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Tuscany - Sacred Routes

Self-Guided Mountain Bike Tour




7 days

Prices from

$1,725 P.P.

Tuscany - Sacred Routes

Self-Guided Mountain Bike Tour




7 days

Prices from

$1,725 P.P.
The Tuscan landscape hosts this fantastic self guided mountain bike holiday. The famous sights of Tuscany are combined with great biking exploring woodlands, hills and valleys with some great tracks and routes that link famous hilltop towns such as San Gimignano, Siena, Pienza. This holiday will enchant with its natural beauty as well as reward with the quality of the riding. While perhaps better known for its rolling hills and quiet roads, Tuscany's long history of trade and agriculture has resulted in an extensive network of trails of all kinds. Thrilling forest singletrack is mixed with scenic country lanes and the rolling landscape gives us challenging climbs and fun descents.
After arriving in Pisa we will drive you through the beautiful Tuscan Landscape, arriving at your first accommodation in the countryside of San Gimignano. Here you'll stay in a stunning Agriturismo surrounded by vineyards where your host will treat you to your first Tuscan tastes. Over the next 3 days you'll bike across forested hills, through vineyards, down river valleys, across streams, past abandoned farmhouses and up to tiny fortified villages. Some rides follow the ancient Via Francigena pilgrimage route and the Eroica roads, hence calling this trip the “Sacred Routes”! The Via Francigena was a trail which once connected Canterbury to Rome, while the Eroica routes are gravel roads used in the Giro d'Italia before tarmac was common.
Midway you'll arrive in Siena, steeped in Italian Renaissance atmosphere. Scattered with great restaurants and superb Gelateria, this is the perfect place to end the first part of the trip. For the next three days you enter the Crete Senesi, where you are in for some thrilling riding along steep valleys, dense forests, rivers and the legendary “badlands”, eroded clay slopes around Siena and Val D'orcia. Here the riding is a roller coaster of tracks and trails riding from lowlands to open ridge views, enjoying descents that will leave you smiling all day!


  • Stay in a Tuscan farmhouses overlooking stunning landscapes
  • Ride The Montagnola trails, location of a well-known Sienese MTB race
  • Sample the best wines of Chianti, Montepulciano and Montalcino
  • Riding down the “Crete Senesi” on a roller coaster ridge ride
  • Enjoy the journey across Tuscany on a variety of terrain
  • Visit the famous hilltop towns of San Gimignano, Monteriggioni, San Quirico d‘Orcia, Pienza

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We loved the variety of the days, enjoying every single day of the trip. It was great! The service was excellent.

Anna, UK


Day 1
Arrival: Pisa - Transfer to San Gimignano
Non Riding Day
  • Meals: Dinner

You will be met at Pisa airport and transferred to San Gimignano. Your accommodation is set in the outskirts of the famous town. With a plunge in the pool overlooking vineyards, the fun is really starting. You will normally have your dinner at the estate.

Day 2
San Gimignano to Monteriggioni
22 Miles / 35 Kms Approx.
  • Meals: Breakfast
  • Ascent: 600 Metres Approx.

Today you set off with a fun off-road section down into the lower valley before looping back towards St Gimignano. You 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. It can be muddy at times!

The destination for today is Abbadia Isola a small medieval hamlet set within stone walls not far from Monteriggioni. After stopping in the square for a well deserved beer you can move on to your accommodation, where you can enjoy a dip in the pool before heading out for dinner.

Day 3
Monteriggioni to Siena
19 Miles / 30 Kms Approx.
  • Meals: Breakfast
  • Ascent: 850 Metres Approx.

You’ll start the day with a steady off-road climb through the Montagnola range which offers great options of trails and routes. This area is a well known destination for the Gran Fondo Sienese MTB race. This area is also ideal for some fun mountain biking, as you 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 leads to the outskirts of Siena. One last push on tarmac and you roll into the old walls of this quiet town. There is time to wander through Siena, visit the Palio Square and Duomo, before heading out to dinner for a mouthwatering Tuscan meal.

Day 4
Siena to Buonconvento
28 Miles / 44 Kms Approx.
  • Meals: Breakfast
  • Ascent: 650 Metres Approx.

Leaving Siena through the ancient town gates you continue your journey south on the Eroica route and into the Crete Senesi. Arriving near the ancient Etruscan hamlet of Murlo, you’ll enjoy a fun ride on narrow trails by the Crevole River, then up a former mining railway track to Murlo itself.

Picking up the Eroica route you head to Buonconvento where you’ll have time to stop for a refreshing break and if inclined visit the fortified walls. A short afternoon section leads to the accommodation.

Day 5
Buonconvento to Pienza
26 Miles / 42 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,000 Metres Approx.

Your mountain bike pilgrimage continues as you head towards Pienza, right in the heart of the Unesco heritage site of Valle d‘Orcia. The route takes you along the ridge lines of the “crete” offering 360 degree views. The trails are a mix of farm tracks and dirt roads, with cheeky steep sections which will get you out of the saddle!

Today is a shorter day, and after joining a section of the Eroica you’ll reach our accommodation in Pienza.

Day 6
Pienza Loop - San Quirico d'Orcia, Bagno Vignoni
23 Miles / 36 Kms Approx.
  • Meals: Breakfast
  • Ascent: 850 Metres Approx.

Different options are available for today’s ride. Whichever way you decide to ride the various terrains and routes will take you to San Quirico d‘Orcia. From here you’ll descend quite steadily on a fast gravel track into the Orcia valley then loop back through fields, dense woods and past castle hamlets, until reaching the medieval hamlet of Bagno Vignoni with its healing baths and home to the legendary water nymphs. After resting and taking time to explore the hot water springs, you’ll head right into the centre of the Unesco heritage site of Valle D‘Orcia.

From there you start a steady climb towards Pienza along some well surfaced strade bianche. Time in Pienza to absorb and visit the local sites, to then carry on back to our accommodation for another relaxing evening. We head into Pienza for dinner.

Day 7
Departure: Pienza - Transfer to Pisa
Non Riding Day
  • Meals: Breakfast

After breakfast we’ll transfer you back to Pisa to say your farewells and savour the memories of a fantastic week on your bikes.

If you wish to spend a day in Pisa at the end of the trip, drop us a line and we can arrange accommodation and may be able to organise a transfer to a hotel instead of the airport.

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The Cycling


Tuscany is a region with rolling hills of cultivated fields, woodland and chalky landscape, with quaint little hamlets dotted on hilltops.

Riding is on a mix of chalky double track or “Strade Bianche” so it can be fast rolling in dry conditions, or of course, get a bit more sketchy in the wet. A mountain bike with off-road tyres is the best choice. The wider tracks will be alternated with some fun, flowing narrower trails that can be rocky and with roots in sections. On the Montagnola range near Siena, fun sections of singletrack can be a bit rocky with limestone making the trails a bit tricky in places.

There are a few steep, and a few long climbs, so fitness is more important than off-road riding skills – of course all the climbing leads to some great descents.


Mountain Biking Grade

Grade 3 - 4: Moderate/ Challenging

25-50 miles / 40-80 kms per day

Aspects of both our grade 3 and 4 trips

For mountain bikers with some experience of singletrack and steeper terrain

May include rocky features and switchbacks

Our grading guidelines have been carefully created based on our many years of cycling experience, as well as customer feedback from our trips. Of course, if you're still struggling to figure out where you fit on the scale, do feel free to give us a quick call and we'll be more than happy to help!

For more information about our grading system click here.

Is this suitable for you?

Trips that are graded as a 3-4, will have aspects of both our grade 3 and 4 trips. If you have experience of off road riding on a variety of terrain, and would like a taste of more challenging terrain, a grade 3-4 trip could be for you. Terrain will include singletrack and steep sections (both up and down) which require more bike handling ability. Shorter technical and demanding features suchs as rocks, roots and tricky climbs will be encountered on occasion on most days. A day’s ride can see you on the trails for around 8 hours (with breaks) and covering between 25-50 miles depending on the terrain. If you’re generally fit and manage to ride frequently this could be the level for you.

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Fantastic trip – the best we’ve done, and it was our twelfth!

Roger, UK

Dates & Prices

Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

2022 26 Mar – 30 Oct.

Season 1 – $1730 – 26 Mar to 14 Apr, 02 May to 24 Jun and 04 Sep to 30 Oct

Season 2 – $1930 – 15 Apr to 01 May and 25 Jun to 03 Sep

Choose your date
Start Date
End Date
Price p.p.
Start Date
Return Date
7 days

Whats Included Tick

A) Accommodation (shared twin / double en suite rooms)

B) Meals as per the itinerary (B=Breakfast, L=Lunch, D=Dinner)

C) Local representative (with welcome meeting)

D) Detailed route notes and maps

E) Luggage transfers

F) Airport transfer on scheduled arrival day from Pisa airport (PSA)

G) Airport transfer on scheduled departure day to Pisa airport (PSA)

What's not Included Cross

A) Bike rental (available if required)

B) Flights and charges for travelling with your bike (if applicable)

C) Meals not stated in the itinerary

D) Single room (available if required)

E) Travel insurance

F) Personal clothing and equipment

G) Personal expenditure (souvenirs, bar bills, hotel facilities etc)

H) Entrance fees to museums and other attractions en route

I) Local tourist tax to be paid at each accommodation (approx 2€ per day)

J) Airport transfers on days other than the scheduled arrival / departure days

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The Essentials

Travel Options

Your tour starts in San Gimignano and finishes in Pienza.

Airport transfers are included in the cost of your tour. We ask that you fly into and back from Pisa airport (PSA). Please aim to arrive between 09:00 and 16:00 and depart between 11:00 and 19:00.

There are no direct flights to Pisa from North America but there are a wide choice of flights with one stop in a larger European airport. Flights from North America typically depart in the late afternoon/evening and arrive the following morning.

Please check with Skedaddle before making any travel arrangements.

Please note If you make travel arrangements that fall outside of the above time windows there may be an additional charge for your transfers.


The majority of our accommodation (shared twin or double rooms) will usually be ensuite in 3 star guest houses, agriturismos or hotels. Occasionally accommodation will include a swimming pool.

The fabulous hospitality will be one of the highlights of the week.

We have an upgrade option available on this tour (5 nights in upgraded hotels). Please select the hotel upgrade supplement at the time of booking.

Bike Hire

If you don’t own a suitable bike or would prefer to avoid bringing your own we have hardtail bikes available to rent. These bikes are typically very good mountain bikes featuring front suspension, disc brakes and good quality components.

We also have electric mountain bikes available on request, these are typically Focus Jarifa 2 Ex Active or Summit E Bikes (or equivalent). It may take us a day or so to confirm availability so please let us know as soon as possible if you’d like to take this option.

We can include a helmet and all necessary spares for the trip. Please request helmets at the time of booking.

If you choose to rent a bike from us you are welcome to bring your own saddle with you, and if you would like to use SPD/clipless pedals you will need to bring these with you.

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