Day 1, Saturday: Arrive in Florence. Transfers to our first hotel, the 3*** La Cisterna near San Gimignano. In the evening, we'll enjoy dinner and chill out over a glass or three of Chianti.
Day 2, Sunday: San Gimignano and Wine Tasting in Chianti (20 miles / 32 Km)
We start our cycling holiday with a 3-mile ride into San Gimignano for a look round before we head off into Chianti itself. Tonight's destination is the Villa le Barone in Panzano. During the afternoon we'll visit Tenuta Fontodi, one of Chianti's top producers, and we'll get our first introduction to the idea of the 'super-Tuscan' wines. These are a complicated result of Italian wine regulation and the national obsession with the flouting of rules.
Day 3, Monday: Chianti Countryside (25 miles / 40 Km)
Today we explore the heart of Chianti Classico, visiting its two most beautiful and important wine towns, Greve-in-Chianti and Radda-in-Chianti. There is a wide choice of friendly, high-quality producers all around here, and we’ll visit vineyards in Greve before lunch and Radda after lunch before we arrive at the Casali della Aiola in the tiny hamlet of Vagliagli. Tonight we eat in the village restaurant.
Day 4, Tuesday: Siena (30 miles / 48 Km)
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 Antica Torre, and the chance to spend the late afternoon nursing a cold beer overlooking the Campo is just one of those moments.
Day 5, Wednesday: Tuscan Countryside (29 miles / 46 Km)
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, Thursday: Brunello di Montalcino Wine Tasting - Italy's Finest Wine (27 miles / 43 Km)
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 stunning 15th century estate of Tenuta Argiano before arriving in Montalcino itself, where we will stay at the Hotel Il Giglio in the heart of the old town.
Day 7, Friday: Our Final Wine Tasting - Vino Nobile di Montepulciano (31 miles / 50 Km)
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, Saturday: Home, transfers back to Florence.
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Europe Italy Outdoor: Land Rambler Bicycle Touring Food & Wine