7 days
From US $2,295
Self guided Heart of Chianti Tuscany Bike Tour
This cycling journey through Tuscany blends rolling hills, vineyard-lined roads, and timeless hill towns into an unforgettable adventure. Starting in the Renaissance gem of Pienza, ride through Montepulciano’s wine-scented streets, Montalcino’s medieval fortress, and Siena’s postcard landscapes. Spin past abbeys, castles, and charming hamlets, pausing for Brunello, Chianti Classico, and Vino Nobile tastings in ancient cellars. The route reveals Tuscany’s many faces—from sun-drenched vineyards to the lunar beauty of Le Crete. Evenings bring rustic feasts of handmade pasta, pecorino, and fruity olive oils, with nights spent in historic villas and palazzos. Each day’s ride promises quiet country lanes, warm hospitality, and breathtaking panoramas.
Self-guided
Casual+ hotels
Pienza
Castellina in Chianti
moderate to challenging
47 km / 29 mi
6
Min. 2, Max. 10
Amerigo Vespucci Airport (FLR)
Amerigo Vespucci Airport (FLR)
Highlights
Explore the Heart of Chianti
Ride through a patchwork of sun-drenched vineyards, cypress-lined lanes, and hilltop hamlets that define Tuscany’s most celebrated wine region. In Castellina and its neighboring villages, discover centuries-old wine cellars, stone piazzas, and the warm hospitality that makes Chianti the beating heart of Tuscan tradition.
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 | 20 km / 12 mi | cycling |
| DAY 2 | Pienza | Hotel Relais il Chiostro di Pienza (4-star) | B | 53 km / 33 mi | cycling |
| DAY 3 | Montalcino | Hotel Giglio | B | 44 km / 27 mi | cycling |
| DAY 4 | Siena | La Villa di STR | B | 56 km / 35 mi | cycling |
| DAY 5 | Castelllina in Chianti | Hotel Palazzo Squarcialupi (4-star) | B | 55 km / 34 mi | cycling |
| DAY 6 | Castellina in Chianti | Hotel Palazzo Squarcialupi (4-star) | B | 55 km / 34 mi | cycling |
| DAY 7 | Departure | B |
Detailed Itinerary
Day 1: Pienza
Arrive in the Renaissance treasure of Pienza and meet your guides for a warm welcome and bike fitting. Stroll through cobbled streets lined with elegant palaces, flower-decked balconies, and sweeping views of the Val d’Orcia. The town’s harmonious design and golden-stone buildings create an atmosphere that feels timeless.
For those eager to start pedaling, enjoy an optional test ride to San Quirico d’Orcia, passing rolling fields and cypress-lined lanes. Return to Pienza in the evening, relax in your charming accommodation, and savor your first taste of Tuscan cuisine, knowing the adventure has truly begun.
Day 2: Pienza
Pedal out from Pienza into the sunlit hills, passing the quiet convent made famous by The English Patient. Glide through the tiny hamlet of Castelmuzio before reaching Montepulciano, a Renaissance jewel filled with grand palaces and panoramic terraces. Pause to sip its famed Vino Nobile and wander its inviting streets.
On the return, stop in Monticchiello, a quintessential Tuscan hill town with stone houses and winding lanes. The ride blends history, beauty, and the gentle rhythm of the countryside, leaving you with lingering vineyard views as you roll back into Pienza for another evening of rustic flavors and warm hospitality.
Elevation gain: 1068m/ 3503ft
Day 3: Montalcino
Ride from Pienza toward the medieval magic of Montalcino, pausing in the thermal village of Bagno Vignoni, where steaming pools fill the main square. Continue through the scenic Val d’Orcia to Castiglione d’Orcia for lunch, then on to the serene Sant’Antimo Abbey, where monks chant daily vespers.
The final climb leads into Montalcino, famed for its Brunello wines and imposing fortress. Soak in sweeping views of the valleys you’ve just crossed, then celebrate the day with a tasting in an ancient enoteca, letting the flavors of the region linger as the sun sets over the hilltop town.
Elevation gain: 920m/ 3018ft
Day 4: Siena
Cycle out of Montalcino along a crest road that reveals some of Tuscany’s most photographed vistas. Pass Monte Oliveto Maggiore Abbey, a 13th-century Benedictine monastery renowned for its frescoed cloister and tranquil setting. Continue into the striking Le Crete region, where rolling green gives way to pale clay domes and rugged gullies, creating an almost lunar landscape.
The road winds through quiet farmland and small villages before leading into Siena. Arrive with time to explore its medieval streets and grand piazzas, soaking in the vibrant atmosphere before relaxing in your villa and enjoying the city’s timeless charm over a leisurely dinner.
Elevation gain: 1035m/ 3395ft
Day 5: Castelllina in Chianti
Leave Siena and follow the scenic Chiantigiana road into the heart of Chianti country. Stop in Castelnuovo Berardenga, a medieval gateway town, before riding through vineyards producing the celebrated Chianti Classico. Pause at Castello di Brolio, a historic castle and winery, and perhaps browse a renowned ceramics workshop near Radda in Chianti.
Continue over gentle rolling hills to Castellina, where the covered Via delle Volte winds beneath ancient walls. End the day exploring the town’s inviting shops and wine bars, then relax in your historic hotel, surrounded by views of vine-covered hills glowing in the late afternoon light.
Elevation gain: 1019m/ 3343ft
Day 6: Castellina in Chianti
Set out from Castellina on a circular ride through the Florentine Chianti. Follow quiet roads to the three historic villages that once formed the Chianti Alliance, passing forgotten abbeys and timeless hamlets. Stop at a local winery to taste supple reds, fragrant olive oils, and fresh honey.
Continue to Greve’s lively triangular piazza, framed by graceful porticos, then ride back via Panzano, where remnants of medieval walls and a castle still stand. Return to Castellina in the afternoon to unwind by the pool or stroll its charming streets, letting the day’s flavors and scenery settle into memory.
Elevation gain: 1019m/ 3343mi
Day 7: Departure
Enjoy a leisurely breakfast in Castellina, savoring the last tastes of Chianti before the journey concludes. Take a final stroll through the cobbled streets, perhaps picking up a bottle of local wine or a handcrafted keepsake.
Transfers are available to Florence for onward travel or an extended stay in the city. As you leave, the rolling vineyards, sunlit hills, and warm hospitality of Tuscany remain vivid in your mind, a reminder of days spent cycling through landscapes rich in beauty, history, and flavor.
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.
Dates and Prices
Single Supplement
From US $790
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
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 Castellina in Chianti, located 27kms or 17 miles from Sienna. You can take either a bus or train, or a direct taxi to reach Sienna.
You can also take a bus or train directly to Florence, located some 55kms ( 32mi) away.
The closest international airport is Florence Airport (FLR), about 65 km / 40 miles, 1.5 hours by car or bus. The airport is good for European and limited intercontinental flights.
The Rome International Airport is about 250 km / 155 miles, 3–3.5 hours by car or train. It is best for long-haul flights.
Siena has no high-speed train service, so the first leg is usually by bus or regional train:
To Florence – Direct bus (1h15–1h30) or regional train (1h30–1h45 with a change in Empoli). From Florence SMN station, connect to trains to Pisa, Rome, Milan, or Venice.
To Rome – Direct bus (3 hours) from Siena to Roma Tiburtina. Or train via Chiusi–Chianciano Terme (~3.5 hours total).
Weather
The best cycling conditions in Southern Tuscany are in spring (April–June) and early autumn (September–October). Days are comfortably warm, averaging 18–25°C (64–77°F), with clear skies and light breezes. Spring brings blooming wildflowers, while autumn offers golden vineyards and harvest scenes. July and August can be very hot, often reaching 30–35°C (86–95°F), making midday cycling challenging. Winter months, especially December to February, are cooler at 8–12°C (46–54°F) with higher rainfall and shorter days. These shoulder seasons provide the perfect balance of pleasant temperatures, scenic beauty, and fewer crowds, allowing riders to enjoy Tuscany’s rolling hills and charming medieval villages at their best.
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
This route is largely on paved surfaces.
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.
