Exploring Tuscany by Bike with Urban Bikery

Exploring the Tuscan Countryside on e-Bike

Tuscany’s cypress-lined roads are straight out of a postcard, weaving their way throughout the countryside as you make your way through, exploring one quaint hilltop town after another. We arrived in Italy about 8 days ago and hit the ground running, making it our mission to explore more and take in a new site, restaurant, experience, or location each day. With the sun shining and us jonesing for exploration, we set out to explore Tuscany by bike with Montepulciano-based Urban Bikery.  I mean, is there a better way to explore the countryside?

For those who are new to e-Bikes and curious about what Tuscan terrain is like, I’m answering those questions below in more depth. First, I’m sharing our itinerary exploring the Val d’Orcia with Urban Bikery’s map system, which helps take the guesswork out of self-guided tours. Unless you already have an in-depth understanding of Tuscany including towns you’re keen on exploring and potential stops along the way, some guidance for your itinerary may be helpful. The folks at Urban Bikery were quick to assist — and it’s all part of the setup for sending guests out to explore. The app is designed for their cyclists, detailing different routes, each with its own stops and information. Each stop along the way links to your phone’s map function so you can use it as a GPS while you’re zipping around.

We set out to explore the Val d’Orcia with stops from Montepulciano to Pienza, and a few pre-planned stops along the way that the Urban Bikery team was kind enough to pre-arrange for us.

The majority of your ride doesn’t happen on the main thoroughfares and city streets but on the country roads that weave their way through the vineyards and forested stretches. It’s worth noting that the terrain is varied since roads are often unpaved and gravelly so it’s a bit of an adventure in some stretches. For anyone that doesn’t have global data, check out options for a WiFi hub (use code SKYROAMTWE for 10% off). We use ours everywhere we go, usually on monthly plans to have internet access on the go.

Stop 1: Monticchiello

After hitting the road, our first stop was the town of Montichiello, situated about 5 miles from our starting point. Much of the joy of this itinerary is that you’re constantly surprised with spectacular views along the way without a windshield as a barrier. When daydreaming of Tuscany, you likely conjure images of the Val d’Orcia with its gentle rolling hills and cypress dotted terrain. It’s a UNESCO-protected area and truly a stunning place to explore. We chose a particularly sizzly summer day (about 100°F) so our ride was a bit more mission-oriented but on a cooler day, this would be the ultimate itinerary to just enjoy in a leisurely way, stopping to take in vistas along the way.

Monticchiello was our first stop, an ancient village with a ton of character and without crowds. It’s considered one of the most authentic and character-rich towns in the Val d’Orcia. The town is rich with history and beautiful facades, but as a stop on this itinerary is also offers some stunning views of the valley below from its elevation.

Monticchiello is small and easy to explore on foot and bike parking is available at the base of the historic center in a car park. Allocate a half hour or so to wander the town’s streets and take in the views before suiting up for the next leg of your ride.

📍 Distance from Urban Bikery to Montichiello: approximately 7.5km (about 4.7 miles)

Stop 2: Lunch at Azienda Agricola CasaGori

After our morning bike ride in the heat, I was very ready for lunch. The team at Urban Bikery was kind enough to get us set up with a lunch reservation at Azienda Agricola CasaGori, an organic and biodynamic farm where they cultivate olive trees, grapevines, beehives, and ancient grains. Just a short distance from Pienza, the food truck on site is set up in a shaded area with views of the vineyards, perfect for a mid-day stop.

Their wines are organic and unfiltered  – that orange-y wine in my hand is their Malvasia! – and make for an interesting switch-up from getting your fill of Vino Nobile in the region. For beer lovers, their brews are available as well for anyone interested in trying something small-batch. And the food…

There are vegetarian options available and the salad I ordered could easily have been made vegan by removing the eggs. All of the components in my salad were cultivated on the farm: farm-fresh tomatoes, eggs straight from their hens, potatoes grown on their land, and other veggies to round it out. After nearly a decade living on a tiny island that has very few organic options, this simplicity and farm-to-table approach is utter perfection for me. Allocate 60 – 90 minutes for lunch with a view. 

📍 Distance from Montichiello to CasaGori: approximately 4km (2.5 miles)

Stop 3: Pienza

Picture-perfect Pienza. During our visit to Tuscany earlier this year, we spent a few days based in Pienza. When I shared photos and stories from the town, the universal response was that Pienza was a fan favorite with its charming facades, stunning vistas, and quaint shops lining the main arteries. The town is small and easily explored on foot in a few hours’ time, though you could spend a day wandering, shopping, and eating your way through.

Pienza marked the furthest destination in our day exploring Tuscany by bike and after wandering through town and stopping for a much-needed granita (there’s also a great gelato spot in town) we were set to make our way back to Montepulciano with a couple of pitstops along the way. If it’s your first time to Pienza, allocate one hour to wander and take everything in, and don’t miss sampling Pecorino di Pienza, the city’s most famous export.

📍 Distance from CasaGori to Pienza: 4km (about 2.5 miles)

Stop 4: Wine Tasting at Fabbrica

After wandering Pienza, we jumped back on our bikes for one final stop: wine tasting at Fabbrica, an organic winery in the Pienza region. The winery produces five wines plus an olive oil, and the somm there treated us to a great tasting of four of their wines (a white, a rosé and two reds). With just a backpack for carrying any purchases, we took home an olive oil from Fabbrica in lieu of wine, though if you’re prepared and have the space, you could easily purchase a bottle of wine to take home.

We took direction from Urban Bikery for this wine tasting stop but if you have other wineries in mind that you’d like to incorporate you can adjust accordingly.

📍 Distance from Pienza to Fabbrica: 5.5 – 6km (approximately 3.5 miles) — we got a bit turned around so were on the higher end!

Stop 5: The Tuscan Road

Alright, here’s the real deal: by the time we were done wine tasting at Fabbrica on a super sizzly day, the thought of biking more than needed to get back to Montepulciano wasn’t doing it for us. The fifth and final stop in our day was slated to be a bike ride down what Urban Bikery lists as ‘Tuscan Road,’ a stunningly dreamy cypress-lined path that looks like you fell into a postcard. If you have the energy and ambition, do it! We felt extremely content after our wine tasting at Fabbrica and made our way back to Urban Bikery to return our bikes instead.

Worth noting: We didn’t need this – though there were a few touch-and-go moments there! – but a rescue van is included with your rental at Urban Bikery so if you run into an unexpected issue along the way, you have peace of mind knowing their team is just a quick call away!

📍 Distance from Fabbrica to Urban Bikery: Approximately 9km (5.5 miles)

The Basics

In total, we cycled just over 30 kilometers while exploring Tuscany by bike, tried five wines (+ two beers!), visited two beautiful towns, cycled through the vineyards, had one farm-fresh lunch, and got a bit of a tan while we were at it. For anyone keen on seeing Tuscany in a new way, biking is a great way to explore. A few details and thoughts to keep in mind:

📍 Pick-Up Point: Via Ricci, 2, 53045 Montepulciano (in the walled historic center of Montepulciano)

🚴🏼‍♂️: Mobility Issues + Fitness Level: I want to point out that e-Bikes are not motorbikes. There’s a bit of an image that using an e-Bike is zero effort and anyone can do it… it’s certainly much easier than a regular bike and makes the hills doable, but there’s still a sizeable amount of effort that goes into cycling, especially with the varied terrain. It helps if you’re familiar with e-Bikes or at least with mountain bikes and shifting gears as a starting point. If you’re someone with mobility issues or issues with balance, I’d probably opt for something simpler.

👟 What to Wear: I mentioned this is still a workout but it’s not Olympic-level cycling so I was fine wearing a tank top, shorts, and athletic sandals. Keep in mind if you’re not an avid cyclist your booty will be feeling it at the end of the day! If you’re more comfortable in tennis shoes, go for it. Avoid flip-flops!

💰 Cost: Price varies based on your chosen itinerary; half-day rentals start at €45 while ‘all-inclusive’ packages range from €99 – 249 and include specified and activities and experiences

👌🏼 Tips + Takeaways: In general, this is a fabulous activity for most visitors who are fairly able-bodied and reasonably fit. Again, you don’t need to be an athlete but a 30km bike ride through the hilly terrain still involves some level of fitness to make this comfortable. A few main takeaways: 1) Try to choose a day with moderate weather. This is tough in the summer but extra-hot days do make it a bit more of a challenge! 2) Bring water! You’ll want water throughout your ride and while you can purchase waters in towns along the way, I’d bring at least one big bottle per person. 3) Wear a hat on sunny days. You’ll be out cycling for quite a while and while the breeze cools you down, you’re still getting a solid dose of sun! Use SPF for your face and wear/take a hat for wandering the towns.

All in all, a success. I’m ready for round two!

Have you used e-Bikes before? Thoughts on exploring Tuscany by bike?