“Luxury” and “e-bike” are two words rarely seen together, but believe me when I say my recent e-bike adventure through Tuscany was extraordinary – and I don’t say that lightly.

The Tuscany area is inundated with generic tours and guides with rehearsed scripts and large groups that don’t feel special at all. Other options force you to consider multi-day bike tours in Tuscany with less than stellar accommodations. Stick around while I tell you all about what made my luxury e-bike experience so special from our charismatic tour guide and high quality e-bikes to the little touches like seeing a baby eagle and enjoying a private wine tasting. Plus, I have a DISCOUNT code at the bottom for anyone who wants to book these experiences as well. You’re welcome!

Table of Contents

• About the Guides
• About the Tour
• About the E-Bikes
• Meeting Point
• Safety Briefing
• Exploring the Chianti Countryside
• Storytelling Stops
• Picturesque Stops
• Bonus Bird Watching Stops
• A Break in Monteriggioni
• Back to the Winery for Lunch and Tasting
• Private Winery Tour
• Who I Would Recommend This For
• Discount Code
• Kat’s Final Thoughts

About the Guides

Roberto and Sara, the owners, were a breath of fresh air. Their passion for e-biking through the countryside was visible with every story told. They were also hilarious and silly making for a contagious upbeat energy throughout our tour. I told them at the end of the tour that we all felt like old friends, and I don’t often feel that way with guides.

Every tour they offer is completely private and personalized—never a generic group outing. Roberto takes the time to understand your interests and activity level to craft a tailored itinerary, whether you’re into history, wine, scenic backroads, or hidden villages.

Roberto was the one at the front leading our tour and telling us stories. Sara would be behind us making sure we were safe from cars (we barely saw any cars, honestly) and blocking the road when we turned. They had headsets to flawlessly communicate with each other before a turn or if any detours needed to be made.

About the Tour

We opted for “The Best of Chianti Classico Senese” which is a newer tour that Roberto started to offer. The loose itinerary consisted of biking through the backroads of southern Chianti passing by vineyards, olive groves, and medieval hamlets before reaching the walled town of Monteriggioni. After a brief stop in Monteriggioni, we would then bike to a winery for a private lunch, tasting, and tour. The tour was estimated to be about 5 hours in total (3.5 for riding, 1.5 for lunch and tasting) with an easy to medium difficulty rating.

When I say these tours are personalized, I mean that even though we chose a specific itinerary, Roberto still reached out to learn about our interests. We mentioned we loved bird watching so he updated the itinerary to include some cool bird stops. I asked if we could visit particularly beautiful locations so I can grab pictures for my social media, so the itinerary included additional stops with stunning views. We could have added other special experiences like truffle hunting or a cooking class, but decided to stick with just biking this time.

About the E-Bikes

We were each provided with a TREK Powerfly+ Gen 5 bike with a Bosch Performance Line CX Gen 5 motor and Bosch Purion 200 display. The bike seats also came equipped with memory foam covers which were much appreciated. The bikes were in pristine condition, brand new, top of the line, and adjusted for our heights. There were also little zip bags in front of the handlebars for smaller items, while Roberto had a saddlebag with a first aid kit and extra waters.

The e-motor was extremely easy to use and had four speed settings in combination with the bike gears. Roberto and Sara would let us know whenever it looked like we needed to shift up or down or give our bikes more juice. Switching between the different speeds of the e-motor was flawless, and Roberto can even control the speed through his phone. The e-motor battery lasted a long time with a starting point of 100% and and ending point of 75% after 3.5 hours of riding (mostly on the highest speed setting).

I have to mention that these tours are family-friendly with the option to add a co-pilot extension, chariot, bench seat, or a regular baby seat attachment.

Meeting Point

Since we were staying at Castelfalfi and rented a Mini Cooper, we opted to meet our guides at the starting point instead of having them pick us up and drop us off. We drove about an hour just to the outskirts of Monteriggioni where we met at a beautiful winery.

Over some coffee and the view of the Chianti hills, we chatted with Roberto and Sara and learned more about them. We spoke about how COVID inspired us to make positive changes in our lives, how they came to start an e-biking company, family life, and the plan for the day. They were both clear about what we expected to see during the tour and encouraged us to ask questions whenever they came up. This was also our chance to make any requests (like additional photo stops, in my case) before we started the tour.

Safety Briefing

After our coffee and chat, it was time to be introduced to our bikes. Roberto and Sara set us up with our own bikes and adjusted the seat heights and helmet sizes for us. We also received instructions about how to shift the gears and use the e-motor in perfect symbiosis.

During this time, we were provided with sunscreen to lather up under the harsh Italian sun. Roberto and Sara came prepared with anything we needed including extra bottles of water and bug spray if needed. A short time later, we were off!

Exploring the Chianti Countryside

For a majority of this tour we biked on unpaved back roads instead of the crowded (and frankly dangerous) main roads. This allowed us to avoid cars, make frequent stops, and see a part of the countryside that others don’t. I honestly felt like we had the whole area to ourselves. We didn’t see another tour group or biker for the first 80% of the experience until we got close to Monteriggioni.

The back roads might’ve been hilly, but Roberto specifically curated this itinerary to go through private (with permission) properties and get up close to vineyards and other special features. We got our fill of the classic Chianti rolling hillside views, avenues lined with Cypress trees, manicured vineyards that stretch for miles, and more. The views did not disappoint!

Storytelling Stops

One of my favorite parts about guided tours is the ability for guides to craft a vivid story of the history in our current destination. Roberto is a master storyteller. He pulls out interesting facts and weaves them in with funny anecdotes and expressive hand movements (he’s Italian after all). We were laughing and smiling throughout the experience.

I don’t want to spoil the itinerary because it’s really special, but I’ll share some of my favorite stops. The first one was in front of a field of ancient grains and a hillside in the backdrop. Roberto told us the history of the Black Rooster symbol of Chianti wine and the competition two towns made for border control. Another stop I enjoyed was at an old vineyard still utilizing ancient farming techniques for the grapes. Roberto knew the owner personally and explained his family specialized in using the branches of a nut tree to hold up the grape vines as they did in the old days. Fascinating!

There were plenty of other storytelling stops including one to an ancient Etruscan bird hunting ground. Another showing us an old guard house with a spectacular view. A stop to pick and smell wild fennel and how that ingredient is used in some wines. The list goes on, and each of them was accompanied by fascinating commentary.

Picturesque Stops

I had asked Roberto if we could make sure to include stops in beautiful locations so I could take pictures for my blog and social media, and he delivered. Each stop was not only interesting from a historical perspective, but it had a stunning view as well.

Roberto and Sara went out of their way to get pictures of myself or me and my husband and took a ton of videos of us riding. Roberto prides himself on offering a complimentary GoPro recording service, and brings a drone for a small charge as well. He brought the drone on our tour and filmed us riding through the Cypress-lined roads of a beautiful winery. Perfect for honeymooners!

Bonus Bird Watching Stops

I don’t know if I’ve mentioned this before, but as my husband and I gracefully age, we’ve taken a liking to birds. What first started as, “oh that one is so cute!” has turned into full blown binoculars with a birds of the region book and trying to get pictures of birds we see. It’s very millennial, I know. When Roberto asked us if we have any interests, I jumped at the opportunity to share how much we love birds.

During this experience we saw a few cool birds and a bird nest. Roberto took us through a forest path to show us a mud burrow in which a particular type of bird rests in and pointed out fox scratches just under the entrance. So cool! Shortly after this, we saw the bird that creates the burrows sitting on some power lines.

As we were making our way through a beautiful private vineyard road, we stopped by an abandoned barn known for housing a particular type of eagle. We were hearing the cries of an animal during Roberto’s explanation, looked down, and saw the cutest little baby eagle crying out and waddling toward us. Sara let us know that the momma was likely looking for it and we should leave it alone before it gets stressed out. It was a memorable encounter!

A Break in Monteriggioni

After biking for about 2.5 hours through beautiful country roads, we started to make our way to the walled town of Monteriggioni. This is one of the most iconic walled towns in Tuscany, and even though it’s not very large it’s worth checking out. We parked our bikes in the main square and sat down for some refreshments.

Roberto and Sara offered us gelato but what we really wanted was ice cold water. Biking under the Tuscan sun is no joke! They both surprised us with a chinotto soda, a traditional beverage made from the chinotto fruit (like a small bitter orange). I personally thought it tasted like cough syrup, but my husband loved it. It was a thoughtful gesture to tie in learning about what grows in Tuscany with a popular beverage.

We could’ve spent more time in Monteriggioni and walked around the top of the walls, but we were starting to get tired and hungry. We hopped back on our bikes and rode back toward the winery just outside the town. This was the only part we were on the main road for, and while Roberto and Sara kept us safe, I’m glad most of the tour was on back roads.

Back to the Winery for Lunch and Tasting

A short while later we returned to the winery and said goodbye to our bikes. The winery had outdoor seating with beautiful views, but the indoor air conditioning was calling our names. Roberto let us know that he arranged a private room for my husband and I to enjoy lunch and a wine tasting and that he would meet us after for the winery tour. We were met by a lovely young man who promptly escorted us to our table.

The winery is on the smaller side, which I much prefer. We didn’t see other tour groups in here (unlike other generic bike tours which take you to tourist trap wineries) but mostly families and locals just looking to enjoy good wine and food. Our host provided us with 4 wines over the course of lunch to taste along with a pencil and paper to take notes or place orders. We used the papers to draw each other.

I have to say, the food was incredible. Way better than I expected for a winery. We were first served a plate of appetizers consisting of hot polenta with ragu (this was so good), cold cuts, sweet melon, olive oil bread, and a bruschetta. Then we were brought out a plate of local cheese cuts and honey along with more bread. For the main course, we were served a plate with two pastas: a rigatoni marinara and a bechamel pesto lasagna. I still dream about that lasagna, it was so good. Chewy layers coupled with the creamy bechamel and salty pesto – drool! Dessert was a basket of almond biscotti with a dessert wine, a lovely end to a great meal.

Private Winery Tour

After about an hour, Roberto came to see how our lunch was and asked if we were ready for our winery tour. Given that we were reaching nap territory, we asked for the express winery tour (perks of having a private tour guide!) and followed our host to the cellar.

The cellar for this winery was small, but we learned a bit about the different barrels they use and the blend of grapes that define the flavors of the wines we tried. It reminded me of the Whiskey Tour we did at Wildflower Farms in New York last year. They had a map of the various Chianti regions and which wines they were known for. We also got to see some barn swallows nesting in the rafters of the cellar entrance. All in all, it was a great short tour that was the cherry on top of a lovely day.

Finally, it came time to say goodbye to Roberto and Sara. We spoke for a bit about their various bike tours and plans for the future. It was like saying bye to old friends! With promises to stay in touch, we headed back to our car for the drive back to our hotel with smiles on our faces.

Who I Would Recommend This For

If you’re reading this blog post, it’s probably because you’re looking for a special e-bike experience (or you just like following along with my adventures – in which case, thank you!) that goes beyond the generic tours on Viator. You’re in the right place!

I would recommend booking Roberto’s e-bike experience if you’re looking to arrange an extra special activity with a hands-on guide. History lovers, people who appreciate culture, foodies, and even those who love animals and nature will find these bike tours right up their alley. I wouldn’t hesitate to recommend these tours to families, honeymooners, retreat-goers, or even solo travelers who want a unique and private e-bike experience.

With all that said, a private e-bike tour comes with higher costs, but you pay for better quality. I would reconsider if you’re on a tight budget, don’t care for history or guiding, or hate nature.

Discount Code

If you’ve made it this far in the blog, thank you. Your taking the time to read my experiences means the world to me. I mentioned that I have a discount code if anyone wants to book these experiences – here it is:

Kat’s Final Thoughts

We spent a total of 9 days in Italy, and this e-bike experience was one of the most memorable things we did on this trip. It hit the sweet spot for us in terms of physical activity, beautiful views, exploring a new area, learning interesting facts, and eating tasty food. We got to meet two of the most genuine people who showed us around Tuscany like old friends.

I know some people look at an e-bike tour and think that it’s way out of their comfort level, but trust me when I say this experience is for everyone. If you have been looking for a way to explore the beauty of Tuscany in a hands-on and fun way, I would highly recommend booking with EBK.