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Tuscan Roads: Renaissance Cities and Road Riding

  • 4.5


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  • 7 nights | 60 miles/day
  • Difficulty Level: 4
  • Self-guided from: €1069
  • View Dates

Tours using road, hybrid or touring bikes:

  1. Mostly flat
  2. Flat with some gentle slopes
  3. Rolling, hilly terrain
  4. Some long and/or steep climbs
  5. Extensive climbing

Tours using mountain bikes:

  1. Mostly flat, wide trails
  2. Some gentle slopes, wide trails
  3. Rolling, hilly terrain and/or narrow trails
  4. Some long and/or steep climbs and/or technical trails
  5. Extensive climbing and/or highly technical trails
  1. Variety: Choose from more than 200 tours offered by local operators in 35 countries.
  2. Advice: Our informed advisors help you choose the trip that's right for you.
  3. Lower cost: You pay local tour company prices—less than what big American companies charge.
  4. Great exchange rates: Pay low rates thanks to the millions of dollars in foreign currency we buy each year.
  5. Convenience: We handle the full booking and payment process.
  6. Support: We’re your advocates from initial planning through final pedal stroke.
Tour Type: Guided Self-guided

Tour description

On this tour, you will be mainly cycling on roads with little traffic, across the hills and mountains in this almost entirely farming and still unknown region of Tuscany. Olive groves, vineyards, cypress-lines roads and wheat fields characterize the landscape in this area.

The point of departure and arrival for your tour is steeped in nature and close to the lovely wine-growing village of Scansano. The other stages are in San Quirico, located in Val d'Orcia, a valley which is part of the wine heritage area, and in the medieval town of Massa Marittima to the North of Maremma.

Our own tour signposting, combined with GPS tracking (available for a fee, upon request only), will make for highly enjoyable road cycling. Moreover, on many of the stages, you have the possibility of choosing between a longer and shorter route. On these tours across this fascinating region, the beauty of the landscape is at the forefront.

Also, you will be cycling through quaint locations such as Pitigliano, Sorano, Pienza, Montepulciano. Last but not least, you will be able to see the ruins of the cloister at San Galgano, as well as fit in a trip to the Mediterranean. It is possible, if you wish, to visit Monte Amiata, the highest mountain in southern Tuscany, standing 1734m high.

The Maremma region will spoil you also from a culinary point of view. Superb food, combined with the excellent Morellino wine will be your reward for uphill cycling during the day.

Daily program

Day 1: Individual arrival at Scansano
Tour information provided and detailed tour briefing at your first hotel.
Overnight in Scansano.

Day 2: Pitigliano (56 miles, 3937 feet gained/90 km, 1200 hm gained)
Up we go, cycling across Maremma. Olive groves, Weinhügel and wheat fields are typical of this region.The first stop in today's tour is the medieval town of Montemerano, after which we move on to the famous Cascate del Mulino in Saturnia. Those who wish will be able to enjoy a first relaxing break with free access to the small spa water springs.

Here we are at the heart of the Etruscan region. This ancient Tuscan population settled in the area long before the Romans. A long uphill ride, about six kilometers long, leads to quaint villages such as Sovana and Sorano, as well as Pitigliano which is the high point of this route. From there, cycling through Manciano, we make our way back to our hotel.
Overnight in Scansano.

Day 3: Scansano – San Quirico (50-62 miles, 4921-7874 ft gained/80-100 km, 1500-2400 hm gained)
On this stage you will be leaving Maremma and, towards the end of the route, the region of Val d'Orcia – listed as part of the world's cultural heritage – awaits you.

The initial uphill cycle ride leads to the medieval village of Roccalbegna, famous for its two large cliffs. Further along the route, there is a possibility to climb the spent volcano and highest mountain in southern Tuscany. Those who do not fancy cycling up its 1738m will have the chance to enjoy a shorter and easier route through Arcidosso.

The destination of today's stage, after cycling through the villages of Castiglione and Bagno Vignoni, is San Quirico d'Orcia. Beautiful views over the hills of Tuscany will be a valuable reward for the day's efforts.
Overnight in San Quirico.

Day 4: Val d'Orcia (53-59 miles, 2953-3937 ft gained/85-95 km, 900-1200 hm gained)
This round tour leads through the beauties of Val d'Orcia. From San Quirico we cycle uphill to the first highpoint: the small Renaissance town of Pienza. Landmarks such as the Cathedral and the Palazzo Comunale are an invitation to stop awhile; it is also well worth tasting some "pecorino," the sheep's cheese whose aroma pervades the whole village.

Turning off at the "San Biagio" junction, it is possible to make a detour into the famous wine resort of Montepulciano. Also here it is worthwhile taking a short tour to Piazza Grande and admire the beauties of the town. The route then leads through the spa town of Chianciano Terme, then Sarteano and on towards Radicofani, whose most famous landmark is the medieval fortress. Cycling through a fantastic hilly route, we make our way back to San Quirico!
Overnight in San Quirico d'Orcia.

Day 5: San Quirico – Massa Marittima (65 miles, 5906 ft gained/105 km, 1800 hm gained)
After a downhill start of the tour, you will be riding uphill to the hometown of Brunello wine, Montalcino. Next, you will be cycling through macchia mediterranea (maquis) in the Val di Merse and the Tocchi nature reserve. One of the high points of this tour is the old cloister of San Galgano. Through the medieval village of Prata and more woodland areas, we finally reach today's destination: Massa Marittima.
Overnight in Massa Marittima.

Day 6: Tour "mare e monti" (62-75 miles, 2297-3937 ft gained/100-120 km, 700-1200 hm gained)
Today's tour starts with an uphill cycle to the old town of Monterotondo Marittimo. A cappuccino break between the medial walls is well deserved. After a downhill ride through the "Colline Metallifere" region, a mining area since Etruscans times, we reach Monteverdi Marittimo.

Enchanting views will be a reward for the uphill cycling effort. You will get more exciting panoramas while riding from Sassetta to Suvereto, on a winding stretch of road through the cork oak forests of Val di Cornia, which is a must-see for any road cyclist. The last third of today's route leads to the seaside at Follonica, with excellent swimming possibilities offered by the beaches of Carbonifera and Torre Mozza.
Overnight in Massa Marittima.

Day 7: Massa Marittima – Scansano (62 miles, 4265 ft gained/100 km, 1300 hm gained)
This final tour is once again characterized by the unique landscape of Maremma. The ride begins with an uphill cycle, about six kilometers long, through woodland. The medieval villages of Roccatederighi and Roccastrada are ideal for a short break.

After a rapid climb to approximately one hundred meter altitude in Campagnatico, you will get an overview of the Ombrone valley. This part of the tour is a straight and flat cycle ride along the "highways." After the final long climb of the week, you will have earned a glass of Morellinowine in the square at Scansano, as well as a relaxing massage and an excellent dinner in your bike-hotel.
Overnight in Scansano.

Day 8: Departure


Saturdays: Apr 7-Oct 13, 2018 (minimum 2 persons)
Low season: Apr 07, 2018 - Jun 23, 2018, Sep 16, 2018 - Oct 13, 2018
High season: Jun 24, 2018 - Sep 15, 2018


Tour package
Per person, double occupancy
High season surcharge
Single room surcharge (1 person/1 room)
Low season
High season
Solo traveler surcharge (1 person in party)
Optional dinner package
Bike Rentals
Carbon road bike
Please note: Instead of operating bicycle tours ourselves, BikeTours.com represents local bicycle tour operators around the world. Review the tour operator's information and terms below, then submit your booking request through BikeTours.com. The primary benefits of booking your tour through BikeTours.com include:
  • Lower cost: You pay local tour company prices—less than what big American companies charge
  • Variety: Choose from more than 200 tours offered by local operators in 35 countries.
  • Advice: Our informed advisors help you choose the trip that's right for you.
  • Great exchange rates: Pay low rates thanks to the millions of dollars in foreign currency we buy each year. Or pay in euros!
  • Convenience: We handle the full booking and payment process.
  • Support: We’re your advocates from initial planning through final pedal stroke.
Contact us with any questions about booking and paying for your tour through BikeTours.com. We look forward to serving you!

Giro di Toscana Terms and Conditions

Cancellation by the Customer/Substitute Participants/Changes to the Reservation
1. The Customer may withdraw from the agreement at any time prior to the start of travel. We recommend that the Customer communicate his or her cancellation in writing. In the event of a cancellation or no-show, we shall be entitled to charge the following fees (percentages refer to the price of travel):

  • Up to 28 days before the start of travel: 20 % / minimum €50,
From 27 to 14 days prior to the start of travel: 30 %
  • From 13 to 8 days prior to the start of travel: 50 %
  • From 7 to 4 days prior to the start of travel: 70 %
  • From 3 days and no-show: 90 %
  • By travel expensen 100% on the travel price.

We recommend a travel withdrawal insurance, please note that the insurance doesn't work for travel expenses. For that case you shall take another insurance.

2. Each registered travel participant may allow a third-party to take his or her place if he or she notifies us thereof in writing up to three days prior to the start of travel. The tour operator may refuse the third party's participation for good cause. The conditions of cancellation above shall apply. If a substitute person takes the registered participant's place, this shall not affect the original contract. We shall be entitled to charge €50 for change fees.

3. Changes to the booking in terms of number or types of rooms, hotel category and type of board shall, providing such is possible in the hotels and there is sufficient capacity available, is basically possible up to 14 days prior to the start of travel. Nonetheless, we will however have to charge you for the time and effort involved. For each change, we shall charge you €50.

I. Conclusion of the Travel Agreement
1. By registering, the Customer undertakes to enter into a travel agreement with the tour operator. Registration shall take place in writing on the form designated for this purpose. A telephonic, oral or other form of registration with us or one of our partner agencies shall be equally binding. Registration shall be carried out by the registering party for all co-named participants. The registering party firmly agrees to these conditions of travel, including on behalf of and for the co-named participants.
2. The agreement shall come into being upon acceptance by the tour operator or its partner agencies upon sending the booking confirmation.
3. Subsidiary agreements and amendments to the concluded travel agreement shall require our written confirmation.

IV. Services
1. With regard to the scope of the contractual services, the descriptions of service provided in the current EUROBIKE catalogue shall be authoritative, but not however any differing statements or promises by intermediary travel agencies, town or hotel brochures or other third parties. The stopover locations are the most frequent and main stopover destinations on the cycling tours. Under certain circumstances, we must require your consent to be placed in towns in the immediate vicinity without any deductions.

2. The price of travel listed is per person based on occupancy in a double bed room. If available, a single bed room can be booked for a surcharge. In some hotels however there are only a limited number of single bed rooms meaning that you may if necessary have to make due with a simpler room or, under certain circumstances, have to go to another hotel or private bed and breakfast. If, exceptionally, no single bed room can be made available, you will have to share a room in a two bed room. In this case you will of course receive a prorated refund.

3. For families, we grant the following discounts off the basic price and extra nights as a third person in a double room with two full paying guests: 0 to 5.99 years old: 100% (any costs incurred shall be paid on site), 6 to 11.99 years old: 50%, 12 to 14.99 years old: 25%, age 15 and up: 10%

V. Liability and Limitation of Liability
1. The tour operator shall be responsible for making pre-travel preparations, careful selection and monitoring of the service providers as well as for the accuracy of the descriptions of service valid for the period of travel at the time our catalogue is printed.
2. Travellers shall take part in our cycling journeys at their own risk. Minors may only participate in a journey when accompanied by a parent or guardian.
3. Every travel participant shall be responsible for ensuring that his or her health is suitable for the requirements of travel.
4. In addition, every travel participant shall be responsible for the observance of traffic regulations.
5. The conditions of carriage of the particular transport companies shall apply to all means of transport (bus, boat, airplane, etc.).
6. If, due to reasons beyond our control (adaptations, renovations, etc.) a scheduled tour cannot take place, we cannot assume any liability.
7. In the event of damage caused solely by one of the service providers selected by us or which is not due to premeditation or gross negligence on our part, then our liability shall be limited, regardless of the legal basis, to three times the price of the journey.
8. In the event of loss or damage to travel luggage, we shall only be liable if the loss or damages is caused by us and is communicated to us immediately after the occurrence. In this event, we shall only be liable for up to a max. of EUR 200.00 per person. We assume no liability for: items which are not usually transported in travel luggage, means of payment of any sort, for visual damage and damage to handles and wheels or damages to pieces of luggage weighing more than a total of 20 kg. We recommend that you take out a travel security package to cover these risks.
Transportation of customer bicycles before, during and after our cycling journeys is possible at the customer’s own risk only. The settings of our cycle carriers are fitted to our rental bicycles, therefore minor damages (e.g. scratches to the paintwork) can occur. Consequently, we cannot be made liable for damages originating from transportation. Above mentioned limitation of liability is also applicable for partner tours and transportation via third parties.
9. If a journey is cancelled due to reasons beyond our control (strike, natural disaster, etc.) or if the minimum number of participants of guided group tours (8 people) and bike & boat tours (15 people or as listed in the offers) is not reached, we reserve the right to cancel the journey up to 25 days before the planned travel date. In this event you shall be notified without delay and will be refunded any amounts already paid to us. You shall not be entitled to any compensation beyond this.

VI. Guarantee
1. Remedies: If the travel service cannot be performed as specified in the agreement, the Customer can demand redress. What is contractually specified shall be based on the one hand on the description of service and on the other on what is customary in the destination country. The tour operator can refuse a remedy if it requires disproportional costs and efforts but shall also be entitled to provide a remedy in the form of services of equal or greater value. Substitute services can only be refused by the Customer for a significant, objectively identifiable reason. The demand for a remedy shall be communicated directly to us or to the guide. The guide shall have no authority to recognise claims.
2. Travel Price Reduction: The Customer may, after returning from the journey, request a reasonable reduction in the price of travel (discount) for the duration of the contractually non-contractually compliant portion of the journey until a remedy is provided by the tour operator. The reduction shall not apply if and to the extent that the traveller, through his or her fault, fails to communicate the deficiency to the parties listed in Item VI (1) in a timely manner so as to enable them to provide a remedy.
3. Any claims must be lodged with us no later than one month after the contractually scheduled end of travel.

VII. Duty to Cooperate
1. If the traveller does not receive the travel documents in a timely manner, he or she must inform the tour operator without delay.
2. The traveller is required, in the event of any issues disrupting the provision of the services as described in the agreement, to take all reasonable steps to contribute to remedying the disruption any to minimise or avoid any damage. The Customer is, in particular, required to lodge his or her complaints without delay to the parties named in VI (1). These parties shall be in charge of providing a remedy if such is possible. If the Customer fails, through his or her fault, to communicate a deficiency, than he or she shall have no claim to a reduction in price.

VIII. Miscellaneous
1. The Customer shall be responsible for complying with all passport, visa, customs and health regulations.
2. We must reserve the right to make changes to prices and services and to correct any mistakes and typographical errors.
3. The invalidity of individual provisions in the travel agreement shall not invalidate the rest of the agreement.

IX. Jurisdiction/Applicable Law
1. The agreement is governed by Austrian Law.
2. The Customer may only bring legal action against the tour operator at its registered place of business.
3. The Customer's place of residence shall be authoritative for actions by the travel against the customer unless the action is directed against general merchants or persons without a general place of jurisdiction in Austria. In this case, the registered office of the tour operator shall be authoritative.


With us, your money is insured!
Pursuant to the Travel Agency Guarantee Decree [Reisebürosicherungsverordnung (RSV)] for all-inclusive journeys offered by the tour operator (registration number 1999/0035 in the Directory of Tour Operators of the Federal Ministry of Economics, Family and Youth, customer funds are secured subject to the following conditions: any payments exceeding those indicated in Item II or previously paid down payments and payments of balances owing may not be demanded nor are they secured. The guarantor or insurer is Volksbank Braunau, 5280 Braunau (bank guarantee no. 5746).
Filing of any claims must be done with the liquidator (Europäische Reiseversicherung AG, Kratochwjlestestraße 4, 1220 Vienna, Tel. no. +43(1) 317 25 00, Fax. no. +43(1) 319 93 67) within 8 weeks insolvency being declared.
Applications for refunds must be submitted, duly documented within 8 weeks of the claim arising. You shall receive a corresponding insurance certificate along with your booking confirmation.

All photos used by permission. ©Giro di Toscana


Ratings Snapshot

  • 5 Star 2
  • 4 Star 2
  • 3 Star 0
  • 2 Star 0
  • 1 Star 0

Average Ratings

  • Overall


  • Difficulty level (Actual vs. expected) 3.8
  • Value 4.8
  • Included meals 4
  • Bikes & equipment 4.3
  • Hotels or boat 4.5
  • Scenery 5
  • Ease of navigation 3.8
  • Tour documents 2.8
  • Local tour company services 4.3
  • Route selection 4.5


John from Naperville September 11, 2017

Beautiful area and challenging riding for average riders

Expect to have a nerve-racking exit/entry from and into the major towns due to traffic and high risk and high speed drivers. Most of the climbing in the area are short, with an occasional multi-mile but gentler climb. The scenery is often breathtaking. Tour book does not offer enough information, such as markets or places to find restrooms in each town.

spokes October 1, 2016

The Standard for Future Tours

My wife and I and another couple took this tour in the middle of September and were very pleased with the experience. We are all experienced cyclists and have high end bikes at home. The bikes we rented were excellent. They were light, stable, comfortable and reliable. They climbed well and were fun on the downhills. We brought our seats, pedals and bike shoes as recommended and that made a big difference on comfort. The bike routes were amazing and very well marked along the way. We uploaded the GPS files sent by the tour operators into a mapping AP called Motion-X GPS, that can be installed easily on a smart phone. We checked the paper version of the turn-by-turn route directions provided by the tour company and Motion-X occasionally, but for the most part were able to find our way just using the symbols posted on sign posts. This allowed us to enjoy the rides without having to constantly stop and look at maps. All rides necessarily started and ended on roads with moderate traffic, but after about 20 minutes we were on lovely, narrow country lanes and roads with few cars or trucks. We loved passing through vineyards, olive tree groves, and the hill-top villages along the way. We live and bike regularly in a hilly part of the U.S. and really enjoyed riding the Tuscan roads, which are moderately hilly. Most of the climbs were short and not too steep, but expect a few challenging climbs along the way. It was great having two nights in the three towns. All of the hotels were nice, comfortable and had some charm. They were all within a short walk of restaurants and other sites in the towns. The owner of the touring company gave us a nice welcome and orientation on the arrival day, and was responsive to some questions we had during the tour. This was an excellent tour and will be the standard by which we judge future trips.

ygto August 12, 2016

Excellent way to explore Tuscany

The communications with BikeTours was excellent, my wife and I were looking at different start date and BikeTours were able to offer that in a short time. We would give the tour 5 stars but there were a few cases for inaccurate information such as stops for food and some road constructions that made us alter our route. A few notes of caution: this is not an easy ride, there are almost no "flats" in Tuscany so be prepared for hard work. It is definitely a ride for experienced cyclists. July in Tuscany is HOT, some days we hit the 97 Fahrenheit and you must be prepared with plenty of water and arranged spots to fill your bottles. In most days we left the hotel early, before breakfast just to avoid the extreme heat. If you choose to go in July- August it is recommended to talk with tour provider to arrange an early breakfast so you are riding on an empty stomach. The rented bike are ok, not great, mine were not tuned so had noise every time I switched to the large chainring (Because the abandoned of hills it never was for a long time). Also make sure you have at large ring at the rear cassette. I had only 27 (Campagnolo) and there were a few times that I wished for 29 or larger

ldf31 May 3, 2016

Can't think of a better way to see Italy!

This was my wife and my first ever bike tour and first visit to Italy. We both have ridden and raced bikes for over 18 years and ride around 100+ miles per week on average, mostly year round, just for context. When looking at tour options we wanted a challenge but also a chance to experience what Italy has to offer and this tour did not disappoint on either account!

First, I would say that dealing with BikeTours up to the last minute of our trip was excellent. They were spot on and timely with directions, from booking to the most minute questions regarding the tour itself. Got to give them two thumbs up for sure.
Giro di Toscana was our local operator and although our contact with them was limited, the contact we did have was super friendly and accommodating. Unfortunately on our last day we missed our train due to a delay in getting our bags. Raimond with Giro di Toscana was quick to address this, checking train schedules for us and even arranged to have us taken to the train station to make up for it...very nice! The bikes we were given were excellent (nice carbon with Campy components), we opted to pay the extra 20 Euros for the GPS (thank God) and everything operated as or better than expected.

As for the tour itself, the riding was a bit tougher than we anticipated in that each stage took a bit longer due to the profile (you can count the flat straightaways on one hand), road conditions which if you're from the US will be unbelievably poor at times, weather (we had some cold temps and rain) and stops along the way to take pictures due to the UNBELIEVABLE scenery and cool small towns and villages along the way. Each days ride took between 4 - 5 hours which seems long given the miles covered but it is what you should expect unless you're planning to time-trial each stage. Also, if you can, get the GPS! I can't fathom how one would navigate this tour with a cue sheet as the only means to get from point A to point B. The tour company puts stickers on most of the signs along the way (which were always nice to see) but this is hit or miss as a few of the stages have two pages worth of turns. This is not a knock on the tour company, it is just a fact of life when dealing with the roads of Italy in and out of small towns and on back roads. There are a lot of turns. This is not a tour for casual cyclists, for sure, but all the hard work made all the great food and sights that much better!

For accommodations, we spent 2 nights each in Montecatini, Volterra and Siena all of which were unique and awesome in their own ways. We really enjoyed the 2 night stay version as it really does give you time to explore and get to know each city a little more intimately. We would say the quality of the hotels in Montecatini and Siena was good and Volterra more like a hostel (clean but dated and spartan). All of the hotels were in great locations with easy access to food/drink and sights and Giro di Toscana made sure our bags were in our rooms each stop which was nice.

In hindsight a few small details could make this a slightly better tour. First, it would be nice to get the routes in advance with the elevations, just to prepare a bit better. From the tour company, they leave a pump each morning for tires but it would also be helpful if they would leave some chain lube (After a few days riding in the rain the chain gets a little squeaky) and a few spare tubes, given the road conditions. We managed fine, but a bit more suggestions on sightseeing/dining along the way or in destination cities may be helpful for newcomers to Italy.

All in all a great tour. Great riding that will definitely leave you feeling like you put in some honest work, unbelievably awesome scenery and towns along the way with three truly unique cities to explore. For our first bike tour we could not have asked for more...what an adventure!