How We Plan Our Travel These Days

April 1, 2011 Blog 5 comments

Mount Cook and Tasman
Well planned holidays are restful and not stressful (breakfast at Lake Tekapo, New Zealand)

We love going on overseas vacations. There is a certain buzz in the air when one is planning and arranging for a trip abroad, regardless of the duration, distance or destination.

In the age of omnipresent online options, choreographing your own holidays is entirely possible. However, one may still want to weigh the pros and cons of DIY versus having a travel agent or travel planner do it for you.
Here’s a general description of how we approach it from a systems point of view.

First, we determine what our budget for each trip is, and the trade-offs that should be made so that we meet a certain predetermined incentive amount in our financial plan. If we go on an expensive long-haul trip during the mid-year, we would opt for a cheaper short-haul one at the end of the year or vice versa. Expenses that should be included are air/ship/ferry tickets, land transport, accommodation, food, sightseeing, tipping and other miscellaneous costs.

Next, we browse the papers to get a good sense of what’s hot and happening in the travel scene. Both The Straits Times and TODAY do a wonderful job of this. I also check out what my travel blogger buddies have recommended to get a good sense of the different places in terms of their natural, cultural, retail and culinary landscapes.

Photos are extremely important as an overseas tour is primarily a visual feast. Searching for pictures under Google Images, Flickr, and individual blogs help one to have a mental perception of the place. I like to look at the photos of an anticipated destination first before going down into the details of what-t0-do.

After we’ve zoomed in to the few options that we’re gunning for, we do a quick scan of available tour packages and itineraries in the market. Fairs like the National Association of Travel Agents (NATAS) travel fair provide a good overview of what’s available and the prices that such packages offer. You may also want to check out the websites of travel agents for individual deals and compare and contrast them.

Here’s where the decision point reaches a fork.

Do we want to go on a packaged tour which saves us some hassle and is priced-to-kill? Do we want to “choose our own adventure” with a completely self-built holiday, booking our own flights, hotels, car, and all? Or do we opt for somewhere in between?

Normally, we’ll evaluate these options based on the following:

1) Ease of transit. Developed countries like Japan, Australia, the US, or Western Europe are normally easier to get around on their own than developing countries. Traffic conditions are also important to consider if you want to self-drive – I don’t relish getting stuck in a two hour jam in downtown Bangkok, Manilla or KL!

2) Cost of package versus time/opportunity cost. While packaged tours often come at a significant discount due to the economies of scale enjoyed by travel wholesalers, they may have strict departure and arrival dates that reduces your flexibility. An example was a tour package to the Canadian Rockies which required one to fly on a Monday and return on a Monday, which meant that one has to take more days of leave and to ‘lose’ one weekend of possible travelling time. If we take a very economic approach, one could even calculate the cost of a day’s leave vis-a-vis using it for a holiday!

3) The tour highlights are next. One has to weigh the advantage of price, convenience, and “being led” vis-a-vis the proposed highlights in the itinerary. If the package covers almost everything you want to see (80/20 rule), at a good price and timing, we’re more likely to sign up for it.

4) Finally, we normally do our own research and work out our sums to determine if the packages, guided or free-and-easy, are really good offers. This will involve making some back-of-the-envelope workings on the costs of individual components like hotels, car rentals, food, attraction/park entrance fees, and so on, matching it against the bundled deal.

If we then decide to go on a free-and-easy holiday after much pondering, we will seek the views of others and garner as much “destination intelligence” as possible. Friends are a blessing here, and I’ve benefited from advice that came from Facebook messages, Linked-in messages, emails, and of course the many face-to-face chats.

Curating a free-and-easy holiday experience involves a fair amount of sleuthing and arranging. There are many websites that can help you with trip planning such as TripIt, Frommers and Google City Tours. For our case, we used a mixture of Microsoft Word and Google Docs.

Perhaps the most important thing to confirm before anything else are your air tickets. Other than Zuji and Priceline, you can also check out the airline websites if you’re looking for specific offers. There is an entire strategy behind this – from determining the best time to fly (both arrival and departure), using of frequent flyer miles versus promo flights, and balancing between cost and comfort. Peak period travel is especially stressful so book your flights early!

After securing your air tickets, you should decide if you want to purchase a land package from the country of travel or to DIY. Again, the same process of cost-benefit analysis could be applied. Popular operators in the Western world include Contiki, Cosmos and Insight Vacations.

We next look at accommodation. My wife does a great job at this, with help from 3rd party travel forums, particularly Trip Advisor where the recommendations of real guests help us to make a considered decision. From our experience thus far, it certainly worked.

If you’re the last minute go for holiday types, you can check out websites like,, or for hot deals and promo packages. Unfortunately, these are often for offpeak periods so it’ll be advantageous if you don’t have to squeeze in with the crowd.

I also use online tools like Google Maps which come with useful distance/time calculators for self-drive vacations. They have neat features where mash-ups of satellite images and photos of destinations are incorporated, making it useful for one to understand the lay of the land.

Hiring of cars (if you’re doing self-drives) will be next. Here, the playing field is so level that Google is probably all you need to help you locate the company that offers the best car deal – with all the necessary insurance, unlimited mileages etc – that is available. There are tonnes of websites offering comparisons across rental companies. Do take note however of the add-ons (GPS, baby/child seats) and what they cost.

Finally, consider all the other elements necessary as part of your holiday – optional tours, entry to museums/zoos, food and drinks, snacks, packing of clothing and toiletries, and so on. If you’re doing free and easy trips, getting a handy guide from Lonely Planet may be useful before the journey.

By Walter
Founder of Cooler Insights, I am a geek marketer with almost 24 years of senior management experience in marketing, public relations and strategic planning. Since becoming an entrepreneur 5 years ago, my team and I have helped 58 companies and over 2,200 trainees in digital marketing, focusing on content, social media and brand storytelling.


  1. hey Walter, next time you can check out too – u can rent whole apartments to stay with with your family – it makes for a nice holiday together, kids can still have their own room while you and your wife can still have yours too. at the same time, there’s usually a kitchen so you can also whip up a quick breakfast or dinner or pack some snacks like sandwiches if needed. 🙂

    anyway, lotsa good and sound tips in here. thanks for sharing! 🙂

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