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For some, planning a trip may seem like a painful burden. But if you are anything like us, planning your trip is almost half the fun. We find that it allows you to build up loads of anticipation and allows you to fully customize your trip according to your personal needs and preferences. The one-size-fits-all approach to trip planning is, in our opinion, seldom successful.

Decisions, decisions, decisions.

When to go? This primarily depends on two things: 1) When can you get time off, and 2) Do you prefer to travel during high-season, shoulder-season, or low-season? With regards to the latter question, we prefer to travel during the shoulder season when possible (typically June or September for North American or European destinations), as there are slightly fewer other tourists around, prices tend to be reduced compared to high season, and the weather is still warm and very enjoyable.

Note: Don’t forget that if your target destination is in the opposite hemisphere to you, the seasons are reversed!

How long should go you? Well, quite frankly this is entirely up to you. If you have your heart set on a specific destination, first figure out your budget and go from there. The same budget could get you a one-week holiday in one area or a three-week vacation in another.

Are you flexible as to your specific departure and return dates? The same flight will cost more or less depending on the day you travel (see our next page on flight information), and many accommodation options increase their stay rates during the weekend. If your dates are not flexible, don’t be too disappointed. Your will life might be much simpler now that you won’t have to bother with trying to figure out the “best dates” puzzle to minimize flight and accommodation costs. Furthermore, if you start planning early, in our experience you can cancel out potential lost flight savings by finding better and cheaper accommodation before all the best places get booked up.

Your itinerary and lodging availability

Before you jump in booking your trip, we generally suggest to being by mapping out your ideal itinerary. In other words, figure out where you would like to stay (which city or area) and for how long. This is particularly important if either your target bases have limited accommodation options or if you would prefer to stay in some sort of specialty lodging. This will allow you to make sure that you can get your preferred accommodations in the order that follows your set itinerary.

Time to start booking?

You will often read that you should always buy your plane ticket first before anything else. We would agree that this is true if you plan on staying in large cities and in standard hotels, where room availability will rarely be an issue. Otherwise, however, we highly recommend first make sure that your preferred accommodation options are available during the dates you wish to travel and this is especially true if you are booking your trip somewhat last minute. Likewise, if you plan on renting a car, make sure there is still availability. In smaller towns, availability can be very limited during the high season.

When should you buy your flights tickets? A quick google search will lead to differing opinions of when the time is right to purchase your tickets. You can also check out the results (below) of a recent airfare study looking into this issue. The bottom line is that the best time to book your flights is highly dependant on both the season and the destination.

Our advice? Make use of Google Flight’s powerful analytics to help you decide when you should buy your tickets. You can look at the history of price fluctuations and get estimates on whether prices should go up or down in the near future. Be sure to check out our flight information page for more details.

Final thoughts

Contrary to most online advice you will come across, we always suggest prior to booking your flights to first check the availability of car rentals and preferred lodging accommodations. You would definitely rather realize that you are having trouble finding options that are to your liking and within your budget prior to having booked your flights!

Don’t forget that cancellation policies matter too. We always recommend booking refundable accommodations, when possible. This allows you to then check back every few weeks to see if the cost of alternative options you were eyeing has dropped.

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