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Your two-wheel Tuscan sojourn

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Brand New Tour For 2020

11-days of sublime cycling through magical Tuscany

Imagine leisurely navigation of Tuscany’s fabled strade bianchi – white backroads – as you immerse yourself in a rolling landscape rich with vineyards, olive groves, wheatfields and golden sunflowers. Now the dream is coming true as you explore some of Tuscany’s most romantic, enchanting corners.

Imagine idyllic days spent visiting legendary hilltop villages with their Etruscan, Roman and Lombard architecture. You’ve seen Tuscany on TV and in travel magazines; now you’re traversing its heart, with the promise of a wonderful hotel and a delicious Tuscan supper after each day’s ride.

Is this real? Of course it is, and for 10 unforgettable days, this will be your world…

Day 1: Arrival at Pisa Airport.

Transfer by minibus or taxi to our base hotel in Pienza.

Day 2: Pienza

After a first Tuscan breakfast, your excitement is rising as we personally equip you with your bicycle and make sure it’s fitted perfectly for the adventure ahead. Then you’re off, exploring this UNESCO World Heritage-rated Renaissance town with its stunning hilltop site overlooking beautiful Val d’Orcia. You’ll soon see what inspired Enea Silvio Piccolomini (later Pope Pius II) to create what subsequently become known as the ‘ideal city of the Renaissance’. Do you enjoy a great steak? If so, make sure to visit Trattoria Fiorella for their melt-in-the-mouth bistecca alla fiorentina…

Day 3: Pienza to San Giovanni d’Asso – 18 miles (29km)

You’ve read all about them, now follow sleepy strade bianchi while navigating the awe-inspiring countryside north-west of Pienza. Enjoy this gentle introduction to the timeless beauty of history-packed Tuscany. As afternoon shadows slowly lengthen over the Crete Senesi’s hills – a truffle lover’s paradise – we reach San Giovanni d’Asso. It's dominated by the twin churches of San Giovanni Battista and San Pietro in Villore, and thirteenth-century Castello Montelifrè housing our luxury boutique hotel with its delightful restaurant and views over the surrounding landscape. We’re in the deep heart of Tuscany; tomorrow we explore further…

Day 4: San Giovanni d’Asso

Over another delicious breakfast we plan the day’s exploration on foot or on two wheels. Will we visit the village’s world-famous truffle museum, covering 250 square metres in the cellars of fourteenth-century Castello di San Giovanni? Or set out on a relaxed cycle exploration of the village’s immediate environs? Or enjoy contemplative time spent in the cool of San Giovanni’s three churches? The oldest dates from the 700s.

Day 5: San Giovanni d’Asso to Castelnuovo Berardenga – 24 miles (38km)

Today our trusty Oro Tours bicycles carry us further north through the gently undulating Tuscan landscape. Let’s make sure to stop awhile among the cream walls and terracotta-coloured roofs of Asciano, with its rich Etruscan, Roman and Lombard history. If time allows, maybe a visit to the travertine architecture of the eleventh-century basilica of Sant’Agata off the Via Roma is on the cards too. Then, leaving this hilltop delight, we’ll cross the Crete Senesi on another sleepy lane to reach Castelnuovo Berardenga, our gateway to the Chianti region, for the night.

Day 6: Castelnuovo Berardenga

The gently rolling, forest and vineyard bedecked, hills invite us to a day’s exploration centred on the comune of Castelnuovo Berardenga. There’s so much to do, ranging from exploring myriad rustic villages and hamlets, to villa visits, a rich assortment of nearby churches and unmissable wine-producing locales – particularly south of Castelnuovo. Take your time and enjoy everything this beautiful part of Siena has to offer your eyes – and, of course, your taste buds.

Day 7: Castelnuovo Berardenga to Castellina in Chianti – 24 miles (38km)

Picture stunning olive groves, vineyards and avenues of majestic cypress trees as you imagine the landscape for today’s gentle ride through Chianti’s heart. Stop off to sample the region’s best-known product, meet the people who lovingly produce this noblest of wines, and enjoy a leisurely picnic amid golden-hued sunflowers – girasoli – en route. Later, as the joyful flower heads follow the afternoon sun, we approach Castellina in Chianti, a well-earned supper of Tuscan specialities and the promise of exploring the medieval village tomorrow…

Day 8: Castellina in Chianti

We awake to another day made for exploration as leisurely or adventurous as you want. Maybe we’ll ride away from this hilltop comune – pretty Radda in Chianti comes highly recommended, as do the views en route. Alternatively, we could discover the myriad gems within Castellina’s boundaries. Whether exploring on foot or in the saddle, the ancient medieval fortifications and protective towers wait to enchant us. Whatever you do, make sure to visit Rocca with its breathtaking views of town and countryside. Later, go underground into the refreshing cool of shop- and restaurant-lined Via della Volte – of course you’ll pause for a glass of local Chianti. Saluti!

Day 9: Castellina in Chianti to San Gimignano – 24 miles (38km)

After breakfast, and still marvelling at Castellina’s charms, today’s ride is a rewarding, curving descent to the Siena plains and on across the remarkably unspoiled Val d’Elsa. By late afternoon, we’ve reached our final overnight stay in San Gimagnano. This impressive town has a well-deserved reputation as ‘the city of beautiful towers’. We’re sure you’ll understand why as you pedal towards the unmistakeable skyline of 14 towers rising from the quintessentially-Tuscan colour palette of its architecture.

Day 10: San Gimignano

As one of Tuscany’s best-preserved medieval towns, San Gimignano delivers the stunning culmination of your cycling adventure. If there’s one place on the tour where we recommend dismounting, it’s here. Of course, you will find time for one last ride on Tuscan time before heading home. But for now, let’s trust our feet for a while, follow centuries-old cobbled streets, and lose ourselves in the delightful shops, restaurants and galleries within its thirteenth-century walls. In particular, be sure to visit the highest tower, the awe-inspiring Torre Grossa on Piazza del Duomo (177ft/54m). It’s a stunning way to finish the day’s exploring and enjoy Tuscany’s expansive beauty one last time before saying ‘arrivederci Toscana!’

Day 11:

Full of memories of Tuscany and its d’oro (golden) hues, and with the taste of Chianti and Brunello lingering on our lips, we bid San Gimignano a fond farewell and transfer direct to Pisa Airport by train or minibus.

Pienza – Piccolo Hotel La Valle

Tuscany’s warm welcome continues at the Piccolo Hotel La Valle with its breathtaking views over Val D’Orcia. Our home-from-home in Pienza is set to delight. It’s a gem in local stone, brick and tile, garnished with giant terracotta pots and only 150 metres from the heart of this UNESCO-rated hilltop town. What a way to begin our magical tour of this fabled region.

After your journey, or another day’s exploration, how about relaxing in the well-appointed roof garden or cosy, well-stocked bar. Come bedtime, as night falls over the magical countryside, dreams are sweet in bright, clean, rooms with wrought-iron bedsteads, wooden floors, flat-screen TV, safety deposit boxes and private bathrooms. Can you feel those workaday cares slipping away already? We thought so.

Your gracious hosts at the Hotel La Valle look forward to helping you make the most of your precious time in captivating, terracotta-roofed Pienza. You’ll find everything you need before and after another day’s wonderful Tuscan adventures.

After a great night’s sleep, plan another day’s activities over a delicious al fresco breakfast and freshly-made coffee on the rooftop terrace. How about a relaxed stroll around town today? The gorgeous central Piazza Pio II is minutes away, as are Pienza Cathedral and the not-to-be-missed Piccolomini Palace. Or will you venture further afield on two wheels? The choice is yours – Tuscany beckons…

San Giovanni d’Asso – La Locanda Del Castello

Welcome to the small hamlet of San Giovanni d’Asso, family-run La Locanda Del Castello and its restaurant in the heart of Tuscany’s Crete Senesi. Make no mistake; a special treat lies ahead within the rugged walls of magnificent San Giovanni d’Asso Castle…

It’s time to relax away happy tiredness at the end of today’s ride. Your room in La Locanda features typical Tuscan design, with beautifully executed brickwork features, exposed wooden beams and gorgeous art. Links to centuries of architectural tradition meet the usual modern appointments – air-conditioning, satellite TV, free Wi-Fi, safety deposit box, and well-equipped private bathrooms with shower. It’s perfect after a fascinating day’s exploring on foot or two wheels – prepare to be spoiled rotten by Massimo and his team.

Tuscan adventures generate healthy appetites. As part of our warm welcome, we’ll find an inviting bar and the cosy Michelin-rated Ristorante del Castello. Try the fresh truffle pastas, artichoke carbonara, other flavoursome regional cuisine and superb wine selection – delicioso. And then there’s the lovely little square right outside La Locanda, with its sublime views over the greens and burnt sienna shades of the surrounding landscape.

Next morning, after a refreshing night’s sleep within the castle’s history-infused walls, what could be better than starting another day’s cycling with a delicious breakfast? Admit it, you could get used to this relaxed Tuscan life couldn’t you?

Castelnuovo Berardenga – Villa Curina

Chianti means delicious wine, beautiful hotels within its wine-production area and a heartfelt welcome from your hosts at Villa Curina, your base in Castelnuovo. Prepare to enjoy a stunning rural location and welcoming traditional rooms in the eighteenth-century villa and its refurbished farmhouses. What a culmination this is to another magnificent day’s exploration.

Arriving at Villa Curina after a fascinating day on Tuscany’s strade bianchi, settle in to your elegantly decorated room at this rural paradise. Note how beautiful antique furnishings meet the modern comforts you expect, such as LCD TV with Sky, minibar, free Wi-Fi and that all-important private bathroom.

Later, unwind with a leisurely walk around the villa’s exquisite parterre garden, cool off in the large outdoor swimming pool, or play some tennis on the hotel court. Then relax with a glass of Chianti – or one of Siena province’s refreshing craft beers – while contemplating tonight’s mouth-watering dinner choices.

Soon, night’s draping its velvety cloak across Tuscany’s rolling countryside and signature olive groves, and you’re reliving the day in the Il Convito di Curina restaurant. Make it extra-special with candlelit al fresco dining on the panoramic terrace as another stunning sunset graces the horizon beyond Siena. Maybe a tour of the hotel’s well-stocked wine cellar will complete another perfect evening!

Castellina in Chianti – Hotel Palazzo Squarcialupi

With a last few pedal turns, we reach the exquisite Hotel Palazzo Squarcialupi along Via Ferruccio and another evening’s well-earned relaxation begins. Picture rustic terracotta floors, a delightful garden with pool, modern rooms, basement spa and Carrara-marbled bathrooms. And a lovely terrace overlooking the Chianti Valley’s vineyards. Welcome to your luxurious, beautifully appointed hotel with its acclaimed views and stories going back to the fifteenth century...

After another day in the saddle, take in the Palazzo Squarcialupi’s imposing Renaissance architecture. What a breathtaking fusion of Tuscan history and modern facilities you’ve found in chic Castellina in Chianti. Savour the exposed beams, eighteenth-century furnishings and quintessential Tuscan ambience, then relive every wonderful mile of today’s ride as you unwind.

Later enjoy a refreshing drink with the magnificent terrace views. Then, if we eschew Castellina’s other restaurants, let’s linger over delicious Tuscan cuisine and wines in the extremely well reviewed ‘Taverna Squarcialupi’ – try zucchini flowers with goat cheese, pici, truffle-based dishes and the hotel’s own Chianti Riserva. It’s all delicious…

Finally, tired, happy and extremely well-fed in the best Tuscan tradition, retire for the night and dream of the wonderful places and experiences awaiting you tomorrow. And in the morning, as the sun rises over this history-packed corner of Italy, start another day with the Palazzo Squarcialupi’s wonderful breakfast buffet.

San Gimignano – Hotel Bel Soggiorno

Bel Soggiorno translates as ‘wonderful stay’. And that’s what’s in store as we reach another superbly located Tuscan destination. Picture a welcoming, beautifully appointed hotel just south of Piazza del Duomo and close to San Gimignano’s history-permeated medieval walls. It’s perfect.

Relax away another day’s happy-pedalling within a Chianti-bottle’s-throw of historic Porta San Giovanni. A restoring night’s rest awaits us in large, air-conditioned rooms – some with balconies and splendid views over the Tuscan countryside that’s charmed us so irresistibly. Naturally, satellite TV, free Wi-Fi and private bathrooms complement comfortable beds at our pied-a-terre in this unmissable city of beautiful towers.

After settling in, we’re exploring again as we navigate San Gimagnano’s cobbled streets and alleys to its hidden corners – even more enjoyable later when the day-trippers have left. Then, if we’re not dining out, and with appetites growing for another ‘fix’ of delicious regional cuisine and fine wines, it’s back to our hotel. It’s suppertime in the on-site restaurant with its terracotta-paved terrace, oak-beamed ceilings and huge brazier grill. Anyone for the Bel Soggiorno’s renowned Fiorentina T-Bone or grilled pork ribs?

In the morning, before more exploration in and around San Gimagnano, there’s a sumptuous breakfast buffet to savour. And ‘views to die for’ from the breakfast room as the sun rises over Tuscany’s wondrous rolling, mist-garlanded hills.

11 Day Tour
(10 nights)

Departure dates Prices
Jun 12, 14, 24, 26 £1,475
Sep 1, 3, 13, 15 £1,475

'1 Night Stops' - 7 Day Tour
(6 nights)

Departure dates Prices
Jun 14, 26 £995
Sep 3, 15 £995

Prices are per person based on two people sharing a double or twin room without flights and transfers.


Triple room: £10 per third person per night.

Infants under 2 years: Sharing bed with parents FREE. Additional expenses e.g. food or cots, to be paid direct to the hotelier.

Children under 12 years: £15 off per night.


Single room: £32 per night.

E-Bike: £20 per day (number of days charged will be one less than the number of nights of your tour).

Tandem: £15 per day (number of days charged will be one less than the number of nights of your tour).


£250 per person

What Your Holiday Price Includes

  • Number of nights bed and breakfast accommodation as specified.
  • Comprehensive information pack and detailed ‘turn by turn’ route instructions.
  • Transfer of luggage between hotels.
  • Support of your Oro Tours representative.
  • Use of our modern lightweight bicycles, supplied with pannier bag and all accessories you may need.
  • All local tourist taxes.

How to Book

  • Please click the ‘Enquire Now’ button, complete and send the form, or, simply call one of our experts on 01584 877596.
  • We shall always speak to you on the phone to take down all the details we need to arrange your ‘Gold Standard’ cycling holiday.
  • We shall carefully research the most convenient and best value travel arrangements for you and, tailor your holiday to your exact wishes.
  • We shall send you a detailed individual quotation for your holiday and travel arrangements.
  • Once you are ready to proceed with your booking, we shall take payment for your deposit (£250 per person). If we have arranged flights and transfers for you, payment for this travel element will also be due at the time of booking – the amount will be detailed on your individual quotation. We accept payment by VISA, Mastercard, cheque and bank transfer.
  • We shall make all your holiday arrangements and, confirm your complete itinerary to you in writing.

Flights and Transfers

Our experts shall be only too pleased to research the most convenient and best value flights for you and, to arrange your airport transfers. Please call on 01584 877596 for an individual quotation, which will be sent to you by email. On acceptance of our quotation, we shall be pleased to book all arrangements for you.

Holidays booked together with a flight are protected by The Travel Trust Association’s ATOL (number: 10300).

Flights and transfers are charged at cost, plus a £20 per person booking fee to cover service and ATOL fees.

Extend Your Stay

If you wish to extend your holiday, with perhaps a short stay in a nearby city of interest, please call our experts on 01584 877596 for help and guidance.

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