Self guided Tuscany Strade Bianche Gravel Bike Tour
The Strade Bianche Bike Tour blends Tuscany’s legendary gravel roads with the region’s rich culture, cuisine, and landscapes.
Starting in Pienza, the “perfect town” of Renaissance design, the journey follows parts of the famed L’Eroica route, weaving through the Val d’Orcia’s rolling hills, cypress-lined lanes, and UNESCO-protected scenery. Riders explore Montepulciano’s Renaissance palaces, soak in the timeless charm of Bagno Vignoni, and climb toward Montalcino, home to world-class Brunello wine.
From there, the path leads through historic vineyards, medieval hamlets, and celebrated gravel sections like Castiglion del Bosco and Pieve a Salti. Siena’s medieval streets offer a cultural interlude before continuing to Chianti, counting castles and village squares along the way. In Gaiole, the Eroica’s starting town, the route visits Castello di Brolio and hidden Chianti hamlets.
Evenings unfold in handpicked accommodations ranging from 15th-century convents to stone manor houses, each rich in character and heritage.
The tour balances challenging rides with indulgent moments. Think espressos in small village cafés, fresh pasta lunches, and wine tastings that reflect the land’s deep heritage. More than a cycling trip, it’s an immersion into Tuscany’s soul, where every climb and coast reveals another layer of history, flavor, and beauty.
Self-guided
Casual+ hotels
Pienza
Gaiole in Chianti
moderate to challenging
42 km / 26 mi
7
Min. 2, Max. 10
Amerigo Vespucci Airport Florence (FLR)
Amerigo Vespucci Airport Florence (FLR)
Highlights
Ride the Legendary Strade Bianche
Cycle iconic white gravel roads, part of the professional Strade Bianche race and the historic L’Eroica route, surrounded by rolling Tuscan hills.
Explore Renaissance Gems
Wander Pienza and Montepulciano, marvel at Renaissance architecture, and soak in timeless piazzas.
Scenic Villages & Vineyards
Pedal past medieval hamlets, cypress-lined lanes, and historic vineyards, with photo stops at castles and chapels.
Itinerary
Brief Itinerary
Meals are indicated as B = Breakfast, L = Lunch, D = Dinner.
Listed hotels are subject to availability and may be replaced with similar alternatives of equal standard.
| Day | Place | casual_plus Inns | Meals | Distance | Activity |
|---|---|---|---|---|---|
| DAY 1 | Pienza | Hotel Relais il Chiostro di Pienza (4-star) | B | 25 km / 16 mi | cycling |
| DAY 2 | Pienza | Hotel Relais il Chiostro di Pienza (4-star) | B | 51 km / 32 mi | cycling |
| DAY 3 | Montalcino | Hotel Vecchia Oliviera Sas | B | 41 km / 25 mi | cycling |
| DAY 4 | Siena | La Villa di STR | B | 58 km / 36 mi | cycling |
| DAY 5 | Gaiole in Chianti | Castello di Spaltenna (5-star) | B | 46 km / 29 mi | cycling |
| DAY 6 | Gaiole in Chianti | Castello di Spaltenna (5-star) | B | 54 km / 34 mi | cycling |
| DAY 7 | Departure | B | 20 km / 12 mi | cycling |
Detailed Itinerary
Day 1: Pienza
Arrive in Pienza, the Renaissance jewel known as the “perfect town". Stroll through cobblestone streets lined with elegant architecture and breathtaking views over the Val d’Orcia. Our local team meets you for a welcome and bike fitting.
If time allows, pedal toward Palazzo Massaini and the hilltop village of Montefollonico, passing vineyards and golden fields along a mix of gravel and paved roads. The ride offers gentle climbs and sweeping vistas that set the tone for the days ahead. Return to Pienza to unwind in your charming hotel and savor your first taste of authentic Tuscan cuisine with local wine.
Surface: 12 km asphalt and 13 km gravel
Elevation gain: 558m/ 1830ft
Day 2: Pienza
Pedal out of Pienza into the rolling hills of the Val d’Orcia, where spring paints the fields green and red poppies brighten the roadside. This is Tuscany's quintessential landscape, made famous by films such as Gladiator and The English Patient.
Follow quiet gravel tracks lined with cypress trees to reach Montepulciano, a Renaissance gem rich with palaces and history. After exploring, tackle a thrilling gravel section toward Monticchiello, a picture-perfect hill town with timeless charm.
Descend into the valley and continue to Bagno Vignoni, famous for its ancient Roman thermal springs. Pause at the Madonna di Vita Leta chapel before returning to Pienza. The route blends cultural treasures, cinematic landscapes, and the warm flavors of Tuscany.
17 km asphalt and 34 km gravel
Elevation gain: 872m/ 2860ft
Day 3: Montalcino
Leave Pienza along a short paved stretch before joining the famed white gravel roads of Crete Senesi toward Lucignano d’Asso, where a quick espresso stop at the tiny village emporio feels essential. Continue through the beautiful Pieve a Salti gravel section, with gentle climbs and sweeping rural views, before arriving in Buonconvento by lunchtime.
From here, tackle the ascent to Montalcino, riding through vineyards and wineries that produce the world-renowned Brunello. The final kilometers reveal panoramic views of the valley you have just crossed. Once in Montalcino, explore its medieval fortress and reward yourself with a glass of local wine before settling into your hotel.
Surface: 17 km asphalt and 24 km gravel
Elevation gain: 855m/ 2805ft
Day 4: Siena
Begin in the heart of Brunello country and ride toward Passo del Lume Spento before entering the celebrated Castiglion del Bosco gravel section, part of the historic L’Eroica route. Pass the vast Brunello estate owned by Ferragamo, then roll into Bibbiano for a coffee stop.
Continue through the La Piana stretch to Murlo, a charming village worth a visit, before tackling the legendary Radi section with its short, steep undulations. Pause for a light lunch at Ville di Corsano, then finish with a scenic paved approach into Siena. End the day exploring its medieval streets and soaking in the city’s atmosphere.
Surface: 32 km asphalt and 24 km gravel
Elevation gain: 1015m/ 3330ft
Day 5: Gaiole in Chianti
Leave Siena via the Pieve a Bozzone gravel section, riding through golden wheat fields and into the vineyards of Chianti Classico. Pass small hamlets like Pianella before enjoying a long, glorious gravel stretch to Canonica a Cerreto and Vagliagli. Count castles and hilltop villages along the way, stopping in Radda in Chianti for lunch.
The afternoon brings a short, scenic ride to Gaiole, following the Eroica itinerary through San Donato in Perano and Vertine. Gaiole is best known internationally as the starting point of L’Eroica, the celebrated vintage cycling event held every October. Riders dress in retro wool jerseys and ride restored steel bicycles along the white gravel roads or strade bianche of Chianti.
Panoramic views, charming medieval lanes, and vineyard-lined roads make this stage unforgettable. Settle into your castle hotel and toast the day with a glass of fine Chianti.
Surface: 12 km asphalt and 34 km gravel
Elevation gain: 923m/ 3028ft
Day 6: Gaiole in Chianti
Start from your castle hotel in Gaiole and ride to the iconic Castello di Brolio, pausing for coffee at the agribar in front of the winery where cyclists and locals gather. Continue on a short Eroica gravel section before meandering along quiet scenic roads to Castelnuovo Berardenga, a village rich in charm and lunch options.
Back in the saddle, visit tiny hamlets like San Gusmé and Villa a Sesta, soaking in their timeless beauty. Return toward Brolio and choose between a relaxed downhill route or a more challenging climb to Castagnoli before descending to Castello di Meleto and back to Gaiole.
Surface: 44 km asphalt and 10 km gravel
Elevation gain: 1013m/ 3323mi
Day 7: Departure
Set out on a short loop from Gaiole to the historic Badia a Coltibuono, riding through peaceful Chianti hills scented with vineyards and wildflowers. The gentle route offers time to savor the scenery and enjoy a final taste of Tuscany’s cycling charm.
Return to Gaiole, where the tour winds down with moments to relax in the village or explore nearby lanes. Hand back your bike and reflect on the landscapes, flavors, and climbs that have defined the journey. Depart by bus to Siena, ready to connect by fast train to your next destination, carrying memories of the white roads with you.
Ready to plan your adventure? Download a print-ready detailed itinerary.
Map
Accommodation
Each hotel has been thoughtfully selected to ensure an exceptional and memorable experience for guests. Should the listed hotel be unavailable, we will ensure an alternative of similar quality.
Hotel Relais il Chiostro di Pienza
Relais Il Chiostro di Pienza occupies a beautifully restored 15th-century convent in the heart of Pienza. The hotel retains historic charm with beamed ceilings, frescoed walls, and terracotta floors while offering modern comfort. Guests can relax in the peaceful garden with a pool overlooking the Val d’Orcia. Its central location makes it easy to explore the town’s Renaissance streets, artisanal shops, and nearby rolling Tuscan countryside.
Hotel Vecchia Oliviera Sas
Hotel Vecchia Oliviera sits in the historic heart of Montalcino, beside the ancient Porta Cerbaia gate. Once an olive oil mill, it has been lovingly restored into a warm and inviting hotel. Guests enjoy comfortable rooms, a charming garden, and sweeping views of the Orcia Valley. Its location makes exploring Montalcino’s wine cellars, medieval streets, and surrounding countryside effortless, offering an authentic Tuscan stay with character and history.
La Villa di STR
La Villa di STR in Siena is a converted 19th-century villa that blends classical Italian design with modern comforts. Recently renovated public areas retain elegant period charm, and a quiet garden offers a relaxing escape. The villa’s location, just a 10-minute walk from Piazza del Campo, makes it ideal for exploring Siena’s medieval streets, vibrant cafés, and historic landmarks while enjoying a peaceful base away from the busy city center.
Castello di Spaltenna
Castello di Spaltenna offers an exclusive retreat in the heart of the Chianti Classico wine region. This historic stone manor provides elegant rooms with stunning valley views, blending luxury with authentic Tuscan charm. Guests can relax in lush gardens, enjoy a pool, and dine at the renowned Pievano restaurant. Surrounded by vineyards and hilltop villages, it is perfect for cycling adventures, wine tasting, and immersing in the beauty and flavors of Tuscany.
Dates and Prices
Single Supplement
From US $1,050
E-Bike Upgrade
From US $120
Couldn't find a trip with convenient dates?
Open your date as a join-in tour or customize further as a private one.
Essential Info
Inclusions
LODGING
All hotels as mentioned in the tour details or similar (subject to availability).
bike
Immaculately maintained bike with helmet, suited to a terrain.
Luggage Transfer
Transportation of luggage from one hotel to another.
meals
Meals as per itinerary. Guests are given the opportunity to dine on their own so that they discover a location independently.
Exclusions
Airport pickup and drop
We recommend to book direclty from airport or hotel.
Beverages
Beverages such as alcohol, tea, coffee, juice at a hotel or restaurant.
Gratuity
Gratuities for your guide team are not included in the trip price.
Bikes
When you have a road and the thrill of a journey ahead of you, it’s imperative to have a good bike to enjoy it. Our fleet majorly consist of the below bikes as a part of this tour. However, sometimes due to height or availability constraints, we may provide a different but similar quality bike.
SCOTT Addict Gravel 20 or similar
Included in your trip price
Canondale Synapse e-gravel or similar
Available at a surcharge
Arrival & Departure Details
Arrival
Your tour begins in Pienza. The nearest major international airport to Pienza is Florence Airport (Aeroporto di Firenze-Peretola, FLR), about 145 km / 90 miles away, which is roughly a 2-hour drive.
Rome Fiumicino (Leonardo da Vinci International Airport, FCO) is about 220 km / 137 miles, 2.5–3 hours by car. It offers far more international connections than Florence.
You can take a high-speed or regional train from Rome or Florence to Chiusi–Chianciano Terme, which sits on the main Rome–Florence line. From Rome, it’s about 1 hour 45 minutes; from Florence, around 1 hour 20 minutes.
You can also take a regional train from Sienna to Buonconvento or Chiusi, but the Siena route generally involves slower trains and more connections.
From Chiusi–Chianciano Terme, take a regional bus (operated by Tiemme) towards Montepulciano and onward to Pienza. The total bus ride is roughly 1 hour, but departures are limited — often only a handful per day, especially on weekends or holidays.
If coming from Siena, you can catch a bus to Pienza via San Quirico d’Orcia, but this route is even less frequent.
Departure
Your tour ends in Gaiole in Chianti, located some 30 kms (18mi) from Siena. After dropping your bikes, you can take a bus to reach Siena. From Siena, you can take a bus to Florence ( journey time around 90 minutes), and from the bus station, a train to the Florence International Airport.
Weather
The best time to cycle the Strade Bianche route is in spring (April–June) and autumn (September–October) when Tuscan landscapes glow with color and temperatures stay comfortable. Spring offers 15–22°C (59–72°F) with wildflowers in bloom, while autumn brings golden vineyards and 16–24°C (61–75°F). Summer (July–August) can be hot, often exceeding 30°C (86°F), making midday rides challenging. Winter (December–February) sees cooler weather, averaging 6–12°C (43–54°F), with shorter days and occasional rain. These shoulder seasons provide the perfect balance of mild temperatures, quieter roads, and beautiful scenery, making them ideal for both challenging climbs and leisurely countryside rides.
January
Offseason
February
Offseason
March
Mixed
April
Best
May
Best
June
Best
July
Good
August
Good
September
Best
October
Best
November
Mixed
December
Offseason
Best
Good
Mixed
Offseason
What to Pack
Packing smart is essential for a safe and enjoyable cycling adventure. From essential biking gear to clothing and travel necessities, this guide ensures you're prepared for any terrain or climate.
Recommended Bicycling Clothes & Gear
- Bicycling shoes or stiff-soled sneakers.
- Padded cycling shorts.
- Short-fingered cycling gloves (personal gloves are ideal).
- Brightly colored cycling jerseys or synthetic T-shirts for visibility.
- Synthetic cycling socks.
- Sunglasses with UV protection.
- Personal helmet (recommended even though provided).
- Personal saddle (optional for added comfort).
- Rain jacket or windbreaker.
- Cycling water bottle (to reduce plastic waste).
Note: Helmets, gloves, and water bottles are personal items, so bringing your own is recommended for maximum comfort and hygiene.
Clothing
- Light, breathable fabrics like cotton or linen.
- Full-sleeved clothing for sun protection.
- Warm layers for chilly mornings and evenings (if traveling in winter).
- Comfortable footwear for non-cycling time.
- Bring a compact rain jacket in case of sudden weather changes.
- Ethnic or modest clothing for exploring towns and temples.
Other Necessities
- Toiletries: Basic hygiene essentials, including insect/mosquito repellent and sunscreen.
- Hand sanitizer and wet wipes.
- Plug socket adaptor.
- Binoculars for wildlife spotting or desert landscapes.
Pro Tips
- Pack light but plan for the varying temperatures: warm days, chilly evenings, and desert winds.
- Use brightly colored clothing for visibility on roads.
- Pack light to leave room for shopping.
Luggage
Please limit your luggage to one medium-sized suitcase and one carry-on bag. Mark your luggage with your name, address, and phone number.
Visa Information
Before venturing on your adventure, make sure you're equipped with essential travel advice, including security updates, local laws, and crucial passport and visa information. Start by visiting the official government website of your home country for accurate and reliable guidance:
- UK Residents: Stay informed by reviewing the Foreign, Commonwealth & Development Office (FCDO) Travel Advice.
- US Residents: Access vital travel tips and updates through the US Department of State Travel Advice.
- Australian Residents: Plan ahead with the latest updates on the Smart Traveller website.
- Canadian Residents: Find comprehensive travel and visa guidance on the Government of Canada's Travel Advice and Advisories.
- New Zealand Residents: Get practical travel advice on the New Zealand SafeTravel website
- Residents of Other Countries: Check with your government or local consulate for tailored travel advice and requirements.
Note: Passport and visa regulations can change at any time. Stay proactive by checking for the latest updates to ensure a smooth and stress-free journey.
Insurance
Medical insurance that covers medical costs in case of an accident during the trip is mandatory to participate in our tours.
We recommend to purchase adequate travel insurance in order to participate in our tours and protect yourself from unforeseen events. Our experience shows that guests who purchase travel insurance—including coverage for all activities on the itinerary, trip cancellation, interruption, delay, baggage damage, loss or theft, personal accident, death and repatriation costs, medical and emergency expenses (including Covid-19), and personal liability—travel with greater peace of mind.
Can I use my credit card insurance?
Yes, as long as it meets our requirements and provides adequate coverage. Ensure you have an emergency contact number and policy number available.
When should I buy travel insurance?
Purchase travel insurance as soon as you've paid in full or booked your flights.
Is proof of travel insurance required?
Yes. You must provide your insurer's name, policy number, and emergency contact via our reservation form. This is mandatory. If you cannot provide proof, you’ll need to purchase insurance before traveling with us.
Does Art of Bicycle Trips sell travel insurance?
We do not sell travel insurance directly, as we believe our customers should have the freedom to choose a policy that best suits their needs. However, we recommend Insured Nomads as a great starting point.
Frequently Asked Questions
We provide an app-based navigation system that can also be used offline. You can download the app to your phone in advance, and we will share the login details ahead of your trip. Since the app works offline, it helps conserve your phone's battery during use.
For minor issues like punctures, the guests are provided with a self-repair kit, which includes tools to help them fix such minor issues. The exact contents of the kit depend on the type of bike, terrain and other factors, and will be communicated to you closer to your date of departure. However, usually such a kit includes tire levers, a spare tube, a patch kit, and a pump, allowing riders to fix the problem themselves. In some cases, the kit may only include a pump or a repair foam.
Self-guided riders are expected to be independent in handling these minor problems. While there are some bike shops along the route, they are limited. If you are unsure about how to repair a puncture, we recommend considering a guided or van-supported trip instead.
For major mechanical failures, such as a cable break, the guests can contact the emergency support number provided. The support team will help coordinate a solution, which could include dispatching a local mechanic, suggesting a nearby bicycle shop for repairs, or sending a vehicle to pick up the rider. Please note that all support services will be provided on a chargeable basis, and assistance may take time, so we advise being prepared for potential delays.
We provide 24/7 emergency support by phone for any medical emergencies during the tour. Our team will assist in coordinating medical care, guiding you to the nearest healthcare facility, and ensuring you receive the necessary support. The national emergency system is reliable and effective, and in the event of a serious accident, contacting them is highly recommended. However, due to our distance from certain areas, response times may be longer. We strongly recommend having appropriate travel insurance, and we will do everything we can to ensure your safety and well-being during an emergency.
The fitness level required for each trip is indicated by the "level" of the tour, which in turn is mentioned on each tour page right next to the price and the trip duration.
Easy: The terrain is mostly flat with a few gentle climbs.
Moderate: The terrain is either mostly flat or consists of rolling hills with a few challenging climbs. There could also be a few days with longer riding distances of up to 75 kms (45 miles)
Difficult: The terrain is mostly hilly with strong elevation gains and/or has long days on the bike. Such trips are recommended for intermediate to advanced cyclists.
Please note that we usually bike around 4-5 hours per day irrespective of the level of the trip.
You can exchange currency at the airport itself, or at ATMs in larger cities. Most commercial establishments will accept international credit cards for payments, though its good to carry some local currency with you at all times.
The meeting time on Day 1 is mentioned in your travel planner shared with you. You can arrive either on the morning of Day 1 depending on the meeting time, or book a pre-tour night to arrive a day earlier.
Yes, we can provide helmets. However, we recommend that guests try to bring their own helmets, as these are items of a personal nature.
Yes, panniers will be provided.
Your luggage will be picked up at the reception of your hotel every morning by 9.00am.
It will be delivered to the next hotel before 5pm. Most of the time it is delivered in the early afternoon itself.
We recommend that you carry no more than 2 bags together weighing up to 15kgs for this trip. You can have one large bag, which contains all your clothing and gear needed for the trip, and one small bag that contains essential items you will frequently need such as passport etc. Please note that once a bag gets loaded in the luggage transfer vehicle, you may not have access to it till later in the evening when you reach the hotel for the night.
For answers to broader questions, please visit our Comprehensive FAQs section.
