Tuscany Getaway: 4 Nights in Siena, Montalcino & Pienza
4 nights from €1340
4.92Cycle through the hillside and to vineyards in the world's most well-known wine region.
We put together this short bike tour for those who do not feel like taking a vacation entirely on a saddle. Each day there will be a choice for short easier bike rides and more challenging ones.
Whether crowned by timeless villages, covered by vineyards and olive groves, or strewn with wildflowers, the hills of Tuscany have one thing in common: they’re perfect for exploring on two wheels. Pedal to lofty hill towns, spin through broad valleys, and follow sinuous country roads past cypress-lined lanes and quiet woodland.
Off your bike, discover unforgettable Renaissance art and architecture, visit winery and cellars: you will be in the heart of Brunello wine land, so savor meals created from the finest local ingredients and relax in charming Tuscan retreats.
Amazing trip, highly recommend
“My brother wanted to do a bike trip for his 50th birthday. After months of research I finally landed on this itinerary and I am so glad we did it! Leading up to the trip bike…” Full Review
“My brother wanted to do a bike trip for his 50th birthday. After months of research I finally landed on this itinerary and I am so glad we did it! Leading up to the trip bike tours staff was very responsive. The info they sent took awhile and wasn’t tailored to our trip, but they make up for that by answering all questions promptly and without making you feel like a burden!! We had some last minute changes they were very accommodating with as well. The local tour company was wonderful! They were very patient with all of our anxieties and questions. We had never done a trip like this and in a foreign country self guided was intimidating. They broke it down for us and it was amazing. The routes they gave us were stunning and we only made a few quick wrong turns. GPS app they use was helpful and easy to use and follow. We were directed to a different hotel than the one we were staying at twice which was a bit annoying but once we found our place it was lovely and so nice to jump in a cold pool after a hot long ride. Their lunch and dinner recs were delicious! And the one time we had an issue where our bike lock wouldn’t unlock they came out to our remote spot and helped! It’s such a magical place to experience by bike! They never made us feel like a burden and were so professional, accommodating and supportive. I highly recommend this trip. It’s totally worth the price.” Less
—Tera Hurst
Very nice experience
“The trip was perfect. The hotels, the bikes and the support team, the routes, everything. I will strongly recommned the trip. The hotels locations, breakfasts, the retaurants recomendetions, the APP to get the indications during the routes.”
—VICTOR GONZALEZ
Awesome getaway!
“”
—Elizabeth
Daily Program
Day 1: Welcome! Benvenuti in Toscana
Pienza the "perfect town" is a remarkable example of Renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it is a treat to stroll about its cobblestone streets. Meet and Greet, we'll fit your bikes and introduce you to each day ride. First loop to San Quirico (14 miles/22 km) to test the bicycle and the equipment!
Overnight in Pienza
Day 2: Vino Nobile di Montepulciano
distance: 33 miles/54 km; elevation: +1068 m / -1070 m
Loop bike tour to Montepulciano and Monticchiello. Start your day with a pleasant downhill, you’ll follow a route checkered with vineyards and cypresses. Highlight of the day is Montepulciano, which is famous for the production of Vino Nobile. Back to Pienza through Monticchiello, another hilltop village.
Overnight in Pienza
Day 3: Montalcino and Brunello wine
distance: 28 miles/45 km; elevation: +920 m / -876 m
Today cycle to Bagno Vignoni, a thermal spa town right before reaching the beautiful Castiglione d'Orcia. Enjoy a long downhill to the monastery of Sant'Antimo. On your way to the Etruscan village and wine town of Montalcino, where you will stay you’ll pedal through magnificent vineyards.
Montalcino is a fortified town which was used as a shelter by Siena nobles during the 16th Century, but today it is even more famous thanks to the production of one of Italian’s premier fine red wines, Brunello di Montalcino.
Overnight in Montepulciano
Day 4: Siena and Palio race
distance: 34 miles/55 km; elevation: +880 m / -1076 m
Ride from Montalcino to Siena. Start with 10 km descent and pass through Buonconvento. Heading northbound to Siena, you’ll be treated to more gorgeous cycling along secondary roads. In the village of Murlo, you can visit the fascinating Etruscan Museum. Continue to Ville di Corsano always on a breathtaking scenery and end up in Siena arch gate Porta San Marco. You'll have time to take a leisurely stroll around this medieval art city in the afternoon and to visit Piazza del Campo, Torre del Mangia and the famous Duomo. Piazza del Campo is famous because here it is held twice a year the disputed “Palio” horse race, which opposes the 17 “contrade” of this fascinating city.
Overnight in Siena
Day 5: End of tour
End of bike tour after breakfast.
Hotels
These are sample hotels and may vary by availability.
Standard hotels
The accommodations are 3-star superior + 4-star hotels.
Pienza: Relais Il Chiostro
Montalcino: Hotel Vecchia Oliviera
Siena: La Villa STR
Luxury hotels - available on request
Pienza: La Bandita
Montalcino: Relais Mastrojanni
Siena: La Certosa di Maggiano
Please note any visitor's taxes are not included in the tour price. These taxes range from €1-5 per person daily, payable to each hotel.
Interested in visiting other areas before or after your tour? Visit our hotels page to learn more about lodging options.
Bikes
Standard touring bike
Frame: Aluminum frame
Fork: Full carbon
Chain ring: Shimano Deore – triple or compact
Cassette: Shimano Deore – 11/34 or 11/36
Brakes: Shimano Deore
Saddle: Selle Italia XO & lady gel
Wheel set: Shimano RS30
Tires: Panaracer close
Weight: 9,5 kg
Size: We can fit riders from 5.0 to 6.4 ft / 1,50 to 1,95 m
Size frame from 46cm to 62cm
Road bike
Frame: Full carbon frame
Fork: Full carbon
Chain ring: Shimano Ultegra compact 50/34
Crank: 172.5 / 175.00 mm
Cassette: Shimano Ultegra or 105 – 11/32 – 11 speed
Brakes: Shimano Ultegra rear and front
Saddle: Selle Italia
Wheel set: Shimano R561
Tires: Panaracer Extreme
Weight: 7,6 kg
Size: We can fit riders from 5.0 to 6.3 ft / 1,50 to 1,92 m
Size frame from 46cm to 59cm
Gravel bike
SCOTT Addict Gravel 20
The SCOTT Addict Gravel has been set up to allow you to ride any road, anywhere and in any weather conditions.
A lightweight Carbon fiber frame, Equipped compact Ultegra, rugged Schwalbe G-One tires and Shimano Hydraulic disc brakes give you a rig that will let you get your adventure on, no matter what.
A cyclocross touring oriented to enjoy the classic strade bianche in Tuscany: Eroica itinerary and Francigena path.
Our gravel bikes are all brand-new, reliable, and well maintained for your ideal cycling light off-road experience of Tuscany.
Size: S, M, L , XL
Gravel bike
CANNONDALE Topstone1 Gravel
Straightforward, reliable and a whole hell of a lotta fun, the Topstone Alloy is a gravel bike crafted for those with a taste for adventure – and value.
Roll light and free, or load it up for a long haul, Topstone’s comfortable ride, confident handling and up-for-anything capability make it the perfect partner on any road, anywhere.
A Lightweight frame and full carbon fork equipped with Shimano GRX 800/600 11-speed shifting
Size: XS, S, M, L, XL
Electric bike
Scott E-SUB Cross 10
E-sub cross 10 as the best for our tours: The SCOTT E-SUB Cross 10’s newly developed frame ePowered by a new 500wh Bosch Internal battery, will get you where you are going faster and more comfortably than ever before.
- Purion Display
- Fork: Suntour Nex-E25 Lo Ds 15mm Ta Tapered
- E-Drive System : Bosch Performance 250w System W
- 500wh Power Tube Battery
- Rear Derailleur: Sram Nx 11 Speed
- Brakes: Shimano Br-M365 Disc
- Size: S,M,L / Man & Woman Model
Electric bike
Scott E-SUB Cross 10
Meet the new Sub Cross eRIDE 10: equipped with the powerful Bosch Performance CX drive unit and a PowerTube battery intelligently integrated into the frame for a slick design.
An adjustable stem and the ergonomic Syncros saddle result in optimal comfort
- Intuvia 100 Display
- Front suspension: Suntour 63mm
- E-Drive System : Bosch Performance CX
- 625 wh Power Tube Battery /
- Rear Derailleur: Shimano Deore 10 speed
- Brakes: Shimano Br-M365 Disc
- Size: S,M,L / Man & Woman Model
Electric bike
E- bike Positive +
Positive + Performance Tecnobike is the elegant and highly performing electric trekking bike.
Equipped with a luggage rack and equipped with a powerful Shimano performance motor, the Positive e-trekking is the ideal bike for getting around for tourism by bike
- Purion Display
- Fork: alloy suspension fork 700C
- E-Drive System : Bosch Active Line Plus
- 500wh Power Tube Battery
- Rear Derailleur: Shimano Altus
- Brakes: hydraulic disc
- Size: S, M / step-through frame
More about electrically-assisted bikes >
Equipment included with bike rental:
- Handlebar bag or map holder
- Helmet
- Water bottle
- Repair kit (mini pump, inner tube, tire levers)
- Computer mileage counter
- Lock (one lock with key per 2 bikes)
Bike Protection:
Bike protection can be purchased at the time of booking. You can read more about that HERE.
Pedals:
The bikes will have toe clips(upon request) or flat pedals. You can also bring your own pedals and shoes, along with the necessary equipment for installing the pedals.
Seats:
If you plan to bring your own seat, please don't bring the seat post. The tour company can assist you with installing.
Helmets:
Helmets are required on this tour. Helmets are included in the tour package; however, we recommend you bring your own helmet for safety and hygiene reasons.
Surface and terrain
Tuscany is a hilly region, but each day you will have a choice for more challenging or shorter, easier bike rides. 90 % are on small country roads( no cycle path). You will encounter a little more traffic when entering the villages and towns, you will see this especially going in and out of Siena.
How to get there
Tour start and end
Nearest airport: Rome Fiumicino or Florence Peretola airports
From Fiumicino airport, take the Leonardo Express train (about 30 minutes) to Termini train station.
From Florence Peretola, take a bus or taxi to Florence station.
To get in Chiusi by train (www.fsitaliane.it) and once in Chiusi, take a bus or taxi to Pienza.
Bus: from Chiusi to Montepulciano, there is a bus every 30 minutes. The bus ride is 40-50 minutes, and the fare is approximately €4 per person. From the bus terminal in Montepulciano, take the bus to Pienza, about a 15 minute ride (this connection is not available on Sundays).
Taxi: from the small train station, the cost is €60-65 per person.
At the tour end, you can easily take a bus or train from Siena to Rome or Florence.
Tips on getting to and from your tour
Loading reviews…
More About This Tour
Related Bike Tours 
Cycling and Cooking in Sardinia
Italy 
Cycling and Cooking in Tuscany
Italy 
Custom and Private Bike Tours in Italy
Italy Related Day Tours
Chianti Classico Florence E-Bike Tour with Wine & Olive Oil Tasting
Florence 
Classic Tuscany Bike Tour
Florence 
Street Food Bike Tour Palermo
Palermo 
Capuchin Catacombs Bike Tour Palermo
Palermo 
Palermo Old Town Bike Tour
Palermo 
Email
Office Hours