This is a guest post by my awesome husband, Henry. Enjoy!
Wine lovers flock to Tuscany in general and Montepulciano specifically. The ancient hill city has made its modern name with wine. However much we enjoy a glass of local red Nobile, we mainly focus on getting outside and into nature, especially in new and beautiful places like southern Tuscany. While the crowds flock to Florence and Siena, with good reason, we gravitate towards smaller areas with a more serene and relaxing ambiance.

Montepulciano sits on top of a hill in the south of Tuscany and on the edge of the Val d’Orcia Nature Park which most people recognize from all the beautiful photos of rural Toscana on Instagram and the web.
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The scenery tugs at the heart with a sublime calmness. Arborvitae line roads and driveways. Tractors till the rolling and undulating hills. Cream-colored stone houses, many converted to modern agriturismos, dot the landscape. And, a gentle haze of woodsmoke and humidity softens the views of the hill towns and adds depth to the landscape views.

The area lacks the transportation network that dots more urban regions. While you can get around by bus, most people rent a car. Driving allows you to navigate between towns quickly but the narrow roads add anxiety to drivers from North America forcing you to watch the road instead of the countryside. Inside a car, you are isolated from the smells and sounds of the countryside. We found a great solution for us. E-bikes!
While many people choose bike tours in Tuscany with large groups, we found that you can easily rent a bike and navigate the area on your own. It takes a bit of confidence but that’s why we want to share our experience with you, to show you how easily you can do your own bike tour.
I personally love the idea and potential of e-bikes. Also, not everyone in the family likes the idea of sweating and grinding our way up hills, me included, on a traditional bike. E-bikes provide a gentle low-impact workout while getting you places you might not go on foot or by traditional bike and without the noise and speed of a motor scooter. This includes places like rolling fields between 600-meter hill towns. Also, e-bikes help protect the environment compared to cars.

How To Rent A Bike In Tuscany
First, we needed to find some bikes. Several companies offer e-bikes and traditional bikes for rent and/or personal tours in this area of Tuscany. We settled on ByEbike, just down the hill from the main gate, Porto Al Prato.
They have a very easy-to-navigate website with an English option and prices clearly listed. Also, other providers required reservations a week or more out and the prices were right. The store was closed when we walked by the first day but Andreas quickly responded to an email and said he could have bikes ready to use in the morning. We sent him our heights so he could have the right bikes for us. We are a tall family (I’m 6’6”) so we knew the bikes might not fit perfectly, which was the case, but Andreas helped us adjust the bikes so they were pretty comfortable.

Most people should be fine with the different sizes he has available. Additionally, Andreas spoke very clear English which was helpful since our Italiano is basic at best.
ByEbike rents traditional bikes as well, they offer guided tours and even custom routes. You will need to bring some sort of ID with you and a credit card as security. There’s a contract to sign, in Italian, but you can pay for the bikes in cash or with a non-Amex credit card. The rate in October 2022 was €40/bike for the whole day which seemed more than reasonable.
Where to E-Bike in Tuscany

I had in my mind just a general idea of riding the gravel roads of the area but no real clue on how to do this. Handily, Andreas gave us a route he uses between Montepulciano and Pienza. I’d hoped to hike the 10 miles to Pienza and take a bus back but this seemed like a better option and I’m glad we availed ourselves of it.
He said it was 50 kilometers which seemed a bit long to me, though I kept that to myself, with a shortcut on the way back that would cut it down to 32 km. Since the bikes have an advertised range of 80 km+, the range would not be a problem. In fact, none of us even came close to running out of battery. However, we also deviated from his route.
Ebikes are much heavier than other bikes and these worked with pedal-assist, meaning you have to pedal to get a benefit. They have regular gears, as well, and 4 “modes” or levels of assist. Eco at the base does a great job on level and moderate slopes and preserves the battery. At the high end, “Turbo” feels like it might leave you behind and really came in handy.
In addition to helmets, and instructions, he provided sturdy locks so we could leave our bikes and stroll around town at our destination. And off we went.

Many people harbor anxieties about Italian roads and drivers. I’m one of those people. I worried that we’d be harassed by constant wild traffic until we could get onto those serene gravel roads I’d dreamed of. However, I personally felt safe the whole time with only a few cars getting close or going fast.
You can’t avoid a bit of traffic getting out of town but cars yielded to us at the round-abouts and intersections per traffic laws. Andreas’ route took us around the base of Montepulciano to the notable Sanctuary of the Madonna di San Biagio, a beautiful building below Montepulciano with views out over the valley beyond. We didn’t take time to go in on this ride but it’s a pretty amazing edifice especially later in the day with late afternoon light bringing out the colors of the stone.
His route took us along some main roads until we got to the small town of Monticchiello where we decided to have some lunch. The cute little hill town sits atop its prominence about halfway along our route and possesses spectacular views.


We hoped to get some food here (we travel on our stomachs) but we could only find a few higher-end restaurants and their kitchens didn’t open until 12:30, so be aware. We decided to snack until they opened and we ended up selecting Osteria La Porta. It has great views out over the countryside and a full menu of delicious food. On the downside, it’s expensive and the portions are small. Not ideal for teens but it did the trick.
To be honest, at this point, we felt like maybe Andreas’ route was a bit too paved for us. While traffic wasn’t heavy, some of us were less comfortable than others. Melynda and Finn decided to head back but to take a small road that was more direct and promised to be gravel and relatively car-free.

Anders and I kept on to Pienza but decided to experiment with a road on Google Maps that seemed to go all the way through. We figured we could backtrack if we hit a dead end, a needless worry. While it included steeper hills, the e-bikes took the brunt of the work and we cruised along quiet gravel roads lined with trees and between fields being worked by farmers. The loudest sound was the crunch of gravel under our tires. Throughout the day, we saw other e-bikers, one large tour group with about 50 people, and a chase/support van. To e-bike Toscana and Pienza seems like a popular activity.
As we climbed back up towards Pienza we merged onto the pavement again but it had very little traffic. Pienza has a larger footprint and a more dramatic look than Monticchiello and as we found a place to park and lock the bikes, I had to wonder why it isn’t more well-known than Montepulciano.

Perhaps it is and I’m just out of the loop. It is certainly popular enough to be filled with other tourists that we dodged as we took a few photos and found some delicious gelato to cool down with. The streets of the town are narrow and held plenty of enotecas and small restaurants in the shade. We didn’t linger too long but I would highly recommend adding this beautiful town to your itinerary if you have the time.


We now had some confidence in route finding and decided to continue our self-directed method on the way back to Montepulciano. If you plug in the destination, Google Maps will direct you along the main roads which we wanted to avoid. To get around this, I merely zoomed in and found one of the many agriturismos in the valleys between us and Montepulciano and then selected “add stop” as many times as needed until I found a good route back. These agriturismos in Val d’Orcia are plentiful and inviting. It’s one of the types of travel I’d like us to try in the future.
Some of these roads were even smaller than our first gravel road experiment and the downhill grades had us riding the brakes but we kept it slow and easy and made frequent stops to take in the countryside. The slow pace allowed us to notice some of the details we’d otherwise miss. The path and sound of an old tractor, the pile of equipment next to an old stone barn. The plume of smoke in the distance. The bark of some sort of bird and the “no hunting” signs beside the numerous small grape arbors along the road, with yellowing leaves and dark purple fruit.

The commensurate uphills begged for us to use our “Turbo” mode and lower gears and took my 215 pounds plus heavy camera gear up the hills without issue. Yes, you still get exercise from the resistance of peddling but the electric motors take the brunt of the work and allow you to focus on the place you are riding through.
As we arrived back at Montepulciano in the late afternoon, with the low light on San Biagio, we opted to go through town and took steep narrow passages up to the main square and back down, again riding the brakes and going slowly in consideration of the pedestrians.

Andreas had left instructions on how to return the bikes to the ByEbikes location in his absence making it as simple as locking them up and dropping the key through an open window.
All in all, we found it incredibly easy to rent a bike in Tuscany and I’m so glad we chose e-bikes to explore. While it was a gentle workout, I still felt like I’d done something physical and earned that glass of Montepulciano wine in the evening.

Clothing For Ebiking In Tuscany
Obviously, the weather will vary, but we got fairly warm in October in the direct sun. In the summer, I would definitely try to leave as early as possible. In the winter, take a jacket and maybe gloves for the wind on your hands. That said, as with most places, layers are the answer.
We checked the weather for the day and knew there was little to no chance of rain or storms. We wore long pants and t-shirts with a mid-weight layer in the morning that we quickly shed. I know I’ve sung the praises of the e-bikes doing the work for you, but you still pedal and it is still exercise. You’ll likely warm up as you ride and cool off on the downhills.
Take water and stay hydrated. Melynda was running a bit colder than the rest of us and kept her layers on.
Where to Stay in Montepulciano
While there are many options for lodging in Montepulciano, we opted for this VRBO in Tuscany. Our small apartment had two bedrooms and was located a very short walk from the Porta al Prado arch. It has ample parking and easy access to the hilltown, and all its wine and gelato shops. You can see a bunch of vacation rentals in Montepulciano here.
Additional E-bike and Bike Rental Options
While we used ByEBike and were very happy with it, there are other providers as well. Here are a few.
- Cicloposse offers rentals and tours, both guided and self-guided, as well as many more services.
- Ebike Tuscany is located in Pienza and has bikes on Offer
- The Urban Bikery is located just off the Piazza Grande in Montepulciano and sells a lot of fashion accessories as well. Call early, they had a waiting list a week deep.
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