Tuscany Cycling Holiday

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

One of our more difficult tours; we start in San Gimignano and finish in Montepulciano.

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.


£1745 PP
  • Single Room Supplement: +£410
  • Transfer from Train Station: +£90
  • Airport Transfer: N/A
  • Self-Drive: N/A


Day 1 Arrive in Tuscany - Fabulous Gourmet Food

Arrive in Florence. Transfers to our first hotel, the 3*** La Cisterna rught 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 Villa Sangiovese in Panzano., right in the heart of Chianti. Chianti is spectacular, but hilly! We'll cycle through vineyards and avenues of cypress trees, lunching in Barberino.

Day 3 More Wine Tasting Deep in the Chianti Countryside

Today we explore the heart of Chianti Classico, visiting its two most beautiful and important wine towns, Greve-in-Chianti and Radda-in-Chianti. T

There is a wide choice of friendly, high-quality producers all around here, and we'll visit a cantine in Greve before lunch, followed by Radda after lunch, before we arrive at the Villa Dievole in the tiny hamlet of Vagliagli.

Tonight we eat in the Villa, and it's amazing.

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 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.

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 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 Il Bersagliere.

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.

Descending from the Abbey, we then face another 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 Il Giglio in the heart of the old town.

Day 7 Our Final Wine Tasting - Vino Nobile di Montepulciano

Another difficult but spectacular day. From Montalcino a relatively easy hop to the Abbey at Saint Antimo, where tarragon was first introduced into Europe by French monks.

The least we can do is stop by to say thank you.

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 'Vin Nobile'.

We'll be introduced to these rich red wines by Elena Falvo at Avignonesi - one of the legends of Tuscan wine, the most prestigious estate we'll visit this week, and a real treat.

Tonight we stay at the Hotel Il Marzocco, inside the old city walls.

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.