Self-guided Super Tuscan Vineyards in Luxury Bike Tour
Super Tuscan wines are wines that broke Italy's rigid wine classification laws, and emerged as some of the finest in the world rivaling the fame of Bordeaux and Napa wines in the 1970s.
We've designed this tour around the theme of these rebellious, yet the finest of Tuscan wines.
Experience the luxury of Tuscany’s famed wine country on this exclusive Super Tuscany Bike Tour, inspired by the celebrated wines that define Italian excellence. Ride premium bikes through rolling vineyards, medieval villages, and Renaissance towns, savoring the perfect blend of adventure and elegance.
Along the way, stay at two exceptional wine relais; Borgo San Felice and Relais Mastrojanni where world-class hospitality meets breathtaking landscapes.
Cycle through iconic Tuscan regions such as the Chianti Classico and hill towns such as Montalcino, and explore the cinematic beauty of the UNESCO listed Val d’Orcia, whose golden fields and cypress lined roads have inspired humans for centuries. Perhaps, you may have seen these landscapes in art or in cinematic masterpieces such as Gladiator.
Indulge in authentic Tuscan flavors: hand rolled pici pasta, pecorino cheese, fresh olive oil, truffles, seasonal vegetables, Chianina beef, and wild boar.
Along the way, taste Italy’s most celebrated wines Brunello di Montalcino, Chianti Classico, Vino Nobile, and bold Super Tuscan blends expertly paired with local cuisine and the perfect espresso. This is more than a bike ride; it’s Tuscany’s essence, served in every mile and every glass.
Self-guided
premiere hotels
Borgo San Felice
Montalcino
moderate to challenging
55 km / 34 mi
5
Min. 2, Max. 12
Florence Airport (FLR)
Florence Airport (FLR)
Highlights
Ride Through Tuscany’s Iconic Landscapes
Cycle past rolling vineyards, medieval villages, and some of Tuscany's iconic highlights such as the Chianti Classico region, Montalcino, and the UNESCO listed Val d’Orcia.
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 | Borgo San Felice | Borgo San Felice Resort Relais and Chateaux (5 Star) | B | 36 km / 22 mi | cycling |
| DAY 2 | Borgo San Felice | Borgo San Felice Resort Relais & Chateaux (5 Star) | B | 52 km / 32 mi | cycling |
| DAY 3 | Montalcino | Mastrojanni Relais | B | 77 km / 48 mi | cycling |
| DAY 4 | Montalcino | Mastrojanni Relais | B | 60 km / 37 mi | cycling |
| DAY 5 | Montalcino | Mastrojanni Relais | B | 49 km / 30 mi | cycling |
| DAY 6 | Departure | B |
Detailed Itinerary
Day 1: Borgo San Felice
Arrive at Borgo San Felice, a beautifully preserved hamlet and winery located in the heart of the Chianti Classico wine region.
Wander its charming piazza, visit the quaint chapel, and stroll along narrow, cobbled lanes steeped in history.
After settling in, enjoy a professional bike fitting before heading out for a warm up ride. Pedal to nearby castelli and explore Castelnuovo Berardenga, a medieval gem with winding streets and the elegant Villa Chigi Saracini. Ride through the vineyards of Chianti Classico, surrounded by rolling hills and cypress lined roads. Savor the first taste of Tuscany’s magic before returning to relax at the relais.
Elevation: +637 m / -632 m
Day 2: Borgo San Felice
Begin the day with a scenic cycling loop through Radda, Badia a Coltibuono, and Gaiole. Pause for coffee in Radda, a hilltop town where medieval charm meets modern Tuscan life. Continue to Badia a Coltibuono, an ancient monastery winery with vineyards dating back over a thousand years, for a guided wine tour and farm to table lunch. Ride onward to Gaiole, famed for hosting the legendary “L’Eroica” vintage bike event. Enjoy the lively atmosphere, local shops, and village charm before returning through vineyard-lined roads.
Elevation: +1160 m / -1159 m
Day 3: Montalcino
Cycle through the serene beauty of Monteaperti, Le Crete, Asciano, and San Giovanni d’Asso. Stop in Asciano for a coffee break amid the striking landscapes of the Crete Senesi. Arrive in Montalcino, world renowned for its Brunello wine and steeped in Etruscan and Roman history. Explore its historic streets before visiting the Abbey of Sant’Antimo, a Romanesque masterpiece with an aura of peace. End the ride at Relais Mastrojanni, where the rolling countryside and fine wines create the perfect setting for an evening of relaxation.
Elevation: +1373 m / -1418 m
Day 4: Montalcino
Ride into the breathtaking Val d’Orcia, a UNESCO World Heritage Site celebrated for its postcard perfect beauty. Enjoy a coffee stop in Bagno Vignoni, a thermal village where ancient baths meet Tuscan charm. Continue to Pienza, the Renaissance “ideal city” envisioned by Pope Pius II, and stroll through its artisan shops and panoramic lanes. Visit the Vitaleta Chapel, one of Tuscany’s most photographed landmarks, before returning through rolling hills and golden fields.
Elevation: +1361 m / -1181 m
Day 5: Montalcino
Cycle toward Poggio alle Mura to visit the striking Castello Banfi, where medieval heritage and winemaking excellence intertwine. Explore the castle’s cellars and learn about the craft of Tuscan viticulture. Continue to Solaria Winery, where the Cencioni family welcomes you for a tour and tasting of their acclaimed Brunello. Ride through vineyards and sunlit hills before gathering in the evening for a farewell dinner at Mastrojanni, raising a glass to unforgettable memories.
Elevation: +1034 m / -1037 m
Day 6: Departure
Enjoy a leisurely morning, whether by sleeping in, walking the estate grounds, or taking one last short loop ride. Bid farewell to Tuscany’s landscapes, flavors, and warmth until your next visit.
Ready to plan your adventure? Download a print-ready detailed itinerary.
Map
Dates and Prices
Single Supplement
From US $1,990
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 brakes 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 Neo All Road Carbon Frame e-gravel or similar
Available at a surcharge
Arrival & Departure Details
Arrival
Your journey begins in Borgo San Felice, a beautifully restored medieval hamlet surrounded by rolling vineyards. The nearest airport is the Florence international airport located 90kms ( 56mi) away, while the nearest major town is Siena, located 26 kms ( 16mi) away.
The most convenient way to arrive from the Florence airport to Borgo San Felice is by taking a taxi from the airport. The drive takes a little over 1 hour.
You can also take a bus or train from Florence to Siena, and from Siena either take another bus or a taxi. Taking the bus from Siena to Borgo San Felice however, can result in a total commute time of around 3 hours.
**Departure **
Your tour ends in Montalcino. The nearest international airport is once again Florence, located some 110 kms ( 70mi) away.
You can take a bus from Montalcino to Siena and from Siena take a train to Florence. The entire journey takes a little over 3 hours.
Alternatively you can take a taxi directly from Montalcino to Florence. The drive takes a little over 2 hours.
Weather
The best weather for cycling in Tuscany is during spring (April–June) and autumn (September–October), when temperatures are mild, skies are clear, and the countryside is at its most beautiful. In spring, average highs range from 18–27°C (64–81°F), with cool mornings and evenings that make long rides comfortable. Wildflowers bloom across the rolling hills, and vineyards are lush and green, creating stunning scenery. Autumn offers similar pleasant conditions, with highs between 21–26°C (70–79°F) and crisp, fresh air. This season also brings the grape harvest, golden vineyards, and seasonal culinary delights, making it a sensory highlight for riders.
Summer (July–August) can be very hot, with highs of 30°C (86°F) or more, so rides are best done early in the day. Winter (November–March) is cooler, with temperatures between 5–15°C (41–59°F), and while still rideable, it’s less ideal due to shorter days and a higher chance of rain. For the perfect balance of weather, scenery, and cultural experiences, late May–early June and mid-September are considered prime cycling windows in Tuscany.
January
Offseason
February
Offseason
March
Mixed
April
Best
May
Best
June
Best
July
Offseason
August
Best
September
Best
October
Good
November
Offseason
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 tour 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.
