5 CRITICAL Questions to Ask Before Planning Your Next Vacation

Photo of Antoinette thinking.

I’ve planned my own vacations for almost two decades to destinations inside and out of the United States and have enjoyed solo, couple, family, and group trips. Every trip is unique; but one thing I learned is if you fail to gather the right Information at the start of the trip planning process, things can go south VERY quickly. That’s why, in this blog, I’m sharing with you five CRITICAL questions to ask before planning for your next vacation along with important things you need to consider.

This is the second post in my How to Plan a Vacation series. If you haven’t read the first post, Five Reasons Why You Need to Start Planning for Your Trip NOW, definitely check it out before continuing with this post.

If you’re ready, grab a pen, paper, tablet, journal, phone, or whatever you need to follow along and take notes because you’re going to want to write this information down or just copy/paste it all from here.

WHERE Do You Want to Go?

Photo of A path along South Beach Miami Florida by Frolic and Courage.
Warm, tropical destinations are my locations of choice!

There are three major types of trips. Local trips are less than a two-hour drive from where you live. Domestic trips tend to be a little further out, at least three hours or more from where you live. They can also take you out of state or anywhere within your country of residence. Lastly, there’s the massive International vacation that take you to an entirely different country. Often called a trip “abroad” or “overseas”.

When deciding where to go, calculate how much time off you have and see if it aligns with your desired location. Local or domestic trips are great for short-term trips (can also include long-term travel, too) or if you have limited time. International trips, however, are best suited if you have at least 3-4 full days up to a few weeks depending on the destination. Most travelers find the longer the distance traveled, the longer the trip needs to be so they can spend more time enjoying the destination instead of in transport getting there.

Here are a few things to consider in deciding where you want to go:

  • Will I hop around to visit multiple locations or just visit one?
  • How long will this trip be? Just a quick weekend adventure? A whole week? A couple of weeks or months?
  • Is my destination primarily indoors or outdoors?
  • Do I prefer to visit a major city, mountains, water, countryside, or travel off the beaten path?
  • Do I have the resources available to visit this destination? Do I need a visa in order to enter this location? Are there certain immunizations I need to schedule in advance? Will this location require a currency exchange?
  • What cultural knowledge must I obtain before my visit? Do I speak the language or am I willing to learn a few key words or phrases?
  • Do I have the right equipment (camping gear, weather-proof clothing, shoes, etc.) for this trip?

Knowing where you want to go is the first of five CRITICAL questions to ask before planning for your next vacation because everything else is centered around the destination.

Now here’s the second.

WHO Are You Going With?

Photo of Hun and in South Beach, Miami by Frolic and Courage.
Who you travel with is everything!

Knowing who you are going with helps shape the overall experience you’ll have and informs cost. People have unique quirks, habits, and their own preferences. Travel has a funny way of bringing out ones personality in, hopefully, the best way possible. At a minimum, you want to know how many people are traveling with you and what are their needs? First, I’d ask myself: Is this vacation going to be a solo trip or a group experience?

If it’s a solo trip, planning will be a breeze! You are the decision maker and don’t need to consult anybody on any aspect of your trip; just be safe and enjoy doing what you want, when you want! I’ve had the honor of taking many solo trips, most notably to my bucket list destination of Paris, France swiftly followed by Madrid, Spain and absolutely LOVED it! Solo traveling, to me, will always be the best form of travel because of the freedom and flexibility you have. It also challenges you to be strong, saavy, and truly understand who you are.

Then we have the group trip. Group trips are kind of like group trips in high school – there are a select few over-achievers that actually do the work while others either reap the benefits or complain. Just kidding (kind of). If you are traveling with other people it helps to have the same travel style or know that you may need to compromise in order to maximize everyone’s experience.

What to consider:

  • Am I traveling with family, friends, or a significant other?
  • How old are my travel companions? Are they older, around 70+ years old? Kids? Same age as me? Will this be a girls or guys trip only, or maybe adults only? Will the vacation include teenagers who tend to get bored easily or babies & toddlers who need naps and strict feeding schedules?
  • What are the personalities of those in my group? Who are the introverts and extroverts? Which are the planners vs. go-with-the-flow-ers? Who is open to new experiences and who needs more encouragement in order to try new things? Are they quick to anger? How do they handle change or things not going their way (or according to plan)?
  • How will each of these individuals interact with each other on this vacation? Will they get along or can I already identify points of friction?

Once you have a good idea of the group (or solo) dynamic, it’s time to talk about money. Who is funding this vacation? What is YOUR budget? What is theirs? Are you traveling with spenders or savers? How much is each party willing to spend and who will pay for what before and during the vacation? Will this trip cause you to go into debt or place you under any financial distress? Do you honestly have the money for this trip? Are you comfortable with the answers to this question?

In addition to finances, there are other important things to consider. Are there any health or mobility concerns or dietary restrictions that can impact the decisions you make for this vacation? What about pets? Are animals going you on this trip? What are their needs?

Knowing WHO you are going with informs what you do, when you do it, where you eat, and where you stay. So…who do you REALLY want to go with on this trip? Think about it, consider all the questions posed in this section, and make a decision early on.

After determining WHO you are going with (if anybody), now it’s time to ask, WHEN you want to go.

WHEN Do You Want to Go?

Photo of the Perfect Day at Coco Cay sign by Frolic & Courage.
What season is your perfect traveling day in?

Knowing when you want to travel is important because there are peak and off-peak seasons that come at different prices and with varying levels of comfort. You are likely to pay more if you travel during a peak season or at the last minute. Are you and your traveling buddies ok with this? Or maybe it doesn’t matter? You decide.

What to Consider:

  • Do you have specific dates in mind or are you flexible?
  • How much time off do you have to visit? What about your companions?
  • Is this a last-minute adventure or do you have more time to plan?

Since we are talking about when you want to go, weather can enhance your mood or spoil it – and everyone has a different definition of what the “perfect temperature” is. I was born and raised in sunny San Diego, California so warm weather is a MUST for my travels. To me, the “perfect” traveling temperature is between 67-80°F. I know other people who love the rain or feel happiest when fresh snow is falling from the sky.

Ask yourself: what season am I most comfortable traveling in? Is it Fall, Winter, Summer, Spring? If traveling with others, what temperatures are they most comfortable in? Summer & Fall are mine, but what’s the perfect season for you? Drop your favorite season to travel in the comments below! A few more questions to consider:

  • Are you traveling to attend a particular activity, festival, holiday, or event, such as a wedding, graduation, funeral, summer break, etc.?
  • Are these dates during peak season or off-peak season?

Deciding when you want to go on your trip and giving yourself time to plan in advance can really set you up to have a debt free vacation. I like to plan 6-8months up to a year in advance so I can have the experience I want to have. In determining when you want to travel for your trip, think to yourself: Do you and/or your traveling crew have money readily available to book NOW? Or do you need time to save? What will my experience be at this time of year?

Speaking of experiences, the next of the five CRITICAL questions to ask before planning for your next vacation is…

WHAT Type of Vacation Experience Do You Want to Have?

Photo of a red curtain at Palais Garnier in Paris France by Frolic & Courage.
What if you want a luxury travel experience and your companions do not?

We all have an idea of what we want to experience, but planning helps make it a reality. As your resident practical travel planning pro, I live to answer this question! Knowing what type of vacation experience you want to have will guide you towards where you visit, the activities you will participate in, and how much money you need to do it. 

What to consider:

  • What is your idea of recreation? What allows you to recharge? What nourishes you? What have you always dreamed of doing at this destination? If you don’t know, research!
  • What type of traveler are you? Luxury? Backpacking? Outdoors? Food? Adventure? Culture? Photography? Do you travel for relaxation, health, or spa treatment?
  • Do you want an all-inclusive experience like at a resort or on a cruise ship, or do you prefer to be amongst the people?
  • Do you travel at a fast pace to see it all or do you enjoy slow traveling at a leisurely pace?
  • Will this be a technology-free trip? Do you expect your traveling buddies to be disconnected as well?
  • Are you an early riser or do you like to go to bed late? Can you tolerate large crowds or thrive in the nightlife scene, or do you prefer quiet space?
  • Do you want to dine in luxurious 5-star restaurants or are you comfortable with street food? Maybe a mix of everything? Do you like to have three meals a day, more, or less?
  • How do you want to get around? Are you ok with public transportation? Taxis only? Private car? Do you even want to rent a car to drive? RV or camper van? Boat? Train? Are you comfortable flying on an airplane? Do you mind walking most days?

If you are traveling with others, do their expectations and comfort level match yours? If so, great. If not, are you willing to compromise? Be really intentional and ask everyone involved in the trip, “WHAT type of vacation experience do you want to have?!” Asking this question BEFORE you book anything can set the appropriate expectations for everyone – they’ll know exactly what they are getting into and what they’re paying for. Doing this AFTER you book or not at all can lead to great disappointment, stress, and frustration on what is supposed to be a vacation.

If your expectations don’t align, consider branching off on your own or planning a trip with those who are in alignment with you. If that’s not an option, you can still travel with the group but be ok with branching off and doing your own thing or prepare to be VERY patient with others.

Like I mentioned before, we all have preferences. Those special preference are likely to be illuminated as you navigate what experience you want to have. this is why the 5th critical question to ask before planning your next vacation is, arguably, the most important.

WHY Are You Going on This Vacation?

Photo of Antoinette wearing an apron at A Punto cooking school in Madrid, Spain.
Answering the “why” question helps you to stay focused when planning for your vacation.

Knowing WHY you want to travel to a particular destination is important because it helps provide clarity when deciding between a wealth of options (and trust me, there are a LOT of options!). It helps you focus on what you want and allows you to navigate through the tedious details of travel planning. It will help sustain you through the ups and downs of the planning process. Knowing WHY you’re going on this trip paints a bigger picture that can shape your experiences and energize you to take action!

What to Consider:

  • Out of all the places in the world, WHY are you traveling to this specific place?
  • WHY do you want to spend your money and time at this destination?
  • WHY are you so inspired to take this vacation?
  • WHY is it important that you go at this particular time?

Everyone has a “why” that drives them. While in London, Hun and I met a middle-aged female solo-traveler. She was friendly, yet a bit reserved and unsure of her place in the group. After our evening bike tour the group started talking about their “why” for London that came in the form of “what brings you to London?” She mentioned quietly to me that she was a wife and stay-at-home mom of a son who just graduated high school and was off to college out of state.

Shortly after graduation, her husband filed for divorce in favor of his secretary, stating he was “only with her because of the kid” and now that the kid was gone, he “did his part.” This short, blonde-haired, meek woman was grieving the loss of her marriage, her newly empty nest, and of her identity. What does this have to do with London? She came to London as the first stop in a three-month trip around the world. She lost her identity and needed to re-discover who she really was outside of these roles and labels she clung so desperately to for the past 18 years. Solo travel, to her, was a means of discovering her true self and the strength she kept hidden inside.

Travel cannot fix your problems, but it can offer you the opportunity to grow, test your limits, and challenge assumptions about yourself and other cultures. When you take a vacation, you come to realize that the world is so much bigger and greater than your tiny corner of the earth. It thrusts you out of your comfort zone then looks you straight in the eye while asking, “what are you made of?”. Out of all the 5 critical questions to ask yourself before planning a trip, answering WHY can be the most powerful…and the one you want to ask yourself first.

Along with why, I’m also going to sneak in a bonus question for thought:

What’s Holding You Back?

I am a zealous advocate for travel, but I wasn’t always this passionate. In fact, I never thought of traveling for a long, dark period of time in my life shortly after college. For years I believed I needed to wait for the right person or people to travel with me. I believed I needed at least $7-10k to go on a European vacation for a week. I believed I only had the time for one vacation a year or maybe every few years. I believed travel was great for other people, but not for me because I didn’t know where to start. Now I know those were lies based on fear, a lack of knowledge, and limiting beliefs.

What’s holding you back from traveling? Is not having enough money holding you back from travel? In this post-pandemic world inflation is at an all-time high, people are resigning in massive numbers, and transportation is insane. I understand travel may be the least of someone’s concerns, but that hasn’t stopped many from fulfilling their dreams.

If money is an issue, try creating a savings plan and set aside whatever money you can, big or small, until you have enough for your trip. You can also responsibly leverage credit card points, search for affordable accommodations, and take advantage of free or reduced price activities to save money. Consider your timing – instead of going now, set your expectations on a future date. I can personally vouch for this because I saved for ONE YEAR to take my 6-day trip to Paris. I want you to know that it is possible for you. I have posts on how I created a monthly budget and how I planned my grocery budget. Managing my finances helped me achieve my travel goals and it may be useful to you, too. If I can do it, so can you! to help you reach your goals.

Is getting time off work a challenge for you? If so, travel around holidays or plan far in advance so you and your employer can make arrangement for your absence. Even if it’s just one or two days, use your vacation time wisely and narrow your activities to those you are most interested in doing or seeing.

What about your health? Do you have a medical condition or diagnosis that prevents you from traveling? Take time to recover and use travel planning as your motivation to stay consistent with your treatment and recovery plan. When you’re healed, you’ll have an awesome trip planned and ready to go! While planning, look for unique, safe solutions to have the best experience possible.

Everyone’s situation is different, but if you can break through any fears or limiting beliefs, you might just have the trip of a lifetime!

Once you’ve answered these 5 questions, now it’s time to actually start PLANNING your trip! In my next post, I’m going to give you an exclusive behind the scenes look at how I actually plan my travels, plus share the resources and tools I use to keep everything organized.

In the meantime, check out the five CRITICAL questions to ask yourself before planning for your next vacation video and let me know which of these 5 questions do you need to spend more time thinking about in the comment below!


Antoinette | Frolic & Courage

You may also like these, too:

Leave a Reply

Your email address will not be published. Required fields are marked *

Discover more from Frolic & Courage

Subscribe now to keep reading and get access to the full archive.

Continue reading