How to Stop Struggling With Your Itinerary & Decide Where to Go

St. Luca's Church, Kotor

St. Luca’s Church, Kotor, Montenegro

I can almost see you there, slumped over your desk, naked bulb over your head, unrolled maps, flight timetables and ripped guidebook pages littering the space, snapped pencils, paper coffee cups and fast food Styrofoam ankle-deep. You’re planning where to go with your round-the-world tickets. And you’re in agony.

While this reenactment may be old-fashioned (Styrofoam? Really?) agony and eyestrain are no strangers to the modern RTW trip planner. Planning where to go on a round the world trip can seem like an insurmountable task but if you’re well-informed and well-prepared, the task won’t force you into a states of geographic and financial comatose.

Here are some guidelines on how to chose an itinerary that’s best for you. Keep them in steady balance and you’ll be good to go.

Idea Labor: Make a List of Your Must-Sees

The first step really in any planning process is to take your bucket-list (for lack of a better term), the one that’s been cascading through your cranium up until now, and write it down. This will galvanize your ideas and separate your dreams from reality, birth them, so to speak. The countries and cities you have a real connection with, as opposed to the ones tainted with caprice, will rise to the surface.

Tip: Be careful of trying to get to every place you’ve ever wanted to go. Omit those that are adding too much to the cost. See Price section below.

How Much Money Do You Have? Let the Budget Lead the Way

There are two sides to every travel budget: the money you save before you leave, and the amount you spend when on the road. The first is known as missed concert events, estranged activity-loving friends and expensive dinners. But the money you’ve saved will determine where you go on your trip. This is also associated with the number of cities you visit, because the more places you put on your itinerary, generally the more expensive your trip.

The second is known as your traveling weakness for expensive day tours, taxi cabs, and unwillingness to sit on the ground to eat lunch. Your daily traveling budget effects where you go because some countries are more expensive by the day. Find out how much you’ll need to save for different places. Budget Your Trip has a handy online calculator to help you figure out how much you’ll be spending on a daily basis, categorized by region.

The Price, or “Fantasyland”

The trip’s overall cost will probably end up spoiling the party for several exotic destinations on your list. But don’t be discouraged, the world is a big place and life is long. And fortunately, like the budget, there are tools out there to help you. Of course we recommend TripPlanner because it’s the best way to gauge how much your custom trip will be. Typically, RTW tickets start around $2500 for a decent 5-stop trip. However, the average AirTreks client spends about $3500 on theirs. This is a good number to plan around since it’s hard to predict where yours finally ends up.

Trips tend to take on a life of their own once your start planning and it’s hard to foresee the final price before the dust finally settles. TripPlanner allows you to adjust your route to get a price your comfortable with before you ever submit it to a consultant. It lets you add and subtract destinations extremely easily, so play around: plug in Harare, then remove it, add Perth, then remove it, and see which one works best for you.

Take a quick look over our Specials page for an instaprice education.

Consider Ambitiousness versus Time

What’s your time period? Do you have 1 month or 6, three weeks or ten? The time you have to travel may allow you to remove items from your list to get the price down, and remember, trying to get to too many places in one trip is just not a good idea. It exhausts you and diminishes the overall quality of the trip. Any seasoned traveler will tell you this.

The Seasonality Reality – Follow the Sun

Adverse weather is a cold certainty and should play a significant factor in deciding where you go. Rainy seasons make sandals unwearable, humidity ruins your hair, and cobblestone strolling in the cold is for chumps. Crowds, floods, snows, and random locust infestations all should be considered. Don’t know when to go somewhere? Turn to This will help to define when it could be raining or when the sun will tan you just so.

Here are a few regions where seasonality should be taken into consideration when deciding where and when to go:

  • India/Southeast Asia – rain and heat can dramatically change the quality of your trip. The monsoon season (Jun – Aug) can inflict misery on the traveler so choose the dates you go wisely. Or even if you go.
  • Europe – It gets painfully hot in the dead of summer and unbearably cold in the winter. High season crowds will force their sweaty shoulders between you and your most fantasized location, so perhaps avoid August at all costs!January will send you back to your hotel at sunset, freezing.
  • Australia/New Zealand – their hot/cold seasons are reversed, but remember, they’re still at the mercy of the Northern hemisphere’s traveling habits. We will pack winter in Australia.

Don’t forget to plan around festivals. If you’ve always wanted to be in Shanghai for Chinese New Year, seasonality will be an important item to plan around.

Panorama - Sonsonate bus terminal 2

Bus terminal, Sonsonate, El Salvador by Ben Beiske

Add a Cup of Variety, the Life Spice

Who doesn’t love the beach? I ask you, who! But think about what each and every one of them brings to your travel inventory: sand. After a half dozen beaches (and an extra kilo of sand in your britches) you’ll be done with the beaches. Keep your nose to the wind and add variety into your itinerary. Beach, mountain, city, jungle, beach, village, canyon, river, city, blimp, beach.

Turn the Internet Upside Down, Shake

In case you haven’t heard, there’s a current travel web explosion happening. There are more websites out there to help you decide where to go than you can shake your 1995 mousepad at. We have our list of recommended travel sites that make the planning a little easier. Match your list with theirs and see if you like the choice. Also, AirTreks has a complete where to go planning guide to help out in just this situation. Yes, it’s on the Internet too.

Get Social

You’ve got 700 followers on Twitter, 350 friends on Facebook (or something) and an unseen hoard on the many social-slanted travel sites on the web, leverage that resource. Ask simple questions like, “I’ll be Tokyo and I’m looking for cheap eats,” or, “how do I find a good Peru jungle trek?”, or, “I need a black market kidney, what’s a good sidetrip from Bangkok?” there will be people to help you out. Travelers in social media are ridiculously helpful.

If you’re on Twitter, search using the hashtag #travel and/or your travel keyword(s). Don’t hesitate to ask questions directly to well-followed users.

If you’re still having trouble, there’s a great event called Meet Plan Go! happening in October, 2011 in 18 locations around the US. Attend, approach, be illuminated!

Have a Good Time, For Goodness Sake

The most important thing to remember, amidst your growing empty wine bottle collection, neurotic 6-hour internet sessions and the dog feeling horribly unloved, is that travel planning should be an enjoyable process. Nobody wants to be sitting in that dark room, gnashing their teeth, with an increased capacity for heartburn. Planning your trip should be almost as fun as the actual traveling. Well, travel without the touts, tourists and nasty cases of gastroenteritis.

Further reading on how to choose your RTW destinations around the web:

From Vagabondish
From Wanderlust & Lipstick

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