Tuscany is one of Italy’s most beautiful regions, so it’s no surprise that cycling in Tuscany is  extremely popular. With its rolling hills, medieval towns, and UNESCO protected countryside, cycling holidays in Tuscany have all the ingredients needed for a unique and unforgettable cycling experience.

Tuscany boasts many fantastic cycling routes. From the rolling hills of Chianti and the Val d’Orcia, to the stunning views from some of the best hill towns in Tuscany, like Siena, Montalcino and San Gimignano, each area has something unique to offer. And that’s before we mention world famous centre of art, Florence.

In this article we speak to Marco who runs Gusto Cycling. He’s originally from Montecatini Terme in Tuscany and has been running bike tours in Tuscany for 12 years. He shares his tips for the best parts of Tuscany for cyclists, Tuscany bike tours and bike routes, information on where to stay, when to visit, bike rentals in Tuscany and more.

Read on to discover the best of Tuscany and plan your next cycling holiday in Tuscany.

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What’s special about cycling in Tuscany?

Biking in Tuscany has it all: great roads, nature, history, art, culture, amazing gastronomy and wine! Tuscany is, quite simply, perfect for a holiday and cycling is the best way to discover it.


Tuscany is home to some of the most beautiful landscapes in Italy, including the Chianti wine region, the rolling hills of Val d’Orcia, and the rugged Tuscan coastline of the Maremma. The region is known for its agricultural heritage, with olive groves, vineyards, and fields of sunflowers covering the hillsides.

History and culture

Tuscany is steeped in history and culture, and a cycling trip through Tuscany allows you to explore the region’s many historic towns and landmarks, many of which have hardly changed for over 600 years. There are famous historical towns like San Gimignano, Lucca, Montalcino, Pienza, Montepulciano and the stunning Piazza Del Campo in Siena, as well as lesser-known towns and villages with many architecturally important and well-preserved buildings and museums provide a rich history to enjoy.

It’s also worth noting that in Tuscany the towns and villages are all quite close together, which means there’s lots of potential for coffee and lunch stops!

If art is your thing, one of the best things to do in Tuscany is learn about the region’s rich artistic heritage, from the Renaissance masterpieces of Florence to the intricate glasswork of Murano.

Food and wine

Another big draw is the food and wine. From fresh pasta dishes to hearty stews and soups, there’s something for everyone to enjoy. And of course, you can’t visit Tuscany without trying some of the local wines, such as Chianti and Brunello di Montalcino.

What you soon realise as you travel or cycle within Tuscany, is the food is different in every local province of Tuscany. For example, the pasta dishes (mostly freshly prepared that day) and the sauces vary a lot, from rabbit, to wild boar to venison. More examples: Livorno is famous for fish soup, Florence is famous for the Bistecca Forentian steak.

The wine regions within Tuscany are also superb. From Chianti, which is located between Florence and Siena, to Brunello di Montalcino, to Vermentino from Montecarlo near Montecatini Terme, or to Bolgheri where the super Tuscan wines of Tiganello and Sassacaia are found.

As such, it’s no surprise that holidays and cycling tours in Tuscany are so popular!

Overview of Tuscany for cyclists

Where is Tuscany?

Tuscany is located in central Italy. It’s bordered by the regions of Liguria to the northwest, Emilia-Romagna to the north, Marche to the east, Umbria to the southeast, and Lazio to the south.

The region covers an area of approximately 23,000 square kilometres and has a population of around 3.8 million people.

Tuscany is divided into ten provinces: Florence, Arezzo, Grosseto, Livorno, Lucca, Massa-Carrara, Pisa, Pistoia, Prato, and Siena. Each of these provinces has its own unique culture, history, and attractions, making Tuscany a diverse and fascinating region to explore.

Florence is the capital of Tuscany and one of the most famous cities in Italy, known for its art, architecture, and history. The city is located in the heart of Tuscany, surrounded by rolling hills and vineyards. Other notable cities in Tuscany include Pisa, home of the iconic Leaning Tower, and Siena, known for its mediaeval architecture and of course the Strade Bianche.

Layout of Tuscany (from a cyclist’s perspective)

When cycling Tuscany, bear in mind that the region is divided into

  • Northern mountain region stretching from Carrara in the north heading eastwards in a line towards the north of Florence. From Montecatini Terme you can head north and visit the ski resort of Abetone at 1700m.
  • Below the mountain range you have places like Lucca, Montecatini Terme, Vinci, Pistoia and then Florence. These offer flatter routes; heading south from any one of these towns you find more lightly undulating, but still iconic, scenery.
  • South of Florence you enter the famous Chianti region which offers stunning countryside views of the many vineyards made famous by Chianti. Nearby is Siena which is famous for the Strada Bianche pro race in early March and a perfect stepping stone to visit Chianti.
  • The west side coastline facing the Mediterranean is mainly a flat coastal region all the way south to Lazio.

Best towns in Tuscany (for cyclists)

When considering your cycling holidays, Tuscany can appear very large; it can be difficult to know which area to focus on and what the best cycling base in Tuscany is for your trip.

In this section I share a range of the best places to stay in Tuscany, based on my experience and knowledge of cycling in Tuscany.

Northern Tuscany

Lucca and Montecatini Terme are two of the best towns to stay in Tuscany. They offer great bases for cycling north into the mountain range. Head west towards the Tuscan coast for flatter coastal roads or south for undulating routes towards San Miniato, Vinci (birthplace of Leonardo) or San Gimignano UNESCO world heritage town.


Lucca is a beautiful Tuscan town surrounded by thick 16th Century walls. The walls are 4km long and you can walk or cycle along them. Lucca is also home to some of Italy’s finest mediaeval and Renaissance architecture, superb dining, antique markets, and summer music festivals. It provides easy access to stunning nearby villas and surrounding hills. There are also some great beaches close at hand! Unlike many towns in Tuscany, it isn’t a hilltop town, so it is ideal for anyone looking for flatter riding options.

Montecatini Terme

Montecatini Terme is famous for being one of the best preserved spa towns in Italy, with its elegant art deco buildings, shops, al fresco bars and restaurants. Its leafy parks and laidback atmosphere give it a feeling of tranquility. It’s also less congested than many other towns in Tuscany. It’s a peaceful place to return to after a day riding your bike. In addition, there’s the unique chance to take the old wooden funicular railway built in 1889 up to Montecatini Alto. It offers stunning views of a wide panorama towards Lucca and within the medieval square there are many restaurants and bars to enjoy the local cuisine.

Mid Tuscany

Siena is a city rather than a town, but it’s perhaps the best city in Tuscany (Florence might have something to say about that but I prefer Siena). Gobsmackingly beautiful, it’s also a base that allows you to head in all directions with varying degrees of changes to the scenery. To the north is San Gimignano, to the west is Volterra, to the north east you find Chianti and in the south is the Crete Senesi region


Siena is one of the jewels in Tuscany’s crown, famous for its beautiful architecture and role in the Strade Bianche. Siena’s heart is its central piazza known as Il Campo, known worldwide for the famous Palio run here, a horse race run around the piazza every summer.

Siena also forms an excellent base for exploring the nearby Chianti countryside, which is famous for its gentle hills and characteristic combination of vineyards, olive groves and forests, dotted with red-tiled farmhouses, mediaeval churches and towers, abbeys, castles and magnificent villas.


Riding here, you’ll experience the beautiful forested Chianti hills as well as the iconic vineyards and olive groves. Chianti is dotted with interesting rural parish churches, monasteries, abbeys, villas and castles, often accessed via ancient dirt roads known here as strade bianche, “white roads”, which are lightly travelled and suitable not only for cars but also for bicycles. The Chianti farm houses themselves are often extremely attractive, often built around the remains of a mediaeval watch tower or even a castle.

Crete Senesi

Crete Senesi means the “clays of Siena”. The distinctive grey colouration of the soil gives the landscape an appearance often described as lunar. The landscape is characterised by barren and gently undulating hills, solitary oaks and cypresses, isolated farms at the top of the heights, stretches of wood and ponds of rainwater (commonly referred as fontoni, literally “big springs”) in the valleys.

Southern Tuscany


Pienza is another popular base for cyclists to stay in. It’s located in the heart of the Val d’Orcia UNESCO world heritage area. Here you have rolling hills and country roads with a mix of tarmac and gravel roads which give the distinctive look of huge open agricultural fields.

Val d’Orcia

Val d’Orcia is an incredible destination in rural Tuscany. This area was declared a UNESCO heritage region in 2004 and it has maintained its beauty for centuries. The rolling hills and beautiful villages in Tuscany have been the subject of many Renaissance paintings. It is full of mediaeval castles, vineyards, and olive groves as well as gorgeous farmhouses, isolated homesteads, roads lined with cypress trees, and golden fields of grain and sunflowers.

On the west side you have the famous Brunello wine region.

To the east you have Montepulciano, another famous historical town also made famous by its many vineyards.

The food is also exceptional, with high-quality items like pecorino cheese, extra virgin olive oil, and delicious wine. Cycling in the Val d’Orcia is an unforgettable journey through amazing panoramas and flavours. This paradise is where many of the most beautiful photos of Tuscany come from.

The routes in the south of Tuscany are a mixture of tarmac and gravel; of course, gravel is what makes southern Tuscany iconic. Here there is less traffic than in the north of Tuscany as it’s mainly agricultural. Scenes used in the English Patient and Gladiator scenes were filmed near Pienza.

Tuscany cycling routes

Below I share some of the best Tuscany cycle rides. They’re also personal favourites of mine. Of course there’s not room here to share all the best cycling routes in Tuscany, but hopefully this provides a good start!

Northern Tuscany: Lucca and Montecatini Terme

Lucca to Montecarlo to Montecatini Terme

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Once you leave Lucca, you are immediately in the countryside. It’s worth stopping to take in one of the most famous of Lucca’s 16th Century villas, Villa Torregiani.

Biking along Tuscany’s many Cypress tree lined minor roads, you pass by many olive groves which produce Lucca’s famous and renowned olive oil. The route has a short climb (the only climb of the day) towards Montecarlo. One side of this small hilltop historical village is full of vineyards and the other side of the village is full of olive groves. There are great views of the countryside from this vantage point; it’s the perfect location for lunch or wine tasting.


  • 12km Villa Torregiani is a stunning villa and photo opportunity.
  • 24km visit the medieval village of Montecarlo for coffee or lunch in the main square. This is the only hill to climb of the whole day and there are many lunch options in the very centre of this medieval village.
  • 38km arrive into Montecatini Terme, a lovely small spa town.

Montecatini Terme to Vinci to San Miniato

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Once you leave Monsummano behind, you’re in the countryside amongst vineyards and olive groves. The route takes in various lovely villages including Lamporecchio and the climb of San Baronto. With lovely views of the countryside, a lunch or coffee at the top of the San Baronto climb is perfect. From San Baronto you have a really nice gentle but panoramic descent to Vinci, the birth place of Leornardo di Vinci. After Vinci you head towards Cerruto Guidi, a well known chianti wine area, which you will cycle past on your way to the historical hilltop town of San Miniato.

San Miniato is the end of the ride and offers great views of the countryside, showing you were you have cycled from. San Miniato is part of the famous Via Francigena pilgrim walk from Canterbury to Roma during the 12th century.


  • 21km Lamporechio village was the home of Vincenzo Nibali, winner of the Tour de France (2014), Giro d’Italia (2013 and 2016) and Vuelta (2010).
  • 22km start of a 3km climb to the iconic village of San Baronto. At the top is a bar and restaurant. You can take refreshments on the balcony overlooking the view of the countryside where you have cycled from.
  • Vinci village – you can visit the museum of Leornardo di Vinci in the old battlement centre (the Museum is very interesting and brings to life the drawings into models).

Mid Tuscany: Siena and Chianti

Siena to Radda in Chianti

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This is a lovely picturesque Tuscany cycling route which starts in Siena and covers vineyards and some of the best villages in Tuscany, including Castellina in Chianti and Radda in Chianti, both in the heart of the Chianti Classico region.

It also takes in Monteriggioni mediaeval walled castle. The route after leaving Monteriggioni is quiet route with a climb to Castellina in Chianti where there’s the opportunity to enjoy a wine tasting at Castello di Fonterutoli. After this you have generous panoramic views all the way to the historical village of Radda in Chianti. This is such a lovely tiny village with enormous character with one high street filled with individual crafts, wine tasting, restaurants and cafes.


  • At 14km visit the walled castle of Monteriggioni
  • At 33km visit wine estate of Fonterutoli
  • At 38km visit the historical centre of Castellina in Chianti

San Gimignano to Siena

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This is one of the most panoramic routes to Siena when cycling from the north. You leave San Gimignano with two climbs, but once on top of the mountain you have a wonderful slow descent and at the same time some of the best views in Tuscany as you head towards the small historical village of Casole D’Elsa.

A gradual descent takes you towards the very small village of Badia Isola – one of the refreshment stops on the famous Via Francigena Pilgrim walk. In the 12th Century it used to be an overnight stop for pilgrims and it’s now a museum to showcase its history.

Not long after this village you come across the stunning Monteriggioni castle; it’s a great place for a refreshment stop.

As you head into Siena it will start to get busy but as you are arriving from the north it’s a quieter route into the city.


  • At 26km visit Castle d’Elsa village – lovely views of the countryside
  • At 43km visit Abbadia Isola located on the Via Francigena, its a lovely village to explore the fortified abbey once a resting place for the pilgrims as they made there way to Rome.
  • At 47km Visit the walled castle of Monteriggioni

Southern Tuscany: Val d’Orcia and Pienza

Pienza to Montepulciano, Montichiello and Pienza

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This is an easy route, with a light, gradual climb to Montepulciano with panoramic views of the countryside. As you enter Montepulciano you can’t help feeling this town has hardly changed since the 15th century, with its narrow streets and bustling shops offering local produce and a hilly walk to the main piazza for a coffee break.

After Montepulciano, you head south, with a section of gravel roads which is typical of some roads in Southern Tuscany, towards the small but picturesque village of Montichiello. Montichiello is a perfect place for lunch. After a great descent towards Bagno Vignoni you return to Pienza via a short climb.


  • 16 km coffee break inside Montepulciano
  • 29 km Montichiello has lovely views and is a good stop for coffee or lunch. It’s worth calling in advance to make sure the Osteria is open. If it’s a nice day, ask to book a table outside on the balcony – it has stunning views.

Pienza to Montisi and Montalcino

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This is a really nice rolling hill route on quiet roads cycling past the small villages of Castelmuzio, Montisi and San Giovanni d’Asso. These are all perched on hilltops offering lovely views of the countryside and are ideal places for a refreshment stop.

Torrenieri village is the start of a 5 kilometre gravel section (used in the Giro d’Italia stage 7 in 2010 – this was one of the most iconic stages on a rain fueled day won by Cadel Evans). It’s now used as part of the L’Eroica long route. L’Eroica is the vintage bike festival held in October every year.

Brunello wine is world renowned and as you head towards the climb to Montalcino you will pass by many vineyards  surrounding the town. The GPS file indicates numerous Brunello wine estates offering wine tasting and light snack options before arriving at the hilltop town of Montalcino. Here you’ll find lovely main squares with lots of cafes and restaurants to eat al fresco as well as dedicated wine shops offering Brunello wine tasting experiences.

Once you leave Montalcino you have a wonderful descent for 12km and cycle around the iconic and highest mountain in the south of Tuscany, Monte Amiata. Thankfully you (mostly) cycle around it, but there is a long climb to 600m elevation before another long descent to Bagno Vignoni. This is an original open air Roman Spring Bath; when you visit the bath you can see hot water bubbles to the surface. The water originates 1,000m below the ground.


From 8 to 20km you pass through three quaint villages, each an ideal stop for a refreshment break.

As you cycle uphill to Montalcino you will see various wines estates. Make sure you book a wine tasting as the wine estate prefer notice in advance.

At 41km arrive in Montalcino beautiful preserved historical hilltop town surrounded by vineyards and wonderful panoramic views of the countryside from many vantage points.

At 72km visit the small village and view the open air Roman spring bath.

Crete Senesi: Castelnuovo Berardenga – Strade Bianche – Bounconvento – Pienza

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Here you enter a new province of Crete Sinesi which is criss crossed by Strada Bianche (see dotted red lines). The sections shown are used in the Strade Bianche Road Race

It has the famous section they call Monte Santa Maria 11.5km section as Fabian Cancellara is honour of the three times winner of the race.


  • At 26km visit the abbey of Monte Oliveto Maggiore large Benedictine Monastery
  • At 35km visit historical town of Buonconvento
  • At 38 – 50km and 54 – 65km experience sections of Strada Bianche route as per the race .

Road quality in Tuscany

An important consideration for road cycling in Tuscany is – what are the roads like?!

Fortunately it’s pretty good news.

Cycling is very popular amongst both tourists and locals in Tuscany. At the weekends thousands of club riders head out in the morning to enjoy the varied riding.

Traffic is generally very considerate to cyclists, there are so many amateur cycle events and professional races in the region that motorists are used to seeing and accommodating cyclists bike riding Tuscany’s roads.

There are few traffic free cycle paths in Tuscany; there are some on the coast but in the interior, cyclists have to share the road with motorists.

In the north, I tend to find mostly smooth roads in the towns to be generally pretty good but I’d suggest staying off the main A roads due to traffic. The surfaces in the south and west are in much better condition as less people live here, there is less industry and it’s rare to see large trucks/wagons on the roads as this part of the region is the agricultural and wine-producing part of Tuscany.

Cycling events in Tuscany

Given how popular bike riding in Tuscany is, it’s not surprising that it’s also home to two major annual cycling events that attract thousands of riders each year:

  • Strade Bianche in early March
  • Tirreno – Adriatico always starts in Tuscany in mid March
  • L’Eroica in early October

Strade Bianche

Strade Bianche is Tuscany’s most famous cycling event. It’s held in Siena over the first weekend in March. It’s swiftly become one of cycling’s most famous races.

On Saturday of the Strade Bianche weekend, you have the opportunity to watch the riders sign on and mingle with spectators and watch the start of the women’s race followed by the men’s race. You have plenty of time to watch the women finish on the famous Santa Caterina climb before heading to the car and going to the 60 km point to the finish at San Martino gravel climb to see the men (and entourage). You can then head to the finish to watch the men climb San Martino.

On Sunday of the Strade Bianche weekend, you can participate with 6,000 riders in the same event with a 90 or 140 km route experiencing the same routes and finish as the pros. There is no other event quite like this that allows you to finish so spectacularly in the main Piazza del Campo. With an array of al fresco bars and restaurants, there are plenty of places to quench your thirst.

L’Eroica, Chianti

L’Eroica is an annual non-competitive vintage cycling event which has taken place since 1997. The idea of the event is to let cyclists experience vintage cycling during the golden years of Italian Cycling in the 40’s and 50’s, with participants using vintage steel bikes, accessories and vintage clothing. To participate you must have a steel bike pre-1987 and wear old fashioned woollen cycling clothes in keeping with the traditional event.

The event starts and finishes in Gaiole in Chianti with the 209 and 135 km route on Saturday and the 106, 81 and 46 km routes on Sunday.

The route is often on “strade bianche”, the white gravel roads Tuscany is famous for. It is held on the first Sunday of October every year. It showcases the stunning Chianti Classico and Crete Sinesi countryside with refreshment stops along many villages offering local specialities such as Tuscan bread dipped in wine, pig fat bruschetta, Ribolita soup, sandwiches, fruit and of course local wine.

L’Eroica is the most popular vintage bike event in the world, with riders coming from as far as America, Australia and South Africa, as well as across Europe. It’s a fun weekend with a huge cycle as well as local stall holders offering many wine and food experiences plus live music.

L’Eroica, Montalcino

This is a recently introduced vintage bike event based around Montalcino.

The organisers felt that riders on the 209km l’Eroica Chianti event in October where the only riders able to see the beauty of this southern region of Tuscany. (On the 209km route, Montalcino is the southern most part of the ride; from here, riders then turn and head towards back to Gaiole in Chianti via Buonconvento and Asciano.)

This new event allows more riders to experience the southern part of the vintage bike event. The organisers created a new event called “L’Eroica Montalcino” offering 46, 70, 96 and 135km routes on the last weekend in May.

Giro d’Italia

The Giro can often be found visiting Tuscany.

One of Italy’s road cycling heroes, the Giro’s three-time champion Gino Bartali even has a cycling museum dedicated to him in Ponte e Ema in Florence. It displays 19th-century bicycles, as well as two bikes ridden by Gino.

Giro d’Italia again visits Tuscany in 2023, with two stages on the Versilian coastline, stage 10 finishing in Viareggio and stage 11 starting in Camaiore.

Tour de France

New for 2024! The Tour de France will start in Florence in homage to the past giants of Italian Cycling, Fausto Coppi, Gino Bartali, Ricardo Nencini, Ottavio Bottecchia, Marco Pantani, Felice Gimondi and the last winner of the Tour from Italy, Vincenzo Nibali.

Hotels (and accommodation) for cyclists in Tuscany

In my experience, most accommodation welcomes cyclists; cycling is a popular sport in Tuscany and it’s a growing market, with a strong trend in demand from tour operators.

There are no specific bike hotels as such, but all hotels tend to offer facilities for bike storage and early breakfast if needed. However, don’t expect mechanical assistance as standard, as these are not bike-specific hotels.

Types of accommodation

Town centre hotels

As Tuscany is such a popular destination, you’ll find great places to stay inside every historical town. Usually they’ll be 3 star establishments and occasionally 4 star.  The challenge is that these towns are small and demand in the summer is very high, so it’s important to book early to secure the hotel.

Italian agriturismos

Agriturismos are also popular in the Tuscan countryside but again especially in the summer demand is high, booking one or two nights is not going to be accepted. They prefer 4 night minimum stays in high season.

Wine estates

Accommodation in castles or wine estates in Chianti or Brunello region are another possibility. They are expensive but are at a level of quality way above any of the hotels in towns. They usually offer their own restaurant, swimming pools, health club and winery to provide an exceptional experience.

Bike-friendly hotels in Tuscany

Below I share some of our favourite cycling hotels in Tuscany; these tie in with the regions above.


Hotel Luna is a 3 star superior hotel that’s very much inside the mediaeval walled town of Lucca. It has characterful rooms and you are close to all facilities and amenities.

In a much quieter location is Hotel San Martino, still inside the mediaeval centre.


Hotel La Villa is a stylish 3-star modern hotel with a fantastic location in the north of the city. It’s easy to cycle to as it’s away from the very centre of Siena but within 5 minutes walk you are in the city

Hotel Minerva is a more traditional 3-star hotel located north of the city but again it’s easy to cycle to. It has a large covered and secure car park for the bikes and vehicles.


There’s not much of a range of hotels in Pienza, but I like these two very good and well located hotels. Both are three star. They are Hotel San Gregorio and Relais Chiostro di Pienza.

The San Gregorio suites are well priced and offer 1 large bedroom and a large room with sofa, table, chairs and a fridge.

The Relais Chiostro di Pienza is located inside the village. It’s a former Franciscan Monastery dating back to the 13th century and offers stunning panoramic views of the countryside as well as an outdoor swimming pool. It has an in house restaurant offering al fresco tables with great views and charming hotel rooms .

Montecatini Terme

Hotel Belvedere is a newly renovated 4-start hotel that only opened in late summer 2022. It has all modern facilities and is in a nice quiet location away from the hustle and bustle of the town.

Francia Quirinale is the other 4 star hotel that’s centrally located close to cafes and bars. It’s old style design offers a nice balcony to enjoy drinks.


You can find other bike hotels in Tuscany in this article.

Bike hire in Tuscany

If you’re looking for bike hire in Tuscany, you’ll be pleased to hear that you can find it in places like Lucca, Montecatini, Siena and Montepulciano.

However many secondary towns and hilltop villages, such as Vinci, San Gimignano, Montalcino, Pienza and San Miniato do not have bicycle rental available.

There are three bike rental shops in Tuscany that I use:


Ruota a Ruota

Via S. Donato,

186, 55100


Colle di Val D’elsa


loc. Pian dell’Olmino, 77

53034 – Colle di Val d’Elsa (SIENA)


Cicli Maggi

Viale Ammiraglio Morin, 79

55042 – Forte dei Marmi


You can expect all Tuscany bike shops to speak English. Also, you can expect them to be open throughout the week, except Sunday. Be aware that most close for lunch from 1 – 3pm.

Bike shops in Tuscany

Occasionally you may need assistance due to a problem with your bike you can’t sort out yourself.

Most major towns have bike shops but secondary towns will not always have a bike shops so be aware to make a note of your routes and locate the nearest bike shop in case of emergency.

Big stores like Decathlon and Nencini sport are available within the region and are also a great source of bike parts and service / repair.

Remember all bike shops are closed on Sunday.

Bike tours in Tuscany

Cycling Tuscany on a self-guided trip is, in my opinion, the best way to see the region. It gives the flexibility of being able to start any day of the week and in any month of the year, with the convenience and time-saving advantages of having a local cyclist and support on hand.

Tuscany cycling tour options: self-guided or add a guide

Via my business, Gusto Cycling, I offer 7 night / 8 day self-guided Tuscany cycle tours. If requested, we can also provide a guide to accompany the clients.

There are two tours, one is Tuscany South and the other is Tuscany North.

These tours give you the opportunity to really immerse yourself in Tuscany via the backroads of the countryside, quaint villages, wine estates, olive groves and enjoy stopping for a cappuccino or lunch with lovely views during the day.

Prices include luggage transfers and routes I’ve personally created along many of the best roads in Tuscany, with distances to suit your group.

Tuscany North (Lucca to Siena or Siena to Lucca)


  • Visit the Leaning Tower of Pisa
  • Stay overnight in beautiful Lucca, the preserved 15th-century walled town
  • Stay overnight in Montecatini Terme, a lovely small Baroque spa town and visit Montecatini Alto with its stunning views and mediaeval setting.
  • Visit Vinci the birthplace of Leornarado di Vinci
  • Stay in quality accommodation, with warm hospitality, all hand-picked by me.
  • Visit and stay overnight in San Gimignano and Siena, both stunning mediaeval towns.
  • I will provide each day a list of places to enjoy a coffee break and lunch so you can maximise your Tuscan experience.

Tuscany South (Siena to Montalcino or Montalcino to Siena)


  • Visit the famous towns of San Gimignano, Radda In Chianti, Pienza, Montepulciano and Montalcino.
  • Bike ride through stunning landscapes, wide-open fields, cypress-lined Tuscan hills, and many of the best wineries in Tuscany.
  • Cycle through the historic wine regions of Tuscany, sampling the best wines of Chianti, Montepulciano, and Montalcino.
  • Stay in quality accommodation, with warm hospitality, all handpicked by me.
  • Visit the wine and the renowned cheese of Pecorino in Montepulciano and Pienza.
  • Cycle along the rolling hills of Chianti and Crete Sinesi, plus cycling through Tuscany’s stunning UNESCO heritage region of Val d’Orcia.
  • I will provide each day a list of places to enjoy a coffee break and lunch so you can maximise your experience.


Distances can vary each day from 35 – 50km. With the odd exception, elevations usually vary from 500 – 1000m elevation. Usually it’s not mountainous but it does tend to get more hilly the further south you go. The reward from these hills is the spectacular views of the countryside.

Bespoke routes

I am always happy to tailor the routes on our Tuscany cycling tours for groups, couples, families – and even this year a couple on their honeymoon who are staying in some of the most spectacular properties in Italy!

We also cater for family cycling holidays in Tuscany. I tend to direct theses type of enquiries to Tuscany south as we can route the tour via much more gravel sections off road allowing to cycle between smaller towns. Also accommodation options means we can provide shorter distances each day.

Rental bikes for the tour

We can supply many different kinds of bikes, depending what our clients are looking for: hybrid, electric hybrid, gravel bikes, carbon racing bikes, electric racing bikes and even tandems!

The bikes are always serviced before delivery to the client’s hotel and we ensure all is well with it.

Mechanical assistance

All bikes are provided with a puncture kit (one inner tube, tyre leavers and Co2 Valve) and we expect all customers to be able to change an inner tube.

In the very rare case there is a need for a mechanic we can dispatch one within a reasonable time frame.

More information​

For more information about Gusto Cycling’s tours, take a look at our website or contact me using the form below:

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When to visit Tuscany

The ideal season to cycle Tuscany is April (average temperatures around 19 degrees), May (average temperatures around 23 degrees) and June (average temperatures around 28 degrees).

Early Autumn in Tuscany is also a good time to visit, from September (26 degrees) to October (21 degrees). During these months, temperatures are great for cycling and al fresco dining. There are also many festivities throughout the May and June period.

The weather is really hot between the end of June to the end of August, and temperatures can reach anything from an average of 32 to 38 degrees with a high humidity factor. During these months, e-bikes can be your best friend.

Even if you come at one of the optimal times of year, I’d still suggest bringing a light rain jacket and possibly a wind jacket if you are cycling down the higher mountains. However, it’s very rare that there is significant wind as the northern mountains of Tuscany block the wind coming from the northern part of Italy.

If you prefer riding in a short sleeve jersey, bring some arm warmers as well as they can be useful for cool early morning starts and are easy to place in your back pocket after an early start in the morning.

Tips for cycling in Tuscany


I always suggest clients try all the food as it’s so varied from town to town. Every part of Tuscany has their own style of ragu, cheese, wine and bread.

For example, in Lucca you would not be offered pappardelle with wild boar meat: that is offered in the south of Siena and Pienza. Also pici pasta and a local speciality dish called cacio e pepe (huge spaghetti with Pecorino cheese) are found in Siena but not elsewhere. Siena is also known for its panforte Christmas dessert.

Meanwhile Pienza is well known for all types of Pecorino cheese. Lucca is well known for olive oil. Florence is known for its ribollita soups.

You get the picture!


Every town has a fountain for access to fresh cold water.


Wine regions include Cerruta Guidi, Chianti, Brunello, Montepulciao and more.

There are now many wine estates in most parts of Tuscany. Many are internationally known like Chianti and Brunello but there are also more regional estates catering for the Italian market.

When visiting wine estates it’s important to book a time slot. Wine tasting and wine tours are becoming more and more popular and invariably they will not be able to add another booking if you just turn up, as staff levels limit more bookings.

Also many wine estates offer light or full lunch with wine tasting again. As before, you need to book in advance if you wish to enjoy a food experience with the wine.


Every restaurant closes one day a week. It’s important if you have a restaurant in mind to check they are open on the day you plan to visit.

Weekends are very busy in the restaurant trade. Sunday is as busy as Saturday so I’d always suggest booking at weekends.

Also a small but important detail! Steaks are always cooked rare to medium rare. If you want it better cooked make sure you advise the waiter taking the order.


Remember shops close for lunch from 13.00 – 15.00. However most cafe bars generally open all day.

If you are wondering what to buy from convenience stores, for the perfect sandwich, you could consider buying fresh cut parma ham, Toscano salami, fennel salami and pecorino cheese from the deli.


If there is a group of you heading to Tuscany and you’re planning to bring your own bikes then I’d recommend booking early and getting a minibus. For example our minibus vans can carry five people and five bikes. Any more than this number and you would need two mini buses. Alternatively, take the easier option and do a self guided tour of Tuscany and arrange for luggage to be transferred each day.

However if you are staying in one location then you can skip the car rental market completely. I’d suggest hiring the racing bikes you need, booking a private transfer to your first night’s destination and have the bikes delivered to your hotel. On the last day take a private transfer back to the airport.

Bike choice

Choosing the right bike for your bicycle tour of Tuscany is important as it depends how comfortable you would be for a week’s cycling.

If you’re looking for a leisure holiday, whilst an aluminium hybrid bike has a great range of gears which give you comfort to cycle and give you the scope to cycle up any hills on your tour, it will be heavy. You can expect front suspension, wide tyres, disc brakes and rear panniers.

For those hiring road bikes in Tuscany, I’d suggest a minimum of 25mm sized tyres. If you plan to cycle on strada bianche roads please advise the bike shop so that gravel bikes are offered. These come with 28- 34mm tyres, giving you much more scope for comfort.


Touring Editore Toscana is a great book – but be aware it’s in Italian!

David Cleveland, author of Bicycle Touring in Tuscany

Public transport

Railway travel in Italy is one of the cheapest in Europe. Bikes are allowed on regional trains; you have to pay extra but it’s not expensive and there are special rail carriages for bike storage. It’s definitely worth booking in advance as otherwise bike tickets are sold on a first come, first served basis so space is not guaranteed.

Useful vocabulary

English is not always spoken outside the main historic and cultural centres of Tuscany, so it’s useful to know a few words of Italian for your Tuscany bike trip:

  • Dove E – where is?
  • Biciclettaio – bike shop
  • Forato – puncture
  • Dove si puo mangiare – where can we eat?

How to get to Tuscany

Pisa and Florence Airport are the two airports in Tuscany. Pisa has many more flights then Florence as Florence has a short runway and so is only allowed to have smaller aircraft.

Alternatively, you can fly into Rome and take the fast Trenitalia or Italo train from Rome to Florence in 90 minutes. There are often four trains an hour to and from Rome to Florence. If you book online it will be cheaper based on set departure times. However, on these fast trains there is no room for bike boxes.

Trains are the best and cheapest option to travel from the airport – www.trenitalia.it offers you the fast intercity trains and the local train services with timings and prices to book online.

Final thoughts

A huge thank you to Marco for sharing so much useful information about Tuscany cycling holidays! If you want to find out more about Marco’s trips and get planning a Tuscan cycling adventure, do head over to his website Gusto Cycling.

Have you been on a Tuscany cycling holiday? How was it? Any tips to share that we haven’t covered here? We’d love to hear from you in the comments below!

Got a question for Marco?

Fill out this form and we will send it to Marco. We aim to get you an answer within 24 hours wherever possible!

We will use this info to send the enquiry to Marco and/or their team. Our privacy policy explains more and here’s a reminder of our disclosure policy and terms and conditions.

Marco Mori

Marco runs Gusto Cycling. He says “I have always been interested in cycling, ever since my uncle took me to see a cycle race in Tuscany when I was 11 years old. This opened my eyes to a new sport and experience. I have been a cyclist ever since, both here in the UK and in Tuscany.

I have spent my whole career in the travel business, working with international tour operators. This gave me a full grounding in managing tours.

I started Gusto Cycling 12 years ago to capitalise on my huge knowledge of Tuscany (all my family is from Montecatini Terme). We offer a unique and a more authentic perspective on cycling in Tuscany via two different tours: Tuscany North and Tuscany South.

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