Experiencing the Real Tuscany: Our Top 10 Tour Highlights

Two cyclists riding through an olive grove in Tuscany

Our Tour of Tuscany is one of our favourites on the tour calendar each year and this most recent tour, shared with a great group of riders and non riding partners, lived up to its reputation of ‘experiencing the real Tuscany’ at every level. From riding the backroads and through small towns and hamlets, to experiencing a diverse range of food and wine experiences in local homes, family run osteria’s and superb restaurants, this is a tour that we love coming back to time and time again. Here we share our top 10 tour highlights.

A cyclist riding past Cypress pine trees in Tuscany

5 Climbs. 1 Day.

What a day. We roll down the hill and out of town and we are straight onto the first climb for the day in the beautiful Chianti countryside. A light tempo to warm up the legs is in order as we roll up the first 7kms, where a beautiful free flowing descent follows. Climb 2 is the hardest of the day with a couple of short lived 18% pinches. If you get your head right before you tackle this one, ease up and take the climb at your own tempo, you’ll have no problem. It’s a great feeling once you finally make it to the top, and this is even heightened by a superb 8km descent. Climb number three takes us up and over into where we stop for a well earned lunch and caffe, while #4 takes us to a little hilltop town before a great descent and a false flat run up to the last climb. With a few guys still feeling fresh, we gave it a nudge on our way to the top, before descending the last collina on our way back to our villa.

A bowl of pasta in Tuscany

Home-Made Pasta Party

Sharing home cooked meals with our host families in Tuscany is one of our favourite experiences, especially when it’s a ‘pasta party’. Enjoying a range of different and delicious pastas from zuppa di ceci to lasagna and ravioli ai funghi, accompanied by a a glass or two of a sensational Chianti Classico Riserva and the obligatory post dinner digestivi, always makes for a fun evening….all while providing the necessary carb loading for the next day’s 5 climbs.

A cyclist riding up a hillin Siena


Siena is an absolute highlight that we never tire of, whether riding or non-riding. Arriving into this very unique medieval city with its spectacular Campo is such a contrast in scenery and tempo after 3 days in the tranquil calm of the green Chianti countryside. It is the perfect stop for a mid ride coffee, but only after we tackle a little chilli pepper of a climb inside the walls, that on this tour took a few riders by surprise. It’s also a fantastic day out on the non riding partner program with a guided tour of the major sights and an insider view into the Palio, the famous horse race that defines the city.

A group of people in a barrel filled room during a Tuscan wine tour

Chianti Degustazione di Vino

Our Chianti degustazione di vino or wine tasting is a lovely, civilized sit down affair where guests are presented with a range of wines to taste. From Chianti Classico to Riserva and Gran Selezione, and often then on to a Super Tuscan or two, this experience is great for not only tasting but also learning about the history, tradition, controlled process and beauty of making this prized and appreciated Chianti wine. The Vin Santo and Grappa are pretty good here too.

Two cyclist riding through a Tuscan town

Montalcino, San Quirico and Pici

A relatively short ride at 70km, but one packed with iconic and quintessentially Tuscan vistas and spirit. Rolling hills, free flowing descents, cypress pine trees, winding gravel roads to stone houses set atop distant hills…… and this is all before we roll through the beautiful main street in the centro storico of San Quirico, where we stop for our mid ride coffee. With only 1425m across the 70km and the bulk of the elevation spread across the 30km between coffee and lunch, it’s easy to underestimate this day on tour. However, the climbing is punctuated with more beautiful views and one of the best descents of the tour. When we arrived into Montalcino, we were all hungry and this was easily fixed with the local speciality of Pici al ragu at one of our favourite little osteria’s. Refuelled and rehydrated, all we had to do now was out-run the possible rain on our last and mostly downhill 17km. Pure magic.

People enjoying a long tuscan lunch

Tuscan Long Lunch

Fresh and flavourful, simple and traditional. Our long lunch takes us on a culinary journey through some of Tuscany’s most wonderful, seasonal tastes. From amazing cured meats to cheese and truffle, fresh tomato and local hazelnut semifreddo, each course is a taste sensation. Taking time out as a whole group to enjoy an afternoon of dining, wining and relaxing Tuscan style, all while soaking in the incredible views, is just the ticket on our rest day.

A plate of pecorino cheese and glasses of white wine

Pecorino Cheese Experience

Engaging with local producers is always a highlight for our non riding guests on tour and our Pecorino cheese experience in the Val d’Orcia, was just that. We not only tasted and learned about the ‘slow food’ production style of this producer’s range of delicious organic cheeses, but also gained an insight into the people that work tirelessly to produce these wonderful products year round. Their family life, passion and love for creating and eating high quality food is certainly infectious.

a man riding a bike in San Gimignano

Our Final Ride into San Gimignano

Our final day on the bike is a major highlight. As we move from the Val d’Orcia, with the terrain and scenery changing as we get closer to San Gimignano, the first glimpse of the silhouette of the 14 towers appears. We slowly edge closer to this magical hilltop town as we ride around it and then descend off the adjacent ridge, climbing the last metres with a 12% pinch or two thrown in. On arriving to the outside walls on Saturday, it was a great experience to regroup before rolling up the ancient cobblestones into the main Piazza together. Such a beautiful finish to 8 days on the bike.

A group of People enjoying aperitivo in San Gimignano

Aperitivo ‘Cheese and Wine Tasting’ in San Gimignano

When the crowds have vanished and we’ve had time out post ride to soak up this beautiful medieval town, we come together for our final and ‘almost favourite’ aperitivo hour on tour. We’re not sure if it’s the pure satisfaction that goes with having ridden 560+km and almost 10,000 metres of elevation, the buzz in the streets or the introduction to Vernaccia di San Gimignano, the sensational local white wine and its accompanying pecorino cheese tasting plate, but this hour on tour is always a highlight.

A group of poeple enjoying a dinner in Tuscany

9 Days With a Great Group

Sharing 9 days of riding, culture, food and wine with a fantastic group of people is always our greatest highlight. We always say that our tours are the bringing together of a collection of experiences that we personally love, but when the guests we share it with, truly appreciate every element, it takes our enjoyment and appreciation for the places we are in, to a whole other level. It continues to inspire us. Grazie.

Saluti to this special group of people with whom we shared 9 great days in Tuscany. If you’d like to join our Tour of Tuscany in June 2020, secure your spot now.

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