8 days
From US $2,395
Self-guided Renaissance Tuscany Bike Tour
This cycle tour has been designed around the picture-postcard landscapes of southern Tuscany that were born out of the Renaissance.
The region was deliberately landscaped in the 15th–16th centuries to reflect Renaissance ideals of harmony between nature and human settlement. Towns like Pienza are literal Renaissance creations, redesigned under Pope Pius II as “the ideal city,” and the sweeping fields and cypress-lined ridges are exactly the kind of vistas painted by Renaissance masters.
Before the Renaissance, Tuscany was beautiful but more rugged and untamed. Val d’Orcia’s transformation effectively gave birth to the orderly, romantic version of Tuscany that travelers still seek today. Its designation as a UNESCO World Heritage Site specifically cites its influence on Renaissance art and its preservation of the idealized Tuscan landscape.
In effect then, this bike tour takes you through the cradle of Tuscany's beauty, the place where the timeless Tuscan look was born.
Ride along quiet cypress-lined roads, past vineyards, olive groves, and hilltop villages like Montepulciano, Monticchiello, and Montalcino, home to the celebrated Brunello wine. Soak in the atmosphere of Bagno Vignoni’s ancient thermal springs, wander abbeys like Sant’Antimo and Monte Oliveto Maggiore, and taste local delights such as pecorino cheese, handmade pici pasta, and robust reds.
Gentle loops and multi-night stays in charming towns let you savor the scenery without constant packing. Each day offers a balance of cycling, history, and indulgence, ending with hearty Tuscan meals and breathtaking sunsets.
Self-guided
Casual+ hotels
Pienza
Siena
moderate to challenging
44 km / 27 mi
7
Min. 2, Max. 10
Amerigo Vespucci Airport (FLR)
Amerigo Vespucci Airport (FLR)
Highlights
Ride through the Val d’Orcia
Cycle past UNESCO-listed landscapes dotted with cypress trees, vineyards, and rolling hills.
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 | 22 km / 14 mi | cycling |
| DAY 2 | Pienza | Hotel Relais il Chiostro di Pienza (4-star) | B | 53 km / 33 mi | cycling |
| DAY 3 | Pienza | Hotel Relais il Chiostro di Pienza (4-star) | B | 54 km / 34 mi | cycling |
| DAY 4 | Montalcino | Hotel Giglio | B | 44 km / 27 mi | cycling |
| DAY 5 | Montalcino | Hotel Giglio | B | 47 km / 29 mi | cycling |
| DAY 6 | Montalcino | Hotel Giglio | B | 31 km / 19 mi | cycling |
| DAY 7 | Siena | La Villa di STR | B | 55 km / 34 mi | cycling |
| DAY 8 | Departure | B |
Detailed Itinerary
Day 1: Pienza
Arrive at Chiusi Chianciano train station in the morning or early afternoon and make your way to Pienza, your home for the next three nights. This Renaissance gem, often called “the perfect town,” charms with cobblestone streets, artisan shops, and irresistible food. Meet your hosts, get fitted for your bike, and head out on a warm-up loop to San Quirico.
Stroll through the Horti Leonini Garden, soak in the Tuscan light, and enjoy your first taste of the Val d’Orcia’s rolling beauty, where every turn reveals postcard-perfect views. End the day with a relaxed evening in Pienza’s welcoming atmosphere.
Day 2: Pienza
Begin with a gentle downhill ride through a patchwork of vineyards, cypress-lined lanes, and timeless villages, including Castelmuzio and Petroio. Pedal toward Montepulciano, famed for its Vino Nobile wine and elegant medieval streets. Pause to explore its historic center and visit a traditional wine cellar beneath the Ricci Palace.
Continue through the picturesque hilltop village of Monticchiello, where stone houses and sweeping views invite lingering. Return to Pienza along quiet country roads, savoring the golden light over the Val d’Orcia. The day blends scenic cycling, cultural treasures, and moments to enjoy the flavors and rhythms of rural Tuscany.
Elevation gain: 1068m/ 3503ft
Day 3: Pienza
Start with a short downhill before weaving through gentle climbs toward the medieval village of Trequanda, crowned by its 13th-century castle tower. Continue to Montisi, a charming hamlet bridging the Crete Senesi and the Val d’Orcia. Ride onward to San Giovanni d’Asso, renowned for its prized white truffles and Renaissance-like landscapes of farms, castles, and rolling fields.
Enjoy peaceful backroads and small districts on the return to Pienza. The route offers a rich mix of history, quiet countryside, and the intoxicating aromas of Tuscany’s culinary heritage, creating a day that is as rewarding for the senses as it is for the legs.
Elevation gain: 791m/ 2595ft
Day 4: Montalcino
Pedal toward the thermal spa village of Bagno Vignoni, where steaming pools date back to Roman times. Continue to Castiglione d’Orcia, dominated by the imposing Rocca A Tentennano fortress. Glide downhill to the serene Sant’Antimo Abbey, where Gregorian chants may echo through its ancient stone walls. The ride then winds through sweeping vineyards on the approach to Montalcino, your base for the next three nights.
Known for its Brunello wine and medieval charm, Montalcino welcomes you with stunning views, atmospheric streets, and the promise of rich Tuscan flavors to end a day filled with history, scenery, and warm hospitality.
Elevation gain: 920m/ 3018ft
Day 5: Montalcino
Follow a scenic crest road through postcard-perfect Tuscan landscapes toward the 13th-century Monte Oliveto Maggiore Abbey. Explore its frescoed cloister and peaceful setting before continuing into the striking Le Crete region, where green hills give way to clay domes and chalk cliffs that create an almost lunar atmosphere.
The route showcases Tuscany’s diversity, shifting from lush vineyards to rugged, open terrain. Return to Montalcino through tranquil backroads, with time to relax in town, sip a glass of Brunello, and reflect on a day that blends art, history, and the dramatic beauty of one of Italy’s most photographed regions.
Elevation gain: 781m/ 2562ft
Day 6: Montalcino
Ride toward the Maremma side of Montalcino, passing the tiny village of Sant’Angelo before descending to Poggio alle Mura. Visit the impressive medieval fortress, now part of the Castello Banfi wine estate, and explore its wine museum, Enoteca, and Taverna. The return route winds through rolling vineyards, with opportunities to stop at small Brunello wineries for tastings.
This shorter ride offers a balance of history, wine culture, and leisurely cycling, leaving time in the afternoon to wander Montalcino’s charming streets, relax with a view over the valleys, and enjoy another evening immersed in Tuscany’s warm and generous spirit.
Elevation gain: 699m/ 2293mi
Day 7: Siena
Begin with a thrilling descent toward Buonconvento, then follow quiet secondary roads north through breathtaking countryside. Stop in the village of Murlo to explore its fascinating Etruscan Museum before continuing through Ville di Corsano toward Siena. Enter the city through Porta San Marco and step into one of Italy’s best-preserved medieval centers.
Spend the afternoon wandering Siena’s narrow streets, visiting Piazza del Campo, the Torre del Mangia, and the magnificent Duomo. Soak in the lively atmosphere and rich history before savoring a final evening in Tuscany, reflecting on a journey filled with cycling, culture, and unforgettable landscapes.
Elevation gain: 880m/ 2887ft
Day 8: Departure
After breakfast, say goodbye to Montalcino’s rolling hills and transfer toward your next destination. For those with extra time, an optional ride into the Chianti hills leads to Castello di Brolio, where sweeping vineyard views and centuries of history await.
Whether cycling or relaxing, the morning offers a final taste of Tuscany’s beauty before the tour concludes. Depart with memories of sunlit roads, medieval towns, and the warm flavors that made each day a celebration of the region’s charm.
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 Sienna. The closest international airport is Florence Airport (FLR), about 85 km / 53 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 trip 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.
