How to Bike the Breathtaking Italian Alps

When I was asked to join an epic 400-mile cycling journey across the Dolomites in northern Italy, I said yes—and decided I’d figure out the rest later.

As a cyclist in Washington, D.C., I ride to work, on the weekends, and on bike-camping trips. My non-competitive cycling and primarily flat stomping grounds mean I was used to an entirely different environment from the one I was planning on tackling. That didn’t stop me from taking on the challenge—and it shouldn’t stop you. With a little bit of training and focus, you can take your cycling game to new heights.

Use these tips to prepare for your own cycling expedition.

Get in the Miles

Snow falls on a cyclist on the road through the Dolomites, where weather can change drastically and quickly.

Photograph by Taylor Burk

I started training in April for my September trip. In total, I put in around 3,000 miles along long flat routes on hot D.C. days. It seems like a crazy number, but, over the five months, it averaged to about 600 miles a month. That equates to roughly 20 miles a day, and you can do more on weekends to give yourself a break during the week. Dedicate some days to your local hills, and you can rack up 3,000 miles pretty quickly.

Focus and dedication to your plan will allow you to have fun on a demanding cycling trip. The climbs in the Dolomites are not a sprint. The trip will take you on a marathon through Italy’s beautiful countryside—and to best enjoy it all, come prepared.

Pack Carefully

What supplies will you need to ride across the Dolomites? This northeastern Italian mountain range rests inside the European Alps and, like many mountainous environments, the weather can change quickly and drastically. During one ride, you might cycle through the rain into a sunny section of the road, and then down from a snowy peak into a warm valley.

You'll be cycling through a full range of conditions, so you need to be prepared for everything. Be sure to pack long cycling pants, a packable wind proof vest and rain coat, a pair of warm cycling gloves, a packable hat, and a balaclava to protect your neck and face. Much of this kit will fit nicely in the back of your cycling jersey, so if you get warm, you can easily shed layers.

Go with an Expert

I'm usually all about planning my own routes, but if I’ll be in a region for a short time, I go with an expert. I cycled this route with DuVine Cycling and Adventure Company, a group that focuses solely on unique and immersive biking trips.

Having that support allows you to cram as much awesome into your time as possible. An expert will know the roads less traveled. They can help you if you get a flat tire in the middle of nowhere. They’ll plan exactly how many miles you should cover in a day and book a comfortable bed for you at the end of each ride. An excellent guide might even get you to the coziest coffee shop in rural Italy and have already ordered you a latte macchiato by the time you’re done taking photographs of the quaint Italian town.

Where’s the adventure in hiring a tour company, you ask? Literally everywhere. You've probably watched clips of the Tour de France or the Giro de Italia, and while you may not go as fast as the professionals, you’ll feel just as tough as you cycle your way across winding roads in the Italian countryside. You’d likely never find these twisting paths without the help of an experienced guide, one who rides the same route and eats at the same local digs on their days off.

Find Your Crew

The bike is a perpetual smile machine—even more so when you’re cycling with an exceptional crew. On a trip like this, the challenges of the route are eased by constant comradery and extensive coffee shop time with your newfound friends.

Together, you’ll cruise through tiny, charming Italian towns. You'll pass apple orchards in the morning, throw snowballs at lunch, and zip through vineyards by dinner. You’ll work as a team to get up each pass, celebrate your hard work at the top, and share stories of your personal growth. While a solo trip has its benefits, joining a group of talented cyclists means you can cheer one another on and share your highs and lows.

Over the course of the week, the journey you once thought impossible slowly becomes realized. You’ll have biked more than 400 miles, covered two times the height of Mount Everest in total elevation, and reached the edge of the Adriatic Sea. With a belly full of local organic cuisine and the support of your new cycling community, you’ll probably start to wonder what else you can tackle—and whether your new friends will join you.

Jon Bowen is a cartographer and cyclist. He and adventure photographer Taylor Burk took this trip through the Dolomites with DuVine Cycling and Adventure Company.