Where should a first-time vagabonder start?

A Chicago-based reader named Ron recently emailed me with a question about a first-time journey. “I am at the beginning stages of planning my long-term travel,” he wrote. “It’s very exciting. The only problem is, there are just to many places to choose from. Can you recommend a list of places to travel for first-time vagabonders?

This is what I told him:

Congratulations on your upcoming travels! No doubt this is an exciting time, as you ponder all the amazing options the world has to offer.

You might start by thinking of places close to home. Not for your long-term journey, necessarily, but for a “warm up.” Road trip to some places near Chicago, or hit some national parks in the West or some cities in the East.

For the big journey, however, I’ll recommend a few places that will make great starting places. I’ll organize them by region:

• Europe: Europe is a natural destination for American travelers, but these days it’s pretty expensive. I’d recommend going to some other part of the world, as you’ll get more for your money.
• South America: Peru or Ecuador make good starting points. Cusco in Peru is especially interesting, as it’s close to places like Machu Picchu, and it’s a great little colonial tourist town where you can study Spanish or see sights or just mix in with other travelers before you hit further flung places. From here you can go overland to Bolivia or Chile or wherever — just remember to go slow and enjoy yourself!
• Middle East: This part of the world is cheap, and has a friendly atmosphere that belies its reputation. Start in Egypt — a tourist-friendly country that can keep you busy for months. From there you can easily go overland to Jordan, Syria, Lebanon, Turkey, etc.
  Turkey, actually, is another great place to start in exploring the Middle East. Israel is an amazing place, but you might need to save it for last, since countries like Syria won’t let you enter if you have an Israeli stamp in your passport.
• Southeast Asia: Start in Thailand — a place I recommend for most anyone, since it has a good combination of inexpensiveness, friendliness, and ease of travel. It’s a great place for vagabonders to start, and after a few weeks or a month you’ll be ready to begin exploring Cambodia, Laos, Vietnam, Malaysia, Indonesia, Burma, China, India, and many other cheap places nearby. If you were to choose just one starting point, I’d recommend Thailand, since it’s a great place to begin a classic Asia journey.
• Australia: This place is more expensive, but very travel friendly and of course everyone speaks English (though language hasn’t been a problem for me in other places). Can be coupled with a trip to New Zealand or the South Pacific.

Those ideas should get you started. You’ll want to follow up with some online and/or library research — but whichever place you choose, you can’t really lose, because they are all amazing places.