8 Days & 7 Nights

4.5

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

Experience the best of classic Tuscany on two wheels, 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 scenery characterised by vineyards, verdant farmland and cypress-lined country roads. Each day you’ll reach traditional villages perched atop rolling hills, where churches, abbeys and monasteries await. Visit the fortified town of Monteriggioni before heading to one of Italy’s most spell-binding locations, San Gimignano, with its many towers. Explore magical Siena, the thermal-spa town of Bagno Vignoni and Pienza, as well as photogenic Montichiello and Montepulciano. You’ll also pass through towns located on the route of the ancient Via Francigena pilgrimage. End each day with a well-earned glass or two of full-bodied Italian red, accompanied by a dish garnished with local pecorino cheese and truffles.

From $1,999.00

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Gallery

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Itinerary

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Day 1 Arrive Poggibonsi and overnight

Your 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.

On arrival at Poggisbonsi train station you will be met and transferred to your accommodation. If you have opted for bike hire your biking fitting will take place in the late afternoon.

Overnight Poggibonsi

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Hotel Villa San Lucchese | Hotel

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.

Day 2 Loop cycle to Monteriggioni, Colle Val d’Elsa and San Gimignano 23 miles / 37 km

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: 575m / 575m (1886 ft / 1886 ft)

Overnight Poggibonsi

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Hotel Villa San Lucchese | Hotel

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.

Day 3 Poggibonsi to Siena 20.5 miles / 33 km

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 52km (32 miles) - ascent/descent: 780m / 630m (2559 ft / 2067 ft)

Overnight Siena

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Hotel Chiusarelli | 3 Star | Hotel

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.

Day 4 Siena to ‘Crete’ to Buonconvento 29 miles / 47 km

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)

Overnight Buonconvento

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Fattoria Pieve a Salti | 3 Star | Agriturismo

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 | 3 Star | Hotel

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.

Day 5 Cycle to Monte Oliveto Monastery and Montalcino 23 miles / 38 km

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)

Overnight Montalcino

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Hotel Dei Capitani | 3 Star | Hotel

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 18^th century “Catasto Leopoldino”. Enjoy the hotel's restaurant, bar, terrace, and a large panoramic garden with an outdoor swimming pool.

Day 6 Loop cycle to Sant’ Antimo Abbey 17 miles / 28 km

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 raod cyclist route is 51km (32 miles) - ascent/descent: 1082m / 1085m (3550 ft / 3559 ft)

Overnight Montalcino

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Hotel Dei Capitani | 3 Star | Hotel

Day 7 Cycle to Pienza, Montichiello and Montepulciano 28 miles / 45 km

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)

Overnight Montepulciano

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

B&B L'Agnolo | Bed and breakfast

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.

Day 8 Onward travel

THIS TRIP'S CARBON SCORE

This trip has a carbon score of 16kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 16kg is equivalent to 6 paperback books in the USA. 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.

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Other Information

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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!

Tour Type:

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!

Activity:

Leisure Cycling | Leisure Cycling

This trip is suitable for:

Solo Travellers, Families with Teens

The minimum age for this tour is: 12 Years

Ideal if you have an interest in:

Foodie

Wine

E-Bike

Activity Level & Terrain

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.

Experience & Fitness

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.

Accommodation & Meals What's Included

Included

7 Nights in hand-picked accommodations
7 Breakfasts
Baggage transfers
Transfer from Poggibonsi train station to the accommodation
Transfer on day 8 from Montepulciano to Chiusi
Welcome briefing and bike hire fitting (if hiring a bike)
Detailed trip info and mapped tracks, via the Macs App
24/7 Emergency telephone support from our office

Excluded

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

Extras

Additional nights along the route
Bike hire (standard 27 gear hybrid)
Upgrade to a road bike or E bike

When to go Travel & Transfers Info & FAQ

Equipment

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.

Travel Insurance

It is strongly recommended that you secure adequate travel insurance.