Take a Cycling Trip to Tuscany Italy in 2018 Image

We’ve been running our unique cycling trip in Tuscany for years now and there’s a reason (actually five reasons) why I always put my name on the staff roster at least once per year. Below I’ve outlined those reasons along with a few of my favorite pictures that help tell the story of what it’s like to tour through Tuscany on a bike.

My Top 5 Reasons to Take a Bike Trip to Tuscany

#1 – The Food

“If Italy can claim Europe’s most tempting cuisine, Tuscany is both its larder and its inspiration. This sun-drenched, vine-lined region is rich in slices of culinary heaven.”
Belinda Dixon, Lonely Planet

Grandma Lia cooking dinner for our riders. She cooks all of the meats over an open fire.

Grandma Lia cooking dinner for our riders. She cooks all of the meats over an open fire.

Tuscans like to source their food locally and it’s prepared Old World style – slowly and with love. You’ll never get bored with typical foods in Tuscany. They enjoy a variety of foods – from meats like rabbit, wild boar and beef, to legumes, leafy veggies, and all sorts of fruits.

Tuscany Cycling House

On our cycling trip to Tuscany we have a mix of eating at our B&B (where the food is prepared by the host family) and eating out at carefully chosen restaurants. When we eat at the B&B, the family prepares the food the same way it has been done for generations. The fruits and vegetables are sourced from their backyard or from their neighbors’. Meats are cooked over an open fire. They pick up their bread and pastries every morning at 7am from the bakery down the road, and we eat family-style in a mill that was built in the 1200s!

Tuscany Cycling Trip - Food

Our riders enjoying dinner after a day of riding the hills of Tuscany.

When we go out to eat it’s not a generic place you’ll find in a tour book. We get off the beaten path and enjoy an authentic dining experience in villages near Siena. These restaurants are run by families who have run them for generations.

Enjoying lunch after our ride to San Gusme (Chianti region)

We finished one of our rides with lunch in San Gusme (Chianti region). We get to start this ride at our home base and ride North into Chianti.

We also organize a cooking class during our trip which is always a highlight. This fun and interactive evening culminates with riders enjoying the food creations that they helped prepare.

Our riders enjoying a tuscan cooking class. This is always a highlight of the bike trip

The Tuscan cooking class during our trip is always a highlight.

I may have an exceptionally excitable palate, but to me the food in Tuscany is worth a trip there on it’s own!

#2 – The Riding

A few years ago, on my first ride in Tuscany, I had two realizations. First, the riding is challenging! There aren’t too many flat roads in Tuscany and if you are on a flat section it won’t last long. The hills are endless and beautiful, so be prepared to climb about 1000 feet for every 10-12 miles that you ride. My second realization was that the roads are awesome and the options for routes feel infinite. The pavement is usually always butter smooth and it seems like every 2 miles there is another turn with more opportunities and adventure.

Making our way to Pienza. You can see Montalcino in the background, that's where Brunello wines are from.

Making our way to Pienza. The village of Montalcino is in the background and that’s where Brunello wines are from.

What I’ve learned about riding in Tuscany is that I have to throw out my old pretenses about mileage and distance on a ride. I do this because sometimes a 30-mile ride in Tuscany feels like a 60-mile ride in Montana. Things are more compact in a smaller area and the up and down riding starts to zap the legs – where as cycling in Montana or Arizona there are climbs, but it’s usually more gradual and longer distances of flat, so you can cover more ground. Instead of focusing on distance while riding in Tuscany I like to focus on time in the saddle and how many villages and cafes I get to explore. :)


Riders regrouping after riding a challenging and beautiful section of the Strade Bianche

Because of all the options I knew there’s probably a “best” direction to ride a route so we partnered up with a local. Andrea Rossi grew up about 10 kilometers from our Tuscany base camp and his local knowledge and experience provides our riders with a Tuscan intimacy that we could never provide without him. I’ve learned more about guiding and finding happiness on the bike from Andrea than any other person I’ve worked with.

Tuscany Cycling Trip Vacation

Adaptability. Part of the beauty of the variety in routes and endless options is our ability to tweak the routes and call audibles during our trips. We have the guides and the route options to make this work for a variety of ability levels. We never want a rider to feel like they are being pushed or forced to go above their comfort level on a ride. Also, a stronger rider shouldn’t be held back to go shorter than he or she wants to. We make sure that adaptability is built into every ride we do. This is something that the Cycling House guides and trip leaders pride themselves on.

The Cafe stop on every ride is mandatory :)

A Cafe stop on every ride is mandatory :)

It’s also important to mention that on every ride that we do in Tuscany, we make sure that a cafe stop (or two) is always built in. Part of the unique experience is stopping in at a tiny little village, going to the only bar in town and grabbing an espresso (un caffe!).

Cycling House Tuscany

Parking the bikes for one of the most important parts of the ride – The Cafe Stop.

The Strade Bianche has become dear to my heart since those first few weeks of riding in Tuscany. Strade Bianche means “White Road,” because of the light color (almost white) of the dirt that winds through the countryside. We have optional sections of these dirt roads that we can ride during our camp. We understand that not everybody wants to ride a gravel road on their road bike and there is no pressure to ride anything out of your comfort zone. But that said, I’ve introduced dozens of riders to the idea of riding the Strade Bianche and I still have yet to see a rider regret having given it a try! After being in Tuscany and riding the Strade Bianche with riders from the area I learned how important these dirt roads are.


Riding a section of the Strade Bianche.

Riding a section of the Strade Bianche.


Some of our riders pedaling gravel roads on a road bike for the first time ever. It's a neat experience that get us completely off the beaten path.

Some of our riders pedaling gravel roads on a road bike for the first time ever. It’s a neat experience that gets us completely off the beaten path.

There is now a professional race that has many sections of dirt similar to the famous Paris Roubaix, but instead of cobblestone it’s Strade Bianche. There are also organizations in Tuscany whose whole purpose is to protect these gravel roads due to growth, expansion, and paving.

Cycling through the alleys of San Gimignano on our trip in Tuscany.

Cycling through the streets of San Gimignano on our trip in Tuscany.

#3 – The People

The people of Tuscany are amazing. In a strange way they remind me of Montanans; Authentic, happy, hardworking and a zest for life. We’ve worked with a family for the past six years that run the B&B Pallazo a Merse near Siena. and I feel like the luckiest guy in the world to be able to partner with and work next to these guys. These folks are an inspiring delight.

We base out of a B&B in the countryside of Tuscany near Siena. It's run by this amazing family that opens up the entire place for just our group. It's full immersion in the family, culture and food of Tuscany.

We base out of a B&B in the countryside of Tuscany near Siena. It’s run by this amazing family that opens up the entire place for just our group. It’s full immersion in the family, culture and food of Tuscany.

Andrea Rossi leading the way.

Andrea Rossi leading the way.

Andrea Rossi (our lead Italian guide) is the linchpin because I hired him years ago to help guide our first trip. After learning more about Andrea he introduced us to his entire family and allowed me and my crew to stay at their B&B about 15 kilometers outside of Siena. Within 10 minutes of being at the B&B with Andrea and his family I knew this would be the place to run our trips from then on. Life with this family is slower. We get to experience full immersion into a Tuscan family, which is unique when you travel. The kids are doing homework, the grandmothers and cooking and doing laundry. Andrea is a wine merchant and is sharing what he does at the dinner table. There is constant cooking and preparation going on in the kitchen.

Cycling House Tuscany

Guido (L) and Sandro are the Father/Son guiding combo in Tuscany. In 2017, Guido was also the recipient of the Staenberg / Cycling House Scholarship which allowed him to experience traveling to and riding in the USA for the first time in his life (he came to our Tucson, AZ camp)

#4 – The Wine

This one kinda goes without saying, but….it’s incredible. Tuscany produces wine that is distributed and enjoyed all over the world. Even if you don’t like wine it’s still pretty impressive to see how it works and where it comes from. I Months after a trip, I find myself going through the wine section at my local grocery store back home, looking for the wineries that I’ve been too. That’s a unique connection and is hard for me to explain; but I bet you will do the same when you return and be brought back to Tuscany every time you’re wandering the wine aisle. One of the most famous Tuscan wines is Brunello which is grown and produced only in Montalcino. It’s really neat to climb up to Montalico and see where the Brunello wine is made. It’s a surprisingly small area for such a famous wine.

Chianti region of Tuscany. We finish one of our rides with this view overlooking some Chianti vineyards

Chianti region of Tuscany. We finish one of our rides with this view overlooking some Chianti vineyards

During the Tuscany trip we always go to a variety of wineries to meet the people who make the wine and to see how it’s produced. It’s the perfect after-ride activity that is engaging, educational, and relaxing.

Cycling House Tuscany

#5 – The Culture

The culture and history that surrounds us while riding through this place can at times leave me speechless. We ride through multiple Unesco World Heritage sites on our Tuscany trip. (https://www.discovertuscany.com/what-to-see-in-tuscany/unesco-world-heritage-sites.html) You can learn about this through a guided tour, but most of the time it’s by osmosis and just being present and allowing yourself to take it all in.

Getting ready to ride

One of the most fascinating things about this country is how localized some of the food and traditions can be. For example, most Tuscans don’t really put balsamic vinegar on their food (that’s produced in the northern part of the country so it’s never been a big part of the meals in Tuscany). They’ll likely have it in their kitchens but it’s rarely used. More common for bread and salad is salt and olive oil (only). I still use both-much to the dismay of our hosts and friends in Tuscany-but I can’t help myself.

Also, did you know that cappuccino should only be ordered in the mornings? If you want a caffe after lunch or dinner it’s customary to order an espresso only. I will usually disobey this rule, again, much to the dismay of the locals… ;)

Checking out a local winery after a ride in Tuscany.

Checking out a local winery production after a ride in Tuscany.

One of the most refreshing things about a bike trip in Tuscany is that once you get off the beaten path you’ll find that life is a little slower. You can’t help but slow down a little bit too. It’s less stressful and I’ve learned from our Tuscan family to decelerate and spend more time with friends and family, and smile more. Life is good.

Catching rainbows from our cycling home base in Tuscany.

Catching rainbows from our cycling home base in Tuscany.

Along a similar line, and I touched on this earlier, I’ve found this odd connection between Montana and Tuscany. To me, true Tuscan people have this can-do attitude that I haven’t seen anywhere else more prominently than in Montana, where I grew up. Tuscans and Montanans have a resilience and life-is-good attitude that is contagious. If something breaks they’ll fix it or figure out some hack to get things done. They work hard and find their work fulfilling and purposeful. Their homes and culture is charmingly rustic – their homes have exposed wood from hundreds of years ago. Their brick and rock is unfinished and rough edged. Food is commonly cooked over an open fire. (Of course, I’m generalizing a little bit here, but I’ve observed this year after year with the folks I meet and work with in Tuscany. It’s pretty inspiring.)

Riding through the walls of Siena, a Unesco World Heritage Site.

Riding through the walls of Siena, a Unesco World Heritage Site.

We’ve helped put together some amazing supplemental adventures to go see and do before or after your trip with us. Every year a few folks always ask why we don’t do a 10-14 day trip and my answer is always that same: After spending 7 days with us we want to give our guests the opportunity to go out and explore on their own. Being off the bike for a few days allows you to walk through Florence or Siena and get a little deeper into these cities and villages.

As you can probably tell, I love this place. I’m already scheming my list of must do rides for our bike trip coming up in May of 2018.  If you are thinking about going to Tuscany or you have more questions about what a bike trip to Tuscany would look like for you, please don’t hesitate to contact me. I love sharing what I’ve learned over the years.


Owen Gue
President of The Cycling House & lover of riding bikes in Tuscany :)

strade bianche
cooked over an open fire
section of the strade bianche
riding the strade bianche