Tuscany Cycling Holiday

Florence • San Gimignano • Vagliagli • Siena • Asciano • Montalcino • Montepulciano

More challenging than our French tours - but the scenery, food and wines of Tuscany make it so worth while! Highlights include Siena and the Abbey of Monte Oliveto Maggiore.

Available Dates 2024:
September 7-14, September 21-29

8 days

7 nights

Evening meals included

Difficulty: Moderate

What to expect

On our Tuscany cycling tour, we'll spend plenty of time in rural Tuscany, exploring Chianti, the Val D'Orcia and Le Crete. But we'll also visit spectacular medieval towns and villages like Siena, Montalcino and San Gimignano.

The food in Tuscany is wonderful, lots of herbs, local olive oil and local specialities. The wines are delicious and fascinating, and we'll explore wines from Chianti, the Brunellos of Montalcino and the Vino Nobile di Montepulciano.

Tuscany also boasts beautiful Abbeys and Duomos and evokes the atmosphere of Dante, Machiavelli and Renaisaance Italy. Some of the highlights of the cycling holiday include the frescos at the Abbay of Monte Olivetto, and Montepulciano, the highest of all the Tuscan hilltop Cities.


£2095 PP
  • Single Room Supplement: +£410
  • Transfer from Train Station: +£90
  • Airport Transfer: N/A
  • Self-Drive: N/A
  • Available Dates 2024:
    June 1-8, August 3-10, September 14-21


Day 1 Arrive in Tuscany - Fabulous Gourmet Food

Arrive in Florence. Transfers to our first hotel, the 3*** La Cisterna right in the heart of San Gimignano.

In the evening, we'll enjoy dinner and chill out over a glass or three of the local Vernaccia di San Gimignano, while enjoying spectacular views across Chianti.

Day 2 San Gimignano and Wine Tasting in Chianti

If you haven't already had the chance to look round San Gimignano, we'll make sure we do before we head off, it's beautiful.

Tonight's destination is the Relais Fattoria Valle in Panzano, in the heart of Chianti. The Fattoria Valle is a stunning villa about 200 metres past the centre of Panzano, and we'll eat at the Relais tonight.

Chianti is spectacular, but hilly! We'll cycle through vineyards and avenues of cypress trees, lunching in Barberino.

Day 3 Wine-Tasting in Chianti 

We start off with a beautiful descent into Greve-in-Chianti, about 5 Km away. We'll spend some time in the central piazza before heading to a lovely surprise, Le Cantine ('The Cellars').

In the Cantine we'll learn about the fascinating history of Chianti wines - how they were devalued, and how their reputation was rescued through the combination of the Gallo Negro marketing label, and the stricter regulations of the DOCG system.

This is a great introduction to Tuscan wines - as well as ordinary Chiantis, we'll be introduced to Chianti Riserva, the story of the Super Tuscans, and the giants of Tuscan wine-making, the Brunello di Montalcino and the Vino Nobile di Montepulciano.

What I love about the Cantine is that we'll be led by one of the staff, wine enthusiasts, who actually know these producers. There really is an interesting story behind Tuscan wines, and nobody knows it like these guys. Our visit will set us up nicely for our week, and the wine-lists at dinner each evening will be a good test!

Leaving Greve, we'll retrace our steps through Panzano, and along the Pesa valley to Radda, another of Tuscany's famous wine centres.

We won't spend so much time in Radda before heading off for our first encounter with Tuscany's famous strade bianche. These 'white roads' are a part of Tuscan culture, but in truth they're no great friend of the cyclist! We'll make our way to the village of Vagliagli, including a tough hill, before a final 7 or 8 Km, mostly downhill, to the amazing Certosa di Pontignano.

Officially it's the congress centre for the University of Siena, but it's a beautiful cloistered abbey run as a hotel. We'll eat at the hotel, and you really must explore the buildings and gardens. Have a look at their photo galley it's a glorious place to arrive at the end of a day's cycling.

Day 4 Stunning, Amazing, Siena

Leaving Chianti we visit Monteriggioni, a beautifully-preserved walled town that served as an advance warning outpost to alert Siena when Florence was on the warpath.

After lunch we spend the afternoon cycling to the main attraction, Siena! Siena itself is a delightful labyrinth built across three ridges and surrounded by a gargantuan wall. We have to be very cunning to approach the town whilst avoiding traffic (anybody who wants to try this without a guide is most welcome, and good luck to 'em!).

This evening we stay at the Hotel Santa Caterina just outside the Porta San Marco, and the chance to spend the late afternoon nursing a cold beer overlooking the Campo is just one of those moments. Possibly my favourite place to sit in the whole world.

Day 5 Deep in the Tuscan Countryside

We leave Siena by a similarly crafty route, and today we're cycling through the green and tranquil (and hilly) countryside of le Crete.

This region is characterised by rolling hills, much less severe than we've been used to, and an unending blanket of vivid green. Our destination is Asciano where we'll stay at the Hotel La Pace.

This quiet little town perfectly sums up this part of Italy. Once ruled by the Scialenghi counts, it was captured by Siena which then destroyed its fortress. It was then taken by Florence, before being taken once more by Siena.

Luckily things have calmed down considerably over the last 700 years.

Day 6 Brunello di Montalcino Wine Tasting - Italy's Finest Wine

A tough day, but spectacular. Leaving Asciano we cycle up to the Abbey of Monte Oliveto Maggiore. A spectacular set of buildings in their own right, and still a working monastery, the abbey houses an important set of frescoes that tell the story of St Benedict. His life story, particularly his part in fighting the barbarian invaders under Totila in the 6th century, is well worth the telling, and the key scenes are captured beautifully in these famous frescoes.

How good are they? This is my favourite place in the whole of Tuscany. That good!

Descending from the Abbey, we'll have lunch in the walled town of Buonconvento before we face the climb to one of the most revered wine towns in Tuscany, Montalcino, home of the famous 'Brunello'.

We'll visit the famous estate of Val di Suga before arriving in Montalcino itself, where we will stay at the Hotel Vecchia Oliviera at the entrance to the old town.

This evening we'll stroll into the City for a very traditional dinner at  the Osteria di Porta al Cassero.

Day 7 Montalcino to Montepulciano

Another spectacular day. From Montalcino an amazing downhill into the Val d'Orcia, a little bit of up & down, and a coffee in the delightful central piazza of San Quirico d'Orcia.

We then visit Pienza, said to be the most perfectly-proportioned town in Tuscany, before our final destination, Montepulciano, the 'other' famous wine town and home to the 'Vino Nobile'.

Montepulciano is my favourite of the Tuscan hill towns. It's the biggest, and the highest (just!), and it feels like a real town, with real people, rather than a theme park. We'll arrive into the town by the Duomo at the top of the town, and we'll have the opportunity to cycle right down the old streets to the  Albergo Il Marzoocco inside the Porto al Prato.

Tonight we stay at the Hotel Il Marzocco, inside the old city walls and eat just across the street.

Day 8 Farewell Beautiful Tuscany

Saturday. Home, transfers back to Florence, Pisa and Bologna.


Please take careful note of the train times. Our transfers are scheduled to meet these designated trains; if these train times are inconvenient, please contact us so that we can be sure of arranging appropriate transfers.