Planning Your Next Vacation?

May 24, 2018

Now that I’ve convinced you that travel is something you ought to get into the habit of doing, it’s time to reveal the biggest downside to travel - it requires a decent amount of planning! All too often I see eager travellers book their travel first and ask questions later. This is a recipe for disaster as travellers soon realize that what they thought would work won’t end up working.


Setting Goals

The first and most important step in travel planning is to set realistic travel goals. How often can you travel in a given year? On Tuesday I proposed aiming to travel at least twice a year. While that goal should be achievable for most, it is also possible to go overboard! 


Towards the beginning of each year ask yourself the following questions: 

  • How often do I want to travel (i.e. every month, every quarter, twice a year?)

  • How much money am I setting aside for these trips?

  • How long should my vacations be?

  • What types of experiences do I want to have this year?

Likely the most important of those questions is how much time and money to budget for each of the trips. Some factors to consider when building your budget is: 

  • Airfare (if applicable) or Car Rental & Fuel Cost 

  • Accommodation (i.e. Hotel/AirBnb/Hostel)

  • Activities (i.e. Shark Diving in Cape Town)

  • Ground Transportation (including airport parking)

  • Gifts and Memorabilia You Want to Bring Back

  • Meals

A common misconception people have about travel is that it’s expensive or requires a lot of time in transit. While the may be true for exotic destinations, there are lots of things happening in your own backyard that might be a short drive/train ride away. For instance, suppose I live in Toronto, Canada. A drive to the Niagara region famous for the Niagara Falls and wineries is a mere 90 minutes. You can get to Ottawa, Canada's capital in 3 hours or Montreal, the cultural capital of Canada, in just 5 hours by train for less than $100 roundtrip. 


Determining the travel experiences you want to have is also important as it helps define where you’ll end up going. Here are the general travel experiences I’ve enjoyed along with the countries I’ve visited:

  • Historical Journey (Egypt, UK, Ireland and Germany)

  • Adventure (Switzerland, South Africa, New Zealand)

  • Arctic Trekking (Iqaluit)

  • Fun in the Sun (Hawaii)

  • Visiting Family/Friends (Saint John, San Francisco)



Do Your Homework


Once you’ve set high level travel goals for the year, the next step is researching each goal you have set. The experience you choose will define the possible locations you want to go to. The key to squeezing the maximum value out of your travel wallet is flexibility in terms of the when you travel, where you travel to and even how you make the booking in the first place. A quick online search should give you a listing of popular travel destinations that serve your purpose. 


Your web search should answer the following questions:

  • What are some destinations that match my travel experience?

  • What is the average transportation cost (i.e. flight or train) to these destinations?

  • How much are hotel in these destinations?

  • What types of activities are recommended and how much does they cost?

  • When is a destination in its high season?

  • Are there logistical considerations for the destination (i.e. seeing the Great Wall of China requires applying for a Visa)?

  • What other costs are associated with the destinations you are considering?


Not all destinations are created equal! Travelling to Orlando will result in quite a different travel bill staying in Honolulu even though you’re aiming for the same experience (i.e. fun in the sun)! Often when you choose travel also plays as much a factor as where you are travelling to, especially when travelling during low season. High and low seasons are usually specific to the destination in the question but are usually cyclical: you’ll pay the most when more tourist are going. For instance, summer months are often high season for many cities in Europe, whereas they are low season in Hawaii. 


Get Organized 


Once you’ve decided your travel goals, have done your background research to determine which destination matches your goals and budget, you'll want to start organizing your trip. One of the first things I do when I start booking travel is to create a spreadsheet to track all of the elements of my travel itinerary. This allows me to take a quick glance at my itinerary. It also lets me spot things I might have missed (i.e. a hotel booking) and prevents me from booking the same thing twice, which is easy to do if you book things months in advance.  Here’s what my spreadsheet looked like for a recent trip to Puerto Rico:



You’ll undoubtedly receive tons of confirmation emails as you start booking your travel. My advice here is to place all of those emails into a single folder. It’ll be a lot easier in Rome to find that hotel booking if it’s all in one spot in your email versus scattered throughout your inbox. Even better print out all your confirmations in the event you lose access to email.





On Tuesday we discussed why travel is important and today we've discussed at a high level how set travel goals and how to plan your travel. Next week we’ll be discussing how to make these travel plans a reality: how to travel deals on flights and hotels and how to find and book activities to the places you’ll be visiting

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