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Designing for Giants

It’s no easy feat to climb six breathtaking giants in the Italian Alps in just four days. If anyone can put the itinerary together, it’s Trip Designer, cyclist, artist and world traveler, Jessica Singerman. Her favorite place she’s been? The Italian Alps. And we can see why. Follow along to see how Jess designed our latest cycling experience, Giants of the Giro, and join us this summer for a truly epic trip. Are you up for the challenge?

Meet Jessica Singerman, Trek Travel Trip Designer

Ride the classic climbs of the Giro on our Legendary Giro Italy bike tour

How did you put this trip together? Tell us about your design process.

On Day 1, the ride up Torre di Fraele is a more gentle climb, although still challenging. It’s the perfect way to acclimate after traveling to the region and it gives people a chance to get used to their new bikes.

Over the course of the next two days, we climb Stelvio, Mortirolo, and Gavia, some of the most challenging climbs in the world. Stelvio’s iconic hairpin turns have inspired cyclists, skiers, mountaineers, and even artists and poets since the mid-19th century. Passo Stelvio is the highest mountain pass in the Giro d’Italia, and during the Giants of the Giro, we will climb it not once, but twice. We will climb the side from Bormio, veer off through Switzerland just before the summit, and then ride up the 48 hairpins from Prato allo Stelvio before descending back into Bormio.

Trek Travel Classic Climbs of the Dolomites Cycling Tour

Passo Stelvio is the highest mountain pass in the Giro d’Italia, and during the Giants of the Giro, we will climb it not once, but twice.

On Day 3, we ride both Mortirolo and Gavia. Lance Armstrong famously said that Mortirolo was the “hardest climb” he had ever ridden, and Gavia brings to mind Andy Hampsten’s grueling 1988 Giro stage win in a blizzard. The stage ended in Bormio, our base for this trip. The reason we ride these two passes on the third day is so that people can make the decision of whether to ride Mortirolo and Gavia, or to stick to Gavia instead. Mortirolo is incredibly steep, so after the two previous days of riding, people will have a good idea of whether to ride it or not.

On the last day, the Bormio 2000 climb is for those guests who want to tick off one last climb before the end of the trip! It’s a short but challenging ride.

What about the Italian Alps is so special?

The landscape is visually stunning, the people are friendly, the riding is second to none, and the food is super tasty. It’s a bicultural region, having been fought over by Austria and Italy, so there’s a lot of history and multiple languages spoken. The region has something for everyone.

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What is the “magic moment” of this trip? Is it a specific climb, the gratification of hard work, or maybe the view from the top?

The views from the top of Stelvio are unreal. Looking down and seeing the switchbacks rise up from the valley to the summit is incredibly rewarding and visually breathtaking. Because of the way the road is built, you can stop periodically along the ride from either side of the pass and see the hairpin turns stacked on top of one another.

Another amazing part of the riding here is simply how long the climbs are. There aren’t many places where we can climb for hours. I love the mental part of climbing like this. Watching your breath, finding your cadence; getting into a rhythm is so satisfying. In the midst of this effort we remind ourselves to look around us, and the breadth of the Alpine landscape is stunning. Riding here is a truly spiritual experience.

There aren’t many places where we can climb for hours. I love the mental part of climbing like this. Watching your breath, finding your cadence; getting into a rhythm is so satisfying.


Learn more about our Giants of the Giro bike tour.



It’s no wonder how the majestic Italian Alps have inspired Jessica in many of her paintings. Below she shares with us three pieces, all sparking creativity from the giants.

“During the making of these, the Italian Alps landscape was absolutely one of my inspirations.”

Oil Paintings inspired by the Italian Dolomites by Jessica Singerman

Top left: The Things I Can’t Reach 1, oil and acrylic on canvas, 40 x 40 inches, 2014
Right: Sweeping Green Blue Air, oil on canvas, 30 x 30 inches, 2014
Bottom left: How to Keep Warm, oil and acrylic on canvas, 40 x 30 inches, 2016

You can learn more about Jessica’s work on her website.

La Gazzetta dello Sport

Perhaps the greatest thing about guiding bicycle trips that interact with big races and follow Grand Tours is the opportunity to travel off the beaten path. We venture to parts of the world that tourists simply do not travel. This was no truer than at Trek Travel’s 2009 Giro d’Italia “Behind the Scenes” trip with the Astana Pro Cycling Team.

It is May 25th, 2009, and the sun is getting lower on the coast of Pescara, Italy. I glance down at my watch: 6:45PM. Dinner is scheduled shortly at a luxurious hotel in Francavilla al Mare, a tiny beach town set on the eastern Abruzzo coast of Italy. This is not just a simple meal, but rather, we have a dinner engagement with the Astana Team.

We had just picked up our crew of Trek Travel adventurers that morning, and immediately experienced an adrenaline-pumped, epic bike ride on the Giro race route. We literally rode up the mountain pass in front of the pros, to the cheers of locals. The Abruzzo region is known for being rugged, and today’s roads were no exception. They were narrow, bumpy, steep and fast. The crowds cheering at the top of our brutal climb were local: I would reckon roughly 98% Italian. But somehow, our group of Trek Travelers, when atop a bicycle, well, we somehow fit right in.
Trek Travel Giro d'Italia Race Vacation
The energy matched the elevation atop our mountain pass, as we eagerly awaited the pros to cross the top. I stood next to a hobbit-sized, elderly, Italian lady with a face leathered and wrinkled by decades of hard work. In her arms she held a stack of bright-pink newspapers. I knew them instinctively: La Gazzetta dello Sport. It’s the title sponsor of the Giro d’Italia, and the inspiration—no truly, the reason—for the race-leader’s pink jersey. The breeze turned chilly as the riders crested the hilltop with much bravado and fanfare. The small, wrinkled hobbit slowly reached her weathered hand in front of her, a pink newspaper clutched in it. As riders prepared for their descent in the frigid, mountain air, they looked around for something warm. Rider after rider eagerly snatched a pink paper from her, stuffing their jerseys with their newly-found insulation. With a smile on her face, she repeated this again and again, barely bothering to look up, as if it were the most natural thing in the world. But of course riders would be chilly on top of a hill; of course they would need something to keep warm on the descent.
Trek Travel Giro d'Italia race Vacation Graham Watson Photograph
I turned our Trek Travel van around the corner to the team hotel, where we met the mechanics who were cleaning and prepping the bikes, and met with behind the scenes support staff who ran us through their process of managing team logistics, the particulars of wrenching from the team car, and shared some of the team’s quirks and lesser-known details.

Then we went inside to enjoy dinner and met with the team managers and some members of the team: Levi Leipheimer (most-improved outgoing personality), Jose “Chechu” Luis Rubiera (kindest cyclist), Jani Brakovic (most gentle, honest rider), Viatcheslav Ekimov (best mullet), and more. After we enjoyed an exceptional Italian feast (many kilos of pasta were eaten that night), we sat around talking and laughing with other members of the team. I had this keen sense that—aside from being able to ride their bike really fast—these guys were just the same as any of us. Here they were, an international group of talented athletes, in a country far from family and friends. An excited group of Trek Travel cycling fans traveled to this small, Abbruzzese town to cheer wildly for them, to share their stories, to encourage them. It was clear that some of our energy and excitement infused back to the team that night.
Giro d'Italia Race Viewing Vacation and Bike Tour
We stopped for a quick round of billiards and a nightcap with the mechanics and support staff before drifting back to our beachside hotel where the group regaled each other with their own perspectives and highlights from a night of excitement and stimulation. Someone remarked that the trip had been a success and that they could go home happy right then and there, which brought a smile to my lips.

Because that was just day one.
Trek Travel Giro D'Italia Race Cycling Vacation
About the Author: Jacob Young, a guide and trip designer who started with Trek Travel at the very beginning, is happiest when showing people new places, a passion he discovered 15 years ago while guiding a friend up Mt. Rainier. When not guiding bike trips, you’ll find him handling logistics for the biggest bike races in North America, or out leading yoga retreats in tropical destinations.


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Activity Level

Level 1:

Road: 1-3 hours of riding. Up to 25 mi (40 km). Up to 1,000 ft (300 m).

Gravel: 1-3 hours of riding. Up to 20 mi (35 km). Up to 1,000 ft (300 m).

Hiking: 1-3 hours of hiking. Up to 5 mi (8 km). Up to 1,000 ft (300 m).

Level 2:

Road: 2-4 hours of riding. 20-35 mi (35-60 km). Up to 2,500 ft (750 m).

Gravel: 2-4 hours of riding. 15-30 mi (25-45 km). Up to 2,000 ft (300 m).

Hiking: 2-4 hours of hiking. 4-8 mi (6-12 km). Up to 1,500 ft (450 m).

Level 3:

Road: 3-5 hours of riding. 25-55 mi (40-85 km). Up to 4,500 ft (1,500 m).

Gravel: 3-5 hours of riding. 20-40 mi (35-60 km). Up to 3,000 ft (900 m).

Hiking: 3-5 hours of hiking. 6-10 mi (9-16 km). Up to 2,000 ft (600 m).

Level 4:

Road: 4+ hours of riding. 40-70 mi (60-110 km). Up to 8,000 ft (2,400 m).

Gravel: 4+ hours of riding. 30-50 mi (45-80 km). Up to 4,000 ft (1,200 m).

Hiking: 4+ hours of hiking. 7-15 mi (11-24 km). Up to 4,000 ft (1,200 m).

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