Cycle the Wine Regions of Tuscany

Cycle the Wine Regions of Tuscany

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8 Days From

$1650

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Tour Overview

Embark on a captivating cycling adventure through the enchanting wine regions of Tuscany with our "Cycle the Wine Regions of Tuscany" tour. This self-guided journey invites you to explore Italy's picturesque landscapes, from medieval villages and hilltop towns to cypress-lined hills and lush vineyards. Pedal through the renowned Brunello wine district to Montalcino, climb to the monastery of Monte Oliveto Maggiore, and unwind in the thermal waters of Bagno Vignoni. Enjoy the panoramic roads leading to Montepulciano, where you can savor the exquisite Vino Nobile wine. With accommodations in charming 2-3 star hotels and agriturismo, including an organic farmhouse, this tour offers a perfect blend of cultural exploration and natural beauty. Equipped with a hybrid bike, pannier, and odometer, you'll traverse well-maintained country lanes and smooth turf roads, ensuring a memorable and invigorating experience in the heart of Tuscany. ...more ...less

Highlights

  • Medieval villages and hilltop towns

  • Explore the Brunello wine district and visit Montalcino

  • Ride through the countryside to Murlo and Le Befa

  • Climb to the monastery of Monte Oliveto Maggiore and visit Sant’Anna in Camprena

  • Relax in the thermal waters of Bagno Vignoni

  • Cycle panoramic roads to Montepulciano and enjoy Vino Nobile wine

  • Cypress lined hills and vineyards

Places You'll See

Wine barrels in a Montepulciano cellar, Tuscany, Italy

Wine barrels in a Montepulciano cellar, Tuscany, Italy

Itinerary

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Day 1 : Arrive Buonconvento

Location: Buonconvento

Accommodation Name: Organic Farmhouse (Agriturismo)

Meals Included: Dinner

Make your own way to Buonconvento. For your 4 nights, you will be staying at an organic farmhouse (agriturismo) nestled amidst the magnificent rolling countryside of the Crete hills south of Siena. This large Tuscan estate produces olive oil, organic cereals and pasta that are used to prepare the typical regional dishes you will enjoy at their restaurant. ...more ...less

Day 2 : Circular ride to Murlo & Le Befa (33km/20.5mi)

Location: Murlo, La Befa, Buonconvento

Accommodation Name: Organic Farmhouse (Agriturismo)

Meals Included: Breakfast, Dinner

A great first ride through the countryside on well kept dirt roads to Murlo. Immerse yourself in the dense woods as you ride by the Crevole River. Continue past steep cliffs to the sweet smell of bright yellow flowers and through an enchanting oak tree forest to La Befa. A short part of the trail is too narrow or rocky to cycle (about 300m) however the exhilarating views are more than worth the effort. Return to Buonconvento.

Day 3 : Circular ride to Montalcino (24.1 or 42.6km/, 14.9 or 26.4mi)

Location: Buonconvento, Montalcino

Accommodation Name: Organic Farmhouse (Agriturismo)

Meals Included: Breakfast, Dinner

Pedal through vibrant fields of sunflowers past Buonconvento to the heart of the Brunello wine district. The Monte Amiata volcano lures above as the surrounding countryside transforms into endless olive groves and vineyards. Ride steeply up to the fortified city of Montalcino where you can visit its magnificent 14th century fortress and Palazzo Comunale, then return to Buonconvento along remote back roads.

Day 4 : Cycle to Pienza (37.7km/23.4mi)

Location: Monte Oliveto Maggiore, Sant'Anna in Camprena, Pienza

Accommodation Name: Hotel in Pienza

Meals Included: Breakfast, Dinner

Climb uphill to the renowned monastery of Monte Oliveto Maggiore with its delightful frescos and botanical garden. After replenishing your soul, follow a winding route past isolated villages until you reach a row of hundreds of cypress trees, inviting you to visit the stunning Sant’Anna in Camprena monastery. Admire the frescos then finish your day in the lovely town of Pienza.

Day 5 : Loop cycle to Bagno Vignoni (27.7km/17.2mi)

Location: Bagno Vignoni, Pienza

Accommodation Name: Hotel in Pienza

Meals Included: Breakfast, Dinner

Today is a relaxing day in which you will travel on smooth country roads to the medieval hamlet of Bagno Vignoni where you can rest and swim in its healing thermal waters, enjoyed by the Romans and home to the legendary water nymphs. Ride back to Pienza along gently undulating hills through unspoiled countryside embracing the essence of Southern Tuscany.

Day 6 : Circular route to Montepulciano (34km/21mi)

Wine barrels in a Montepulciano cellar, Tuscany, Italy
View of Montepulciano, Tuscany, Italy

Location: Pienza, Monticchiello, Val d'Orcia, Montepulciano

Accommodation Name: Hotel in Pienza

Meals Included: Breakfast, Dinner

From Pienza, travel along immensely panoramic roads past the medieval stone-built hamlet of Monticchiello. Ride up a remarkable limestone ridge and enjoy breath-taking views of the Val d’Orcia. Gather your strength as you make the climb up to Montepulciano. Upon arrival, celebrate with a glass of the famous local Vino Nobile wine before freewheeling back to Pienza.

Day 7 : Cycle to Pieve a Slati via Lucignano d'asso (24km/15mi)

Location: Orcia Valley, Lucignano d'Asso, Pieve a Salti

Accommodation Name: Organic Farmhouse (Agriturismo)

Meals Included: Breakfast, Dinner

The ride today is mostly on gravel road, gentle rolling hills in the most beautiful countryside of the Orcia valley. Half way you can stop in Lucignano d'Asso, a tiny village on the L'eroica cycle route. Then you ride back to the organic farm of Pieve a Salti where you spend your last evening.

Day 8 : Transfer to Buonconvento, trip concludes

Location: Buonconvento

Meals Included: Breakfast

After breakfast a short transfer takes you down to Buonconvento (arrange the time with the reception in advance), where you can catch the local bus or train to the airport for your onward journey.

What's Included

  • Accommodation
    4 nights 3 star agriturismo

  • Hybrid bike, pannier and odometer

    A hybrid bike, pannier, and odometer (1 per 2 bikes) are provided.

  • Vehicle transfer on day 8

    Vehicle transfer is provided on day 8.

  • Luggage transfer

    Luggage transfer is included for 1 bag per person not weighing more than 20kg.

  • Digital information pack

    A digital information pack with a navigational app (usable offline) including route notes and maps is provided. A smartphone is essential.

  • Emergency hotline

    Access to an emergency hotline is included.

What's Not Included

  • Evening meals, all lunches & beverages

    Evening meals, all lunches, and beverages are not included.

  • Entrance fees

    Entrance fees are not included.

  • Travel insurance

    Travel insurance is not included.

  • Travel to the start and from the end point of the trip

    Travel to the start and from the end point of the trip is not included.

  • Personal expenses

    Personal expenses such as laundry and phone calls are not included.

  • Tourist taxes

    Tourist taxes are not included.

  • E-Bike, rear bags & odometer

    E-Bike, rear bags, and odometer are not included and must be pre-booked.

  • Solo traveler or single room supplement

    A supplement will apply if you are traveling solo or book a single room.

  • Guide

    A guide is not included as this is a self-guided holiday.

Grading

Moderate trip on hilly terrain, very little shade on roads (Daily climb 350 to 750m). The rides follow mostly well asphalted country lanes and smooth turf roads (approx. 35% of the time) with very little traffic. More traffic near larger towns. *Please note that by Italian law, you can ride an electric bike if you’re 14 or over. For cyclists 14-18 years, wearing a helmet is compulsory. ...more ...less

Mode of Transport

Travel includes hybrid bike with pannier and odometer, vehicle transfer on day 8, and luggage transfer (1 bag per person not weighing more than 20kg).

Accommodation

Enjoy 7 nights in 2-3 star hotels and agriturismo, including stays at an organic farmhouse nestled amidst the rolling countryside of the Crete hills south of Siena.

Check out our Q&As

  • What type of bike is provided for the tour?

    A hybrid bike with a pannier and odometer is provided for the tour.

  • Is luggage transfer included in the tour?

    Yes, luggage transfer is included for one bag per person not weighing more than 20kg.

  • Are meals included in the tour package?

    The tour includes 7 breakfasts, but evening meals, all lunches, and beverages are not included.

  • Is there a guide provided during the tour?

    No, this is a self-guided holiday, so a guide is not included.

  • What kind of accommodation is provided during the tour?

    The tour includes 7 nights in 2-3 star hotels and agriturismo, including stays at an organic farmhouse.

  • Is there an emergency contact available during the tour?

    Yes, access to an emergency hotline is included in the tour.

  • What is the terrain like for the cycling routes?

    The trip is moderate on hilly terrain with very little shade on roads. The rides follow mostly well asphalted country lanes and smooth turf roads with very little traffic, except near larger towns.

  • Is it possible to use an electric bike on this tour?

    Yes, you can ride an electric bike if you’re 14 or over, but it must be pre-booked.

  • What is the policy on helmets for cyclists under 18?

    For cyclists aged 14-18 years, wearing a helmet is compulsory by Italian law.

  • Self-guided holidays - inclusions

    We have designed our self guided walking and cycling tours to include a number of elements to help you enjoy your holiday more, while leaving out some things to give you more freedom to tailor the trip to your needs and interests. Refer to the Trip Notes for more information on the specific inclusions for each trip. What’s included: - Detailed Route Notes - Accommodation - Luggage transfers - Any scheduled transfers as per Trip Notes - Emergency support - Some meals (mostly breakfasts) What’s NOT included: - Transport to/from start/finish points - Most meals - Any entrance/park fees - Travel insurance - Personal expenses along the way - Unscheduled transfers required during the trip

  • Trip Grading & Preparation

    Match your level of fitness & requirements Please read this information carefully to find out which grade is most suited to your level of fitness and requirements. To make the most of your Walkers' Britain holiday it is essential and your responsibility to choose a trip that is well within your capabilities. All our active holidays are graded and clearly marked in each trip description. All mountains have uphill and downhill sections and by definition walking and cycling demand some effort. However all things are relative, and these grades assume that you are a reasonably active person who enjoys walking or cycling. Few trips are extreme and most allow ample time for sightseeing and enjoying the scenery. If in doubt about the grade of any holiday, please contact us for advice or request the tour dossiers, you can also chat with our team about the right travel insurance for you. Grade 1 – Introductory These trips involve walking for four to five hours per day or cycling for 15-50 km per day at a slow but steady pace. You will need a reasonable level of fitness and good health. Suggested Preparation 30 minutes of aerobic-type exercise (either road cycling or jogging), three times a week for three months leading up to your trip. Grade 2 – Introductory to Moderate These trips involve a combination of what is described in our Introductory and Moderate levels. The emphasis is on introductory activity but including several moderate stages. Grade 3 – Moderate These adventures involve walking for up to six hours per day or cycling for up to 65 km per day, at a steady pace. You will need a good level of fitness and be in good health. Suggested Preparation 45 minutes of aerobic-type exercise (road cycling or jogging) three times a week for three months leading up to your trip. Grade 4 – Moderate to Challenging This trip grading involves a combination of what is described in our Moderate and Challenging levels. The emphasis is on moderate activity but including several challenging stages. Grade 5 – Challenging These active holidays involve walking up to nine hours per day in mountainous terrain with steep ascents and descents, pass crossing & alpine weather conditions, or cycling for up to 80 km per day over undulating terrain, with some steep and sustained hills. You will need an excellent level of fitness, be prepared to carry a daypack weighing up to 8 kg and be completely comfortable in adverse weather conditions. Suggested Preparation 1 hour of aerobic-type exercise five times a week for three to six months leading up to your trip. We also recommend regular hill walking with a pack in variable weather conditions or road cycling.

  • Route notes

    While our tours vary in terms of difficulty, route finding is made simple and convenient with our specially prepared package of maps and route notes. On many of the walks it is easy enough to navigate carefully using the route notes provided with a cursory glance at the map. As holidays reach the higher grades, you will need to take more care and we would expect you to have at least some knowledge of using a compass. Maps for our tours also vary considerably, from up-to-date GPS referenced additions, to old map copies which may still be the only ones obtainable for a particular area. The differences in style, grade and destinations of our tours are features that make them of continual interest and delight to our walkers & cyclists. Each set of route notes can contain the following elements relevant to the route: History and information on the region and the route you are walking. Detailed maps including points of interest and accommodation. Detailed step-by-step descriptions (with pictures) of the route and information on detours/optional additions. Transport timetables and information for getting there and away. Safety information and advice. Contact details of accommodation, transport, local representatives and emergency support. Advice for things to do along the way. Suggestions for dining and self catering.

  • How our self-guided holidays work

    Self guided walking and cycling holidays offer freedom, independence and choice, allowing you to tailor your holidays in the UK & Europe to your interest and travel style. Our detailed Route Notes will contain all of the information you need to plan how you would like to approach each day, giving you the freedom to set your own pace. As you are not limited by the constraints of group travel, you are free to shorten or lengthen your walk as the terrain permits and can even take a day off, although you may need to travel onto your next accommodation by taxi or public transport in order to do so.

Reviews of this operator

Marguerite Carter (Google Reviewer)  

We found Walkers Britain on...

19-Jul-2023

We found Walkers Britain on google. Their communication and information was excellent. The hikes were well marked with signs. Local tourist office was excellent as well. we bought the half price rail pass which was great but probably should have got a full pass for the amount of travel we did. We loved all the hikes we did based at Meiringen Swizerland. The Hotel Accomodation at the Albach Hotel was a great location and we were well looked after. Meals were excellent. We were charged the tourist tax at the end which was mentioned ...more ...less

David Grogan (Google Reviewer)  

The Cotswolds by bicycle was...

29-Jun-2024

The Cotswolds by bicycle was a wonderful experience. Walker's Britain had selected charming B&Bs that had good facilities and pleasant owners. The biking routes were well chosen to have little to essentially no traffic, with minimal time on busy roads. The English countryside and its villages is one of the wonders of the world. ...more ...less

Iain McNeil (Google Reviewer)  

We recently visited Madeira for...

17-Apr-2024

We recently visited Madeira for a walking holiday organised by Walkers Britain. Everything from transfers and accommodation to the interactive mapping app showing the routes for our daily walks was excellent. The walks themselves were easy to moderate grade and combined places of interest with trails alongside lavadas, taking us through a variety of beautiful plants and vegetation. The bonus at the end of the trip was a night in a fantastic small boutique hotel downtown Funchal. ...more ...less

ted Mckim (Google Reviewer)  

Great hike, a chance to...

14-Oct-2024

Great hike, a chance to see England like few others have seen it, transporting the hiker back it time by centuries in some places. More tiring than expected, but worth every step. The weather cooperated for the most part and the bags always arrived at the hotel/inn on schedule. The food and ales were great (surprisingly), and the accommodations were good to satisfactory - with one exception. ...more ...less

Elaine Spencer (Google Reviewer)  

We did the 16 day...

23-May-2024

We did the 16 day rambler coast to coast walk organised by Walker's Britain, it was an amazing trip which was very well planned meaning all we had to do was follow the provided gps coordinates and walk to the next lovely accommodation where our bags were waiting to us. We met some lovely people from all over the world, had an amazing time and would definately use Walker's Britain again. ...more ...less

Terry Welch (Google Reviewer)  

Amazing walk! Take a...

06-Oct-2024

Amazing walk! Take a couple of different guide books with you in order to make route finding easier and use your GPX files. Walkers' Britain was very helpful and responsive to our questions. Excellent customer service!

Douglas Schiff (Google Reviewer)  

Three of us (ages 67,...

30-Nov-2022

Three of us (ages 67, 69, 71) - just finished the Coast to Coast trail - the 13 days of hiking version. We loved it. It was, at times, quite difficult (particularly the 24 mile day followed by a 20 mile day) - but wonderful. The accomodations done for us by Walkers Britain ranged from very good to simply outstanding. We were extraordinarily lucky to have 20 minutes of rain 1 day only. We were a little sorry we hadn't chosen a 1 day longer version and/or built in a rest day in Richmond. Also, we used the GPS files almost exclusively - very important. ...more ...less

Lauren Cuttler (Google Reviewer)  

Very happy with Walkers Britain....

11-Sep-2024

Very happy with Walkers Britain. We did the Coast to Coast in northern England. Trina, who did all the arrangements, was easy to work with, l thought prices were reasonable, loved the GPX maps that came with other resources and it was reassuring to know if there was an emergency on the walk there was someone to call. ...more ...less

Michael Howard (Google Reviewer)  

Most of the problems were...

07-Sep-2023

Most of the problems were created by the weather over which you have no control. The organization of shelter, food, and baggage transfer were very good. I found the navigation in the book a bit of a problem but as I refused to use the GPX system offered, I have only myself to blame. All in all, I felt I got my money's worth on this trip and have no hesitation in recommending it to others. ...more ...less

Marc Torrey (Google Reviewer)  

We just completed the self-guided...

18-Oct-2022

We just completed the self-guided tour of Haute Provence. We found the hiking more strenuous than expected, but well worth the effort in terms of scenery and natural beauty. The staff at the selected hotels and restaurants were all pleasant and helpful. We thought September was a good time to visit the area, as it wasn't too hot, there were no active wildfires, and we didn't have to deal with any mud. We will definitely consider Walker's Britain on our next Europe trip. ...more ...less

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Book with Confidence

  • Low Deposit

    Walkers' Britain requires a minimum deposit of 250 GBP per person or the full booking value, whichever is less, with the final balance not due until 70 days before departure.

  • Cancellation Policy

    We don't charge a cancellation fee, here is a summary of walkers' britain charges.

    Up to 70 days before tour starts: Forfeit 100% of deposit.

    At 69 days before tour starts: Forfeit 50% of booking price.

    At 35 days before tour starts: Forfeit 100% of booking price.

Cycle the Wine Regions of Tuscany

8 Days Starting and ending in Buonconvento, Italy

Visiting: Buonconvento, Murlo, La Befa, Montalcino, Monte Oliveto Maggiore, Sant'Anna in Camprena, Pienza, Bagno Vignoni, Monticchiello, Val d'Orcia, Montepulciano, Orcia Valley, Lucignano d'Asso, Pieve a Salti ...more ...less

Tour operator:

Walkers' Britain

Tour code:

JTS

Group Type:

Independent

Guide Type:

Self Guided

Physical rating:

moderate

Age range:

14-

Tour operated in:

English

Activities:

Cycling, Walking

From: $1650 (USD)

NB: Prices correct on 17-Mar-2025 but subject to change.

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