Self-Guided Walking Tours & Biking Tours

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Self-Guided Classic Tuscany Cycle Tour


  • Cycle the rolling Cypress tree lined Tuscan hills
  • Dine in the buzz of Piazza di Campo, Siena
  • Ride amongst the vineyards of Montepulciano
  • Poolside relaxtion 'Under a Tuscan Sun'
  • Sample the gelato of San Gimignano

Experience the very best of classic Tuscany on a self-guided cycle tour. Take to two wheels and cycle bella Italia, discovering picture-postcard Medieval and Renaissance hill-top villages, accompanied by sumptuous cuisine and the famed Chianti, Brunello and Nobile wines.

Each day you will be cycling at your leisure through impossibly pretty scenery, characterised at first by vineyards and verdant farmland which lead to contrasting cypress-lined country roads, the UNESCO World Heritage Landscape-listed Val d’Orcadia and the grey hues of the ‘Crete’ region.

Your Tuscan adventure starts with an incredible first day’s cycling; visit the fortified town of Monteriggioni, before heading to one of Italy’s most spell-binding locations—San Gimignano with its many towers. Each day you’ll reach traditional villages perched atop rolling hills filled with stunning red brick and earthen-coloured buildings, with roofs baked by the Tuscan sun. Highlights include magical Siena, the thermal-spa town of Bagno Vignoni and Pienza, as well as photogenic Montichiello and Montepulciano.

Cool churches, abbeys and monasteries await you, where Gregorian chants drift through the air and create a special ambience. Take time to reflect at the Monte Oliveto monastery and peaceful abbey of Sant’ Antimo. You’ll also pass through towns located on the route of the ancient Via Francigena pilgrimage. And the end to each perfect day’s cycling? You’ll certainly have earned a glass or two of full-bodied Italian red accompanied by a dish garnished with local pecorino cheese and truffles! Tuscany is well known for its steep hills and therefore this trip will appeal to those with a good level of fitness, with daily distances ranging from 35 to 46 kilometres.

DAY 1: Arrive in Poggibonsi and transfer to Staggia

Your Tuscan cycling adventure begins in the lovely village of Poggibonsi, in the heart of Tuscany's rolling landscape. Relax and unwind at your lovely villa; take a tip in the pool, wander around the exquisite gardens, enjoy a glass of wine on the panoramic terrace, or perhaps take a stroll around the picture-postcard Tuscan countryside.

We recommend flying to Florence or Pisa airport, then you can take a train to Poggibonsi (1hr or 1h16 respectively). You’ll receive a welcome briefing and bike fitting later today (the latter if you have opted for bike rental).

Overnight: Poggibonsi

DAY 2: Loop Cycle to Monteriggioni, Colle Val d’Elsa and San Gimignano

Following a delicious breakfast, depart on a loop cycle from Villa San Lucchese, heading towards the classic fortified town of Monteriggioni, its distinctive round shape dominating the surrounding Sienese plain.

Continue to Colle Val d’Elsa which is home to glass-blowing artisans, and perhaps visit one of the workshops.

Next comes a highlight of your trip—cycling to the famous medieval town and UNESCO World Heritage site of San Gimignano, with its many towers. Ensure you allow yourselves a few hours to stroll through this photogenic town and pick up a memento of your Tuscany trip.

Return to the lovely Villa San Lucchese for a second night’s stay.

Cycle: 35km, total ascent approx. 600m

Overnight: Poggibonsi

DAY 3: Cycle through Chianti to Siena

Bid farewell to your hosts at Villa San Lucchese and start your cycle through Chianti’s winding scenic roads to your next destination. You’ll be travelling through a landscape of verdant vineyards with superb wineries—your destination is beautiful Siena.

Reaching the cobbled streets of Siena, why not treat yourselves to a well-deserved gelato on one of Italy’s most famous squares—the Piazza del Campo. It is here in the shell-shaped town square that the Palio horse race is held twice a year.

Siena is a UNESCO World Heritage site and one of Italy’s must-see attractions. The city is well-known for its wine and cuisine, art, museums and medieval Duomo architecture—soak up the atmosphere and revel in the ambience of this charming historic town.

Cycle: 40km, total ascent approx. 450m

Overnight: Siena

DAY 4: Cycle through the ‘Crete’ to Buonconvento

Climb on board your bike for another day’s memorable riding through the winding roads of Chianti. You’ll see the landscape change from vineyards to the linear cypress-crested hills near Buonconvento of the ‘Crete’. Pass through the little village of Murlo en route to your traditional accommodation.

The ‘Crete Senesi’ consists of a range of hills, woods and villages; the literal translation is ‘Senese clays’; their grey colour giving the landscape an almost lunar air. The region is known for its black and white truffles and hosts a festival and museum celebrating this rare and delicious delicacy.

Cycle: 39km, total ascent approx. 800m

Overnight: Buonconvento

DAY 5: Cycle to Monte Oliveto Monastery and Montalcino

The day starts with the most challenging ride of the tour, with fairly steep slopes until you reach the asphalt. Head to the tranquil red brick Monte Oliveto Maggiore - this large Benedictine monastery dates from 1313. With its drawbridge, Cyprus-lined alley and botanical medicine gardens it will no doubt prove to be yet another highlight of your tour.

Cycle onwards to your hotel in Montalcino, the winelands of the delicious Brunello red. Almost unknown until 20 years ago, Brunello di Montalcino is now one of the most famous Italian wines and you should certainly try it yourselves!

Cycle: 46km, total ascent approx. 850m

Overnight: Montalcino

DAY 6: Loop Cycle to Sant’ Antimo Abbey

Enjoy an easier cycle as you descend the trail to the beautiful and peaceful church of Sant’ Antimo. With luck, you may be able to listen to the Gregorian chants of the monks.

The name of the abbey may relate to Saint Anthimus of Rome, as the story goes that his relics were moved here during the late 8th Century. In its hey-day, the abbey had authority over 38 churches from Pisa to Grosseto and control of around a thousand farm estates throughout Tuscany.

The area is also known for its Chiusure artichokes and Montalcino honey as well as a unique grappa from Brunello grapes. Sheep’s milk is used to produce a special type of pecorino cheese. Tuck in!

Cycle: 32km, total ascent approx. 450m (there is also an alternative route available for road bikers which is through Bagno Vignoni, in which case the total ascent is 1000m and level 'strenuous').

Overnight: Montalcino

DAY 7: Cycle to Pienza, Montichiello and Montepulciano

Cycle through Val d’ Orcadia National Park, where you’ll find  the hill-top town of Bagno Vignoni dominated by a square with a large thermal bath, drawn from a volcanic aquifer. From here, continue to the renaissance town of Pienza, village of Montichello before arriving at the famous wine producing town of Montepulciano.

Cycle: 45km, total ascent approx. 700m

Overnight: Montepulciano

DAY 8: Transfer to Chiusi and onward travel

This morning you’ll be transferred to Chiusi train station, for onward travel.

Additional Nights and Extensions

We can add additional nights before, during or after your cycle and would recommend adding a few days extension to Florence. Alternatively this trip combines well with our walking tours of Florence, Rome and the Cinque Terre or even the Via Francigena pilgrimage.


You will stay in rooms with private facilities in charming hotels, one countryside agriturisimo and a bed and breakfast. All properties are chosen for their excellent location, charm, warm welcome to cyclists and spectacular views. Some hotels have swimming pools.

We will always try and accommodate you at the locations detailed below, but on occassion, especially during peak season, we may have use an alternate accommodation of equal or higher standard. 

Single Rooms & Solo Cyclists

If you're travelling with family or friends but prefer your own room, a single room This trip is suitable for solo travellers although there is a solo supplement payable. Single rooms are available. A single supplement is payable.


The delicious Tuscan food and wine is undoubtedly a highlight of this holiday. The price of your holiday includes two dinners (one at Villa San Lucchese and one at Pieve a Salti), and breakfast each morning.

Lunches and dinners (excluding aforementioned) are not included but available at your hotel or nearby restaurants.




B&B l'Agnolo - Montepulciano

Located in the heart of Montepulciano. This once grand home is now a beautiful small and comfortable Bed and Breakfast, still displaying the ornate high fresco ceilings and wonderful surroundings. Expect a warm welcome during your stay in this unique bed and breakfast.







Villa San Lucchese - Poggibonsi

The stunning 4-star Villa San Lucchese is a restored 15th Century villa whose origins date back to 1300. In summer, dine al fresco on the terrace with expansive views, or wander around the beautiful gardens. Included in your stay is one dinner here at Villa San Lucchese.







Hotel Dei Capitani - Montalcino

Hotel Dei Capitani is fantastically positioned in the centre of the Medieval town of Montalcino. You will delight in the wonderful panormaic views over the Tuscan countryside, from the beautifully designed swimming pool and terrace area. You can expect a warm welcome during your stay in this charming Hotel.







 Fattoria Pieve a Salti - Buonconvento

Fattoria Pieve a Salti - Buonconvento

A traditional Tuscan agriturismo, offering total tranquility and overlooking the incredibly beautiful Tuscan countryside. Enjoy the vast array of facilities on offer, with outdoor swimming pool, spa, horseriding and the rustic restaurant which serves excellent home-grown food from the estate.







Hotel Chiusarelli - Siena

The building is a Neoclassical villa which was built around the 1860s and became one of the first hotels in Siena. In 2010, it was completely restored, maintaining its original style. In the magnificent frescoed halls, guests feel like they have gone back in time. Hotel Chiusarelli adds a gastronomic note to your stay in Siena with its Restaurant “Gli Orti di San Domenico”, where you can dine in a charming atmosphere, tasting typical recipes and dishes from traditional Tuscan cuisine.




Our Cycling Tuscany: Chianti & Siena tour is available from March to early November. You can start your holiday on any date in the season. 

Time of Year

We offer this trip from March to early November when the spring, early summer and autumn days are perfect temperature for cycling and capturing the essence of Tuscany's colourful landscapes. During the hotter summer months it's worth considering hitting the road earlier in the day.

Grade, Terrain & Navigation

This cycling tour is graded easy to moderate depending on the choice of
route. Each day you can choose the difficulty, with the longer/steeper
routes requiring a reasonable level of fitness. The routes follow
surfaced country roads and secondary roads. Near larger towns there are some
roads with more traffic. Please always be mindful of other road users at all times. Our tried and test route notes together with easy to follow maps are supplied. Should you require any assistance, 24/7 telephone support is provided.

Baggage Transfer

Your bags will be collected from your accommodation each day and moved onto your overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

Bike Hire

Bike hire is available as an optional extra. Choose from a Hybrid bike (Shimano Alivio 27-gear with 13kg aluminium frame), or a Road bike (Bianchi Via Nirone with Shimano Sora 27-gears). Bikes are equipped with rear rack, 1 rear pannier, odometer, pump, repair kit, water bottle and map folder. If you do opt for bike hire, then we will need your height and inside leg measurement in order to allocate you the correct equipment. A welcome meeting and a bike fitting will be on your first evening.


Your information pack has a detailed equipment list which includes standard cycling gear such as helmet, good shoes, warm and waterproof clothes and a day pack

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.

General Information

The distances and ascent/descents are approximations of the recommended routes.  This Cycling Tuscany; Chianti & Siena tour is not for beginners; Tuscany's rolling landscape means some of the rides are more challenging than others. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat, sunscreen. Your information pack has a detailed equipment list which includes standard cycling gear.

Travel to/from Tuscany

We recommend flying to Florence or Pisa airport.

By train: 

You can take a train from Florence or Pisa to the start of your trip at Poggibonsi (1hr and 1h16 respectively).

At the end of your tour you will receive a transfer to Chiusi train station, from where you can take a train to Florence (1h26) and then either a bus or a taxi (latter is approx. EUR20) to the airport. If flying out of Pisa then you can take a train from Chiusi to Pisa (2h40 approx, changing at Florence).

For train timetables visit

We supply detailed public transport information in your information pack, which you will receive when your booking is confirmed.


  • 7 Nights accommodation in rooms with private facilities in hotels, an agriturisimo (country hotel) and a bed and breakfast accommodation
  • Transfer on Day 8 from Montepulciano to Chiusi
  • 2 Dinners (at Villa San Lucchese and Pieve a Salti)
  • 7 Breakfasts
  • Information pack, route notes & maps
  • Baggage Transfers
  • Welcome briefing and bike hire fitting
  • 24/7 Emergency phone support


  • Lunches, dinners (except on 2 nights aforementioned), snacks and drinks
  • Travel to Poggibonsi / from Chiusi
  • Travel insurance
  • Admissions or entrance fees
  • Public transport or additional transfers
  • Rental of bike/s


  • Bike Hire: 27-gear hybrid or road bike, with rear rack, 1 rear pannier, odometer, pump, repair kit, water bottle and map folder
  • Additional night/s at any of the accommodations on the way or other destinations in Italy
  • Solo cyclist or single room supplements

We are often asked the following questions and I hope that you will find the answers useful.

Please don’t hesitate to contact us for more advice from our clients and team.

How fit do I need to be?

This cycling holiday is graded moderate and involves cycling 35-46km each day so you should enjoy an active lifestyle to get the most from this holiday. There are significant ascents as the towns and villages are at the top of hills.

What happens if I can’t cycle a stage?

We use a dedicated local service to transfer your baggage and they may be able to move you, your bike and baggage to the next stop in case of emergency. Local buses can also sometimes take bikes.

When is the best time of year?

Spring in Italy is sublime and April, May and June are absolutely lovely. Autumn is probably my favourite time of year as the landscape is made up of a gold and red pallet so September and October are unmissable. July and August can be very hot so you will have to start early to miss the heat of the day, although the towns and villages are buzzing which is great. You can view weather details for the region here.

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised. Tuscany is extremely popular especially during July/August. You will find up to date availability on our website and we will always try and accommodate your plans so just ask.

What personal equipment do I need?

You will need normal cycling clothes, waterproof jacket and trousers and some warmer cycling clothes, a full detailed kit list will be included in your info pack. 

Do I need to bring my own helmet?

Some local laws require cyclists to use a helmet. Please check to ensure you are abiding by the law. Helmets are not usually included in your bike hire for hygienic reasons. We recommend you bring your own or buy one from the rental bike service.

Which is the best airport?

We recommend flying to Florence or Pisa airport, then you can take a train to Poggibonsi (1hr or 1h16 respectively). See for further information on rail travel. 

What happens if I can't cycle a stage?

You can use public transport or local taxis to continue to your next overnight stop.

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