Cycling past a small farm in Vietnam's countryside

Trip Planning Step 1: Define YOUR Perfect Experience

If you search “how to plan a trip,” you’ll find a zillion and one suggestions. But most trip planning tools skip over this MOST important first step: defining YOUR perfect travel experience. Without YOU and YOUR goal clearly in mind, your planning will be all over the map.

Trip planning 3-step process: infographic

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The #1 most important question to ask when planning a trip is THIS: “When I’m back at home, what will make me say, ‘Now THAT was a fantastic trip’?” 

Starting with the dream – the outcome you want – will be your compass to guide all the details of planning your trip and making decisions that’ll help bring that dream to life.

Then, consider what you know about your trip – and yourself. How will you prioritize between the time and money you have with the things you want to see and do? What do you already know about the trip you’re planning, and how will it guide the rest of your planning? How well do you understand your default travel style?

By the end of this post, you’ll be able to write at the top of all your travel planning documents the experience you’re planning for – which will make everything else fall neatly in line.


  1. Identify your GOAL: Your trip planning compass
  2. Prioritize your CONSTRAINTS: Time, money and activities 
  3. Clarify what you know: WHERE, WHEN and WHO
  4. Understand your default TRAVEL STYLE

After Step 1, there are only 2 more steps in the trip planning process:

Not quite ready to move from dreaming to planning? Create your EPIC travel bucket list!

1. Identify your GOAL: Your trip planning compass

Compass guiding you along the beach at sunset

Photo credit: Denise Jans from Unsplash.

Every trip starts with a dream; a fantasy. An experience you want to have.

So, trip planning should obviously start there.

FIRST: Ask yourself the #1 most important question in this entire post: “When I get back from my trip, what will make me say, ‘That was a FANTASTIC trip’?” 

Maybe life has been crazy, and you really just need to rest and recharge – or reset with an incredible adrenaline rush. Maybe you’re eager to explore and learn, immerse yourself in another culture, and meet new people. Or, maybe you really just want to create amazing memories with your family or friends.

Whatever comes to mind, write this at the TOP of your trip planning documents. THIS is your compass. To keep you steady and true as you plan all the fun – and very distracting – little details.

NEXT: jot down a few descriptors of the feeling you want to have while on your trip. (Yup, my husband would be rolling his eyes, but just go with it!) What’s the VIBE you want to capture from the destination? At one with nature? Glamorous? Sophisticated? Chill? 

THEN: make a simple list of the 3 most important things you want to see and do. If you only see and do these three things, will you meet your goal? If not, reevaluate them!

2. Prioritize your CONSTRAINTS: Time, money and activities

Trip planning constraints triangle: time, money, activitiesNow, this next step is about adding some practicality to your goal. I’m sorry. If only the sky were the limit (sigh).

But, this step is actually really helpful. By identifying your biggest constraints, you can make better planning decisions … which will lead to a better travel experience. 

Your ability to realize your goal (i.e. QUALITY) is impacted by 3 constraints: TIME, MONEY and ACTIVITIES. (If you’re into project planning, yes – this follows the project management constraints triangle!)

When you think about your goal – the experience you want on your trip – how will you negotiate between the time you have, the money you have, and the activities you want to see and do? Which two are your biggest constraints? I.e. most limited; most defined; most firm; most important.

Don’t get bogged down in budget details at this stage. Budget is always a constraint to some extent, so pick your two biggest constraints based on which will have the “last say.” Will money/cost stop you from adding a day so you can see your top 3 activities? If the answer is no, your top constraints are likely Time/Activities. If yes, your top constraints are Money/Time or Money/Activities. 

TIME/TIMING: Trip planning with limited time or firm timing

Are you limited on time to see everything you want to see? Maybe you can’t get all the vacation time you’d like. Or, you can only get time off during a specific season. Be prepared to sacrifice on cost or activities.

Here are some ideas to make the most of your time:

  • Spend the extra money to cut to the front of lines for things you really want to see or do.
  • Book a “highlights” tour to see a lot in a short amount of time. (Hop on/hop off bus tours are great for this; plus, they double as transportation.)
  • Pack snacks and meals (like bagels or sandwiches) to eat on the go.
  • Chop down your top 3 list so you can see 1 or 2 in depth.
  • Modify your top 3 activities to make the most of the timing of your trip.

MONEY/COST: Trip planning with limited money

Is money (or the lack of it) a key factor in what you see and do? You’ll likely need to sacrifice some of your time and activities.

Here are some ideas to make the most of your money:

  • Plan your trip during low season.
  • Wait for last-minute deals for what you most want to see and do.
  • Spend more time walking or taking public transit to get where you’re going.
  • Plan a few meals in.
  • Modify your top 3 list to free or cheap activities.

ACTIVITIES/SCOPE: Trip planning with must-do activities

Are there certain things you’re willing to spend a disproportionate amount of time or money on to experience to the fullest? If there are certain things you just have to see and do, you’ll need to give enough time and money to do them.

Here are some ideas to make the most of your activities:

  • Plan your trip during the best season to experience your top 3 list.
  • Schedule enough time off to take in everything you want to see and do.
  • Allow extra time in case you want to explore something more in depth.
  • Pay for better tickets or access to your top 3 activities.
  • Budget extra for conveniences or impromptu purchases that make the most of your top 3 activities.

Realistically, trip planning is a series of negotiations between these constraints to get to your “quality” experience. Deciding which hotel to book. How many meals to eat out and where. But before you get to these details in Step 2, consider how these constraints guide your planning process overall.

3. Clarify what you KNOW about your trip: WHERE, WHEN and WHO

Pins mark your destination on a map

Photo credit: Capturing the human heart from Unsplash.

Clarify what you know and don’t know about your trip to map out the boundaries for your trip planning process.

THREE KEY FACTORS to clarify at the beginning of planning your trip are: 1. WHERE you’re going; 2. WHEN you’re going; and, 3. WHO you’re going with.

How you answer each of these questions will help narrow down the experiences available to you. For example, visiting New York City with children will be very different than with your closest friends. As is visiting in summer versus winter.

If you know WHERE: Trip planning with your destination in mind

You have it in your head that you just have to visit a certain place. You might know who’s going with you and you might not.

If you know WHERE you’re going, here are some great questions to help you consider the experience you’re after:

  • Why do you want to go to this destination? What are you most excited to experience for yourself? For example, is it a certain vibe, like the Hollywood glamor of Los Angeles or the colorful diversity of New York City? Is there something specific you just have to see or do?
  • When is the best time to visit so you can see and do what’s most important to you? Are certain activities only available during certain seasons or days of the week?
  • Who would you absolutely love to see this place with? Who’d want to see and do the same things? Or, would it be more fun to visit this place alone? With a tour group?

If you know WHEN: Trip planning with your timing in mind

Many people can only vacation at certain times of the year because of work or school. Teachers are an obvious one, as are students and families.

Or, maybe you only travel during low season. The most affordable time to travel is typically just after Christmas and New Years. Early spring and late fall are also more affordable times. Just keep in mind that certain activities might not be available.

So, if you know WHEN you can go but are flexible on where, here are some questions to consider:

  • Where would be fun to travel to in the season you can go? Would certain places be super-fun over Christmas, or even in summer when there’s lots of tourists? Maybe especially fun when there’s lots of people? Is weather a factor, like hurricane season, rainy season, or extreme-cold winter season?
  • If you have a short amount of time, where could you go that would be fun and not feel rushed? Would you prefer to fly somewhere or finally explore a gem close to home? If you could only experience one or two things, what would they be?
  • Who could go with you at that time? Where would they want to go?

If you know WHO: Trip planning with your companions in mind

Or, maybe you’re planning a trip with someone specific: your family, your closest friends, or your retired parents. Or, maybe you’re heading out on your own.

Who you travel with – or don’t travel with – will have a big impact on the types of experiences you can have. If you’re traveling with specific companions, put them in the center of your planning; pick a destination and a time that you’ll all love. Make the most of what you enjoy doing together, rather than trying to squeeze your travel companions into a trip they’d hate. (Then you’ll just hate it, too. And maybe resent them for it. Don’t do it!)

If you know WHO you’re traveling with, here are some questions to start your planning off right:

  • What types of things do you enjoy doing together? What things don’t you enjoy doing together? Do you know their travel styles, preferences and limitations? (More on this in the next step.)
  • Where might you go that features the things you most enjoy together? What types of destinations fit your styles and limitations? Where wouldn’t be a good fit?
  • When would be the best time to go? Does it need to fit in with work schedules? School? 

Traveling with your MOM? Check out: 11 Practical Tips + 5 Reasons to Take that DREAM Mother-Daughter Trip Now

4. Understand your travel style: Preferences, rhythm and limitations

Meeting kids on a bike ride near Hoi An, Vietnam

Meeting kids in Vietnam

Now’s the time to take a closer look at YOU – your travel style. 

Your travel style will shift a bit depending on where you go (and why), who you go with, and limitations you face. However, everyone has a default style: how you’d travel if everything was up to you. So let’s look at that first.

Here are the top 3 questions to ask yourself about your travel style:

  • What do you look forward to MOST about a vacation? (Sleeping? Relaxing? Meeting locals or other travelers? Learning about the area?)
  • What do you hate doing on vacation? (Grocery shopping? Driving? Sleeping in?)
  • What do you tend to talk about most after a trip? (How much time you spent on the beach? What you saw? What you ate? Who you met?)

Now we’ll dig a bit deeper …

Preferences: How do you like to spend your time and money?

The most obvious way to define your travel style is your preferences – how you like to spend your time and money. 

So, what types of experiences do you prefer to spend your limited time and money on? Again, the destination and purpose of your trip will definitely clarify this more, but by default, you’ll have some preferences. 

Here are some questions on how you like to spend your time and money:

  • What are you willing to spend more money on? What are you NOT? For example, a nicer hotel in a nicer location. Cabs instead of public transit. Nice meals. Better tickets to your priority activities.
  • What are you willing to spend more time on? What are you NOT? For example, exploring something in depth versus scanning a bunch of things. Relaxing by the pool or on the beach, or people-watching at a cafe. Searching for your perfect travel treasures.
  • What types of activities make you happiest? Experiencing a new culture and learning something new. Pushing your limits on some crazy adventure. Surrounded by a busy urban center versus amazing scenery. 
  • How busy and pre-planned do you like to be? Action-packed days versus slow, relaxed days. Plan as much as you can, or figure it out along the way.
  • Do you like the thought of meeting locals and other travelers?

What’s your vacation rhythm?

Then there’s your daily rhythm. How you operate on vacation may be very different than at home, or it might be pretty similar. Some people love “stopping to smell the roses” while others love the whirlwind tours (I’m definitely the latter!).

Consider these questions about your vacation rhythm:

  • Do you tend to stay up late and sleep in, or go to bed early and wake up with the sun?
  • In the morning, do you like to get going right away, or lounge around with your first coffee? Realistically, how long does it take you to get ready?
  • When it comes to meals, do you need a big breakfast every morning? Would you rather eat regular meals or snack throughout the day?
  • In the evening, would you rather be out at a show or a pub, or relaxing back at your hotel?

What are your personal limitations?

Personal limitations are part of your travel style, too. I don’t like to think about limitations or the idea of them holding me back; but, acknowledging your limitations can help you account for them so your trip goes smoother.

Physical limitations can be obvious and not. For example, I’ve learned that I get pretty grouchy when I’m dehydrated; so now I always carry water with me (or better yet, a sports drink).

Here are some questions to consider about your limitations (and ideas to address them):

  • Does jet lag hit you hard? Plan a day to relax when you arrive.
  • Do you get bad car sickness from twisty roads? Maybe sit out that crazy road to Hana tour in Maui or plan a lot of stops.
  • Do you get tired with too much walking? Let a taxi, hop on/hop off bus, or carriage ride do most of the work for you … plus lots of coffee shops.
  • Do you get cranky if you don’t eat, drink or sleep enough? Plan to eat, drink and sleep more … and warn your travel companions to tell you when you need more!
  • How much quiet or solo time do you need? At what times during the day?

Your travel style is likely to evolve – and be refined – over time, different travel experiences, and changing life circumstances. I encourage you to reevaluate your travel style before planning each trip.

Remember to SHARE this post with your TRAVEL COMPANIONS!

Summary and Resources

Too many trip planning tools completely skip over this first step of defining your perfect travel experience. But, before you can get what you want, you have to KNOW what you want!

Taking even five minutes to consider your answers to the sections above will help you build a more cohesive, super fun trip.

If you’re traveling with others, I encourage you to at least talk through the points above with them, too (not a chance would my husband actually do it himself!). Get a sense of what you’re dealing with before you start building it out.

Practice thinking through the travel experiences YOU want … create your travel bucket list!

Travel personality quiz!

Here’s a fun way to end this post: has a short and fun trip matcher quiz to get you dreaming. It matches you up with a travel experience: a destination, accommodation options, fun activities and places to shop. It’s worth a few minutes for some inspiration!

(Apparently my mantra is, “never stop growing;” that’s definitely me!)

Continue to Step 2 and 3 of the trip planning process:

Or, take a look at an example of how to plan your trip based on the experience you’re looking for:

Trip planning 3-step process: infographic

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