Self guided Hill Towns of Tuscany in Luxury Bike Tour
This journey through Tuscany blends cycling, culture, and cuisine into an unforgettable adventure. You ride past cypress-lined roads, vineyards, and hilltop towns that look like Renaissance paintings come to life. Starting in Pienza, the purest Renaissance town, you explore Val d’Orcia and roll through landscapes so striking they’ve earned UNESCO recognition. In Montalcino, Brunello wines and ancient abbeys enrich the experience before you continue through the lunar-like terrain of Le Crete and into Siena, a medieval jewel alive with art, history, and the famous Piazza del Campo.
The route then winds into Chianti, where castles and vineyards mark the way to Gaiole, birthplace of the legendary L’Eroica race. Each day’s ride balances effort with reward—tasting local wines, strolling ancient streets, and relaxing in handpicked retreats. From a stylish palazzo in Pienza to a serene monastery in Siena and a castle estate in Gaiole, your nights echo Tuscany’s layered history with comfort and charm.
By the time you cycle among Chianti’s medieval towns like Castellina and Radda, the rhythm of Tuscany feels like second nature. The final morning invites one last ride or a quiet farewell, leaving you with vivid memories of hills, heritage, and heartfelt hospitality.
Self-guided
premiere hotels
Pienza
Gaiole in Chianti
moderate to challenging
56 km / 35 mi
4
Min. 2, Max. 10
Amerigo Vespucci Airport Florence (FLR)
Amerigo Vespucci Airport Florence (FLR)
Highlights
Cycle Through Val d’Orcia
Pedal across UNESCO-listed landscapes of rolling hills, cypress-lined roads, and timeless villages. Stops include Bagno Vignoni’s ancient thermal waters and Montalcino, home of Brunello wine and medieval charm.
Discover Siena’s Medieval Splendor
Arrive in Siena through the scenic Le Crete, Tuscany’s “Badlands.” Explore its medieval streets, the grand Piazza del Campo, Torre del Mangia, and the Gothic Duomo.
Stay in Historic Retreats
Nights unfold in unique properties that reflect Tuscany’s history—an elegant palazzo in Pienza, a monastic sanctuary near Siena, and a castle estate in Chianti.
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 | premiere Inns | Meals | Distance | Activity |
|---|---|---|---|---|---|
| DAY 1 | Pienza | La Bandita Townhouse | |||
| DAY 2 | Pienza | La Bandita Townhouse | B | 68 km / 42 mi | cycling |
| DAY 3 | Siena | Certosa di Maggiano | B | 56 km / 35 mi | cycling |
| DAY 4 | Gaiole in Chianti | Castello di Spaltenna (5-star) | B | 44 km / 27 mi | cycling |
| DAY 5 | Gaiole in Chianti | Castello di Spaltenna (5-star) | B | 57 km / 35 mi | cycling |
| DAY 6 | Departure | B |
Detailed Itinerary
Day 1: Pienza
Arrive in Pienza, the purest Renaissance town in Tuscany, and feel its charm right away. Meet the Cicloposse team for a personalized bike fitting, then set out on an optional warm-up ride to Bagno Vignoni. This ancient village, known for its Roman thermal waters, invites you to explore its unique square built around a steaming stone pool.
As the sun dips, wander Pienza’s cobbled streets, admire sweeping views over Val d’Orcia, and settle into La Bandita Townhouse. The evening unfolds with Tuscan flavors, warm hospitality, and the excitement of starting a cycling journey through some of Italy’s most enchanting landscapes.
Day 2: Pienza
Glide down into the rolling pastures of Val d’Orcia, a UNESCO World Heritage landscape that looks painted by Renaissance hands. The ride challenges and rewards with climbs to Castiglione d’Orcia and sweeping descents past the serene Sant’Antimo Abbey. Vineyards lead the way into Montalcino, home of world-renowned Brunello wines and medieval charm.
Pause in San Quirico d’Orcia to explore the manicured Horti Leonini Gardens before returning to Pienza. Every pedal stroke brings you closer to Tuscany’s heart, where history, culture, and wine blend seamlessly with breathtaking scenery.
Elevation gain: 1391m/ 4563ft
Day 3: Siena
Cycle through Le Crete, a fascinating region where Tuscany’s lush hills give way to dramatic clay domes and chalk cliffs, an almost lunar landscape. The road unfolds with ever-changing views, drawing you toward Siena’s medieval gates. Enter the city and feel the timeless atmosphere of narrow lanes, brick palaces, and soaring towers.
Spend the afternoon strolling Piazza del Campo, scene of the legendary Palio horse race, and marvel at the striking Gothic Duomo. Siena’s rich history and vibrant life surround you at every turn, offering the perfect mix of art, culture, and authentic Tuscan soul.
Elevation gain: 961m/ 3152ft
Day 4: Gaiole in Chianti
Leave Siena behind and ride toward Chianti, passing through Castelnuovo Berardenga, a medieval town that opens the gateway to vineyard country. The route winds past castles, forests, and hills that echo Tuscany’s storied past. Stop at Brolio Castle, once a battleground between Florence and Siena, and soak in views of endless vines.
The road leads into Gaiole in Chianti, birthplace of the legendary L’Eroica vintage cycling race. The town’s lively spirit, combined with the stunning surroundings, sets the tone for days of discovery in the heart of Tuscany’s wine country.
Elevation gain: 831m/ 2726ft
Day 5: Gaiole in Chianti
Pedal into the famed Chianti hills, where vineyards and forests unfold in an almost impossibly beautiful panorama. The ride carries you to Badia a Coltibuono, an abbey dating back to the 11th century, before continuing through Lucarelli to Castellina. Explore the medieval walkway of Via delle Volte, peering out over countryside framed by arrow slits in stone walls.
On the return, pause in Radda, another hilltop gem steeped in wine traditions. This day blends challenging climbs, rewarding vistas, and village charm, creating an unforgettable cycling loop through the very soul of Chianti.
Elevation gain: 1066m/ 3497mi
Day 6: Departure
Savor a leisurely breakfast at Castello di Spaltenna, surrounded by vineyards and timeless Tuscan beauty. Choose between a gentle farewell ride to San Sano and Ama, or linger in Gaiole, a village rich with cycling heritage as the home of L’Eroica.
Reflect on the week’s adventures, from Renaissance towns to Chianti castles, and the friendships built along the way. The tour closes with the warmth of Tuscan hospitality still fresh in memory, leaving you with the sense of having lived not just a journey, but a story woven into Tuscany’s hills.
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.
La Bandita Townhouse
La Bandita Townhouse sits in the heart of Renaissance Pienza within a 500-year-old palazzo once home to nuns. This boutique retreat blends historic character with stylish design, creating a warm, lived-in atmosphere. The townhouse feels like a local’s residence, offering intimate hospitality, inviting lounges, and locally inspired cuisine. Guests can unwind with a glass of wine, savor Tuscan flavors, and immerse themselves in the authentic rhythms of village life.
Certosa di Maggiano
This former 14th-century Carthusian monastery offers a rare blend of history, tranquility, and refined elegance. Just outside Siena’s medieval gates, the estate preserves its monastic soul while reimagining it into luxurious, uniquely styled rooms. Guests can stroll peaceful gardens, relax by the pool, and dine on regional delicacies. Certosa di Maggiano creates a serene haven where heritage meets comfort, making it a perfect base for exploring Siena’s art, architecture, and culture.
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 $990
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.
Hybrid bike with disc brake or similar
Included in your trip price
SCOTT Addict Gravel 20 or similar
Available at a surcharge
Scott E-SUB Cross 10 or similar
Available at a surcharge
Canondale Synapse e-gravel bike 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.
