When contemplating a life on the road, one of the first questions is “Where do I go?”. Once one is out there, this question becomes “Where do I go next?”

Sitting in the Suburban Extended Stay Hotel in Jacksonville, Florida today, I am asking myself that question. This is the end of the third major leg of the Southern Swing 2013, and I now must decide how to finish the last leg of the Swing. I have ridden about 4000 km, 620 km in just the last week as I pushed up the Treasure Coast of Florida, to meet my final mail drop.

The author and world traveller Josh Calhoun in Fort Pierce, Florida.

I have stayed with friends in Boca Raton and Fort Pierce, dodged the fans going to the Daytona 500 race, and set personal records for same-day distance (180 km) and average speed (22 km/h, loaded), thanks mainly to fair weather, smooth roads and stiff tailwinds.

I have let my speaking schedule and the location of friends and family determine where I go, but you may not have the same spread of acquaintances (or not want to see them!) as I, nor have work destinations that are scheduled well in advance.

It is only necessary to lay out the first “trip.” If you want to live and work on the road, but continue to return to home base in between long outings, that’s a great way to go. It is happening to me without any planning in 2013 and 2014. My friends back home are as happy to see me every six months as I am to see them.

Here are some other ways to decide where to go:

1. Visit a series of major destinations you have always wanted to see. These could be capital cities, famous landmarks or natural wonders, or places you read about or dreamed of in the past.
2. Visit everyone on your Christmas card list or with whom you are in correspondence. You could use your parents’ list if you don’t have one of your own. Choose a dozen people from your contacts database. Pen pals tend to be distant; so do many Facebook friends.
3. Make a religious pilgrimage. This does not even have to have a religious meaning for you personally. The major destinations of pilgrimages are often famous anyway, and it’s the journey that counts, not the destination.
4. Visit a favorite teacher who moved far away. Maybe pick one from elementary school, another from middle school and one from high school.
5. Visit the “old country” if your parents or grandparents emigrated to where you live now.
6. Visit school classmates or friends who moved far away.
7. Visit every state, province, territory – however your country is divided up.
8. Follow the Tour de France, TransAmerica Trail, TransCanada Trail, Giro d’Italia, Vuelta de España, Continental Divide, or other major bicycle or hiking route. In the Americas, this will involve camping, more than the “credit card touring” that I used on the Southern Swing 2013.

Once you have one or more ideas for a route, you can check the details for logistics, cost, etc. Of course, shortly before you finish one “trip”, you can begin planning the next one.

I will continue to use the “friends and family plan” in designing my travel to major engagements, but I am looking to be more flexible. For one, I have decided that I should spend more time in each place, especially where there are friends to see, or when I happen to ride more than 100 km to get there.

Next week, I will report on how I decided to end the Southern Swing 2013, and begin preparations for the Northern Trek 2014, which will take me through the rest of this year. I will be making some changes based on my experience so far. Please send in your questions and comments, because I am writing this blog for you.

Smooth roads and tailwinds,

Jonathan.