Cycling Tuscany: Chianti & Siena
- Cycle the rolling Cypress tree lined Tuscan hills
- Dine in the buzz of Piazza di Campo in Siena
- Ride amongst the famous vineyards of Montepulciano
- Poolside relaxation under the Tuscan sun
- Sample local wine and delicious cuisine en route
Itinerary
Day 1 Arrive Poggibonsi and overnightYour Tuscan cycling adventure begins in the village of Poggibonsi, in the heart of Tuscany's rolling landscape. Relax and unwind at your 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.
After arrivng you’ll be met by one of our local representative's for a welcome breifing and bike fitting (the latter only if you opted for bike rental).
Villa San Lucchese Hotel in Poggibonsi, is a romantic Historic Villa from XV century and today a 4 stars Hotel near Siena, whose origins date back to early 1300.
Following a breakfast, depart on a loop ride from heading towards the classic fortified town of Monteriggioni, its distinctive round shape dominates the surrounding Sienese plain. Continue to Colle Val d’Elsa, home to glass-blowing artisans, and perhaps visit one of the workshops.
Make sure to allow plenty of time for exploring the hilltop UNESCO Heritage Site of San Gimignano town, with its many towers. After your fill of the town head back to your countryside villa for a relaxing evening.
Ascent/descent: 558m / 558m (1830 ft / 1830 ft)
Villa San Lucchese Hotel in Poggibonsi, is a romantic Historic Villa from XV century and today a 4 stars Hotel near Siena, whose origins date back to early 1300.
Cycle Chianti’s winding roads through a landscape of verdant vineyards with superb wineries to the beautiful city of Siena. On 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 famous 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, Tuscan cuisine, art, museums and medieval Duomo architecture—soak up the atmosphere and revel in the ambience.
Ascent/descent: 408m / 261m (1338 ft / 856 ft)
Alternative longer route is 50km (31 miles) - ascent/descent: 733m / 586m (2404 ft / 1922 ft)
Situated in Siena city centre, so perfect for exploring on foot. Built in around 1870 as a Neoclassical villa, it was restored in 2004, keeping its original style as well as its beautiful, frescoed common rooms. The hotel has a restaurant, bar, terrace, and small garden to relax in.
Today the landscape changes from vineyards to the linear cypress-crested hills near Buonconvento of the ‘Crete’. Ride 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 gives the landscape an almost lunar air.
The region is known for its black and white truffles and hosts a festival celebrating this rare and delicious delicacy.
Ascent/descent: 576m / 659m (1889 ft / 2162 ft)
This agriturismo has been converted from farm buildings into a stunning country hotel including both an indoor and outdoor swimming pool, garden, spa with sauna, steam room and massages available (additional charges apply; advance bookings recommended). The agriturismo is in a natural truffle zone, so this is often on the restaurants menu along with local wines and organic produce grown on the farm.
Hotel Ghibellino is a family-run property in the centre of Buonconvento. It has a large terrace on the third floor providing a great view over the historic village. Cakes, fresh fruit and cold meats are served as part of the buffet breakfast.
Begin with the most challenging ride of the trip as you head for the tranquil red brick Benedictine monastery of Monte Oliveto Maggiore, dating from 1313. Complete with drawbridge, cyprus-lined alley and botanical medicine gardens it will no doubt prove to be another highlight of your trip.
Cycle on 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. We recommend trying a glass (or two!).
Ascent/descent: 597m / 235m (1958 ft / 771 ft)
Located in the medieval town centre of Montalcino with magnificent views of the Tuscan hills, this charming small hotel is situated in part of the 18th century “Catasto Leopoldino”. Enjoy the hotel's restaurant, bar, terrace, and a large panoramic garden with an outdoor swimming pool.
Enjoy an easier ride today as you descend to the peaceful Abbey of Sant’ Antimo, with luck, you may be able to hear the monk's Gregorian chanting. 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 the Brunello grapes and a special type of pecorino cheese. Tuck in!
Ascent/descent: 408m / 408m (1338 ft / 1338 ft)
Alternative longer route is 50km (31 miles) - ascent/descent: 1000m / 1000m (3280 ft / 3280 ft)
Located in the medieval town centre of Montalcino with magnificent views of the Tuscan hills, this charming small hotel is situated in part of the 18th century “Catasto Leopoldino”. Enjoy the hotel's restaurant, bar, terrace, and a large panoramic garden with an outdoor swimming pool.
Cycle through Val d’ Orcadia National Park, where you’ll find the hilltop town of Bagno Vignoni dominated by a piazza complete 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 for your final overnight.
Ascent/descent: 858m / 831m (2815 ft / 2726 ft)
Our hosts offer a warm welcome to all guests to their extraordinarily charming B&B. Rooms are museum-like, decorated with period Italian antiques and frescoed ceilings while on the other hand there are renovated bathrooms with modern fittings.
After a delicous breakfast you’ll be transferred to Chiusi train station, for your onward journey. If you'd like to extend your stay in Tuscany you can check out other cycling or walking holidays in the region.
This trip has a carbon score of 7kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 7kg is equivalent to 1 single running shoe (not even a pair!). Here at Macs, we pride ourselves on being a responsible travel company and continue to adopt, develop and innovate ways to positively impact the environment. Find out more information about how we've carbon counted our trips.
Other Information
Is it for me?Indulge in the very best of classic Tuscany on two wheels, enjoying fantastic wine and authentic cuisine. This trip requires a good level of fitness and offers cyclists a taste of the delights of Tuscany, with its fascinating abbeys, Renaissance towns and delicious food, whilst burning off any extra holiday calories!
Classic Routes | If you’re the active, outdoorsy type, who’s interested in taking on the great routes of the world or looking for a challenge, then our Classic Routes are for you. We’re talking the West Highland Way in Scotland, the world renown Tour Du Mont Blanc and Germany's Moselle Cycle Path, to name but a few!
Leisure Cycling | Leisure Cycling
Solo Travellers, Families with Teens
The minimum age for this tour is: 5 Years
This cycling tour is graded moderate based on the shoter routes available. Each day you can choose the difficulty, with the longer/steeper routes requiring a reasonable level of fitness (in line with a moderate to strenuous grade). The grade is determined on the basis of the entire trip. Individual days may vary in terms of difficulty, i.e some rides may be slightly more difficult or easier than the overall grade. The routes follow surfaced country roads and secondary roads. Near larger towns there are some sections on busier roads.
This cycling tour is suitable for relatively fit regular cyclists seeking an active holiday. You'll spend much of the day in the saddle experiencing a region and discovering its variety. The terrain is rolling with some longer and steeper ascents/descents, with daily total elevations ranging from 408m to 858m 1338ft - 2814ft. E-bikes are available for hire should you want to have battery-powered assistance for the hills.
Overnight in charming hotels, one countryside agriturisimo and a B&B. All properties are chosen for their excellent location, charm, warm welcome to cyclists and spectacular views. Some hotels also have swimming pools.
We always try and accommodate you at the locations detailed below, but on occassion, 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, it's possible to request a single room. This trip is suitable for solo travellers although there is a solo supplement payable.
Meals
The holiday includes breakfast each morning. Lunches and dinners are not included, so you are free to choose where you wish to dine in the afternoon or the evening.
- 7 Nights in hand-picked accommodations
- 7 Breakfasts
- Baggage transfers
- Transfer on day 8 from Montepulciano to Chiusi
- Welcome briefing and bike hire fitting (if hiring a bike)
- Information pack and route notes with maps
- 24/7 Emergency telephone support from our office
- Travel to Poggibonsi / from Chiusi
- Bike hire (standard hybrid or upgrade to a road bike or E bike)
- Dinners, lunches, drinks & snacks
- Entrance fees for attractions
- Travel insurance
- Additional nights along the route
- Bike hire (standard 27 gear hybrid)
- Upgrade to a road bike or E bike
You can begin on any day of the week from March to the end of October. Spring, early summer and autumn days are the perfect temperature for cycling and capturing the essence of Tuscany's colourful landscapes. During the hotter summer months it's worth hitting the road earlier in the day, or reconsidering dates if you don't enjoy the heat.
By Air: We recommend flying to Florence or Pisa airport.
By train: You can take a train from Florence or Pisa to the start of the - Poggibonsi (1hr and 1h16 respectively). For train timetables visit Tren Italia.
At the end of your holiday we include a transfer to Chiusi train station.
By Air: From Chuisi you can take a train to Florence (1h 26) and then either a bus or a taxi to Florence Airport. If flying out of Pisa then take a train from Chiusi (2h 40, changing in Florence).
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.
Your information pack has a detailed equipment list with essential kit and handy suggestions.
Bike Hire
Bike hire is available as an optional extra. Choose from a Hybrid bike (Shimano Alivio 27-gear with 13 kg aluminium frame), or a road bike (Bianchi Via Nirone with Shimano Sora 27-gears) or an E bike. Bikes are equipped with rear rack, 1 rear pannier, odometer, pump, repair kit, water bottle and map folder. If you opt for bike hire we will ask for your height to make sure your bike is the perfect fit. A welcome meeting and a bike fitting will be on your first evening.
It is strongly recommended that you secure adequate travel insurance.
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.
You can use public transport or local taxis to continue to your next overnight stop.
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.
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.
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.
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.
We recommend flying to Florence or Pisa airport, then you can take a train to Poggibonsi (1hr or 1h16 respectively). See www.trenitalia.it for further information on rail travel.
You can use public transport or local taxis to continue to your next overnight stop.
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