How To Plan A Trip: Important Questions To Guide You

July 11, 2021
how to start planning a trip,how to plan a trip

I’ve done several posts focusing on different aspects of how to plan a trip, but this one is following the immortal advice of Fräulein Maria (you know you want to sing it…)

I wanted to back up and focus on the very beginning stages of how to plan a vacation or trip (yes, there’s a difference), particularly when it’s your first time, or when you’re not fully sure of really critical details…you know, like where to go, when you want to travel, what your personal “travel style” is.

In other words, this is focused on how to START planning a trip.  As I’ve mentioned before, an amazing trip depends on what it means to YOU, what you were hoping to get out of it.  A chill long weekend vegging out at the pool can be just as perfect as a week in Thailand—it’s all about the expectations you had and what types of things you enjoy.

How to Plan a Trip: Important Questions to Help Guide You | If you're wondering how to plan a vacation or trip, these key questions will help inspire you and guide you through the process...from identifying your travel style, where to go, how flexible you are, and more. Trip planning tips and travel itinerary planning to start planning a trip now!

And while I wish I could simply give you a formula for how to plan a trip, every person is different.  I can’t tell you what *you* or the people you’re traveling with will love.

Instead, over the years I’ve identified some key questions that you can ask yourself to help guide your decisions and help you get to the most enjoyable version of your trip possible.

This is part of a series on how to plan epic trips.  I’ve linked to the others at the bottom of this post, and you can also download my free e-book for dozens more trip planning tips on flights, housing, itinerary, and more!

How to plan a trip: questions edition

Hopefully these questions will really get your brain juices going and help you narrow in on the travel ideas that really excite you.  If you’ll be traveling with other people, they make great conversation starters as well.

What is your travel style?  What do you love and hate?

This really can be summed up in “know thyself”.  There is no one right way to travel, or right kind of trip.  Do you like a jam-packed itinerary and seeing as much as possible?  Do you like to make sure you have plenty of time to just chill and drink some coffee while people-watching?

If you know your personal travel style well already, then my advice is not to ignore your gut when planning.  For example, I sometimes try to convince myself that I like more raw, “roughing it” type trips in less-developed countries, and while they can be valuable experiences, they never are my favorites.

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When I ask myself these questions, I have to acknowledge that I’m not into big cruises, camping, museums, or (generally) group trips/tours.

I like to splurge sometimes on luxury, unique, or adventure options on many of my trips.  I prioritize food and drink exploration, beautiful architecture and landscapes, with self-guided, fast-paced travel that almost always includes alcohol 🙂  I always look for a way to be on a boat, and I occasionally love a lazy beach vacay.

If you DON’T know your travel style, it’s really worth it to try and figure it out.  Some of that is trial and error, experimenting as you travel.

For example, the next time you’re going somewhere (even if it’s just a quick local weekend trip), choose one activity that you’d normally never think of.  A cooking class, a segway tour, a boat trip, visit an offbeat museum, stay in a different type of accommodation for a night…you get the drift.

Having it be just one element of your trip makes it lower-commitment in case you don’t enjoy it.

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What do you want out of the trip?

Beyond just your personal travel style, it’s important to know what you want out of the trip.  If it’s amazing photos, then rainy season can be dicey.  Is it pure relaxation, parking yourself under an umbrella at the pool?  Adventure?  An epic story you can tell friends later?

Are you traveling alone or with a companion, or trying to coordinate a bigger group (whew, let me tell you about the logistics of family trips…!)??  That will impact everything from housing options to transportation logistics, so take that into account very early on.

As an example, I was planning a (sadly aborted) Greek Isles trip with my aunt and two cousins, but then she asked about inviting all our other aunts and uncles…I was like WHOA okay, island hopping and all the logistics on tiny islands may not be the best idea with 8+ people, so let’s look at a different destination.

Are you already set on a specific place?  Sometimes the hardest thing to figure out is where you want to go.  If you’re hardcore dreaming of a getaway to Bali, that’s one thing and quite specific enough.  But if it’s more vague like “I really need a beach vacay” or “an amazing girls’ trip”, then you’ve got some more work to do.

How to Plan a Trip: Important Questions to Help Guide You | Trip planning tips and travel itinerary planning to start planning a trip now!

You might also like:  A Travel Bucket List for Your 30s

Where do you want to go?

This is almost a subset of the previous one, because the two go hand-in-hand.  Do you have a specific destination in mind or are you a bit lost on WHERE to go??

I go into greater detail on some tips that can help you choose a destination in my post on my travel planning process, but here are a few initial thoughts.  First, I always recommend keeping a running list of places you’d like to visit…anytime you read an article, a friend gives you a recommendation, etc., just throw it in a running Word doc or email draft.

You can also do Google and Pinterest searches for specific attributes (e.g. “chill solo beach vacation”, “south american itinerary using public transportation”, “best roadtrip itineraries in Europe”).  I use Google Flights “map search” sometimes when I know my dates but not where I’m going.

Obviously in the world we live in right now, specific COVID testing/vaccine/quarantine requirements are a critical factor in where you can go, so make sure to research that as well.  I’ve found this constantly updated post from Smarter Travel helpful.

How to Plan a Trip: Important Questions to Help Guide You | One Girl, Whole World

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How flexible are you?

This is super critical, and now we’re starting to really get down to brass tacks.  Ideally you’ve chosen a destination, but even if you’ve narrowed it down to a few, it’s now important to “pressure test” what’s feasible and what will fit your needs best.

One aspect is timing…are you set on exact dates or even an exact time window?  How much time can you take off work, and is there a day or two of wiggle room?  These all affect how you search for flights and what flight times and dates will work for you—and obviously affects costs.

Are you okay with shoulder or off-season to avoid crowds?  Or are you wanting peak season due to a specific event (e.g. cherry blossoms in Japan) or ideal weather (like avoiding monsoon season in southeast Asia)?

Another thing that impacts both costs and timing is whether you prefer to go as direct as possible, or if you can accept longer travel times and more layovers to get better deals.  Again, asking yourself all these questions as you plan can help you hone in on the best times and right costs for your specific needs.

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How open are you to winging it a bit?  

Personally I believe you want to go “off script” sometimes.  If you only approach travel as checking the boxes on someone’s “must do” list, then you’re going to miss out on some amazing experiences.  But this goes back to knowing yourself—for some people, the idea of that is really stressful.  I still recommend doing it in some way though!

It might be as simple as stopping on a road trip whenever something takes your fancy (for me, that’s basically any roadside farm or food stand), or building time in your itinerary to just wander little streets or sit at a café with a drink and people-watch.

This is also why you don’t want to cram your itinerary so tightly that you don’t have any room to let things just…happen.

I’ve had so many absolutely delightful experiences that were unplanned, where I went with my gut.  From a whole day spent exploring a local’s favorite spots in Costa Rica, to discovering a ruined castle on a seaside cliff in Scotland or stumbling upon the best rooftop bar in Lisbon, I’ve never regretted having time built into my itinerary to seize on a local’s recommendation or great find.

But you don’t ONLY have to wait for things to happen.  When I’m researching before a trip, I always do some searching for “unique things to do” or “local secret favorites” in wherever I’m going.  Take a chance on something that doesn’t have gobs of reviews, an interesting cultural experience, or something outside your comfort zone.

how to start planning a trip...questions like how to make time for spontaneity

What does epic mean to you?  

This is closely related to the previous point.  As I discuss further in my post on how to many any itinerary at least a little epic, “epic” means something different to everyone.  And to me, even something different depending on the trip.

The question to ask yourself could be…when I come home, what types of experiences will I love telling people about??  It might be a cool secret thing, a big bucket list adventure, or an accidental find.

Epic might be splurging on something really well-known but expensive…a luxurious afternoon tea in London, a glacier boat trip in New Zealand, the Norway in a Nutshell fjord tour, or snorkeling between continents in Iceland.

Or something that just takes more effort to plan or get to…like seeing Petra lit up by hundreds of lanterns at night, marveling at Argentine’s Iguazu Falls, or taking a boat to Scotland’s tiny epic Isle of Staffa.

For me it also often means finding a bucket list item to experience while I’m there…seeing the Northern Lights, sailing along Turkey’s coast, or going on an African safari (which I’m still dying to do!).

But “epic” doesn’t have to mean massive or expensive.  Trips can be epic in many small ways.  I love taking a small-group walking food tour in a new city to explore the cuisine.  Often transportation can add a unique twist, like a cool train ride or even hopping on a ferry for a different view.  Getting out into nature, maybe for a beautiful hike, is great.  Or staying in an interesting residential neighborhoods.

Just do something that you’ll want to tell people about later!

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Now, what do you need to know?

To be fair, this is less about getting started, and is further down the process of how to plan a trip, and I have a separate post outlining my own process from inspiration to realistic itineraries.

But once you’ve either settled on a destination and time, OR when you’re getting close and just need help deciding, there are some amazing resources out there to help—particularly the TripAdvisor forums.  In most cases you won’t want to start asking the forum questions *too* early in your planning process.  There are two main reasons for this.

First, if you go on there just asking super generic questions (“what should I do in Paris?”) without having done your own research, the forum folks will get annoyed with you because they can’t really help and you’re just wasting their time.  Second, you need to have a good idea of what you’re looking for/trying to do before their advice will be useful to YOU.

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So I’d say seek out advice…but take it with a grain of salt.  Obviously everyone will have their own experiences and opinions, and they can be helpful but only you know what truly works for you.

As an example, I often get told that my itinerary is too ambitious and I’m trying to cram in too much, that I’m going to feel rushed.  But go back to question #1—I know myself well enough to know that my “normal” speed is most people’s “rushed”, so I thank them for their input, take specific ideas to tweak it, and move on.

Here are examples of the types of questions/advice that can be especially useful in the TripAdvisor forums:

  • “Here is the rough 4-day itinerary I’m thinking, can you help me figure out what doesn’t work or any additions?”
  • “I’m trying to figure out whether to fly into Rome or Florence for this itinerary, which would you recommend?
  • “Need help with clarity on visa requirements & customs process in Argentina”
  • “Best ways to get to Cappadocia that aren’t flying, within 10-day Turkey itinerary”

As you can see, make sure you already so some research and have info for them to react to, and then ask questions with some specificity.  Plus, make sure you give them any pertinent info about yourself, your travel companions, likes/dislikes, and budget.

how to start planning a trip,how to plan a trip

So now that we’ve talked about the big questions that can help with how to start planning a trip (INSPIRATION), the posts below dive into the actual PROCESS I use and how I plan individual elements of my trip!

My Travel Planning Process: Inspiration, Research, & Realism

How to Find (& Choose) the Right Flight For You

How to Pick the Perfect Hotel or Rental Every Single Time

How to Create Epic Itineraries…Whether Weekend Getaway or Bucket List Trip

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How to Plan a Trip: Important Questions to Help Guide You | If you're wondering how to plan a vacation or trip, these key questions will help inspire you and guide you through the process...from identifying your travel style, where to go, how flexible you are, and more. Trip planning tips and travel itinerary planning to start planning a trip now!

Comments (1)

  • Elina Brooks

    April 5, 2023 at 4:13 am

    I love traveling to different countries with friends, but this year, I have decided to go on a solo trip for the first time and chose Kenya as my destination. I’m thankful you told us to also be flexible during our trip since approaching travel as checking boxes on a to-do list will make us miss out on amazing experiences instead. I’ll make sure to keep this in mind while I look for a Kenya vacation planner to hire and help me with the preparations I need for my trip.

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