Ask Gadling: Making a five-year travel plan

This week’s Ask Gadling question comes from Ryan in San Diego.

“How do you choose where to go? I haven’t traveled all that much, but I want to. My friends all just want to go to Hawaii to relax and I don’t really know where to start. Are there certain places I have to go to be considered “well-traveled”? I’m not rich, but I can take a vacation or two per year.”

Gadling: Hey Ryan, I totally get the wanderlust thing. I mean, I love Hawaii, and everyone should go there, but I understand the desire to see the world. You’ve already taken the first step by figuring out that you can take one or two vacations per year. What you can do now is make yourself a five-year travel plan. Here’s how:

Make a list.

One or two vacations per year for five years is seven or eight destinations. There are no hard and fast rules for where you have to go to be “well-traveled,” but to be able to participate in most travel-related conversations, I would say you should definitely hit France, Italy, India, China, Japan and at least one country in both Africa and South America. If you have domestic cities you’d like to see, consider hooking them onto your international trips with couple-day layovers.

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Rather than just blindly choosing which one to visit first, lay out the plan. Do you have a friend living abroad in one of those places? Go there sooner rather than later, in case they move. Are you planning to move to the east coast in two years? Save your western Europe destinations for after that; it will be cheaper to fly. Furthermore, are you in a good position to add destinations? For example, when you go to Africa, investigate a safari company that will take you through several countries. You could also try to plan two longer trips to Europe and Asia and country-hop there, as well. Traveling to multiple destinations per trip will actually save you money in the long run, if you’re planning to hit all those destinations eventually anyway.

Amass information.

At this point, you should have a list of destinations and a vague idea of what year you’ll be going to them. Now, the real research starts. Find out what the weather will be like and plan your trips by season. Find out what goes on in Italy in September/October, or what festivals are in India in February. Ask friends and family what they recommend doing in your various destinations, and be sure that whatever activity you want is available at the time of year you’re visiting. This may sound like a lot of work, but it can be fun — just keep in mind that you’re actually going to get to go to these places and do these things. Keep the excitement of it all in mind.

Enlist friends.

Your friends may be beach bums by nature, but gauge their interest about your destinations. They may surprise you, and it can be good to have a traveling companion. Maybe you’ll have a different one for every trip — and that’s fine. It’s also fine to go alone, or make friends with locals and other travelers while you’re there (then you don’t feel alone, like you’re not sharing your experiences with anyone).

Get specific.

Now comes the really hard part: making concrete decisions. Take a look at your first two trips. Decide on your cities, and go ahead and book your hotels. If you’re doing this blindly, it can feel very intimidating, but just keep in mind that no matter where you stay, it will probably work out just fine. Google every potential hotel to see what guests have said about it. Perhaps the most important thing to keep in mind when booking a hotel in a strange city is transportation; like, if you’re not renting a car, stay somewhere near the city center and decide in advance how you’re going to get there. Do they have an airport shuttle? Is there public transportation available? If you are renting a car, you may be able to save money by staying somewhere a little out of the way, but check online to see that previous guests aren’t reporting muggings and kidnappings in the area.

The first trip is the hardest (most intimidating), but by the second, you’ll probably be addicted — and feeling well-traveled.

The feeling of being well-traveled doesn’t come from crossing countries off a list, but from the act of planning your trip and the experience of seeing all your decisions, blind and otherwise, come to fruition. It comes from truly exposing yourself to and immersing yourself in something completely new. Good luck planning your next five years of travel!

[Photo credit: Annie Scott]