2027 EDITION – COMING SOON
Tuscany - Chianti and the Strade Bianche
More Than a Cycling Tour
Five Days Through the Chianti Hills and the White Roads of Siena
Everyone has seen the postcard of Tuscany. Almost nobody has ridden it. This is the Tuscany of the Chianti hills, of cypress-lined roads that climb to a medieval village and drop into the next valley of vineyards, of the white gravel Strade Bianche that the professionals race every spring and that most visitors never even find. You do not see this from a car window on the way to Florence. You see it from the saddle, slowly, with a glass of Sangiovese waiting at the end of the road.
The route runs 200 km over five days through the hills between Siena and Florence, staying in two five-star hotels, one of them a castle from the twelfth century. Mornings are for the bike, when the light is low over the vineyards and the white roads are empty. Afternoons are for the good part: a long lunch at a Chianti winery, handmade pappardelle, the towers of San Gimignano, the shell-shaped square of Siena. The support van is always behind you with your bags and your water, so all you carry is your legs. Short days on the bike, long lunches. That is the whole idea.
Six Days From the Costa Smeralda to La Maddalena
DAY 1
Arrival in the Chianti Hills
You fly into Florence and we bring you south into the Chianti hills, to Hotel Le Fontanelle, a stone villa set among vineyards with the whole valley falling away below the terrace. There is time to fit your bike with Rodolfo and spin an easy loop through the vines to shake off the flight. Tonight is the first long table of the week: Tuscan bread, aged pecorino, a bottle of Sangiovese from the estate down the hill. Nothing hard today. Tuscany starts slowly, the way it should.
DAY 2
The Heart of Chianti
We ride out into the classic Chianti, the roads between Gaiole and Radda where cypress trees line the climbs and every ridge has a stone farmhouse or a small castle on it. The riding rolls up and down all morning, never for long, always with vineyards on both sides. Lunch is at a wine estate, long and shaded, with a tasting of Chianti Classico and a plate of handmade pappardelle. We roll back with the light going gold on the hills. Around 50 km, and you will want to stop for a photo on every one of them.
DAY 3
The White Roads into Siena
Today you ride the Strade Bianche, the white gravel roads that cross the bare clay hills of the Crete Senesi south of Siena. These are the same sectors the professionals race every March, and on a quiet summer morning they are yours alone, pale ribbons of road rolling over golden hills with a single cypress on the skyline. The gravel is smooth and the views are enormous. We finish by rolling into Siena itself and its great shell-shaped square, the Piazza del Campo, for an espresso in the shade. This is the day you came for.
DAY 4
Monteriggioni and the Towers of San Gimignano
We ride north through the hills, past the perfect ring of medieval walls at Monteriggioni, a whole town still wearing its fourteenth-century towers like a crown. Then on toward San Gimignano, the hill town famous for the stone towers its rival families built taller and taller against each other eight hundred years ago. We leave the bikes and walk up through the gates for a gelato in the main square, said to be the best in Italy. Tonight we move to Castello del Nero, a twelfth-century castle turned five-star hotel, for the last night.
DAY 5
Departure from the Castle
A slow last morning: breakfast on the terrace of the castle, a final espresso, and time to swap numbers before the road home. When you are ready, we handle the short transfer back to Florence airport. Bags are packed, bikes are boxed, nothing to organize. You go home with brown legs, a phone full of cypress trees, and a list of roads you already want to ride again.
The Man Behind the Roads
Rodolfo Massi won a stage at the Tour de France in the Pyrenees. He won a stage at the Giro d'Italia. He wore the King of the Mountains jersey - the polka dots - through the same cols you'll ride on this trip.
He's not a tour operator who studied a map. He's a former professional who spent his career on these exact roads. He knows where the gradient kicks, where the wind hits, where to stop for the view that nobody else knows about. And he knows something most guides don't: how to make a climb feel like a gift instead of a punishment.
Today, Rodolfo takes a handful of people each year through the mountains that shaped his life. Not to race. Not to suffer. To feel what it's like to ride roads that were built for something extraordinary - with someone who lived it.
Massi's "Service Course" Treatment
We handle every logistical detail so your mind remains completely free.
Note: flights, medical insurance, room upgrades and personal expenses are not covered.
Worried You're Not Fast Enough?
Read This
Every single person who books this trip asks some version of the same question:
"Can I actually do this?"
Yes. Here's why.
This is not a race. There is no pace to hold and no group to keep up with. Rodolfo has guided riders of every level through these cols - from people who train five days a week to people who ride on weekends when the weather is nice.
The support van follows the group every day. If you hit a wall, you can still enjoy the view in the van without judgment. If you want an e-bike for the bigger days, several guests choose exactly that every trip.
The only thing that matters is that you enjoy riding. If you're worried about being a burden, that worry itself is proof that you're the kind of person this trip was made for: someone who cares about the experience and the people around them.
the investment
5 days across Tuscany with Rodolfo Massi. Luxury accommodation, all dinners, airport transfers, full ride support, and mechanical service included.
TUSCANY
2027 Edition — Coming Soon
5 days
4 nights
Siena to Florence
Limited to 12 spots
your piece of mind
Will I slow the group down?
What about my luggage and transfers?
What happens if the weather is bad?
Do I need an insurance?
How do I pay?
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