Months Available
We craft 100% custom journeys with a private team and exclusive and culinary experiences, giving riders and companions the freedom to travel in their own style.
Our Tuscany gravel we don’t just guide tours; we curate private entries into the authentic heart of Italy. We believe that a journey should be as exhilarating for the one in the saddle as it is for the one exploring the village.
The Experience While riders conquer the legendary Strade Bianche and the rolling ridges of Val d’Orcia, their companions are immersed in a parallel world of curated luxury. From private viewings in hidden artisan ateliers to olive oil pressings in historic estates and quiet moments in sun-drenched spas, every guest experiences Tuscany at their own pace.
Our Promise We blend rugged adventure with discreet, effortless luxury. With 24/7 support, expert local knowledge, and stays in hand-picked boutique resorts, we remove the logistics so you can find the connection. This is Tuscany as it was meant to be seen: authentic, uncompromising, and shared together. Italy with Italians. Experience the Unreachable.
Our Essence:
EXAMPLE Itinerary
No two trips are ever the same, but this will give you a taste of what your private journey will be like.
Day 1
Distance: 30 km (18 miles)
Short Ride Available
Elevation: +500 mt (1640 ft)
Meals: L, D
Accomodation: Borgo San Felice
Welcome to Chianti: Vineyards & Cypress Lanes
Cyclist: The first pedal strokes roll out from Borgo San Felice onto pale gravel that hums under the tires. Vineyards open in neat lines, cypress trees mark the horizon, and the road curves gently toward San Gusmè. A quick espresso, a nod from the barista, then you glide back through warm light and stone farmhouses. Evening brings a quiet terrace, local dishes, and the first sip of Gran Selezione—exactly the right pace for day zero.
Non-Rider Activities: Either relax in the hotel’s private gardens and spa
or take a walk through the vineyards and olive groves to the village of Lecchi in Chianti, with wine and olive oil tastings along the Via Francigena
Day 1 - Welcome to Chianti: Vineyards & Cypress Lanes
Cyclist: The first pedal strokes roll out from Borgo San Felice onto pale gravel that hums under the tires. Vineyards open in neat lines, cypress trees mark the horizon, and the road curves gently toward San Gusmè. A quick espresso, a nod from the barista, then you glide back through warm light and stone farmhouses. Evening brings a quiet terrace, local dishes, and the first sip of Gran Selezione—exactly the right pace for day zero.
Non-Rider Activities: Either relax in the hotel’s private gardens and spa
or take a walk through the vineyards and olive groves to the village of Lecchi in Chianti, with wine and olive oil tastings along the Via Francigena
Distance: 30 km (18 miles)
Short Ride Available
Elevation: +500 mt (1640 ft)
Meals: L, D
Accomodation: Borgo San Felice
Day 2
Distance: 60 km (37 miles)
Short Ride Available
Elevation: +1,100 mt (3608 ft)
Meals: L, D
Accomodation: Borgo San Felice
Strade Bianche & Brolio Castle
Cyclist: The white roads feel iconic from the start—firm, rhythmic, inviting. The climb to Brolio threads through vineyards before the castle crowns the ridge with big views over the Chianti hills. Rolling terrain carries you toward Monti in Chianti with a few short, sharp ramps that wake up the legs. It’s classic Chianti riding: tidy gravel, tidy curves, a touch of dust on your ankles.
Non-Rider Activities: Either private tour of the village of Siena and curated shopping or walk the hills of Gaiole along the Via Francigena, passing chapels and hidden villages like San Sano, with local product tastings
Day 2 - Strade Bianche & Brolio Castle
Cyclist: The white roads feel iconic from the start—firm, rhythmic, inviting. The climb to Brolio threads through vineyards before the castle crowns the ridge with big views over the Chianti hills. Rolling terrain carries you toward Monti in Chianti with a few short, sharp ramps that wake up the legs. It’s classic Chianti riding: tidy gravel, tidy curves, a touch of dust on your ankles.
Non-Rider Activities: Either private tour of the village of Siena and curated shopping or walk the hills of Gaiole along the Via Francigena, passing chapels and hidden villages like San Sano, with local product tastings
Distance: 60 km (37 miles)
Short Ride Available
Elevation: +1,100 mt (3608 ft)
Meals: L, D
Accomodation: Borgo San Felice
Day 3
Distance: 70 km (43 miles)
Short Ride Available
Elevation: +1,350 mt (4429 ft)
Meals: L, D
Accomodation: Borgo San Felice
Oaks & Medieval Villages: Radda and Gaiole
Cyclist: Shade pools beneath the oaks, and the gravel changes texture—compact here, pebbled there—asking for a smooth hand. Lecchi’s stone houses and fountain invite a quick stop before Gaiole hints at L’Eroica heritage. The road rises to Radda in soft steps; views widen, and the pace finds its groove. The return is all soft S‑bends between vines and wheat fields.
Non-Rider Activities: Either cooking masterclass with the estate chef and vertical wine tasting of Gran Selezione wines or historic walk from Radda to Castellina in Chianti along a section of the Via Francigena, passing churches and medieval villages.
Day 3 - Oaks & Medieval Villages: Radda and Gaiole
Cyclist: Shade pools beneath the oaks, and the gravel changes texture—compact here, pebbled there—asking for a smooth hand. Lecchi’s stone houses and fountain invite a quick stop before Gaiole hints at L’Eroica heritage. The road rises to Radda in soft steps; views widen, and the pace finds its groove. The return is all soft S‑bends between vines and wheat fields.
Non-Rider Activities: Either cooking masterclass with the estate chef and vertical wine tasting of Gran Selezione wines or historic walk from Radda to Castellina in Chianti along a section of the Via Francigena, passing churches and medieval villages.
Distance: 70 km (43 miles)
Short Ride Available
Elevation: +1,350 mt (4429 ft)
Meals: L, D
Accomodation: Borgo San Felice
Day 4
Short Ride Available
Crete Senesi to Pienza: Lunar Lines
Cyclist: The landscape shifts: clay waves, solitary farmsteads, and wind moving freely over open ridges. Asciano offers bread and a pause; Monte Oliveto Maggiore adds quiet cloisters if you fancy a short detour. Between Chiusure and San Giovanni d’Asso, the gravel rolls in long, undulating stretches. Pienza appears at the end like a well‑composed postcard—clean lines, warm light, a door opening at La Bandita.
Non-Rider Activities: Either private tour of Montalcino with Brunello Riserva tasting or walk through the Crete to Monteroni d’Arbia along panoramic trails, with honey and olive oil tasting at local farms
Day 4 -Crete Senesi to Pienza: Lunar Lines
Cyclist: The landscape shifts: clay waves, solitary farmsteads, and wind moving freely over open ridges. Asciano offers bread and a pause; Monte Oliveto Maggiore adds quiet cloisters if you fancy a short detour. Between Chiusure and San Giovanni d’Asso, the gravel rolls in long, undulating stretches. Pienza appears at the end like a well‑composed postcard—clean lines, warm light, a door opening at La Bandita.
Non-Rider Activities: Either private tour of Montalcino with Brunello Riserva tasting or walk through the Crete to Monteroni d’Arbia along panoramic trails, with honey and olive oil tasting at local farms.
Short Ride Available
Day 5
Short Ride Available
Val d’Orcia UNESCO: Icons & Wide Horizons
Cyclist: Set off early for gentle light and quiet roads. The Vitaleta Chapel rises between fields like a bookmark between sky and page; San Quirico invites a pastry stop before you drift down to Bagno Vignoni, where steam hovers above the old stone pool. The return climbs smoothly, with tidy gradients and broad views. Back in Pienza, everything feels proportionate and calm.
Non-Rider Activities: Either artisan shopping in Pienza (cashmere and leather) and relax at the thermal baths in Bagno Vignoni or walk along the Via Francigena from Pienza to Bagno Vignoni, through cypress trees, golden fields, and medieval churches, with a pause at the natural thermal baths.
Day 5 -Val d’Orcia UNESCO: Icons & Wide Horizons
Cyclist: Set off early for gentle light and quiet roads. The Vitaleta Chapel rises between fields like a bookmark between sky and page; San Quirico invites a pastry stop before you drift down to Bagno Vignoni, where steam hovers above the old stone pool. The return climbs smoothly, with tidy gradients and broad views. Back in Pienza, everything feels proportionate and calm.
Non-Rider Activities: Either artisan shopping in Pienza (cashmere and leather) and relax at the thermal baths in Bagno Vignoni or walk along the Via Francigena from Pienza to Bagno Vignoni, through cypress trees, golden fields, and medieval churches, with a pause at the natural thermal baths.
Short Ride Available
Day 6
Short Ride Available
Wild Maremma to the Tyrrhenian Coast
Cyclist: Today is a transition you can feel: from clay to woodland, from inland breeze to a hint of salt. Roll out toward Buonconvento, then climb patiently through shaded hills and small hill towns where fountains still matter. Near Vetulonia, Etruscan echoes meet olive groves; the first breath of sea air arrives like a quiet promise. L’Andana greets you with long pines, still water, and space to unwind.
Non-Rider Activities: Either guided tour of Massa Marittima and relaxation in the Medici villa park or hike along scenic trails toward medieval villages, following a section of the Maremma Via Francigena, among centuries-old pine trees and sunflower fields.
Day 6 - Wild Maremma to the Tyrrhenian Coast
Cyclist: Today is a transition you can feel: from clay to woodland, from inland breeze to a hint of salt. Roll out toward Buonconvento, then climb patiently through shaded hills and small hill towns where fountains still matter. Near Vetulonia, Etruscan echoes meet olive groves; the first breath of sea air arrives like a quiet promise. L’Andana greets you with long pines, still water, and space to unwind.
Non-Rider Activities: Either guided tour of Massa Marittima and relaxation in the Medici villa park or hike along scenic trails toward medieval villages, following a section of the Maremma Via Francigena, among centuries-old pine trees and sunflower fields.
Short Ride Available
Day 7
Short Ride Available
Bolgheri & the Super Tuscans: Poise and Flow
Cyclist: The Viale dei Cipressi is a living colonnade; the Macchia della Magona brings dappled shade and a touch of sandy gravel that rewards light handling. Between Bolgheri Alto and famed vineyards, everything feels orderly and elegant: neat rows, whitewashed walls, gentle rollers. You climb with a broad breath and descend in smooth lines—riding that simply feels good.
Non-Rider Activities: Either 4×4 Super Tuscan Wine Safari and boutique shopping in Bolgheri Alta or walk through vineyard lanes and dirt roads in Bolgheri, visit private wineries, enjoy sunset views, and taste Sassicaia or Ornellaia.
Day 7 - Bolgheri & the Super Tuscans: Poise and Flow
Cyclist: The Viale dei Cipressi is a living colonnade; the Macchia della Magona brings dappled shade and a touch of sandy gravel that rewards light handling. Between Bolgheri Alto and famed vineyards, everything feels orderly and elegant: neat rows, whitewashed walls, gentle rollers. You climb with a broad breath and descend in smooth lines—riding that simply feels good.
Non-Rider Activities: Either 4×4 Super Tuscan Wine Safari and boutique shopping in Bolgheri Alta or walk through vineyard lanes and dirt roads in Bolgheri, visit private wineries, enjoy sunset views, and taste Sassicaia or Ornellaia.
Short Ride Available
Day 8
Meals: Breakfast (B)
Farewell, Tuscany
A last easy spin or a slow breakfast with warm bread and ripe fruit. The shuttle traces familiar lines between pines and fields. Tuscany lingers in small details: a dry‑stone wall, a cypress shadow, a fine dust that feels like a souvenir on your shoes.
Day 8 - Farewell, Tuscany
A last easy spin or a slow breakfast with warm bread and ripe fruit. The shuttle traces familiar lines between pines and fields. Tuscany lingers in small details: a dry‑stone wall, a cypress shadow, a fine dust that feels like a souvenir on your shoes.
Meals: Breakfast (B)
YOUR TRIP, YOUR WAY
Fully custom dates, routes, hotels, and difficulty levels. A private team dedicated only to you. Exclusive cultural and culinary experiences for riders and non‑riders alike. This is the freedom of a journey built entirely around your style.
Our Identity
Italy With Italians
Astrocycling was born from the desire to share the authentic Italy: the quiet backroads, the timeless villages, the flavors that tell a story, the warm smiles, and the traditions that still shape everyday life. It’s a way of traveling that blends elegance with simplicity, taste with slow living, discovery with genuine human connection.
Testimonials
Robert Shapiro
A MUST DO. The whole experience was truly unforgettable. From building the customized itinerary that suited our group of 4 couples, to the immersive feel of experiencing local Tuscan culture…I can’t recommend Astro enough!! Everything was top quality but relaxed and approachable.
They were adaptable when changes needed to be made, and definitely made sure each person felt well taken care of. This was my first cycling trip in Italy and I can’t wait to book another with Astro to explore a different region. I thought it would be a really hard challenge to do all of the hills but the bikes and guidance were amazing. And the VIEWS. Takes your mind off of the quads!
We went in mid September which felt like the perfect time of year. Thank you for everything Fabrizio and your amazing team!
Krista Deady
Heath Golden
Debbie Kindford
Kent Gonnerman
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