This story originally appeared in the March 2012 issue of Canoe & Kayak.

When a perfect storm of career failure, a deteriorating relationship and a gnawing sense of angst left him adrift, Glenn Charles remembered a few glorious moments he spent in a sit-on-top kayak. Within months, Charles found himself in Seattle with a sea kayak, some paddling gear and $500 to his name. The year was 2009, and he set a goal to paddle north to Alaska on a “journey of spiritual discovery and life simplification.” The 1,700-mile Inside Passage epic proved to be just that. “I knew I was getting in over my head, but I also knew this was something I was supposed to do,” says Charles, formerly of Washington, D.C. “I learned how to kayak as I went. When I finished I realized that this nomadic life was the way I want to live—one trip to figure things out turned into a new calling for life.” — Conor Mihell

Mission: To travel 50,000 miles by sea kayak and bicycle in five years, essentially tracing much of the perimeter of the North American continent. After paddling the Inside Passage in 2009 and the U.S. Atlantic coast in 2010, Charles, 48, is about 12,000 miles into his goal. He’s starting 2012 with a circumnavigation of the Sea of Cortez.

Boat: Nigel Dennis’s 17.5-foot Explorer (now manufactured by Sea Kayaking UK) has been used to circumnavigate Iceland, New Zealand, South Georgia Island and Great Britain. This solid expedition cred sold Charles on the uncompromising design, and he managed to buy a secondhand Explorer from a neighbor. “The learning curve was steep,” admits Charles, who carried up to 25 days worth of food and gear on the Inside Passage and endured hairy conditions off the Outer Banks of North Carolina. “But I’ve been lucky that my first boat was an Explorer. I don’t feel the need for anything else.”

Blades: Charles splits time between a bent-shaft Werner Cyprus and a Superior Kayaks carbon-fiber Greenland paddle, averaging 18 to 25 miles per day. “I love the Greenland paddle for the simplicity of the blade,” Charles says, “but in bigger conditions, I still prefer the bite of a Euro blade. The obvious benefit of switching between the two is that the stroke is different and uses different muscles.”

Apparel: When he wore out his first Kokatat expedition drysuit after thousands of miles of paddling, Charles was surprised when the manufacturer replaced it free of charge. “I wore it every day of the Alaska trip and almost every day of the Atlantic trip,” he says.

Shelter: Most of his nights have been spent cocooned in a Black Diamond Tripod bivy beneath an ultralight, 8-by-10-foot sil-nylon tarp made by Oware. “It’s all in the vein of simplicity,” he says. “You really can travel this way in comfort and it creates so much flexibility.”

Camera Bag: The Watershed Ocoee that protects his digital SLR camera and travels in his cockpit is “the best drybag I’ve ever owned,” Charles says. “It’s the only bag that stays 100 percent dry no matter what.”

Mountain Bike: Charles has ridden more than 5,800 miles across the Western states. He’s now toying with an ambitious 1,000-mile solo cycling and packraft epic this summer with a Salsa Mukluk and an Alpacka Raft Alpaca, from Icy Straits to Anchorage on Alaska’s “Lost Coast.”

Follow the journey and read about the gear Charles uses at