Wondering how to start planning for a trip? 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.
The #1 most important question to ask when you start planning a trip is THIS: “When I’m back at home, what will make me say, ‘Now THAT was a fantastic trip’?”
This vision – the outcome you want – will be the compass to guide all decisions in the trip planning process. And these decisions are the details that’ll make your vision happen.
How you start planning for a trip can make it easier or harder to get the trip you want. So, take the time to seriously think about what you want. How can you make it happen, given your travel constraints? Your travel companions?
The post below walks you through this.
- Identify your GOAL: Your trip planning compass
- Prioritize your CONSTRAINTS: Time, money and activities
- Clarify what you know: WHERE, WHEN and WHO
- Understand your default TRAVEL STYLE
Still stuck in the dream phase? Create your EPIC travel bucket list!
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1. Identify your GOAL: Your trip planning compass
Every trip starts with a dream; a fantasy. An experience you want to have.
THIS is right where you should start when planning for a trip.
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 you’re craving some rest and relaxation. Or maybe an incredible adrenaline rush. Are you eager to explore and learn, be immersed in another culture, and meet new people? Or to create amazing memories with family or friends?
Whatever comes to mind, write this at the TOP of your trip planning documents. This is your compass to guide all your decisions. 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, re-evaluate them!
Get Your FREE Trip Planning Template when you subscribe to our email list. A 6-page fillable PDF that walks you through steps 1-3.
2. Prioritize your CONSTRAINTS: Time, money and activities
Now, 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 in how to start planning for a trip. By identifying your biggest constraints, you can make better planning decisions to make the most of what you’ve got. And this will lead to a much better travel experience.
Your ability to realize your travel 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. Yup, I know I’m a planning geek. But it works!)
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. But you should pick your two biggest constraints based on which will have the “last say.” If adding a day to your trip is the only way to see your top 3 activities, would you add a day? If the answer is yes, your biggest constraints are likely Time and Activities. If no, your biggest constraints are likely Time and Money or Activities and Money.
Below are ideas on how to start planning for a trip, based on your biggest constraints.
TIME/TIMING: Trip planning with limited or firm timing
Are you limited or locked in on the time you have for your trip? 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? Will it stop you from staying longer, or from seeing your top 3 list? You may need to sacrifice on time/timing 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 MUST see or experience to the fullest? If yes, be prepared to sacrifice some time and money to make them 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
Clarify what you know and don’t know about your upcoming trip. This gives boundaries to your trip planning process … very helpful when you start planning for a trip.
THREE KEY FACTORS to clarify when you start planning for a trip: 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 in summer will be very different than in winter. As is visiting with children versus your closest friends.
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 when you’re going and who’s going with you, or you might not.
Questions to ask if you know WHERE you’re going:
- Why do you want to go to this destination? What are you most excited to see or experience for yourself? Is it a vibe you’re after, like Hollywood glamor on your first time to Los Angeles? The colorful diversity of Queens in New York City?
- 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.
Questions to ask if you know WHEN you can go:
- Where would be fun visit in the season you can go? Have you always wanted to experience Christmas in a certain place? Would certain places be super-fun in summer when there’s lots of tourists? 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. Close friends. 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. Make the most of what you enjoy doing together, with timing that works well for everyone. Don’t try 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!)
Questions to ask if you know WHO you’re traveling with:
- What types of things do you enjoy doing together? What things don’t you enjoy doing together?
- Where might you go that features the things you most enjoy together? 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
Now’s the time to take a closer look at YOU – your travel style. How to start planning for a trip includes a little reflection on what you like and don’t like.
Your travel style will shift a bit depending on where you go (and why), who you go with, and limitations you face. But everyone has a default style: how you’d travel if everything was up to you. So let’s look at that first.
And yes. It’s a good idea to discuss your answers with your travel companions!
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 something?
- What do you hate doing on vacation? Grocery shopping? Driving? Getting up early?
- 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 …
Your travel preferences
The most obvious way to define your travel style is your preferences – how you like to spend your time and money.
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.
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?
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!).
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?
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 limitations right when you start planning for a trip allows you to account for them. So the actual 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.
Questions 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. And plan for people-watching at coffee shops.
- Do you get cranky if you don’t eat, drink or sleep enough? Plan to eat, drink and sleep more. And come up with code phrases your travel companions can use to gently 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. Time, travel experiences, and life circumstances tend to do this. I encourage you to re-evaluate your travel style as part of how you start planning for each trip.
Get your FREE Trip Planning Template! This 6-page fillable PDF walks you through steps 1-3.
Summary and Resources
Too many trip planning tools and processes completely skip over this first step. How to start planning for a trip MUST include defining the travel experience you want. Before you can get what you want, you have to KNOW what you want!
Even just taking five minutes to consider the sections above will help you build a more cohesive, super fun trip.
If you’re traveling with others, it’s a good idea to discuss the points above. Even better: go through them individually, and compare and negotiate afterwards. Get a sense of what you’re dealing with BEFORE you start planning for your trip.
Consider the travel experiences YOU want … create your travel bucket list!
Travel personality quiz!
Here’s a fun way to end this post: AirBnB.com 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 the trip planning process with steps 2 and 3:
- Trip Planning Step 2: Build Your Itinerary and Book
- Trip Planning Step 3: Count Down with Your Ultimate Checklist
Or, take a look at an example of how to plan your trip based on the experience you’re looking for:
- Comparing Maui’s 4 popular places to stay: how the place you stay can make or break your trip.
- Finding your ideal NYC experience in this 3-part series.
- Seeing 5 VERY different sides of Montreal on this 5-day itinerary.
Remember to SHARE this post with your TRAVEL COMPANIONS!