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How to Plan a Vacation the Right Way

October 22, 2019

How to Plan a Vacation the Right Way

The first snow of the season has arrived and I can’t help but think about how badly I need to plan a vacation for this winter. But where should I go? When should I go? How will I get there and what should I plan to do while I’m there?

Planning a trip can become overwhelming quickly. The world is a big place and there are so many places to see and things to do! So what is the best way to plan a trip to eliminate the overwhelming feelings AND ensure that your final destination meets your expectations? 

 Instead of choosing a location and then creating your travel plan, how about creating a travel plan and then choosing a location that fits your travel desires?

Below are the eight key questions to ask yourself  in order to plan a vacation that suits you well. 

1. For how long am I going to travel?

Is this a weekend getaway, a month long vacation or a six month sabbatical?


2. What activities am I interested in?

Are you mostly interested in city exploration including sight-seeing, shopping, and refined experiences such as eating at nice restaurants? Or are you looking to spend time in the outdoors: camping, hiking, climbing, beach going, etc.? Or is it a bit of both?


3. What is my overall budget?

For now, understanding your overall budget is most important instead of designating a specific amount for airfare, for example. This is because the breakdown of expenses can vary significantly based on where you decide to travel.

For example, airfare from the US to Indonesia might make up the majority of your budget,  but once you arrive accommodations and food will be inexpensive requiring only a small portion of your budget.

On the contrary, traveling from the US to Canada may require less of your budget, but the food, accommodations and activities will consume more of your budget.


4. Do I care if I speak the local language(s)?

For some, traveling to locations where they don’t speak the local language is not a big deal. For others, this is a deal-breaker. What do you prefer for this trip?


5. What’s my preferred travel rhythm for this trip?

When you plan a vacation, consider whether you want to be on-the-go the entire trip with multiple activities lined up for each day or whether you are looking for a slower-paced trip with few activities planned. Or is it a bit of both?

If you’re looking to be busy, then you’ll want to make sure your destination has a lot to offer. If you’re looking for a slower-paced trip, you’ll have more flexibility when choosing your destination.


6. What kind of weather am I looking for?

Based on the activities you’re looking to participate in, what kind of weather do you prefer? For example, if you’re planning to spend all of your time at the beach, are you okay with regular afternoon showers as is common in many tropical locations? Or do you desire hot, sunny weather all day long?


7. What time of year am I going to travel?

The time of year along with the type of weather you prefer will play an important role in choosing your destination. 


8. Do I care whether I vacation in a location during their high season, shoulder seasons or low season?

This decision will greatly impact your experience. Below are generally the pros and cons for each season, although they may vary based on your destination. Which one do you desire for this trip?

High Season

Pros: ideal weather for the location; many services and activities available

Cons: the busiest tourist season; accommodations and services will be more expensive; reservations may be required for accommodations, restaurants and activities & tours (sometimes months in advance)

Low Season

Pros: few visitors; accommodations, food and services will be less expensive and may not need to be booked in advance

Cons: Many locations completely shut down during low season. Therefore, there may be limited options for activities, accommodations and restaurants. The weather may be poor to unmanageable or unsafe for travel: monsoon season, hurricane season, extremely hot, extremely cold, etc.

Shoulder Season (in between high season and low season)

Pros: Accommodations and activities are less expensive than during the high season and don’t need to be booked as far in advance, if at all; many activities and services are available; fewer visitors than during the high season; the weather is better than during the low season.

Cons: The weather might not be as good as during the high season; the availability of services and activities might be limited


Awesome! You’ve completed the eight key steps to plan a vacation that meets all of your desires!

Wondering what to do next? Download your free How to Plan a Vacation the Right Way worksheet to put your responses into action!  

Happy Trip Planning!



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