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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: €789
  • 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

This tour combines road cycling through a unique, hilly landscape with staying in historic artistic and cultural cities in the region of Tuscany.

On the Giro "Classico" you will experience the beautiful Tuscan landscapes in all of its variety. The fascinating climb to the Etruscan site of Volterra, a trip to the Mediterranean, and to Castellina in Chianti are "highlights" of the week. You will also visit the charming landscape of Crete, south of Siena and the town of San Gimignano with its many towers.

The point of departure and arrival is the spa town of Montecatini Terme, in northern Tuscany which is a hub providing ideal connections. The journey continues through the next stages, in a two-day rhythm, giving you a chance to relive your impressions while sitting down to enjoy a tasty dish of pasta and a glass of Chianti wine in one of the typical local trattorias.

Daily program

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

Day 2: Vinci roundtrip (47 miles, 2625 feet gained/75 km, 800 hm gained)
The tour starts by leading you through flat and then slightly hilly terrain. This unique cultural landscape follows the wine route known as “Strada dell‘Olio e del vino del Montalbano“, all the way to the small medieval village of Vinci, where you can visit the Leonardo Museum and the birthplace of the famous Renaissance artists. Cycling along olive groves and grapevines, the return trip starts with a long climb which will give you a fantastic, worthwhile sight of the Monti Pisani mountain range and of the Valdinievole.
Overnight in Montecatini Terme.

Day 3: Montecatini Terme – Volterra (56-68 miles, 4265-5249 ft gained/90-110 km, 1300-1600 hm gained)
Today’s stage will lead you initially through woods and nature reserves, before crossing the Arno valley and reaching the first short climbs. We will then be cycling southwards, through small medieval villages. This means a full immersion in the hilly landscapes of Tuscany; from a distance it will already be possible to discern today‘s stage destination, Volterra, at a height of 531m above sea level.
Overnight in Volterra.

Day 4: Cecina roundtrip (65 miles, 4593 ft gained/105 km, 1400 hm gained)
Enjoying a wonderful view, we will be cycling downhill from Volterra and then continue along the Cecina valley towards the “Costa degli Etruschi“. The sandy beach and the true-blue Mediterranean at Marina di Cecina will be your reward for the effort you have put into the steep climb to Guardistallo. The road is lined with the tallest cypress trees in Italy and the hilltops covered in vines and olive trees around Bibbona offer another glimpse of pure Tuscany before a final ascent leading to the Etruscan site.
Overnight in Volterra.

Day 5: Volterra – Siena (50-59 miles, 3937-4921 ft gained/80-95 km, 1200-1500 hm gained)
After a brief visit to Volterra and a long excursion around the valley, the route today leads through the hilly landscape, first of all to the town of San Gimignano, which beckons you to pause in its medieval setting. The second part of this stage is an excursion through the wine hills of the “Colli Senesi“, cycling by the “Castello di Monteriggioni“ before we reach the destination of today’s stage, Siena, which will require a final climb.
Overnight in Siena.

Day 6: "Crete" roundtrip (62-75 miles, 2297-3937 ft gained/100-120 km, 700-1200 hm gained)
South of Siena the bizarre, as well as fascinating landscape known as the “Crete”, is well worth a visit by bicycle. Continuous ups and downs lead you to Asciano. Quiet roads with charming views pass through Buonconvento and continue across the forest area known as Montagnola. With Siena as a destination in sight already during the final few kilometres, today’s tour ends in the city of the “Palio“.
Overnight in Siena.

Day 7: Siena – Montecatini Terme (68 miles, 3937 ft gained/110 km, 1200 hm gained)
The first part of this “royal stage“ includes the world-famous wine production area of ”Chianti Classico“. The climb to Castellina, leads to the highest point in the tour, 630m above sea level. From a landscape viewpoint, this area looks like an extensive garden, with vineyards, olive groves, cypresses and woodland all harmoniously intertwined. Cycling through the hometown of Leonardo da Vinci and the wine production area of Montalbano, we will make our way back to our point of departure in Montecatini Terme.
Overnight in Montecatini Terme.

Day 8: Departure

Route map

Maps reflect your approximate overnight locations and do not reflect your actual cycling route.


Saturdays: Apr 6-Oct 19, 2019 (minimum 2 persons)


Tour package
Per person, double occupancy
Single room surcharge (1 person/1 room)
Solo traveler surcharge (1 person in party)
Bike Rentals
Carbon road bike
Hybrid bike
Extra Nights, Montecatini Terme
Per person, double occupancy
Single room surcharge (1 person/1 room)
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!