//Tour of Tuscany
Tour of Tuscany 2018-05-28T14:36:02+00:00

Tuscany Cycling Tour

A land of beauty, elegance and dreams

Tour of Tuscany

Tuscany; a land of beauty, elegance and dreams. Where the colours of the landscape and the flavours of the traditional cuisine change with the seasons, and the slow rhythm of life is felt with each encounter, ride and meal.

To the cyclist who ventures into this world, it is heaven. Urged by a sense of adventure and the discovery of magnificent views at every turn, you can expect long, warm days on the bike surrounded by incredible panoramic views of rolling hills, olive groves, vineyards and medieval hilltop towns, all while embracing the winding roads, challenging climbs and exhilarating descents.

Rediscover your taste for adventure as you pedal along quiet country roads and cobblestoned streets, enjoying the history, culture and of course the cuisine of this spectacular region.

Tuscany is where our journey began and a place we invite you to share with us as we create a truly authentic experience of our favourite areas to ride and eat in this ancient land, where the art of living is represented through tradition, generosity and talent.

Come ride, eat and drink like a Tuscan. You’re in for an unforgettable adventure.

2nd to 10th June 2018
th to 23rd September 2018

14th to 22nd June 2019

14th to 22nd September 2019

AUD $5,995.00 per person twin share

9 days / 8 nights

Group size: 12 guests

Non-Riding Partner Program Available




Daily rides through the stunning Tuscan landscapes of Chianti, Montalcino and San Gimignano – we’ll do a different ride each day and have you exploring some of the most spectacular areas of Tuscany including the rolling hills around Chianti, the open landscapes of the Crete Senesi and the UNESCO world heritage listed Val d’Orcia, the famous Strade Bianche and more.

Daily Rides:
Day 1 – Lecchi: 25km & 470ms – The perfect introduction to Chianti with the idyllic rolling hills and one long climb, striped with vineyards and backed by dense wooded forests.
Day 2 – Castellina: 54km & 1000ms – It’s time for you to explore the cypress lined roads of Chianti made famous by its wine, with beautiful winding descents and climbs with incredible panoramic views.
Dy 3 – Buonconvento & the Crete Senesi: 69km & 1200m – Today you track south on your way to the centre of the Crete Senesi: a hilly, almost bare lansdcape that is truly magnificent, on your way to one of the most beautiful towns in Italy, Buonconvento.
Day 4 – Montalcino: 71km & 1455m – Today’s ride will take in five distinct climbs as you get to see first hand the truly majestic Val d’Orcia that was included as a UNESCO World Cultural Landscape in 2004, on your way to the mesmerising Montalcino.
Day 5 – Café ride: 39km a& 570m – Today is a bit of a rest day on the bike with a traditional coffee shop ride.
Day 6 – Montepulciano: 90km & 1680m – Your longest day, setting off in the direction of Umbria and traversing through a picture post card landscape through the villages of Montisi and Castelmuzio, before reaching one of Tuscany’s prettiest towns, Montepulciano.
Day 7 – Certaldo: 79km & 1170m – This is a truly typical tuscan day on the bike where you will encounter undulating quite country roads with olive groves and vineyards vying for dominance, as you wind your way to beautiful Certaldo.
Day 8 – San Gimignano: 53km & 1100m – This is another day of incredible views from the bike, with many considering this the most beautiful part of Tuscany. A magical atmosphere all set amidst the rolling hills, woods, olive groves and vineyards as you roll in to San Gimignano with it’s 17 towers, before a free flowing descent to cap off an amazing week of riding.

*We will also be providing a light riding option for each day of the Tour to accommodate guests who may want to ride less km’s and climb less metres.

Comprehensive back-up and support on all rides – a local ride guide will join us in each location with an intimate knowledge of the surrounding areas, ensuring your riding experiences are truly local, and take in many of the quiet back roads in this beautiful region. Rides are fully supported with a support vehicle, mechanic and your safety as our priority.

Full A’QTO cycling kit – designed by AQTO and made in Italy, this exclusive kit for our Travel guests will see you riding in style and comfort through the Tuscan hills and surrounds

Transport to and from Florence upon arrival and departure – you will be picked up from Florence and driven back on departure, and all your transport needs for the week are taken care of, including the transporting of bikes and bike cases, and transport for non-riding partners to various activities


A hand picked selection of boutique hotels and family-run villas across Tuscany – to enjoy Tuscany is to appreciate its diverse accommodation options so we’ve personally selected three different places to stay, based on their best fit to the area we’ll be in; we will stay for 2 nights in a charming boutique hotel which dates back to 1300 in the centre of medieval Radda in Chianti, a tranquil hilltop farmhouse with incredible views across the Tuscan Valleys and medieval hill towns of Montalcino and Buonconvento for 4 nights, and finally a quintessentially Tuscan B&B immersed in vineyards and olive groves, and perched high in the Hills surrounding Certaldo and San Gimignano for our final 2 nights.

Enjoying the distinctly different areas of Tuscany and their varied recipes – The lure of the Tuscan table is immense; characterised by its close association with the land, Tuscan cuisine is earthy, simple in style, and reflective of the region’s changing seasons and peasant traditions or ‘cucina povera’. We will take you on a food safari of Tuscany that takes in all the very best it has to offer from simple organic produce, grown on our host properties, to exquisite gastronomic dishes at a selection of family run osterias and restaurants.

Daily buffet breakfast – a daily, home made Italian feast with magnificent local produce will keep you going for hours on or off the bike

Welcome dinner – we’ll be celebrating the start of our week in authentic Chianti style at one of Volpaia’s most highly respected restaurants. Situated amongst vineyards with spectacular views, this dinner will see us launch our week in style

Traditional, home cooked Tuscan dinners – home cooked meals in Tuscany using their wonderful seasonal produce and traditional cooking methods is a ‘must do’, so we’ll be enjoying the best of this region’s home made cuisine with our hosts and guest chefs across each of our locations, whose hospitality is all tried and tested by us, and second to none.

A never to be forgotten Tuscan lunch at one of Montalcino’s premier restaurants – this is our personal ‘off the bike’ highlight for the week – a long Italian lunch where the hours pass by slowly and time has no meaning – our hosts at this restaurant will delight with their incredible food, wine and hospitality, as we sit back and enjoy great conversation, while overlooking the spectacular Tuscan countryside.

Aperitivo hour each day – this is one of our favourite daily rituals in Italy and we’ll be sharing it with you each day; whether it’s in a bustling piazza or by our pool, we’ll enjoy a range of aperitivi as we watch the world go by.

A winery tour of a superb Montalcino Estate – A private tasting and personal tour of the cellar of a celebrated Brunello di Montalcino estate, run by a very special family. 

A wonderful Finale Dinner on Saturday evening – after a week of sensational riding, food, wine and friendship, we’ll enjoy a relaxed dinner as a group at Certaldo’s premier family-run osteria, where the food and wine are simply exquisite.

Warm, engaging Italian hospitality – your hosts, Damian Hancock and Nancy De Losa will lead you through the week, sharing their warm, open entertaining style.  Combining Damian’s experience in leading group rides with their huge passion for Italian food and culture, means you’ll feel right at home in every town we visit. Nancy’s Italian heritage and fluency in speaking the language makes for a smooth experience with the locals each day. You’ll relish the experience that comes from their meticulous planning and attention to detail in all areas on and off the bike

Generous free time to explore all that this magnificent region has to offer – we believe a big part of the enjoyment of being on tour in Tuscany is being able to spontaneously duck into our local towns to enjoy a glass of wine and cheese in the piazza or a spot of shopping, or to wander off into the Tuscan countryside and explore places on foot or bike that take you on your own little exploration, or take a day trip to a surrounding town such as San Gimignano, Siena or Volterra. Whatever it is that you would like to do, there will be free time set aside for you to enjoy your own slice of heaven.



  • Price: $ 1,995.00 Quantity:
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“WOW! What a week you organised for us in Tuscany. This is what we loved so much; Your attitude to making sure we enjoyed every moment… Thank you both so much for the experience of a lifetime.”
Brian & Lyn Hosking
“A perfect world is a life where I don’t have to think about anything other than riding my bike and eating wonderful food. Nancy and Damian are perfect hosts and create an ideal setting for this to happen.”

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