Where To START Planning a Vacation: The Experience

Wondering how to start planning for a trip? Where you should start planning a vacation is with the EXPERIENCE you want. This is the most important step in getting a trip you’ll love.

Most trip planning processes skip over this first step. But how else can you align your travel planning decisions, if you don’t first define the outcome you want?

This vision will be the compass to guide all decisions in the trip planning process. And these decisions are the details that’ll make your vision a reality.

So, take the time to seriously think about what you want.

The post below walks you through this.

Where to START Planning a Trip: Define the Experience

Start planning a vacation with the end in mind. Then, consider how key factors will affect the experience you want, and plan for them.

Here’s how to start planning your trip with the experience in mind:

• Articulate your GOAL: What’s most important?
• Identify your PRIORITIES and CONSTRAINTS: Time, money and activities 
• Clarify what you know: WHERE, WHEN and WHO
• Understand your default TRAVEL STYLE

Once you clearly define the travel experience you want, you’ll build your travel itinerary and book the key pieces. Then, use our ultimate vacation countdown checklist to get out the door without forgetting a thing.

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1. Articulate your GOAL: What’s most important?

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.

Begin by asking yourself the #1 most important question when you start planning a vacation: “When I get back from my trip, what will make me say, ‘That was a FANTASTIC trip’?”

Are you craving some rest and relaxation? An 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.

Then, write down how you want to feel on your trip. (Yup, my husband would be rolling his eyes, but just go with it!) What’s the VIBE you want at your destination? Glamorous? Low-key? Adventurous?

Next, 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. A 6-page fillable PDF that walks you through the entire travel planning process.

2. Identify your PRIORITIES and CONSTRAINTS: Time, money and activities

Now, this next step in starting to plan a vacation will add some practicality to your goal. (I’m sorry!)

But, this step is actually really helpful in how to start planning for a trip. By identifying your biggest priorities and constraints, you can make better planning decisions to get the most from your trip. And this will lead to a much better travel experience.

Your ability to realize your travel goal (i.e. QUALITY) is impacted by three constraints: TIME, MONEY and ACTIVITIES. (You’ll recognize this model if you’re familiar with project planning. Yes, you can use it to create the best travel experience ever!)

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 most want to see and do? Which two are your biggest priorities or constraints? Are some most important, firm, or very limited?

Don’t get bogged down in budget details at this stage. Budget is always a constraint to some extent. You should pick your two biggest constraints based on which will have the “last say.”

If the only way to see all of your top 3 activities is by adding a day to your trip, would you do it? If yes, your biggest priorities are likely Activities and Time. If no, your biggest priorities are likely Time and Money.

Below are ideas on how to start planning for a trip, based on your biggest priorities and constraints.

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 from work. 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. They also 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. This might mean #4 replaces one.

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.

Trip planning with must-do ACTIVITIES

Are there certain things you MUST see or do to get that experience you identified when first starting to plan your vacation?

If yes, be prepared to sacrifice some time and money to make them happen.

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, planning a trip is a series of negotiations between these priorities and constraints to get to your “quality” experience. Deciding which hotel to book. How many meals to eat out and where.

Get a sense of how these will affect your decisions at the start of planning a trip.

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

Clarifying what you know and don’t know about your upcoming trip gives you boundaries to your trip planning process. Very helpful when you start planning a vacation.

Clarify THREE key things when you start planning a trip: WHERE you’re going; WHEN you’re going; and, 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 traveling with your kids compared to your best friends.

Trip planning if you know WHERE

At the start of planning a vacation, you may already know where you want to go. You’ve been dreaming of a specific travel destination and you’re ready to make it happen.

Maybe you know when you’re going and who’s going with you, or maybe you don’t.

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?

Trip planning if you know WHEN

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 New Years. Early spring and late fall are also more affordable times. Although certain activities might not be available.

Another reason that timing may guide you at the start of planning a trip is if your top 3 activities are season-specific. Examples are cherry blossoms in Japan. East Africa’s Great Migration. Oktoberfest in Germany.

Questions to ask if you know WHEN to go:

• If you’re limited to a specific season, where would be fun to 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?

Trip planning when you know WHO

Maybe you already know who will be going with you. Your significant other. Kids. 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 pretty big impact on the types of experiences you can have. If your kids or in-laws are coming along, you might want to save your romantic getaway plans for another trip.

Consider what activities you and your travel companions enjoy doing together, and create an amazing experience around that. Beware the temptation to squeeze your companions into a trip they’d hate. (‘Cause you’ll hate it then, too.)

Keep your travel companions clearly in mind when you’re starting to plan your vacation.

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?

You may also like:

• TIPS for Traveling with AGING PARENTS
• How To Plan a ROMANTIC GETAWAY: 29 Tips
• Trips to Take with MOM and Trips with DAD

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 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 travel 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? Exploring or learning something new?
• 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.

When starting to plan a vacation, pay attention to what you still talk about from past trips.

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!)

Embrace your vacation rhythm when starting to plan your trip. You might be willing to sacrifice one relaxed morning or late night for something you MUST see or do, but likely not every day.

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 holding me back from something I really want to see or do. But, acknowledging limitations right when you start planning a trip allows you to account for them. Then, the actual trip will go smoother.

Physical limitations can be obvious and not. Some have trouble walking long distances. I’ve learned (the hard way) 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. 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 the entire travel planning process.

Summary and Resources

Too many trip planning tools and processes completely skip over this first step. How to start planning a vacation MUST begin with 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, SHARE this post with them! Then compare your answers to plan a trip you’ll all love. (And come out still liking each other.)

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:

• Build Your TRAVEL ITINERARY and Book the Key Pieces 
• Your Ultimate Vacation Countdown Ultimate CHECKLIST

Or, jump into How To Plan a ROAD TRIP You’ll Love in this step by step guide.

Remember to SHARE this post with your TRAVEL COMPANIONS!

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