Where did you start and where will you finish?
I started in Deadhorse, which is a town at the northern end of the Alyeska Pipeline at Prudhoe Bay on the Arctic Ocean.  Ideally I’ll make it to the souther tip of Argentina, in Tierra del Fuego, in particular the city Ushuaia which is considered the southernmost city in the world.  Nothing is set in stone though, I may well find something along the way worth stopping for.  I try to focus on the journey itself, as the idea of so many thousand miles left can be overwhelming.

How long do you expect it to take?
I expect this to take up to 18-20 months. With many different options for routes and places to stop along the way, it is hard to guess when I’ll get to Argentina.

How many miles between Alaska and Argentina?
This entirely depends on the route you take.  From reports of other cyclists who have done similar trips, around 15-20,000 miles.

How can you afford this trip?
I do my best to live frugally.  You might be surprised how cheap life on the road can be; you don’t have to pay rent or utilities, and generally don’t spend money on entertainment like you would in a city.
One of the best ways to keep costs down is to avoid paying for lodging.  This means I camp out as much as I can.  Most touring cyclists’ philosophy is to rough it at night in your tent and spend money on better food instead!  I also have found places to stay along the way through the awesome hospitality exchange website couchsurfing.org and the cyclist-only one warmshowers.org.

What inspired you to make this trip?
I fell in love with bicycle touring doing shorter trips around the Midwest, but always had time constraints and had to be back in Chicago by a certain time. I’d been following blogs of dozens of other cyclists doing long distance tours (in particular, those cycling in the Americas), and was captivated by the idea of packing up my life in Chicago and leaving on a trip with no set schedule. One cold winter night almost 2 years ago something clicked and I told myself “I’m going to do it [try to bike from Alaska to Argentina]“.

What has been the most memorable part of the trip thus far?
Of course, the people I’ve met along the way. I’ve encountered so many kind strangers that have offered me food and places to stay. And I’ve run into many other cyclists headed in all directions, and it is always fun to hear their stories. As for places, generally the more rugged and remote ones, although more challenging, are more rewarding.  Places that come to mind are the Dalton and Denali Hwys in Alaska, the Cassiar Hwy in British Columbia, the Kananaskis area of the foothills of the Canadian Rockies in Alberta, the canyonlands of southern Utah, the mountains of Michoacan, higher elevations in Central America.  So basically mountains.

How far do you typically bike in one day?
Between 50-60 miles, though since I’ve gotten to warmer and more challenging terrain, more like 40-50 miles. Any more and I’m really motivated or have a great tailwind, any less it is usually because of bad weather, difficult terrain, or having arrived at a suitable stopping point for the day.

Has anyone else done this?
Before the trip, I made contact with several cyclists who I had followed online who had done or were doing a similar trip corresponded a little.  I also found several people online (mainly on crazyguyonabike.com, which is the most frequented cyber-community for touring cyclists) who were planning on starting the same trip I was this summer, so we talked about cycling together.  For about the first month and a half I cycled with Baptiste, in British Columbia we split ways and he went down the Pacific Coast and I stayed in the mountains (MT, WY, UT and AZ).  I keep tabs on him and other cyclists on the road mainly by their blogs and an occasional email.

Do you have plans for life after your trip?
Nope, no plans. But at the very least return to Chicago to reconnect with friends and eat some deep dish pizza.