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From the Olympics to Cross Country USA: Meet Lynn Jennings

Part 1: In October, our group of cross country riders reached the coast of the Atlantic and completed an incredible 3,784-mile journey by bike. Among them was one of the most accomplished women’s long-distance runners in U.S. history, Lynn Jennings. The three-time Olympian and world cross-country champion took on a new challenge this fall and embarked on a 47-day journey from Portland, Oregon to Portland, Maine. Get to know Lynn firsthand as she writes about her experiences on the open road across America and stay tuned for more entries soon.

For as long as I can remember I have been happiest moving outdoors with birds, forests, flowers and any kind of water. For years I moved through the world on two feet testing my limits and my willingness to endure the training to be the best runner in the world. Being a world-class runner is not for the faint of heart and somehow I came through it all intact and still kicking and with my love of the outdoors all the stronger.

When I discovered serious cycling in my forties, I found an even better way to move through the world — so many places to cycle, so much time to be on a bike. I fully embraced, as Henry James wrote, “Try to be one on whom nothing is lost.” The very notion of traveling the world on two wheels means moving through one environment after another with eyes, heart and mind wide open.

Portland to Portland 2022 was the ultimate expression of so much of what I hold dear. Being brave enough to try something new and challenging. Being willing to train hard and strong for 8 months to prepare for it. I was ready for anything to happen. I had this sense that I would thrive no matter how challenging it all was, that beautiful days and tough days would combine to create an unforgettable adventure. Improbable as it seems, I was certain I would be in my element every single day.

Sharing my experience on Portland to Portland 2022 will, I hope, show how we are always capable of more than we think, we are always more resilient than we think. I was the best version of myself every day on this trip and I can think of nothing better than inspiring someone else to give it a go.

Stay tuned for more from Lynn.

See the trip


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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 Explorer and Luxury hotels. Rest assured, no matter which hotel level 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