Difficulty
Duration
9 Days
Distance
kms (or)
kms
Elevation Gain
m (or)
m
Country
Italy
Welcome to the Tuscany: Cycling Through Wine Country, a curated week of cycling through one of the world’s most storied regions by Barnowl Adventures. From the vine-covered slopes of Chianti to the UNESCO landscapes of Val d’Orcia, this ride blends gentle to challenging cycling with the full sensory richness of Tuscany — its food, wine, history, and warm hospitality.
We start in the heart of Chianti Classico, staying in a charming farmhouse-style hotel surrounded by vineyards. From there, we follow quiet backroads to medieval towns like Volpaia, Radda, Gaiole, Siena, Pienza, and Montalcino. The first four days are spent exploring the rolling hills of Chianti before moving to Siena for a relaxed day in the city, then onward to the cinematic landscapes of Val d’Orcia for the final three nights.
You can’t be in Tuscany and miss out on the gastronomic experience it offers! Food and wine are at the heart of this ride. Throughout the week, we stop at handpicked local eateries, wineries, and cafés — the kind of small, family-run spots that let you taste Tuscany like a local, with authentic flavours, friendly faces, and the occasional delicious surprise.
If you enjoy cycling, culture, good food, and even better wine, this is the perfect week on two wheels.
Fly - In
Florence Airport Peretola
Fly - Out
Florence Airport Peretola
Quick Navigation: Pricing & Dates | Highlights | Itinerary | Inclusions & Exclusions | Gallery
GIRONA
Ride Snapshot
Distance
Elevation Gain
Distance
Elevation Gain
Tour Fee
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Twin Sharing € 3,700
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Single Occupancy € 4,500
🗓️ 25 Sep - 3 Oct 2026
HIGHLIGHTS
- Cycle through Chianti Classico and the stunning Val d’Orcia
- Taste Chianti, Brunello and Pecorino at authentic local stops
- Explore medieval gems like Siena, Pienza, Volpaia and Montalcino
- Relax in Bagno Vignoni’s unique thermal spa setting after the ride
Itinerary
Day 1: Welcome to Chianti
Meet in Florence and settle into your private transfer to Castellina in Chianti. Once we reach our hotel, we set up the bikes, shake off the travel legs, and head out for the perfect Chianti warm-up ride
It’s a classic introduction to the region — rolling vineyards, short punchy climbs, stone farmhouses, and those sweeping views that Tuscany is famous for. We stop for coffee in Lecchi, then return to Radda via a different scenic route before rolling back into Castellina. In the evening, we gather for a relaxed welcome briefing followed by a hearty Tuscan dinner.
- Private transfer from Florence to the heart of Chianti
- Scenic warm-up ride through vineyards and rolling countryside
- Welcome briefing followed by a traditional Tuscan dinner
Day 2: The Road to Volpaia
Distance
48 kms (or) 82 kms
Elevation Gain
1040 m (or) 1600 m
Night Stay
Hotel Colle Etrusco Salivolpi
Meals
Breakfast, Lunch, Dinner
After a leisurely breakfast at our hotel, we roll out from Salivolpi towards Radda and then ease into the beautiful climb up to Volpaia. This tiny, fortified medieval village dates back to the 12th century and feels almost suspended in time — stone lanes, quiet corners, and cellars built right into the village walls. It’s one of the most atmospheric hamlets in all of Chianti Classico, perfect for photos and a slow coffee break.
Volpaia is also home to Castello di Volpaia, an organic winery known for its high-elevation vineyards and elegant, balanced Chianti Classicos. After Volpaia, we roll down towards Lucarelli for lunch at a small countryside spot that feels wonderfully local. From here, it’s an easy return to our hotel — unless you’re in the mood for a little more exploring, in which case the long option is right there for you.
The medieval town of Castellina in Chianti is a 10-minute walk from our hotel. It’s a compact, charming hilltown with a few lovely spots worth exploring. The little piazza, wine shops and gelaterias make it a relaxed, easy place to stroll before dinner.
- Ride through the heart of Chianti via Radda and Volpaia
- Explore the beautifully preserved medieval hamlet of Volpaia
- Optional extended ride for those seeking extra miles
Day 3: Chianti Classics
Distance
41 kms (or) 60 kms
Elevation Gain
860 m (or) 1400 m
Night Stay
Hotel Colle Etrusco Salivolpi
Meals
Breakfast
Today we head south-east into the central Chianti spine toward Panzano and then Greve in Chianti. The short option is a friendly out-and-back that gives you the iconic Greve piazza coffee stop and easy rolling roads back to Castellina. The long option continues the loop via Dudda / Lucolena and then climbs toward Radda again before descending to Salivolpi — more vertical, more villages, and more panoramic ridge riding.
In the evening, we stroll into Castellina town for a relaxed Chianti Classico tasting, featuring small producers and the traditional styles that define this historic wine region. Lunch and dinner are on your own today, giving you the chance to explore the cafés, wine bars, and trattorias around Castellina at your own pace.
- Choose between an easy spin or a more challenging ridge loop
- Classic piazza coffee stop in one of the region’s most loved towns
- Guided tasting of traditional Chianti Classicos in the evening
Day 4: Gaiole: Heart of Eroica Country
A ride that threads the central Chianti hilltowns. After rolling through Radda, we settle into a forested climb — a shaded, peaceful ascent through oak and chestnut trees — before it opens into a smooth, flowing descent straight into Gaiole in Chianti.
Gaiole was once one of the three capitals of the old Chianti League, alongside Castellina and Radda. Today, it’s a bit of a cycling pilgrimage spot — the starting point for the Strade Bianche and L’Eroica routes — with a relaxed piazza, stone buildings, and an easygoing rhythm. We’ll stop here for a coffee and soak in the atmosphere.
After Gaiole, we continue our ride toward Siena, where the evening is free to explore the city on foot.
- Ride the classic Chianti thread linking its iconic hilltowns
- Pause for a leisurely lunch in Gaiole, a historic town with deep cycling roots
- Spend the evening wandering Siena’s timeless streets
Day 5: Siena: Cafés & Cobbles (Rest day)
Siena is one of Italy’s best-preserved medieval cities. The fan-shaped Piazza del Campo is a masterpiece — the stage for the iconic Palio horse race — and the Duomo stands out with its striking striped marble façade and richly decorated interior.
Today is yours to soak it all in: wander the narrow alleys, climb the Torre del Mangia for sweeping views, explore the Duomo Museum, or simply linger over panforte and an espresso in the Campo.
It’s pure medieval charm — cobbles, porticos, and that unmistakable Sienese atmosphere.
Lunch and dinner on your own.
- Full day to explore the historic city of Siena.
- Wander medieval lanes, museums, and local cafés
- Free time for lunch and dinner at your own pace
Day 6: Across the Crete Senesi
Today we roll into the Crete Senesi — those dreamy, sculpted clay hills just south-east of Siena. About 27 km into the ride, our first coffee stop is in the Asciano village piazza — a laid-back break where we can sip, snack on some local treats, and soak in the quiet vibe before cruising onward towards San Quirico and Bagno Vignoni.
About Bagno Vignoni: This little village has been a place to unwind since Etruscan and Roman times, all thanks to its naturally hot springs. Instead of a regular piazza, the centre of town is a steaming 49°C thermal pool — the Renaissance-era Piazza delle Sorgenti. Your hotel, Albergo Le Terme, sits right beside it and includes spa access, so you can slip straight into a long, easy soak after the ride. Perfect way to end the day.
- Ride into the stunning Crete Senesi and some of Tuscany’s most photographed landscapes
- Enjoy an espresso in the relaxed piazza of Asciano
- Finish in Bagno Vignoni, where the “piazza” is a steaming thermal pool
Day 7: Pienza & Beyond
We roll out from Bagno Vignoni for a relaxed loop through the heart of the Val d’Orcia. First stop: Pienza, perfectly perched above the valley with postcard views at every turn. This is also the landscape made famous by Gladiator — the golden wheat fields where Maximus walks in his dreams were filmed just outside town, between Pienza and San Quirico. Pienza is also famous as the capital of Pecorino di Pienza, the sheep’s milk cheese that’s been crafted here for centuries — you’ll likely spot it in local shops and markets, often still aged in traditional caves.
From Pienza we follow the soft, rolling ridgelines toward San Quirico d’Orcia, a quiet medieval village with cypress-lined lanes and a lovely Romanesque collegiate church. We’ll stop here for lunch, and for those who’d like, there’s an wine tasting at a tiny family-run winery right inside this charming village — hosted by a warm, elderly couple who’ve been making and pouring wine here for decades. It’s the kind of intimate, old-world experience that feels straight out of rural Tuscany.
After San Quirico, gentle roads lead us back to Bagno Vignoni, wrapping up a mellow and scenic loop through the Val d’Orcia
- Ride past the iconic filming locations of Gladiator.
- Stop for a leisurely stroll through Pienza, a charming Renaissance village overlooking golden Tuscan valleys
- Taste the region’s famed Pecorino cheese
Day 8: Montalcino: Land of Brunello
Today’s highlight is Montalcino, a classic hilltown dominating vineyards famous for Brunello di Montalcino
We start our first climb straight from our hotel in Bagno Vignoni, climbing toward the Castiglione d’Orcia. At the top, we’re rewarded with a long, flowing descent that lets us soak in the views of the Val d’Orcia. We eventually arrive at a classic medieval hilltown perched above vineyards, world-famous for Brunello di Montalcino — one of Italy’s most prestigious reds.
We’ll stop in town for wine tasting and lunch, surrounded by vineyards rolling down toward the historic center. After soaking in the scenery and enjoying some Brunello, you’ll have time to wander the streets, peek into small shops, or simply take in the medieval atmosphere before we ride back to Bagno Vignoni along scenic roads.
- Ride through Val d’Orcia toward the iconic hilltown of Montalcino
- Climb and descend through some of Tuscany’s finest landscapes
- Lunch and Brunello tasting in the heart of it all
Day 9: Until Next Time
After breakfast, check-out and a private transfer back to Florence (timed to flights/trains).
Other Info
Inclusions
- 8 nights’ accommodation
- All breakfasts, 5 dinners ( D1, D2, D4, D6, D8) and 5 light lunches ( D1, D2, D4, D7, D8)
- Daily guided rides with ride leaders
- Support van with water, fruits & electrolytes
- Mechanical support
- Daily route briefing and GPS files
Exclusions
- Airfare or travel to/from Florence
- Bike rental (available at additional cost)
- Travel or medical insurance
- Lunches on Day 3, Day 5 and Day 6
- Dinners on Day 3, Day 5 and Day 7
- Alcoholic beverages (unless specified)
Fitness & Preparation
This tour is designed for riders comfortable with hilly, rolling terrain. While the routes include climbs and descents, the pace is relaxed with plenty of stops — for coffee, wine tastings, or to wander through medieval towns like Gaiole, Pienza, and San Quirico along the way.
Participants should:
- Arrive with a well-maintained bicycle and be familiar with basic on-the-road fixes such as flat repairs.
- Using a GPS navigation device such as a Wahoo or Garmin is mandatory. While a guide will ride with the group, riders are responsible for following the route. All route files will be shared in advance.
- The daily distances aren’t as long as some of our other rides, but the terrain is hilly, so you should be comfortable with both climbing and descending.
- Ride with peace of mind knowing a dedicated support vehicle is always with the group, ready to assist with mechanical issues or injury.
Weather
Late September is one of the best times to ride in Tuscany. Expect warm days with golden sunlight, perfect for exploring vineyards and hilltowns on two wheels. Average daytime temperatures range between 20°C and 26°C, with cooler mornings around 12–15°C.
Rain is possible but generally light and infrequent, so it’s wise to carry a light rain jacket and a wind vest for the occasional gusty ridge or shaded descent.
Travel & Logistics
Arrival:
We’ll arrange a group pickup from Florence train station at 9:30 AM on 25th September 2026. The transfer to Castellina in Chianti takes about 90 minutes. Riders arriving by air can easily reach Florence train station via train or taxi from Florence Airport (FLR).
We recommend arriving in Florence a day earlier to allow time to recover from travel and get into the Tuscan rhythm. This additional night’s accommodation in Florence is not included in the tour cost.
Departure:
On 3rd October 2026, after a relaxed breakfast, we’ll transfer everyone back from Bagno Vignoni to Florence train station for onward travel or flights.
Bike Rental
For riders who prefer not to travel with their own bikes, good quality road bikes are available for rental during the bike tour.
Road bike: Scott Addict 30 for €300 for the trip (Carbon frame, Shimano 105 mechanical groupset, hydraulic disc)
E bike: Cervelo Rouvida for €560 (Full carbon, Shimano GRX 12 speed, hydraulic disc
Repairs & Safety
Basic spares and tools are carried by the guide and on the support vehicle, though we cannot guarantee having spares for every conceivable problem. Carrying a basic tool kit, a spare tube and a pump while riding is recommended.
Wearing a helmet is required on all our biking adventures and is non negotiable. If you do not wear a helmet you will not be allowed to cycle. Your tour leader is trained in first aid and emergency rescue, but to a large degree you must be responsible for your own safety while riding.
