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Meet Our Team: Jacob Young

“I thought, ‘Well, I’ll give this a shot for a year or two, then I’ll get a real job.’ I’m coming into my 14th year, having guided in amazing places all over the world, and couldn’t be happier.”

Meet Trek Travel cycling guide Jacob Young
Tell us your story. How did you end up at Trek Travel?
At a dinner party one night, a friend mentioned this new company—a new branch of Trek Bicycle that was taking people on super nice bikes to super nice places. I thought, “That’s way too good to be true.” As I was job hunting in the post 9/11 mayhem, I wasn’t having much luck. I had guided a few friends up Mount Rainier, and it felt life changing to show someone a new place, to see them achieve something they didn’t know they could: I was hooked. Somehow, Tania saw something in me through the reality-TV-style hiring process and gave me and 13 other lucky guides a job. I thought, “Well, I’ll give this a shot for a year or two, then I’ll get a real job.” I’m coming into my 14th year, having guided in amazing places all over the world, and I couldn’t be happier.

How did you get into cycling?
Fifteen bucks at a yard sale in New Hampshire scored the 12-year-old version of me a grey Peugeot and my first taste of freedom. Granted, I was riding in cut off jean shorts at the time, and mountain biking quickly became my passion, but that was my humble beginning. I had never worn a chamois until two weeks before my interview with Trek Travel! Track & Field and Cross Country are the sports that put me through university, and it was there that a passion for endurance sports was born. Trek Travel was really the transition from running to cycling for me.

How has your guiding experience impacted your life?
Beyond meeting incredible people, and the travel, I’ve become really good at eating out. This skill only becomes apparent when I eat out with my non-guiding friends (and could be its own future blog post). Also, being able to read people is one of the finest skills a guide can hone, and I like to think that my temperature gauge of people is finely tuned.
Meet Jacob Young, Trek Travel tour guide and transportation director for pro cycling races
How do you spend your off-season?
I am fortunate enough to wear a few different hats. I currently toggle between working as Transportation Director for some of the biggest bicycle races in North America, as well as helping lead yoga trips in sunny, tropical destinations. Through the years, I’ve bartended, worked retail, edited manuscripts, taught yoga, coached high school track, tutored English, lived in Italy, became a Carmichael Training Systems coach, landscaped, and briefly held the title of Global Logistics Manager for a hand-warmer company.

Do you have a favorite vacation spot?
My current favorite place to travel is the Veneto region of Italy, known as the foothills of the Dolomites. The food and wine are amazing, the terrain is varied, and the tourists are few.
Meet Trek Travel cycling guide Jake Young
Tell us about a highlight during your time guiding.
Some years back, I was guiding in New Zealand with my good friend Jon Vick (currently rocking as the Event Manager for Trek Bicycles). We had some guests who wanted to go skydiving. Near Lake Wanaka, I made a couple calls and learned that the local establishment would not only give us guides a commission if guests signed up to skydive, they would also comp our skydive. JV and I “jumped” at this opportunity, and the fist bump at 15,000 feet before the adrenaline rush confirmed that this would remain a highlight for the rest of my life.

What advice would your give our readers when planning a vacation?
Prepare to make new friends. Also, spend multiple days in a row on your saddle. (Speaking of saddles, they are very personal things, so I recommend you bring one that works for you.) Most importantly, come with an open mind. “Trip of a lifetime” is quite the moniker to live up to. I feel lucky when guests tell me we have exceeded their expectations, and can’t wait for the next time to do it again.
Meet Trek Travel tour guide Jacob Young

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What is the Difference?

Ultimate Luxury:

Savor some of the most spectacular, 5-star properties in the world. Exuding luxury and elegance, these one-of-a-kind accommodations offer the chance to rejuvenate at award-winning spas, dine at Michelin-starred restaurants, and more.


Enjoy luxurious accommodations handpicked for a refined experience. From signature spa treatments to delicious local cuisine, you’ll be more than provided for; you’ll be pampered.


These handpicked hotels provide relaxation and fun in a casual and comfortable environment. Delicious cuisine and great service mix perfectly for a memorable stay.


On select cycling vacations, you’ll stay at a mix of hotel levels, from Explorer to Luxury to Ultimate Luxury. Rest assured, no matter which level of hotel you’re at, our trip designers carefully select every accommodation.

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).

What are your trip styles?

Classic - Reserve:

Savor the finer things as you relax in luxurious 5-star accommodations and wine, dine, and ride in some of the most unforgettable destinations around the world.

Classic - Signature:

Explore beautiful destinations by bike, enjoy extra inclusions, savor delicious local cuisine, and enjoy the perfect mix of accommodations.

Classic - Discover:

Enjoy a casual cycling vacation with fantastic routes and comfortable accommodations.

Ride Camp:

Train like the pros in some of their favorite riding destinations.

Pro Race:

See the pros in action at the biggest cycling events of the year.

Cross Country:

Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.


Enjoy a bike tour on your schedule with just your chosen travel companions.

Single Occupancy

Sometimes it’s more convenient and comfortable to have your own room while on vacation. We understand and that’s why we offer a Single Occupancy option. The additional price guarantees a private room all to yourself