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Trail riding in Tuscany

Day 1 1 : UK - ROME - CATELL'AZZARA

Day 2 2 : castell'azzara - 5 hours riding, day 3 3 : castell'azzara - pitigliano - 5 - 6 hours riding, day 4 4 : pitigliano - poggio buco - 5 - 6 hours riding, day 5 5 : poggio buco - poggio conte - 5 - 6 hours riding, day 6 6 : lamone forest nature reserve - lake mezzano - 5 - 6 hours riding, day 7 7 : lake mezzano - castell'azzara - 5 - 6 hours riding, day 8 8 : castell'azzara - rome - uk, dates & prices, price details, price includes, support team, accomodation, price doesn't include, accommodation, equestrian info, guide & local team, minimum riding ability, tacking ability and participation, trip conditions and requested experience, equestrian equipment, travel info, packing list, sustainable tourism.

• Travel light. It's a little known fact, but the lighter you pack, the better for the environment as heavy bags will produce higher emissions (when flying a plane or driving a car!).
• Reduce plastic waste. Take your favorite reusable bottle with you. Avoid single-use bags, cups, or straws.
• Preserve nature. Always take your rubbish with you during the ride and recycle them. Leave all the flowers or plants as you found them, and never get too close when observing wildlife. Make sure to use eco-friendly products such as body wash or laundry detergent (if camping) to protect both your skin and the environment.
• Choose your experiences carefully. Respect animal life by not participating in any activities that abuse wild animals (shows, elephant rides, etc.).
• Support local populations. Buy local handicrafts, be respectful of customs, and learn about the culture of local communities.
• Share! Raise awareness among your family and friends about sustainable tourism.

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Tuscany, Italy

Buckle up, globetrotters: we’re about to fulfill every mouth-watering, sun-soaked, romantic cliché that the word ‘Tuscany’ conjures up!

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Buckle up, globetrotters: we’re about to fulfill every mouth-watering, sun-soaked, romantic cliché that the word ‘Tuscany’ conjures up! Guides and hosts, Gio and Patrick, have created a five star getaway with history, scenery, food, wine and hospitality that rival even their horses for dreaminess.

If you’re coming for the riding, you can’t go past the week-long Tuscan Trail, where you’ll set out on long rides to beaches, ancient villages, vineyards, forests and a heaven-sent thermal lake. Like a fine wine, the itinerary is well-rounded, with an oh-so-satisfying blend of thrilling, varied riding, technical terrain, spectacular views, sightseeing, siestas and scrumptious feasts. Does it count as an adventure when the vino is this good, and you’re drinking it from a crystal glass? We say YES!

If you’re a beginner rider, or perhaps eager to balance saddle time with off-the-horse pleasures, then the Tuscan Escape is for you. Four nights and five lazy days to spend however you please: half-day rides to and from the estate, swimming, tennis, yoga, massage, reading, napping, gawping in disbelief at your dreamy surrounds… not to mention visiting some of the fabulous local attractions at your doorstep.

And if you happen to be in Italy in the summer months and can coincide your travels with the full moon, then our leisurely Full Moon Trail is available to you!

If you’re keen for a glorious ride, in glorious company, astride a phenomenal trail horse in heavenly surrounds, then let yourself sink back into the warm embrace of bella Toscana. You deserve it!

• Horse Breed: Mostly Quarter Horses, Paints, Appaloosas and Criollos, all surefooted, versatile and perfect for trail riding.
• Pace: The pace varies from a walk right through to a canter depending on the terrain.
• Weight Limit: A maximum of 90kg/198lbs. *If you are above this weight limit, please contact us for a further assessment.
• Type of tack: Super comfortable, Italian-made Western saddles and a mixture of snaffle and shank bit bridles, all tailored to the individual horses.
• Seasons: February to October
• Group size: A minimum of 2 and a maximum of 7 riders for the Tuscan Escape and Tuscan Trail itineraries. A maximum of 6 riders for the Full Moon Trail.
• Time in Saddle: Tuscan Escape: From 1 to 6 hours per day. Tuscan Trail: From 1 to 7 hours per day. Full Moon Trail: From 1.5 to 6 hours per day.
• Riding Ability: Tuscan Escape: Beginner to advanced. Tuscan Trail: Intermediate to advanced. Full Moon Trail: Intermediate to advanced.   Not sure what your riding ability is? Watch THIS video to find out.
• Accommodation: Three stylish, tasteful and luxurious apartments occupying a glorious traditional old Tuscan farmhouse. There is one three-bed, one two-bed, and one single bedroom apartment, all equally charming, and all studded with sumptuous furnishings and exceptional artwork. The apartments have their own kitchens, laundry facilities and rain showers, plus WiFi, a swimming pool, and a garden terrace for outside cocktails and entertaining. All of the beds are king sized, so please note twin share is not an option - if you share a room, you’ll share a bed!
• Ride Length: Tuscan Trail: 7 days, 6 nights (6 riding days). Tuscan Escape (for 2025): 5 days, 4 nights (4 riding days). Full Moon Trail (for 2025): 4 days, 3 nights (3 riding days)

The price includes all riding activities outlined in the itinerary; accommodation; all meals (from first day dinner through to last day breakfast); alcoholic beverages (within reason); housekeeping mid-week; use of tennis courts, swimming pool, and all facilities at the farmstead; national park fees; internal transfers within the itinerary (except for the Full Moon Trail where logistical support is not provided).

The price does not include international or regional flights; travel insurance (compulsory); and transfers to/from the ride. For the Full Moon Trail, logistical support is not provided, and with almost every meal located off-site, each guest most have a hire car as their own means of transportation.

DEPARTURE DATES & RATES

The Tuscan Escape

October 7 to 10, 2024

4 days, 3 nights (3 riding days)

The Tuscan Trail

October 21 to 27, 2024

7 days, 6 nights (6 riding days)

November 4 to 7, 2024

November 18 to 24, 2024

December 2 to 5, 2024

February 3 to 7, 2025

5 days, 4 nights (4 riding days)

*Beginner to advanced riders.

February 16 to 22, 2025

*Intermediate to advanced riders.

February 27 to March 3, 2025

March 20 to 24, 2025

April 15 to 19, 2025

April 23 to 29, 2025

May 16 to 20, 2025

May 25 to 31, 2025

Full Moon Trail

June 10 to 13, 2025

July 9 to 12, 2025

August 8 to 11, 2025

September 6 to 9, 2025

September 21 to 27, 2025

October 3 to 7, 2025

October 12 to 18, 2025

October 24 to 30, 2025

REMINDER: There is no twin share option available – all of the beds are king-size. For this reason, solo travellers MUST pay the single supplement price. If you share a room, you’ll share a bed!

NB: Whilst every effort is made to ensure guests with gluten intolerances are looked after with alternate food options, we advise against Coeliacs booking this ride and our ride partner will not be held legally responsible for any cross-contamination or small traces of gluten being found in any meal. It is Italy after all, a place that was practically founded on gluten!

WHAT IS INCLUDED IN THE PRICE?

The price includes all riding activities outlined in the itinerary; accommodation; all meals (from first day dinner through to last day breakfast); alcoholic beverages (within reason); housekeeping mid-week; use of tennis courts, swimming pool, and all facilities at the farmstead; national park fees; internal transfers outlined in the itinerary (for Tuscan Trail & Tuscan Escape only. No logistical support offered for Full Moon Trail).

WHAT IS NOT INCLUDED IN THE PRICE?

The price does not include international or regional flights; travel insurance (compulsory); and transfers to/from the ride. For the Full Moon Trail, no logistical support is provided, guests will need their own car for transportation.

Accepted payment is by credit or debit card only. Depending on the ride you choose to book and your country of residence, there will be a 1.2% to 2.9% surcharge.

*Please note, this is a suggested itinerary only and subject to change due to weather and other influencing factors. Changes will always be communicated clearly, and more often than not, the result of something even more amazing happening that you won’t want to miss!

‘Oh my God, where do I even begin? It was a dream come true altogether. I had my first horse riding holiday, and I picked the perfect place for it! Not only the ranch and the horses, but also the hosts themselves made this a very special experience. It is their ambition that the globetrotters have the perfect holiday and enjoy themselves, so everything is arranged perfectly for our comfort. And the dogs are the absolute sweetest things!  I would like to offer a personal testament to the claim that even beginners can learn to canter comfortably on this ride. I started a bit nervous on a horse that was quite excited to canter, so the host made us switch horses and let the group ride ahead while he and I had a bit of a private lesson. My confidence significantly increased, and after just a few minutes, I was cantering comfortably. By the end of the day, my friend and I had a little sprint ahead of the group with a huge smile on our faces! I will never forget these rides, and I hope to book the longer format ride in the future.’

‘If you want a luxury horse riding holiday combined with spectacular Italian hospitality, including the opportunity to learn about life in Europe from two gorgeous authentic hosts – go to Tuscany. You will not be disappointed for one second of this experience other than, of course, the day you have to leave! The hosts, Patrick and Gio are the most gorgeous, hospitable folk I have ever met in the business who just made everyone feel so welcome & safe. They love what they do, and it shows in every way they care for the group. Everyone was so looked after & their attention to authentic Italian hospitality was flawless! These two guys are special. Gio extended himself at every request – even helping me plan the rest of my trip around Italy! Nothing was too much of a bother and they both made us all feel like the ranch was our home. I will truly treasure every aspect of my stay & will surely go back for more!’

Christina W

‘The Tuscany ride is an absolute dream. Gio and Patrick, the hosts, have created a slice of heaven that exceeds all my expectations in terms of quality of horses, variety of the ride itinerary, and comradery amongst fellow guests. The food is sensational! There is a personal chef for dine-in meals, and the hosts took us out to the best small hole-in-the-wall local restaurants for our dine-out meals. I love how Gio and Patrick explore and support other small businesses in the area doing extraordinary things. The quality of accommodation is comfortable, and the decoration is tasteful. Meeting new people and horses and having experiences while solo traveling is so rewarding. As a mom of three and a small business owner, my time is pretty busy, but the quality of horses and friendships I made on this trip is so worth taking time away for. I feel so refreshed upon returning home. I rode Naira, who took the best care of me and was so brave and surefooted. Walking through a medieval town on horseback and galloping across the Italian countryside are core memories I will cherish forever.n horseback and galloping across the Italian countryside are core memories I will cherish forever.’

Susan Fitzpatrick

‘What an incredible week in Tuscany! We stayed in a luxurious accommodation that had a pool. Every day, we got to go on spectacular rides through olive groves, pristine countryside, and even mountain villages for lunch. We even had the opportunity to ride along the beach. We had a wonderful time having lunch at the family home and enjoying a picnic in the hills. The horses were well-trained, calm, and happy to canter and move when we wanted.’

Barbara Pingree

‘I am thrilled to have gone on the first Tuscany trip. It was an incredible experience that exceeded all my expectations. I had almost cancelled the trip due to a rough patch that I had gone through just before leaving, but little did I know that this experience would help me heal and bring a smile to my face. The hosts were two of the most wonderful and gracious people I have ever met. From the moment I arrived and met them, I felt a sense of peace. The location was breathtaking, the horses were remarkable and so well taken care of, the dogs were like family, and the accommodations were five-star! And then there was the authentic Italian food. Being of Italian descent, I can say that this was the real deal! The riding experience was amazing. The horses knew their job, and the guides were always attentive to our needs. From riding through the olive trees to galloping on the beach, every moment had us all smiling. I cannot recommend this ride enough, and in fact, I plan on returning next year!’

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Saddle up for a horseride around Tuscany

Love horse riding? Then you’ll be glad to hear that there are plenty of opportunities to get in the saddle during your holiday in Tuscany. Check out our tick list of the trails to follow on horseback and the stables we recommend for a good day’s trekking.

Via dei Cavalleggeri

The Via dei Cavalleggeri, or Horseman’s Way, is a 210km route once used by the cavalry that links the watchtowers that line the coast between Pisa, Livorno and Grosseto and crosses regional parks including the Maremma and San Rossore.

The Horse Trail of the Sacred Forests

A romantic landscape of historic landmarks, including the castle of San Niccolò and the abbey of Vallombrosa, awaits riders who join The Horse Trail of the Sacred Forests in the Casentino valley.

Amiata Horse Trail

The Amiata Horse Trail features two paths, one 30km long, the other 80km long, both of which wander the slopes of the mountain of the same name, dipping through ancient chestnut woods.

San Jacopo Trail

On the San Jacopo Trail, near Pistoia, you can break up the journey by visiting important sights, such as Vinci, birthplace of Leonardo da Vinci.

Terre di Siena

Immerse yourself in the countryside around the beautiful city of Siena on the Terre di Siena trail, which takes riders through secluded woodland and vineyards, passing a number of ancient churches along the way. Recommended stables in Tuscany include Rendola Riding near Montevarchi, Club Ippico Senese near Monteriggioni and Maneggio La Fiaba near San Vivaldo. Check out this villa on a racehorse-breeding farm, one of four available to hire through To Tuscany at Agriturismo Legi.

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Brigands Trail

8 Days   |  From £1240pp

Italy ( Best airport: Rome Ciampino / Rome Fiumicino)

Contact us now on WhatsApp with any queries you have about this trail.

Explore the charm of Tuscany, crossing vast, unspoiled territory without restrictions. Riding alongside lakes through unchanged villages admire the castles, palaces and archeological sites that dot this region. Your Italian guides at this family run castle will lead you along some of the hidden trails used by the “Brigands” (outlaws) to escape 200 years ago.

The castle offers a perfect location for an authentic country holiday in the south of Tuscany, where you can explore the picturesque neighbouring historic towns of Orvieto, Sorano, Pitigliano and Bolsena.

Short on time? Take a look at the Tuscany Short Break .

This trail consists of 4 half day rides and one full day ride; however the riding can be tailored to suit individual requirements and abilities. For those who want to improve their riding there are instructors on site to offer tuition in one of their sand arenas. There are also special intensive training programs with lessons in flatwork and showjumping available on request. The equestrian centre is a perfect place for family holidays, with riding programs and summer camps available for children aged over 5 years old.

During July and August it is too hot to run the full day trail, so instead a half day trail will be offered with a massage at the wellness centre.

Level of Riding and Fitness

All riding abilities are catered for and your stay will be tailored to your specific requirements. Beginner and novice riders will be offered a mix of tuition and easy trail rides, more experienced riders can enjoy a full day trail ride as well as lessons and half day rides. The weight limit is 100kg.

Guides and Group Size

Group sizes are between 1-6 riders. Groups are separated based on ability.

The horses are a mixture of thoroughbreds, warmblood crosses and ponies, ridden in English tack.

Accommodation and Dining

This splendid 17th century castle, Castello di Santa Cristina, has been the property of the Caterini family for generations. It is located in Southern Tuscany half way between Orvieto and Siena, closely bordering with the regions of Umbria and Tuscany and one and a half hours away from Rome.

The castle’s 18th century ivy-covered farmhouse and out-buildings have been carefully restored over the past ten years to retain their authenticity. Now they offer fantastic accommodation, in 8 self-catering cottages and 14 private bedrooms. All rooms are furnished with original pieces and offer you the chance to enjoy a unique holiday in Italy.

The ground floor of the farm house opens onto the main terrace which overlooks the swimming pool (open from 1st June). On the ground floor there is a large “taverna” with brick vaulted ceilings. The space is divided into three main areas: dining room, billiard room, ping-pong room, plus a large kitchen available for all the guests and equipped for cooking courses.

There is also a wellness centre onsite providing a range of holistic and Ayurvedic treatments with a qualified physiotherapist.

Get a free Brigands Trail mini-brochure in PDF format.

8 days / 7 nights / 5 riding days £1240pp

Seasons 2024

Low season: 10th April – 15th June and 17th Sept – 12th Nov High season: 16th June – 16th Sept

During July and August full day rides are not possible due to high temperatures. Instead half day rides will be added.

Prices are based on two sharing a double room. Twin room reduction (room size: 10 m2): £40 per person per week Single supplement: £125 per week

BEGINNERS: 6 lessons or easy treks. Reduction of £200 NON RIDERS: £430 reduction

Flights & Airport transfers

Transfers can be arranged from both Rome airports

FCO Airport – €320 return (max two people) CIA Airport – €330 return (max two people)

Surcharge for transfers required before 09:00 or after 18:00; €20 (per person, paid locally)

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• All meals including wine
• Riding - 4 half day rides and 1 full day ride
• Guided tour of the castle
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Brigands Trail - Payment, Cancellation & Booking Terms

Cancellation policy

Payment & Cancellation Terms Holidays are confirmed with a 20% non-refundable deposit. The full balance is due 56 days before the start date.

If you cancel your booking less than 56 days before the start date of your trail we are entitled to receive full payment, less refunds as follows:

42 days or more before booking date – 50% 30 days or more – 30% less than 30 days – nil

Book with confidence – Covid Guarantee: if ride operator is closed/you are unable to travel – due to lockdown: 1/ The deposit is reissued as a rebooking voucher to rebook anytime. 2/ Any balance payment will be refunded to you in full within 1 week of departure date.

Insurance All saddletravel.com customers are required to take out appropriate travel insurance that covers horse riding and holiday cancellation. Proof of insurance details will be required during the booking process.

Brigands Trail - Riding Declarations

Dressage and Trail in Tuscany (2024) - IT-SR04

Rates note:, transfer and other charges:, itinerary for dressage and trail in tuscany.

Climate for Dressage and Trail in Tuscany

What to bring for dressage and trail in tuscany, video for dressage and trail in tuscany, google map for dressage and trail in tuscany, average tour ratings for dressage and trail in tuscany.

Accommodations for Dressage and Trail in Tuscany

This trip can accommodate special dietary requests.

Dressage and Trail in Tuscany

Visa requirement for dressage and trail in tuscany.

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Memories of Tuscany

Published: February 11, 2021

Rides in Italy can easily meet the criteria for a successful riding holiday: beautiful scenery and countryside to ride through, interesting history and culture, delicious local food and wine, good horses and elegant accommodation. This is all easily apparent from the photos and clips Louise Palmer was kind enough to share following her Tuscan Villages & Vintages ride in September 2017. Enjoy the memories below!

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Tuscany, Italy   Travel Guide

Courtesy of Peter Zelei Images | Getty Images

10 Best Things To Do in Tuscany, Italy

Updated Apr. 24, 2024

Sipping local wines and dipping bread into just-pressed smooth olive oils is one of the main things to do in this Italian region. Luckily, there are numerous wineries where you can to do this, such as  Ciacci Piccolomini d'Aragona in Montalcino

• All Things To Do

Florence Florence free

Firenze, Tuscany's capital city, is known for its Renaissance art and architecture. You can climb to the top of the Duomo , gaze at Botticellis at the Uffizi Gallery , tour the Galleria dell'Accademia  and stroll through the Boboli Gardens for a taste of the 13th through 16th centuries.

But this city isn't just for art and architecture connoisseurs: There are quaint shops, delicious restaurants and decadent hotels. And with its red roofs, cobble stone streets and narrow alleys, it's also a very picturesque place to spend a few days. Be sure to hike to the top of the Piazza Michaelangelo, located across the Ponte Vecchio, for incredible city views and live music. Bring a bottle wine and watch the sunset — you won't want to miss it. For more information on this city, visit our Florence travel guide . 

Siena Siena free

Siena vies with Florence for the title of the most charming city in Tuscany. While Firenze is known for its Renaissance influence, Siena exemplifies the Gothic era, and you'll find that near-pristine Gothic architecture fills the city. One of Siena's main attractions is also a UNESCO World Heritage Site: The breathtaking Piazza del Campo is a city square that sits at the base of three majestic hills. While you're there, climb to the top of Torre del Mangia (a part of the Palazzo Pubblico) for an awe-inspiring view of Siena.

As for museums, visitors find the Museale di Santa Maria della Scala and the Museo Archeologico are each worth a few hours of their time. And when it comes to churches, recent travelers recommend visiting several: the Siena Cathedral (or Il Duomo) for its beauty; the Cathedral of the Assunta for the surrounding landscape; and the Abbazia di Monte Oliveto Maggiore for its wine cellar. 

Lucca Lucca free

Located in northwest Tuscany and less than 20 miles from Pisa, this town is famous for its 16th-century walls — recent travelers recommend riding a bike atop them to get the best views. Or consider climbing to the top of the Guinigi Tower where you can overlook the entire city.  There's also a rendition of the Duomo, called the  Cattedrale di San Martino.

Luca is also praised for its native son Giacomo Puccini, who composed such operatic masterpieces as "Madame Butterfly" and "La Bohème," so art is aplenty.  And art aficionados recommend popping into L.U.C.C.A. (Lucca Center of Contemporary Art) or strolling by the art show every third weekend of the month by the Piazzetta San Carlo to see local works of art. 

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Cinque Terre Cinque Terre free

Cinque Terre is a group of cinque (five) villages — Monterosso, Vernazza, Manarola, Riomaggiore and Corniglia — strung along cliffs that overlook the Ligurian Sea. Since it became both a UNESCO World Heritage Site and national park in the past couple of decades, the area has been saved from the commercialism that pervades most European cities today.

Visitors like to hike Cinque Terre's leafy crags; Via dell'Amour is a popular (and well-paved!) walk that connects Manarola with Riomaggiore. The trail with the best ocean views is from Vernazza to Monterosso. Unfortunately, this hike is also the most challenging and isn't for the faint of heart, as the trail (or lack thereof) is unpaved and involves lots of climbing under and over various terrain. To avoid the crowds and the heat, recent travelers recommend hiking in the morning. And if you're not up for hiking from town to town, you can always catch the train that runs along the coast and stops at each town. 

Sovestro in Poggio Winery Sovestro in Poggio Winery

Sovestro in Poggio Winery is a farming estate filled with fields of grapes and olives. The estate produces wines like the Tribolo and Chianti, as well as its own extra virgin olive oil called Bagatto. Like many of the estate wineries, Sovestro in Poggio also contains overnight accommodations. Recent visitors are almost unanimous in their praise for this estate, saying the scenery was "breathtaking," the food was "delicious" and the wine was "perfect."

You'll find Sovestro in Poggio Winery in central Tuscany in the small town of San Gimignano. Although some recent travelers say the experience here is expensive, most say it's worth it. Reservations are mandatory for all visits. For more information, visit the estate's website . 

Ciacci Piccolomini d'Aragona Ciacci Piccolomini d'Aragona

Ciacci Piccolomini d'Aragona produces wines, grappas and olive oils in a beautiful swath of southern Tuscany. The estate itself dates back to the 17th century, making it a great stop for historians as well as gourmands.

If you plan on visiting this winery, you'll want to be sure to take a guided tour. Recent visitors rave about the talented tour guides and their abundant amount of wine knowledge  — you'll be a wine connoisseur by the time you leave.  Tours give visitors access to all three of the wine cellars where you can learn how wine is produced.  You'll find the winery in Montalcino on the hills flanking the Orcia River. For more information on this winery, visit its website . 

Castello del Trebbio Castello del Trebbio

Castello del Trebbio hosts everything from a winery to a restaurant (and cooking classes) to accommodations. It's hard to pin down just what visitors like most about the experience. Some say its the family-run winery with simply tasty wine and olive oil. Others say the 12th-century castle's ambiance is the coolest, while some find tasting different Chianti vintages and learning to make Italian pasta the most satisfying part about this estate winery.

And here's an interesting historic tidbit: This castle was once owned by the Pazzi family, the arch enemies of another powerful Italian family, the Medicis. You'll find this winery on the outskirts of Florence .  Weddings are held here frequently, so be sure to call ahead for reservations.  For more information, visit its website . 

Castello di Verrazzano Castello di Verrazzano

Visitors to the Castello di Verrazzano say its mix of warm hospitality, scenic beauty and delicious wine that is absolutely divine. Dating back to the 14th century, the estate also produces olive oil, honey, grappa and balsamic vinegar. So if you want to bring back a few souvenirs, Castello di Verrazzano has you covered — just know that you can buy the same wines cheaper at the local grocery store.

Many recommend booking the three-hour winery tour with lunch rather than just the winery tour itself, saying the food makes it worth the extra time and money. You'll learn how to properly pair and taste wine during the multicourse lunch. But if you're a vegetarian, recent travelers recommend skipping the lunch as the majority of the meal is different kinds of meats and not worth the extra cash. 

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Castello di Volpaia Castello di Volpaia

Castello di Volpaia is much more than a winery — it's an entire village, and a 11th-century one at that. The former churches, homes and underground passages have been converted into wine cellars, bottling plants, tasting bars, olive presses and even an underground wineduct. Visitors can even do some hiking in the surrounding countryside; the Enoteca (or shop) sells hiking itineraries, some of which can take up to three hours to finish.

Guests rave about this estate nearby the breathtaking Radda di Chianti.  You can also stay overnight in the castello's apartments or villas. You'll discover several delectable dining options around town and, of course, plenty of wine tastings. Various cooking and food classes are also offered, such as lessons on combining food and wine and how to serve Italian style. For more information on this winery, visit its website .

The Leaning Tower of Pisa The Leaning Tower of Pisa

Oh, the Leaning Tower of Pisa — so touristy and yet so fun. Each day, hordes of visitors come to the small northwestern Tuscan town of Pisa to take pictures "propping up" its tower. Some do it with their entire bodyweight while others hold it with a finger. Even just watching other tourists take pictures is pretty entertaining. 

At about 183 feet tall, the tower leans at about four degrees, meaning that at the top, it's displaced nearly 13 feet from its bottom. Yikes! And yet, it's still architecturally sound enough for visitors to walk up its nearly 300 steps to the top. And spying the exorbitant price of walking to the top ( € 18 EUR), most travelers recommend snagging a few free pictures from the ground level. 

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Classic Tuscany

Self-guided leisure bike tour, prices from.

This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.

E-BIKE HIRE AVAILABLE

• All Cycling Holidays
• All Leisure Cycling Holidays
• Europe Leisure Cycling Tours
• Italy Leisure Cycling Tours
• Tuscany Leisure Cycling Tours

• Staying at Tuscan farms overlooking stunning countryside
• Visiting the famous towns of Monteriggioni, Radda in Chianti and Siena
• Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
• Trying delicious, regional dishes
• Sampling the best wines of Chianti, Montepulciano and Montalcino
• Absorbing the atmosphere of San Gimignano – a UNESCO World Heritage Site

Back to Top

Arrival into Pisa airport and transfer to San Gimignano (transfer approx. 1.5 hours). Depending on your arrival time and local arrangements we may arrange for your local representative to meet you either tonight or tomorrow morning to fit you to your rental bikes (if renting) and conduct your welcome meeting. Details will be confirmed for you ahead of your departure. After checking into your accommodation you will have the rest of the day to explore the local area and get prepared for your first day of cycling.

• Meals: Breakfast
• Ascent: 500 Metres Approx.

The fascinating town of San Gimignano is the town of towers and is one of the prettiest and best-preserved medieval settlements in the whole of Italy. San Gimignano is also known for its white wine, Vernaccia di San Gimignano, which is grown in the area. The old town is a UNESCO World Heritage Site. We recommend taking a walk through its narrow streets – a great opportunity to absorb the Tuscan atmosphere. Back on the bikes you will descend towards the plains of Colle Val d‘Elsa. You’ll ride past woodland and cultivated fields making your way towards the hill-top town of Casole d‘Elsa. The last few kilometres are challenging but the views from the top of the hill will certainly outweigh the effort. You’ll have some time to wander through this authentic medieval town, far away from the tourists and clichés of Tuscany. The accommodation is set just outside the walled centre, a short walk into town and where you can enjoy an evening drink. We recommend watching the sunset from the bastions overlooking the hills of Tuscany.

• Ascent: 450 Metres Approx.

You’ll leave Casole d‘Elsa on a rolling road passing small stone villages scattered throughout the countryside. Sections of the route are part of the Via Francigena, the pilgrimage route from Canterbury to Rome. This ancient road will lead you straight to your accommodation, in an ancient medieval village, surrounded by vast vineyards; an ideal place to taste the local wines. A short cycle away from your accommodation you’ll find Abbadia Isola.

The fields surrounding Abbadia Isola were once a large swamp or bog that accumulated rain water from Monte Maggio. ‘Isola’ refers to an island or the only solid piece of land on which the original ancient hamlet was built. The Abbey of St Salvatore was founded in the 11th century and was an important strategic crossroad on the Via Francigena between Florence, Fiesole, Siena and Volterra. Now the Abbey is surrounded by flat fields filled with sunflowers in summer, and it’s an easy-going and enjoyable cycle from your accommodation.

• Ascent: 600 Metres Approx.

Today is the toughest stage of the week, with a roller coaster ride through the northwestern side of Siena and into the Chianti region. Don’t worry though, each new climb will be rewarded with a fantastic descent!

The first climb takes you to the Castle of Monteriggioni with its 13th-century architecture. The massive walls here are linked with Dante’s Divine Comedy and, at that time, served as a defensive stronghold of the town of Siena against rival Florence. A gentle stroll through the narrow streets is a must, as well as a cycle round the fortified walls. Back on the bikes, you’ll head towards Castellina in Chianti. You will soon realise you are cycling in wine territory as you pass acre after acre of vineyards. Castellina in Chianti is well worth exploring on foot; its importance is not only connected to wine, but also to the abundance of Etruscan sites found in this region.

Such rich archeological heritage justifies a visit to the territorial museum for Chianti Senese, its collection including findings not only from the township of Castellina in Chianti, but from Castelnuovo Berardenga, Gaiole in Chianti and Radda in Chianti as well. Leaving Castellina, another 11 Kms will take you to Radda in Chianti, a beautiful medieval town enclosed in large defensive walls.

Today’s route will be a gentle roller coaster through the Chianti region of oak forests and vineyards. The day will start with a gentle descent past vineyards towards Gaiole in Chianti, where you can take a slight detour to visit the town. The birthplace of Chianti Classico, Gaiole is celebrated in its own right.

In medieval times it was one of the three capitals of the Chianti League, along with Castellina and Radda. The hilltop town is set among oak and chestnut forests but also surveys vineyards and olive groves. As a former military stronghold, Gaiole is ringed by medieval castles and fortified abbeys. Today Gaiole is also known as the birthplace of the “Eroica” (1997) a vintage cycling event, that brings thousands of riders in the region cycling along the “strade bianche“. Gaiole is a perfect stop for a long lunch, before cycling back to Radda in Chianti.

Today’s route will be a gentle roller coaster through the Chianti region of oak forests and vineyards. The day will start with a gentle descent, the landscape changing from oak forests to cultivated fields as you make your way towards Siena.

This whole region is dotted with castles, once defensive systems but now privately owned by wine producers. Your route will then take you past Meleto, San Donato in Perano and Brolio Castle. You’ll follow a mixture of tarmac and “strade bianche” (gravel roads) as you get closer to Siena, with glimpses of bell towers and churches.

Entering Siena from the Porta Romana will lead you straight to the heart of the city, Piazza del Campo, where the famous Palio takes place. There will be time to wander through Siena in the late afternoon, with a visit to the Palio Square and the Duomo, before heading out to dinner for a mouthwatering Tuscan meal.

Today you’ll say ciao to this beautiful part of Italy and we’ll transfer you back to Pisa airport for your outgoing flight. (Transfer approx. 1.5 hours.)

The Cycling

Tuscany is a region with rolling hills of cultivated fields, woodland and chalky landscape, dotted with hill-top hamlets. Riding is mostly on quiet tarmac roads (95% – shared with traffic, can be busier in the summer months) and some well-beaten gravel roads (5% – mostly strade bianche), with days involving riding up to hill-top towns. You will find certain sections have some steeper more challenging climbs. Day 4 riding up to the Chianti region will prove the most challenging following a roller coaster route.

We recommend hybrid bikes for this tour, but it’s possible to cycle the route on a road or gravel bike, bearing in mind there are some short gravel sections.

If you’re wanting to spend more time exploring the towns and villages along the way, then an e-bike is a great idea to cover the miles a little quicker. An e-bike would also help those in need of a little boost (particularly if riding in September when it can get quite hot) to cover some of the longer distances, and cheeky climbs mid-week. Please note – E-bikes are generally heavier than hybrid bikes, so worth considering when handling the bike.

For more information about riding an electric bike on our holidays please click here

Leisure Cycling Grade

Aspects of both our grade 2 and 3 trips

Suitable for those looking for some cycle friendly routes

Some modest climbs

Possibly sections of varying terrain (eg. forest tracks, gravel paths etc)

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 2-3, will have aspects of both our grade 2 and 3 rides. These tours are still suitable for those perhaps who have recently got into cycling, and offer an array of accessible, cycle friendly routes, cycle paths and quiet roads, however there will be some days / sections where you may have to tackle some ups and downs, the occasional steeper climb and perhaps some varying terrain (forest tracks, gravel paths etc). Suitable for those with a decent level of physical fitness, looking for some leisurely rides with occasional (achievable!) challenges along the way.  

For more information about the grading of this holiday in particular, please check out the terrain section which will give you some specifics of what to expect on this tour.

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.

2024 25 Mar – 30 Oct

Season 1 – $1650 03 Apr – 17 Jun / 04 Sep – 30 Oct

Season 2 – $1945 25 Mar – 02 Apr / 18 Jun – 03 Sep

Alternatively for a great value holiday choose one of our scheduled departures below.

Secure Your Holiday With A Deposit

Book now with a $250 deposit and nothing more to pay until 60 days before departure. Choose a date to start your booking and see all prices, including bike hire and single room supplements.

Whats Included

A) Accommodation (shared twin / double en suite rooms) in small hotels / agriturismi / guesthouses

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

C) English-speaking local representative (with either an in person or video welcome meeting)

D) Access to the navigation app for holiday information and navigation

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)

H) Financial Protection through ABTOT

What's not Included

A) Bike rental (available if required)

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

C) Single room (available if required)

D) Travel insurance

E) Meals not stated in the itinerary

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 locally – Approx. 2€ per day)

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

The Essentials

Travel options.

Your tour starts in San Gimignano and finishes in Siena.

Airport transfers are included in the cost of your holiday. 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 12.00 and 19.00.

If you are joining one of our scheduled departures we will provide arrival and departure times, along with suitable flight options, as and when more flight schedules are released.

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.

Accommodation

The majority of your accommodation (shared twin or double en suite rooms) will be in a mixture of 3 and 4* hotels, guesthouses and agriturismi.

We have an accommodation upgrade option available on this tour, if you’d prefer to stay in 4* hotels; this will include an upgrade on 4 nights of 6. Please select this supplement at the time of booking.

If you don’t own a suitable bike or would prefer to avoid bringing your own we have bikes available to rent. These bikes are typically Focus Univega Geo hybrid bikes (or equivalent).

We also have electric bikes available to rent on request; these will typically be Focus Univega GEO 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.

Rental bikes will be provided with a pannier rack and 1 bag, a puncture repair kit, spare inner tubes (2), a bike lock, a bike pump, a water bottle holder and a phone mount.

We can provide a helmet locally on request, please let us know if you’d like to rent one when you make your booking. It is possible to bring your own saddle and / or pedals, but please let us know in advance.

News, Reviews & Stories

Customer story: *trinis take on tuscany.

Excellent! All aspects of the cycling tour were excellent from the initial contact and followup emails back and forth in the months preceding our trip to the details provided at the very start of the trip in San Gimignano. Instructions were clear and the self guided maps and information provided were accurate and relatively easy to follow. Great bikes! Solid, easy to ride and well tuned. We were surprised somewhat to see that the tires provided were slicks instead of tires with some tread. We were a little concerned on the first day when it rained that the roads would be slippery but it wasn’t an issue. Overall, yes, good value for the money.

Hassle free holiday Tuscan scenery was awesome! Representatives were excellent. I needed some bike repair at the end of day 4 in Siena and it was done after a single text message with no hassle at all. No errors on the map and easy to follow!

True to the descriptions! Excellently described and true to the descriptions. A full and thorough briefing at the start of the trip and great directions (map and words) – we never got lost once. Excellent service during the booking process and on arrival, through to the taxi transfers to and from the airport. The ride from Casole D‘Elsa to Abbadia Isola (and for our changed itinerary) through to Monteriggiano was excellent – lovely road through some amazing countryside (though the whole week could be described this way) but we had a cappuccino stop at the restaurant recommended en route. Questions answered promptly and well and nothing was too much trouble. A really excellent trip – so well organised and made easy work (despite the hills & heat) of the beautiful Tuscan countryside. Thank you very much to all the team!

Fantastic views Bikes were great – good quality and well set up. The route planning and maps worked fantastically and we didn’t get lost once. Superb arrangements and communication. Everything happened as you said it would and at the time it was arranged. The ride into Sienna was a favourite – as there were some fantastic views.

Great accommodation.. Both of our tour guides were extremely knowledgeable and helpful. They were always available. The standard of the accommodation was better than I have come to expect on ski holidays. It was my first cycling holiday, but it won’t be my last, and Skedaddle will definitely be top of my list!

Brilliant! Really enjoyed every aspect of the holiday. Great scenery, wonderful food, brilliant guides!

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