Secrets of San Gimignano Cycling(Trip #60756)

Tour Overview

This 8-night cycling holiday is, quite simply, outstanding in every way: the rich scenery, the fantastic hotels, the local cuisine, the exceptional wines.. the list goes on!

You’ll start off in Volterra, a beautifully preserved hilltop gem whose eclectic mix of Etruscan, Roman and Renaissance art and architecture has inspired artists and writers for centuries. From here, you pedal east through a timeless and kaleidoscopic landscape of ochre-coloured hills, verdant vineyards and stunning rolling countryside towards San Donato, a sleepy wine hamlet overlooking San Gimignano. The cycling is truly glorious as you continue via mediaeval Colle – optional day trips to Florence and Siena – and coast on towards honey-coloured Pancole, nestled in the Tuscan hills. It’s then on along traffic-free strade bianche, shady forests tracks and high undulating ridges – sweeping views out as far as Corsica on a clear day! – and a real sense of achievement as you loop back to Volterra for your final night.

Superb *** and **** hotels – all with panoramic sparkling swimming pools – are an added highlight throughout this holiday. In Colle, you stay in a fabulously restored c14 Benedictine abbey, complete with original frescoes, while Alessandro’s friendly hotel in Pancole is renowned for its gastronomic cuisine – see if you can spot the photo of Tony Blair eating here last summer! Of course, you are in the heart of some of Europe’s finest wine country too, so you’ll never be short of tasting opportunities.

Day by Day Itinerary

Day 1 Arrive in Volterra

We meet you at Pisa airport and take you to Volterra (75mins) where you’ve time for a dip in the pool and a wander round its tangle of cobbled alleys and hidden squares before dinner.

Day 2 Volterra to San Donato 24km/14mi or 34km/21mi

Spectacular views sweep infinitely across the open countryside as you leave Volterra and pedal along the pretty Era Valley. It’s a haven for wildlife and offers fantastic bird spotting opportunities. You’ll pass the ancient Momialla thermal baths before the landscape softens with vines, olives and crumbling farmhouses as you enjoy a gentle downhill whizz towards San Gimignano. Ice creams on the Piazza della Cisterna are highly recommended before heading up to San Donato where dinner is served in the flower-bedecked courtyard.

Day 3 At San Donato

Cycle or taxi (5kms) to San Gimignano where a regular bus service departs for mediaeval Siena (40mins). Considered by many to be simply the most beautiful city in Italy, it’s well worth climbing the Torre del Mangia for unrivalled views of the town and surrounding Sienese countryside. Or relax with a chilled vernaccia before lunch in Il Campo, the town’s harmonious scallop-shaped piazza. If you prefer to stay put for the day, our tranquil hotel has a fabulous pool and extensive gardens.

Day 4 San Donato to Colle di Val d’Elsa 33km/19mi

Continuing east past fields ablaze with sunflowers, and with the inimitable towers of San Gimignano forming a breathtaking backdrop to your route, you arrive in Casole d’Elsa, a beautiful village characterised by ancient vermilion-hued buildings and blessed with stunning balcony views from its hilltop position. Take time to explore its C12 church (frescoes by Gano da Siena), piazza and impressive fortress. Perhaps have lunch here – there are a couple of decent trattorie – safe in the knowledge it’s easy, flat pedalling for the rest of the day! It’s then on to your ssss hotel, a beautifully converted C12 Benedictine Abbey with lovely pool and gardens.

Day 5 At Colle di Val d’Elsa

A visit to Florence is a “must” today as the regular bus service (1hr) stops just outside the hotel. Explore its maze of honey-coloured alleys, admire Brunelleschi’s Duomo, take in the treasures of the Uffizi or savour a gelatoin the Boboli Gardens. (Shopping is highly recommended here too by the way!)

Day 6 Colle di Val d’Elsa to Pancole 29km/16mi

It’s gentle pedalling through poppy fields and olive groves before passing the lovely Basilica di San Lucchese (a C14 convent resplendent with original frescoes) and an exciting freewheel down into the old town of Poggibonsi. You then follow the official, and mainly off-road, Chianti Wine Route – masses of tasting opportunities (don’t forget that we can collect any purchases for you) – virtually all the way to Pancole.

Day 7 At Pancole

If you fancy a day off from cycling today, then the pool here is simply gorgeous – nice lunches served on the geranium-scented terrace too! There’s also a small enoteca where you can taste local cheeses, olive oils and wines. The more energetic might want to cycle (or taxi!) past orchards and vines to Boccaccio’s birthplace, stunning Certaldo. Take the funicular to its mediaeval centre for spectacular views across the Val d’Elsa.

Day 8 Pancole to Volterra 25km/15mi or 32km/18mi

A peaceful strada bianca takes you first through the forests of the Castelvecchio Nature Reserve - last time we were here, we spotted a pair of hoopees circling overhead. You’ll then continue heading west along a panoramic ridge, passing a string of C18 villas - stunning views across the rich open countryside. You might like to stop for lunch on the terrace at the Prato d’Era restaurant – the homemade asparagus and parmesan risotto is to die for! It’s then your final last stretch back up to Volterra for a well deserved glass of celebratory prosecco on the sun-baked terrace before dinner!

Day 9 Leave Volterra after breakfast

We take you to the station for your train to the airport or to Florence/ Siena/ Pisa if you’re having an add-on city break before heading home.