12 Questions to Ask Before Planning a Trip

Planning a trip should be exciting, but for many people it quickly becomes overwhelming. One minute you’re looking for flights, the next you’ve got 27 browser tabs open, conflicting advice from social media, Google and AI, and no idea where to start. It’s rarely the destination that creates overwhelm. It’s usually the planning process itself, leading to analysis paralysis or decision fatigue.

Travel is also quite subjective and there is no one size fits all when it comes to an itinerary. That’s why it’s really important to take the time to think about the kind of trip you actually want before you get started. 

After more than 25 years of planning my own trips, including complex multi-country itineraries, I’ve found that the biggest difference isn’t having more information, but knowing how to tackle it.

The best trips don’t start with booking flights, rather they start with asking the right questions. These are the 12 questions I recommend asking before planning a trip, so you can create an itinerary that suits your priorities, budget and travel style.

Why ask questions before planning a trip?

Preparation and research is key to a successful vacation. That’s not to say that you have to plan absolutely everything, but know your options, understand what works for you and how to manage the practicalities so you can start to plan with intention and get excited about your holiday. 

Travel planning may feel like a checklist of things to book and in some ways that’s true, but let’s reframe this to think about it as a set of principles. There’s a logical sequence you can adopt to pace research and know what you need to book and when. Once you answer these questions, you’ll start to think does this suit me instead of what should I do.

A shorter 6 question version exists as a free download for anyone who wants the fast version first.

12 questions to ask before planning a trip

Pace & Energy

1. How many big activity days vs. rest/wander days do I actually want?

Most people over-plan and come home needing a holiday from the holiday so baking in rest days is important. Depending on where you’re going, you want to factor in travel days. Going from destination to destination can eat into a day, so factor this in accordingly. I often don’t plan anything on a travel day so that I can either rest upon arrival or have nothing planned to just walk and explore the surrounding area where I’m staying. 

2. Am I a plan-every-hour traveller, or do I want room to wander?

I get it, some people like a spreadsheet itemising everything and document to the hour like their life depends on it. That’s ok if that works for you. Personally, I don’t want any kind of schedule and prefer to know what I want to cover and what I’m willing to forego, in order to have free days to explore at leisure. 

3. What’s my honest tolerance for early starts and long travel days?

Don’t be aspirational. Honestly, what are you willing to accept to avoid exhaustion. If you’re a morning person and like to make the most of the daylight hours, then great – you can often avoid crowds this way although you might encounter local peak hour delays. Night owl, no problem – factor that into the equation and choose afternoon/evening activities and bake in rest for your mornings. It’s all about knowing how you like to operate and taking that into your vacation as well as daily life.

The FOMO is real and you’re probably thinking I may not come back here so I need to do as much as possible. See every sight, museum, book every restaurant in advance and take all the day trips. BUT, I would urge you to reconsider. 

You will likely burn yourself out and return home more exhausted than when you left. This is really the whole idea behind slow travel – designing days around how you actually want to feel, not how much you can fit in. Yes, the memories and inspiration may hold you in good stead for a short while but very quickly you’ll be booking in the next round of leave or PTO to recover after daily life kicks in. 

For example, I spent 3 days in Milan and shock horror did NOT visit Lake Como. I wanted to but I also wanted to enjoy Milan properly. The thought of visiting Lake Como on a packed train with every other tourist did not excite me so I chose to stay and enjoy the city itself – best decision. 

Planning tip: Build in one deliberate ‘nothing’ day for every 3-4 days of travel and treat it as part of the plan, not a fallback.

Budget & Priorities

4. What’s my total budget ceiling, and what does it actually need to cover?

Budget is a really important consideration before planning a trip, as this can impact your choices. Just know, there are ways to make your budget stretch further and even the most expensive cities have free ways to enjoy it. It’s about reframing what matters to you and what you want to do. Think about typically how much you would spend per day including transport, food, activities, any extras such as shopping. 

5. Where do I want to spend more -comfort (flights/hotels) or experiences (food/tours)?

We all value different things when we travel. Some people happily spend more on a beautiful hotel and save on activities. Others don’t care where they sleep but will splurge on incredible food or once-in-a-lifetime experiences. Location, transport options and doing something on your own versus organised tours is another consideration.

6. What would make me feel this trip was worth the money?

This isn’t your budget. It’s an emotional question – even if you spent over what you’d expected, what would make it worth it to you?

For me, it’s less about the total spent and more about whether I walk away feeling like the money went toward something that actually mattered. An incredible experience, a unique souvenir, an unforgettable meal I still think about, rather than just ticking off another sight because it was there. Again, that doesn’t mean expensive either; it’s about the value you place on something.

Feeling overwhelmed already? Download my free 6-question checklist and work through the essentials in under 10 minutes.

Non-negotiables

7. What’s the one thing that would ruin this trip if I missed it?

Once you decide on all the various sights, activities, food spots you want to visit, work out what you absolutely must see and what you’re willing to forego if time/energy/pace won’t allow and that you will be ok missing. Naming this upfront gives yourself permission in the moment and protects what’s important to you from the beginning, allowing you to plan around it.

8. What am I not willing to compromise on (dietary, mobility, climate)?

Practical constraints can quickly derail a trip if you don’t think about them before you leave.

If you have specific requirements, take the time to research your options in advance. That might mean checking restaurant menus for dietary needs, knowing how to communicate food allergies or sensitivities in the local language, understanding the availability of public bathrooms, or planning transport options for days when you’re tired or have mobility considerations.

Don’t overlook the climate, either. Heat, cold, humidity or altitude can have a bigger impact than many people expect, especially if you’re managing a health condition or travelling with someone who has additional needs. Thinking about these practicalities now means fewer surprises later and a more enjoyable trip.

9. Who am I travelling with, and what do they need that I don’t?

This matters more than you might think as travelling solo vs travelling with a partner or friends can quickly create resentment and silent compromises among the party. It influences all levels of planning from accommodation choice, to dining, to managing activities and even just general flow requiring a lot more coordination, which can be exhausting. Discuss with your group upfront as having a plan makes a real difference which is something I’ve explored in more depth here.

Planning tip: Write down your non-negotiables before you start researching, as it’s far easier to protect them from the start than to claw back time for them once your itinerary is already full.

Flexibility & Risk

10. How much do I want locked in advance vs. decided as I go?

The reality is many popular tourist sights get booked out and often need to be booked in advance. Even those that are booked, still require waiting in long queues to enter so worth deciding what you absolutely must do/see versus what you think you must/do see. Personally, I would choose 1 or 2 maximum activities per destination that you don’t want to miss and book those, again at a time that’s convenient for you. The rest, you can decide on the go and if you can’t get in, there are lots of other options to consider (particularly since you’ve already researched them or even better you might choose to just wander and get lost for a few hours). 

11. What’s my backup plan if something falls through?

In order to avoid disappointment or stress, having done research for options can help greatly so decide how much backup-thinking you want now, calmly, vs. mid-trip under stress.

12. How much uncertainty can I actually tolerate before it stops being fun?

Understanding your risk tolerance can help guide how much structure vs spontaneity to build into your plan. Travel is exciting but there is a lot that’s out of one’s control ie weather, traffic, delays etc. Know your options, have a plan B and understand what to do if things don’t go your way. 

Planning tip: Book only the 1-2 things you genuinely can’t risk missing and leave everything else open, and trust that a good backup option usually exists.

Before planning your next trip, ask yourself these 12 questions

Planning a trip can be stressful. We look forward to the vacation but once you open 27 tabs and begin researching, the excitement quickly turns into a chore. I built this list of questions to help cut through the noise and get you thinking about what you actually want from the trip, not just what you think you should see and do. 

This isn’t an exhaustive list, but I hope it helps you frame your planning around your own needs and how you want to feel when you get home. Sometimes the anticipation of a trip can be more exciting than the trip itself, so manage expectations and know what you’re after from the start. 

Want the fast version? I’ve put together a free, six-question checklist — the short version of everything above, ready to work through in ten minutes. Get the free checklist here.

Prefer to skip the DIY step entirely? I run 45-minute sessions where we work through your specific trip together, and you walk away with an actual plan. Find out more about working with me here.