent: 500 m
    Meals: Breakfast, dinner  

    Streets of Buonconvento

  • Your mountain bike pilgrimage continues! Head towards Pienza, right in the heart of the UNESCO heritage site of Valle d‘Orcia. The route takes you along the ridge lines, offering 360 degree views. The trails are a mix of farm tracks and dirt roads, with steep sections which will get you out of the saddle. Today is a tougher day in terms of ascent, and after joining a section of the Eroica, you’ll reach your accommodation in the heart of Pienza– the perfect base for two nights allowing you to explore some cultural and historical sites as well as small Tuscan shops, wine bars and restaurants.

    Distance: 26 miles / 42 km
    Ascent: 1000 m
    Meals: Breakfast, lunch  

    Mountain biker on a gravel road with rolling hills and the walls of Pienza in the background

  • Your group can choose between different options for today’s ride depending on the preferred terrain—all the trails lead to San Quirico d‘Orcia. Descend quite steadily on a fast gravel track into the Orcia valley and loop back through fields, dense woods and past castle hamlets, until you reach the medieval hamlet of Bagno Vignoni with its healing baths and home to the legendary water nymphs. After resting, head to the center of Valle D‘Orcia and start a steady climb towards Pienza. Absorb and visit the local sites before indulging in another delicious Tuscan meal at one of the carefully selected local restaurants.

    Distance: 25 miles / 40 km
    Ascent: 900 m
    Meals: Breakfast

    Riding through scenic meadows of Tuscany

  • After breakfast, your guides will take you back to Pisa to say your farewells and savor the memories of a fantastic week on your bike!

    Driving: 2h 45min
    Meals: Breakfast

    Group posing in front of a church

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Meet your guides

Naomi Lindfield
5.00
Naomi Lindfield
Main guide in Skedaddle Italia
Originally from Sardinia, Naomi has been with Saddle Skedaddle since 2000, working hard to build the company into what it is today. Bikes have always been part of her life and have given her a sense of freedom since she was a child riding her tiny bike around the Sardinian countryside. The freedom combined with the exploration and the journey is what she loves the most!
Saddle Skedaddle
5.00
Saddle Skedaddle
Saddle Skedaddle was founded by a couple of MTB pros (Paul and Andrew) while trapped in a snowstorm during their year-long biking adventure in Chile. They believe travel should move you and that there’s no better way to see a place properly—its people, culture, and natural wonders—than by bike. Saddle Skedaddle currently runs tours in 36 destinations, offering adventure junkies incredible places to tour on two wheels.
5.00 (4 reviews)
Thank you, Skedaddle, for inventing this tour.
Sarah (source: Guide's website)

What an opportunity to see the Tuscan countryside in such an intimate way as cycling / mountain biking. How else could we get a guided tour – the best trails, lodging and meals all figured out for us?

When one guest lacked stamina the first day, Skedaddle got him an e-bike and for the rest of the days he did great. When another guest needed stitches a guide took her to the hospital in the van right away. These are examples of good service.

Excellent riding!
Mike (source: Guide's website)

Excellent riding – Hard to single out one day. The mix of technical and fitness was great and I particularly enjoyed the climbing (I know, I am weird). Great planning by the guides when the original route was not suitable due to the weather – we had a great day around Montalcino.

All the scenery was stunning
Becky (source: Guide's website)

All the scenery was stunning, so all days were enjoyable. The last day in particular as it was the only real day with any singletrack was most enjoyable in terms of MTB riding.

Great
Ian (source: Guide's website)

A truly memorable trip and has already got us planning to revisit the area. The crew on the ground were excellent and nothing was too much trouble. The cycling was a little harder than I imagined (as was the amount of wine we drank!!), but such great company and organisation/pace mean that it was still a holiday and not too much of a grind. The accommodation/food/routes were all stunning. Thanks so much. A dopo!

Things to know

  • What you get on this adventure:

      • 1 or 2 English speaking MTB guides, depending on the size of the group
      • At least one guide qualified in First Aid
      • Accommodation (shared twin / double en-suite rooms)
      • Breakfast, 3 lunches and 2 dinners
      • Support vehicle and luggage transfers
      • Airport transfer on scheduled arrival day from Pisa airport 
      • Airport transfer on scheduled departure day to Pisa airport (PSA)

    Mountain bike and helmet rentals are available for an added fee. Please let us know if you need to rent any gear upon checkout.

    What’s not included:

      • Flights and charges for traveling with your bike
      • Meals not stated in the itinerary
      • Single room — available upon request
      • Personal expenditure (souvenirs, bar bills, hotel facilities etc)
      • Entrance fees to museums and other attractions en-route
      • Airport transfers on days other than the scheduled arrival / departure days
      • Insurance — recommended
      • Guide gratuities — optional
  • Tuscany’s technical terrain, complete with loose, steep single tracks is one of its strongest selling points. That said, even the most experienced among the group can count on it to push their limits. You’ll need to be able to bike 25-50 miles / 40-80 km per day. 

    You will be biking on a mix of chalky double track or “Strade Bianche”. The wider tracks will be alternated with some fun, flowing narrower trails that can be rocky and with roots in sections. Sections of singletrack can be a bit rocky with limestone making the trails a bit tricky in places. You will have to manage a few steep, and a few long climbs (followed by fantastic downhills), so fitness is more important than off-road riding skills.

    This tour is perfect for mountain bikers with some experience of singletrack and steeper terrain. If you’re generally fit and manage to ride regularly this could be the level for you.

  • As this tour is aimed at regular cyclists who have a degree of off-road experience, singletrack and steeper terrain, it is not suitable for mountain biking beginners.

  • Here’s what you’ll need:

      • Comfortable riding or athletic clothing, moisture wicking or synthetic material 
      • Everyday clothes for  sightseeing and dinners
      • Sneakers or sport shoes
      • Breathable outside layer or jacket
      • Biking gloves
      • Sunglasses
      • Helmet (can be rented)
      • Backpack 
      • Daypack with snacks
      • Plenty of water, water bottle or hydration bladder
      • Toiletries (sunscreen, hand sanitizer, bug spray, toilet paper, etc.)
      • Camera

    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.

    Your guides allow one main piece of luggage per person, other than your bike and a small day pack. Your main luggage should preferably be either a backpack or ‘sports bag’ so as to assist in transportation. The day pack may be useful for carrying your additional outer-layer clothing, camera and snacks.

    You will be able to leave extra gear or spare kit in the support vehicle during the day, meaning there is no need to carry any equipment other than that carried on your normal day ride. In the vehicle there will be some space for tired bikers as well, allowing the chance of a well-earned break if needed.

  • If you don’t own a suitable bike or would prefer to avoid bringing your own, your guides have hardtail bikes available to rent. These bikes typically feature front suspension, disc brakes and good quality components. You can also rent a helmet and all necessary spare parts. 

    If you are bringing your own bike, a mountain bike with off-road tyres is the best choice. Best options is a front suspension or full suspension mountain bike with a wide range of gears and tyres with an appropriate level of tread for this trip. Keep in mind that the vast majority of airlines will charge you to transport your bike. Please contact your airline for specific details.

    In case you’re renting a bike, you are welcome to bring your own saddle with you or SPD/clipless pedals.

  • The majority of accommodation will be in a shared twin or double room with an ensuite bathroom. You’ll stay in 3 star guest houses, agriturismi (immersive farm stays) or hotels. An Italian agriturismo will usually serve guests food that was prepared from raw materials produced on the farm or from other local merchants. Occasionally accommodation will include a swimming pool. The fabulous hospitality will be one of the highlights of your week!

  • Tuscan cuisine is primarily about simplicity. Breakfasts will typically consist of a range of breads, jams and cakes. Lunch will be served as a buffet of fresh local treats often supplemented with a pasta dish. Dinners will be at a local restaurant or your accommodation. Generally speaking these consist of antipasti (a selection of appetizers), a pasta course, a main course of meat or seasonal vegetables finished off with a sweet dish, fruit, coffee and liqueurs, all washed down with the great local wine.

    Vegetarians and people with specific dietary requirements can generally be catered for. Please indicate at the time of booking if you have any dietary requirements.

    Italian wines and food expect all tour participants

  • ​​Late spring and early autumn are probably the best months to cycle in Tuscany as the temperatures are very pleasant without being too hot. Expect temperatures around 20-25°C / 68-77°F, but some days may be as warm as 30-35°C / 86-95°F. 

    It can get chilly at night so make sure you bring something warmer as well. Occasional rain showers can be expected, especially in the hillier areas.

  • Group sizes and prices:

      • The group size for these group tours are usually between 6 and 16 participants and 1 to 2 guides, depending on the size of the group. 
      • It takes a minimum of 6 people for this tour to operate. 
      • The cost does not decrease as the group grows. 

    Mountain biking in Tuscany can be arranged for bigger groups. Contact us prior to booking.

    Min. age requirements:

      • If you are older than 18, you’re good to go.
  • To get to Pisa where your adventure begins, most people fly into Pisa International Airport. Group airport transfers are included in the cost of your holiday and both the arrival and return transfers from Pisa airport will be coordinated with the group flight schedule.

    Once you and your guide agree on the details of your itinerary, your guide will suggest the best arrival time and place to meet, usually at the airport. The tour starts in San Gimignano and finishes in Pienza.

    Please note that if you make travel arrangements that fall outside of the scheduled transfer windows, there may be an additional charge for individual transfers.

  • We highly recommend that you cover all your bases with both emergency medical and travel insurance. With medical insurance, if you have an accident or medical emergency on or off the mountain, you’ll avoid paying out of pocket for costly expenses. This covers everything from hospital treatments to emergency air transportation and more.

    Travel insurance covers canceled flights, natural disasters and other scenarios that may interrupt your travel plans. 

    We also expect you to respect local regulations and take measures to protect yourselves, your guides, and the communities you’re traveling to. For more information on travel recommendations and restrictions in Tuscany, Italy please refer to the official pages of the Italian Government

    If you need assistance selecting the right insurance for your group, let us know and we will be happy to help!

  • Secure your place with a $250 deposit due upon booking. The remaining amount is paid 3 months (90 days) prior to departure. If you book less than 60 days before departure full payment is due on booking. Depending on how far in advance you cancel you will be entitled to the following refund:

      • If you cancel up until your balance due date (90 days before the trip), you will forfeit your deposit
      • If you cancel 89 to 30 days before departure, a 50% refund of the trip price will be made;
      • If you cancel less than 30 days before the departure date, no refund will be given.

    If you need to transfer a booking to another person, or change a person on the booking, you will need to write an email with details, at least seven (7) days before your trip. There may be an administration charge to cover the cost of this transfer or change.

    Your guides reserve the right to change the itinerary or cancel the trip if they feel it would be unsafe to operate it or under any other circumstances beyond their control. They may also have to cancel your trip if the trip doesn’t reach the minimum number of participants. If this is the case, they will let you know 4-8 weeks before departure, but certainly no later than 20 days in advance.

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