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Writer's picturejessicadanielstrav

Plan Your Best Vacation by Asking Yourself These 5 Questions

This post is to help you help me help you plan your next vacation!


I have had many clients ask me “Jess, where should I go on vacation?” or "whatever you think budget should be" and better yet "whenever is the best time to go."


Well, these are loaded questions! I can tell you all the amazing places I would love to go to or what price I would be happy to spend on a trip or when I went to so-and-so. But none of these answers would be the right ones for your vacation.


Your vacation should be customized to your wants and needs so you’ll need to KNOW your wants and needs!


Pretend you are a travel agent and ask yourself these 5 important questions to get a start on your vacation planning (because if you don’t ask them then I will!).


“A journey of a thousand miles must begin with a single step.” Lao Tzu

WHERE To Go On Vacation?


If you’ve ever searched where to go on vacation you’ll find that the answers are not always the most helpful. Thousands of search results will only make you feel more overwhelmed when all you want to do is get out of your daily stress.


Even if you don’t know an exact destination or location you can narrow to a general area. Think of the scenery that you want to wake up to in the morning, activities that you would enjoy during the day, food that you’ve been dying to try. You can break it down into smaller choices as well:

  • Beach or mountain

  • City hustle or relaxing resort

  • Places you’ve been or a new adventure

  • Domestic or international

  • Longer distance or short travel


For example, if you know you want to go to Mexico but are not sure which region, you can think about the landscape (rocky beach vs white sand), area experiences (shopping/cenotes/ruins/whale watching) and financial decisions (luxury vs budget). You will find that the Riviera Maya might be a better choice for your adventurous family of 5 to go to Playa del Carmen rather than the luxury vibe of Cabo.


WHEN To Go On Vacation?


Ya’ll, travel agents do not have the time nor the energy to research every day of the month to find you the best dates for your trip. Too many personal preferences come into play when making this decision so YOU need to have an idea of when you would like to travel. A few date ranges can be managed and price compared, but please don’t say “summer” or the month of March. Every time I’ve tried to accommodate these vague dates, the client always realizes there really are more specific dates they’ve had in mind that fit their schedule best.


Tip: If you have flexible dates you will still need to know what dates work for you but are flexible on your departure and arrival dates. This can sometimes be really helpful in accommodating your budget.


Things to consider when choosing when to go on vacation:

  • High season vs Low Season for the determined destination

  • Your personal calendar

    • Remember to check if there is an important meeting or school function you might be missing

  • Holidays

  • Budget

    • Budget can determine if you are planning a quick trip or an extended stay, if you want to go during high season or low season, experience holiday festivities and more!

  • Weather

    • Trying to get away from cold weather? Don’t mind going when it’s “wet season”?

How Much?


This question is usually the hardest for most to decide on, but also the most important.


Your vacation budget does not need to be set in stone when first planning your trip, but you do need to consider what is the best price range for you and the members of your traveling group.


Please, please do not say “whatever is cheapest.” A few reasons why this won’t work:

  1. Cheap does not equal good. No matter your vacation expectations, you are still spending your hard earned money. Don’t squander it by being unhappy with an unsatisfying hotel room or cheap transportation but a whole day lost of relaxing at the beach.

  2. Everyone’s definition of cheap is different. What you may consider a budget could be completely different than what I think of. This is also important to understand if you’re going with a group.

”Travel is the only thing you buy that makes you richer”

Tips:

  • A little research will go a long way. Do a quick search for flights so you know what your base price will need to be.

  • Consider what type of accommodations you’ll be happy with aka what amenities you need.

  • Do you want to stay in one spot or adventure out. Transportation and activities can add up, especially if you don’t budget it in.

  • Never spend more than you can afford

  • Think of the things you would rather splurge on and the things you would rather have a stricter budget for.

What do you want TO DO?


Asking yourself what you would love to do on your next vacation can help determine where and when you want to go on your trip, which will also assist your budget planning.


Examples of vacation to-do’s are:

  • Sightseeing a new city

  • See mountains and go hiking

  • Go to a new hotspot with nightlife

  • Snorkeling with exotic fish

  • Spa day

Even if you don’t want to do anything (leave me by the pool for the day!) knowing this can set your vacation expectations.



“A vacation is having nothing to do and all day to do it in.” – Robert Orben


What have your past EXPERIENCES been?


Knowing what you’ve liked or disliked in the past can greatly help decide what you want to do on this next vacation.


For example, on our last trip we scheduled our itinerary to the max and quite frankly some days were just too much. So, our next vacation is planned with more free time, more pool days and more drinks! I’m also the type of person that has a hard time deciding what I want but can easily eliminate the options that I don’t want and this information is just as helpful.


Go down memory lane with what made your last trip a good or bad experience:

  • Did you enjoy the hotel/resort/rental that you stayed at?

  • Were the food choices adequate?

  • Were there enough activities to do?

  • Did you have enough time to see the area?

  • Did you like flying/driving last time?

  • Do you want the same or different climate?

You don’t have to have all the answers or even know what questions to ask–that is why I’m here to help! But to curate the best vacation experience you do need to have an idea of where you want to travel, when you would like to go, what an ideal price range looks like and have a few thoughts on how you want to get the most out of your time and money.


The world is a big place but together we can discover the best destination for your next vacation!



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