When to go: Timing your itinerary

| July 7, 2009 | 18 Comments
compass When to go: Timing your itinerary

When to go?

“I learned that we can do anything, but we can’t do everything… at least not at the same time. So think of your priorities not in terms of what activities you do, but when you do them. Timing is everything.”

—Dan Millman

As Doug Lansky writes in his book,  First-Time Around the World: A Trip Planner for the Ultimate Journey, “on a long trip you can’t be everywhere at just the ideal time. And it’s not worth trying.” I think that’s sage advice and notable for what it demands from the traveller—flexibility. While you can’t be everywhere at the ideal time, you can take steps to ensure that you are at least somewhere during some of those ideal times. Lansky’s advice is even more relevant when considered in the context of Dan Millman’s above quote—”we can do anything, but we can’t do everything”. That’s important advice for a backpacker.


When planning your itinerary, it’s likely that weather will be among your primary considerations. In an effort to make such planning easier, Babakoto.eu has developed an Excel travel planner. Their travel planner encompasses weather data from a number of countries and includes information about the best periods to travel in respect to average temperature and rainfall. Hence, the travel planner allows you to plan your trip through one or more destinations and can provide you with a starting point from which to consider your itinerary—from the perspective of weather at the very least. As an added bonus, Babakoto.eu’s planner allows you to estimate and track your expected costs per destination—and for your entire trip.

Owing to Kathryn’s distaste for cold and dreary weather, we’re going to do our best at chasing the summer around the globe. So our itinerary, while not dictated by weather, will be at least somewhat motivated by it!


Another of Doug Lansky’s best tips is that you need not consider the ideal time to visit a certain location, but rather if there are any dates that you should absolutely avoid. Often you need to plan around local holidays and events. In 2002, I discovered that the start of my trip through China coincided with Golden Week. I had suddenly found myself in the midst of no fewer than 120 million Chinese on the move, filling seats in every plane, boat, train, bus and car available. I hunkered down in Beijing to wait it out.

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Of course, I made the most of my time in Beijing (and area), but missed seeing other parts of China I might have otherwise accomodated. Of course, you might want to schedule your holiday around a festival. Basing your travels on not just a place, but a place blazing with all of the sights sound and smells of a festival can certainly enhance your experience. Often, planning to attend festivals take some advanced effort, as cities and towns often fill up with reservations long before the festival, think the Carneval in Rio de Janeiro and Salvador, or the Great Migration in Tanazania, or even World Cup in South Africa next year.

Keep abreast of world events and celebrations with Rough Guide’s exhaustive list of holidays and festivals for the year 2009—check out their site here. Or check out the book itself here—World Party: The Rough Guide to the World’s Best Festivals. Rough Guides’ book doesn’t include everything, but you will you will find the classics—Rio Carnival, Glastonbury and Mardi Gras—as well as smaller events such as Scotland’s Common Ridings and Australia’s Birdsville Races. Highly recommended.

Cost of travel

Remember that domestic air travel costs remain reasonably constant the year round, apart from the occasional rounds of special fares that arise depending on popular travel times betweend destinations. Some holidays such as Thanksgiving, Christmas, or New Year include a semi-hidden surcharge. Because there are fewer discounted seats available, they sell out early; hence, if you’re considering  traveling at these popular times, you will likely end up paying more than if you travel just a week prior.

While the days when students could hang out at the airport and fly ‘standby’ for dirt cheap prices are long gone, when you book your travel is now often more important than when you actually travel. Guesthouses, hostels, airlines and cruise ships offer generous discounts if you book your accomodations or tickets very early—or at the last minute. Traveling this way allows you the option of travelling at a discount rate. However, there are risks.

High season, low season, shoulder season

Many people who complain about crowds in high season are those that seek out the the most crowded sites of the most crowded cities in the most crowded months—only to complain about the crowds. You could be in Paris in July and walk ten blocks behind the Louvre, step into a café, and be greeted by Parisians who act as though they’ve never seen a tourist. A lot of tourists stick to the small section of the city covered by their Let’s Go, Lonely Planet or one of the many available tourist maps. Wander out into the areas outside of the margins of the guidebook and you’ll find yourself among the locals!

The alternative, of course, is to consider travelling during low season. While low-season travel is very easy on the wallet, it’s important to remember that tourist destinations have off-season slow periods for a reason—the weather may turn out to be unfavorable during certain seasons and attractions or activities may be curtailed. Unending rain during the monsoon season in Inida or 110-degree summer temperatures in Arizona might not be worth the aggravation. And some places—especially those at elevation—may be completely inaccessible in the winter.

There is a sweet spot in that liminal space that haunts both high and low season—and it’s termed ‘shoulder season’. This period between high and low season sees prices drop, but offers similar advantages to high season. Here you need not worry that prices are being inflated by demand; rather, they come closer to being based on value. For North America and Western Europe, the months of April, May, September and October are considered prime travel time for those of us (ie backpackers, vagabonds and long term-travellers) who don’t have to worry about schedules and holidays.

Ann Shields at Travel and Leisure writes: “No significant shoulder seasons fall within January, February, July, and August, but prices drop immediately after the holidays in January”. She chronicles a few “Shoulder Season Travel Secrets” in her article—among them Japan in May. She writes, “peak hotel rates have come down after last month’s cherry blossom celebrations, and the humidity has yet to kick in.”


Ultimately, I would caution against overplanning. Of course, it pays to do your research—have a number of cities chosen, keep in mind some seasons to avoid, but avoid the temptation of overplanning.  Like Per Andersson, editor of Vagabond Magazine, I suggest that it best to read novels and classics set in the place in which you’ve decided to travel, but don’t start planning beyond that. Per writes, “If you make a detailed itinerary, then you take away the excitement. And then it’s easy to get disappointed because you often have to break with your plans”.

For Kathryn and I, the most important question that we face is not: “Where are we going to go?”, but rather “Where do we begin?”.  The only thing that we’re committed to thus far is a departure date—the first week of July 2011. Aside from that, we’re keeping in mind Dan Millman’s advice—”we can do anything, but we can’t do everything”. That’s important advice for a backpacker.

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About the Author ()

For nearly ten years now, Daniel of Two Go Round-The-World has explored how travel captures our imagination and engages our deepest emotions. One half of the duo that maintains the widely read Two Go Round-The-World blog, Daniel treats his subjects not only as works of art but also as symbols of the cultural and political forces that inspire them. Check him out on Google+.

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  1. Victoria says:

    We’ve been through all this thinking, it’s nice to read a post laying it out so clearly. Another consideration for us was culture shock for our children. We are travelling clockwise around the Pacific, so that we can start with Disneyland, followed by Hawaii, NZ and Australia, so that we can be in English speaking, culturally similar countries to the UK first. Once we are used to spending 24hrs a day together, carrying our stuff, sharing rooms, moving frequently etc, we will move onto Asia, which is naturally more challenging because of the language and cultural differences. We are also chasing the sun!

    • Daniel says:

      Certainly, planning for a family introduces a higher level of considerations. Interesting that you’re choosing english-speaking, but progressively more exotic places as introduction to world travel for the family. I think that’s exactly how I would go about it. In regards to culture shock—I’ve dealth with it before as an adult, and it can be tough sometimes. One of the hardest things I had to deal with, though, was reverse culture-shock after having been away for one-and-a-half years. That was a whole new realm of weirdness. My wife Kathryn is putting together a post on her experiences with culture shock when we lived and travelled together in Korea—before our marriage!

  2. Tim Morrison says:

    Insightful post, I would say costs, time zone (whether you like to gain time or lose time) and weather (maybe you like cold weather activities?) will affect RTW routes the most.

  3. Daniel says:

    Thanks for the comments, Tim. Despite being Canadian, I’m not too fond of cold weather activities—hockey included. Just don’t tell my government; they’ll take away my passport. Looking forward to hearing about your new gear. I’ve got a forerunner and dig it. And so want that Camelbak pack you’ve featured. Sweet.

  4. Hey there! I popped over here via your link on TravelBlogs. :)

    Thanks for the link to the Rough Guide’s list of holidays around the world. I hadn’t run across that particular website before and I think it’ll be handy for our trip to India later this year.

    During our 18 month round-the-world trip, we often followed the warmer weather and tried to keep informed about the holidays/elections/major events going on in the country we were in (and going to next). We don’t book our rooms ahead when we travel, so it can be good to know when the BIG event is going to take place in the next town over.

    That said, this past December we found ourselves in Mexico City over the festival of the Virgin de Guadalupe. I’m happy we didn’t realize that before booking our plane tickets, otherwise we might have waited a few more weeks to travel there…and we would have missed out on some amazing moments. :)

    • Daniel says:

      Cool. I like TravelBlogs. Great site. Glad you found that link of use—lost a lot of time at that Rough Guide site, too! Just now reading your blog, Jessica. First of all, it’s one of the nicest designed sites I’ve come across. Laid out beautifully! I’d like to learn more about your itinerary, so I’ll dig deeper into the blog. First off, am off to subscribe to your RSS feed and will link to you from our links page. Appreciate the comment. I apologize in advance, but I’ll likely have lots of questions! Thanks for dropping in.

    • Thank you so much for the kind words about our site! That’s really wonderful to hear. And thanks for the link on your links page too. (We don’t have a links page at the moment…otherwise I’d do the same. But I’ll definitely make sure to keep your link handy whenever someone is looking for a RTW blog!) :)

      We love nothing more than to chat about our RTW trip, so feel free to drop us a comment or send us an email as you guys plan. It’s always fun to compare notes with fellow travelers. Our RTW ended in 2006 (gosh, I can’t believe it’s been that long ago!), but we still travel outside of the country multiple times each year and enjoy sharing those adventures on our blog too. (We just got back from Colombia, hence the string of Colombia related stories on the front page right now!) We like to think we have two homes now: one in Cape Cod, and one in our backpacks. :)

      I’m really looking forward to reading your site both during your preparation and when you’re on the road!

  5. Akila says:

    Dan – Great post. I am actually going to write a similar post (gosh, the number of posts that I want to write is exponentially increasing) but focus more on the specific details of how we planned our route. This is a great guide and I will link over to it in our post.

    • Daniel says:

      Akila, looking forward to your post. And thanks in advance for the link. It’s much appreciated. As our planned departure date draws closer (still so long away), we’re going to drill down to more specifics. I’m really interested in what motivated you to choose the itinerary that you did, so I’ll keep a close eye on your RSS feed! I said this a while ago on the BootsnAll forums, but when considering a choice for domain name, I found yours to be one of the best out there. In thirteen letters it captures exactly what your site is about, and it wraps it in a pun, too. Solid.

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