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Around the World on Two Wheels: Annie “Londonderry” Kopchovsky

As the first woman to ride her bicycle around the world, Annie “Londonderry” Kopchovsky challenged world views on women in cycling and paved the way for many greats to take to two wheels after her.

In 1894, Annie was like most 19th century women, a 23-year-old mother of three, a dutiful housewife and not necessarily a cyclist or an outspoken advocate for women’s rights. But when a pair of strangers bet that a woman couldn’t possibly ride the globe on a bicycle in fifteen months, she decided to take on the challenge.

She left her home and family in Boston and began her journey in full skirts with a 42-pound bike dead set on proving that women were not only strong, physically and mentally, but that they could provide for themselves. To finance her journey she took on sponsorships–carrying advertisements on her clothing and bicycle, and even changing her name to “Londonderry” as promotion for the Londonderry Lithia Spring Water company.

Annie Londonderry Trek Travel Cycling Vacations

As her route wore on through Europe, North Africa, Asia and the South Pacific, she acquired a lighter bike (20lbs lighter) and evolved her wardrobe from traditional women’s clothing to a men’s riding outfit. She, admittedly, loaded up her bike aboard a few steamships and trains at key points in the journey, but despite that still crushed her way through thousands of miles of rough terrain, camping outside and fending for herself every step of the way.

Eventually she made her way back to the states by way of San Francisco and returned to Boston 15 months to the day after she departed. According to Peter Zheutlin, author of Around the World on Two Wheels, “What Annie accomplished with her bicycle in 1894-95 was a tour de force of moxie, self-promotion and athleticism. Though she was a skilled raconteur and gifted self-promoter with a penchant for embellishment and tall tales, she was also, as the evidence shows, an accomplished cyclist who covered thousands of miles by bicycle during her journey.”

Annie Londonderry Trek Travel Cycling Vacations

Upon her return, Kopchovsky went on to become a popular and vocal advocate for both cycling and women’s rights. Speaking around the country about her adventure and throwing in some fantastical tall tales along the way.

The New York World remarked in 1895 that her trip was “the most extraordinary journey ever undertaken by a woman,” and we can be sure that what started as a bet became an immeasurable impact on the attitudes about women and an inspiration to women of that time and today.

Annie Londonderry Trek Travel Cycling Vacations


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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