Travel is fun.

Travel planning is where things can go off the rails fast.

People come to me all the time and say, “We want to go somewhere fun, warm, affordable with stuff to do,” then look at me like I’m supposed to magically know the rest.

Here’s the truth. A great trip doesn’t start with a destination. It starts with a conversation.

These are the 25 questions I ask before I plan any trip. For my own crew and for my clients at Take Time To Travel. They’re not trick questions. I’m just trying to figure out who you are, how you live, and what kind of trip will actually work in real life. I do not always ask All of the things…sometimes it just isn’t needed. But it is great guideline!

As you read through these, think of it like sitting across from me with a cup of coffee while we talk this out.

The Big Picture

1. What is the real purpose of this trip?

One of the first things I ask you is, “What is this trip really for?” Is it a collapse on the beach, a bucket list adventure, a couples reset, a family memory builder, or a solo sanity break. If you tell me “relax” then hand me a list of ten cities, we’re going to have a little talk.

2. How do you want to feel when you come home?

I’ll ask, “When you walk back in your front door, how do you want to feel?” Rested, energized, inspired, proud that you finally did the thing. Your answer tells me if we’re building a spa week, a food tour, or a “check ten things off your dream list” kind of trip.

3. What kind of scenery does your soul need right now?

I’ll ask about what you want to see every day. Ocean, mountains, city lights, desert, forest, little Christmas village. If you’re burned out, I probably won’t send you to the busiest city on earth. If you’re bored, I’m not sending you somewhere that goes to bed at 7 p.m.

4. How far are you really willing to travel?

I ask this very plainly. Are you honestly up for long flights, layovers, and time changes, or are you going to be grumpy before we land. “Once in a lifetime” sounds cute till half your vacation is spent in airports.

5. Is this your dream trip or someone else’s?

I’ll gently ask, “Do you really want to go here, or did social media decide that for you?” I want to know if this is your dream, your spouse’s, or your friend Carol’s “must do” that you got roped into.

Time, Money and Adult Reality

6. How many true vacation days do you have?

I always ask how many days you can fully unplug. Not “I’ll just check work email in the mornings.” Travel days count. If you have five days off, I am not building you a ten day itinerary. I like you too much for that.

7. What is your real all in budget?

When I say “budget,” I mean flights, hotel, food, tips, transport, tours, souvenirs, airport parking, pet sitter, all of it. I ask this so I can protect your wallet and your blood pressure. Your budget is a boundary, not a suggestion.

8. Where do you want to put the bulk of your money: flights, hotel or experiences?

I’ll say, “If we have to choose, do you want the nicer flight, the nicer room, or more money for tours and fun?” Your answer helps me decide where to splurge and where to save.

9. What are you willing to trade to get the price you want?

I ask about your tolerance for early flights, longer layovers, staying a block off the beach, traveling off season. There is always a trade. I need to know what is a hard no for you.

10. How do you feel about travel protection for this trip?

You will hear me ask, “If something went sideways, could you afford to lose this money?” If the answer is no, then we talk seriously about travel protection. I see what can go wrong more than you do. I’m not trying to scare you, I’m trying to protect you.

Who’s Going And What They’re Really Like

11. Who is actually traveling and what are they like on a normal Tuesday?

I ask you to tell me about each person. Ages, personalities, energy levels, any health or mobility stuff. I am not planning for the fantasy “we’ll all be easygoing and flexible” version of your family. I am planning for the real humans you live with.

12. What is everyone’s travel style?

I’ll ask, “Do you like a structured day or do you want room to wander?” Maybe one of you loves museums and another only cares about food and views. I’m listening for how to balance those styles so no one is quietly seething by day three.

13. What are each person’s non negotiables?

I always ask, “If you had one thing on this trip that absolutely had to happen, what would it be?” One fancy dinner, one spa day, one ballgame, one day by the pool. I try to protect those things in the plan.

14. Who is the least flexible person on this trip?

I never phrase it quite that blunt in front of them, but I’ll ask enough questions to figure it out. If Grandma can’t walk hills or your toddler needs a nap, that shapes the entire plan. I build around the most limited person so everyone can still enjoy themselves.

Comfort, Pace and Expectations

15. What is your honest energy level these days?

I ask you to be real with me. Are you in “let’s hike all day” shape or “let’s stroll and then sit down with a drink” shape. I don’t care what you did in your twenties. I care about what your knees and your back say now.

16. How many hotel or rental changes are you comfortable with?

I’ll say, “How often are you okay with packing up and moving?” Every hotel change eats up time. Sometimes it is better to stay in one spot and do day trips than hop to four places in six nights.

17. Do you want more guided help or more freedom?

I ask how you feel about tours, transfers, and guides. Some folks feel safer and more relaxed with structure. Others want as much independent exploring as possible. Your comfort level tells me how “handled” this trip needs to be.

18. How do you feel about crowds, lines and noise right now?

If you tell me you’re peopled out, I am not dropping you into the middle of a festival or the busiest theme park week of the year. I ask this so we don’t book you into a situation that drains you instead of filling you up.

Safety, Accessibility and Practical Stuff

19. Do we need to plan around any health, mobility or comfort issues?

I always ask directly about stairs, walking distance, heat, altitude, long days, long rides. If you have MS, bad knees or anything else that can flare, I want to know so I can build breaks and choose smarter locations.

20. Have we talked honestly about weather and daylight where you want to go?

I’ll check and then say, “Here’s what it really feels like that time of year.” Monsoon season, hurricane season, early sunset, wildfire risk, or 100 degrees in the shade. Weather changes the whole vibe of a trip.

21. Are your documents ready to go?

I will absolutely ask, “When does your passport expire?” and “Do we need visas or special documents for the kids?” It is not glamorous, but it is the difference between “bon voyage” and “you’re not boarding this flight.”

22. How comfortable are you with the local language and culture?

I ask how you feel about navigating menus, money, and transportation. If that stresses you out, I lean more into private transfers, guides, and organized sightseeing so your vacation feels like a vacation, not a scavenger hunt.

The Little Things That Make A Big Difference

23. What are your top three ‘if these happen the trip is a win’ moments?

I’ll say, “If these three things happen, you’ll come home happy. What are they?” Northern Lights, one perfect beach day, a special meal, a kid’s big reaction. I build your schedule around those anchors.

24. What do you absolutely not want to deal with on this trip?

I ask about your “nope” list. Cooking, driving, big group decisions, budget fights, long lines, early mornings. Knowing what you want to avoid helps me narrow down the right style of trip.

25. Do you actually want to plan this yourself, or do you want me to handle it?

Yes, I really ask this. You can absolutely Google your way through and book every little piece yourself. You can also cut your own hair. Sometimes it works. Sometimes it’s a hat situation. My job is to take these answers and turn them into a trip that fits your life.

Why I Share My Questions

When I sit down to build a trip, I am not throwing darts at a map. I am walking through these questions, listening for who you are, then matching that to the right destination, timing, and style of travel.

If you want to grab this list and talk it over with your spouse, your best friend, or your kids before you call me, please do. The more honest you are with your answers, the better I can do my job.

This is the behind the scenes part of travel planning I love sharing on Journeys With Jani, because travel is more than pretty photos. It is about making memories on purpose.

And when you’re ready for someone to take all these answers and turn them into an actual itinerary, that’s where I come in. You bring the dreams. I’ll handle the details.

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