To Plan or Not to Plan? Compromising Your Travel Style

If you’re like me, a compulsive list maker and organiser, you’ll understand that the planning of a holiday, road trip, day trip or anything big or exciting in your life, needs to be planned down to a T. If you’re like my boyfriend, the complete opposite, and believe the best thing about going away is the spontaneity and excitement of a new place, then my idea of planning is probably your idea of a nightmare. I find myself constantly trying to talk to him about what we’re going to do, what we’re going to eat and what days to do what, and he just doesn’t seem interested. I’ve bought two travel guides for our next trip, and he hasn’t read a page. I guess the planning is all down to me then. Don’t get me wrong, I do understand his point of view, but for me, I need to plan. I hate the idea of not knowing about any of the local restaurants, and accidentally getting stuck going through McDonald’s drive-thu’s every night. I like to know the distance between places, and check out the public transportation or roads and have routes planned out. I like to know the prices of museums, wildlife, water and theme parks, and have the tickets for those booked. I like to know where the supermarkets are, what time the bars and clubs are open ’til, and most importantly, how much money we can spend in a day. If you’re travelling with someone who just isn’t about all of this intensive planning, then allow me to offer you a few compromises which might help you still feel comfortable and content with your planning, but still have a go-with-the-flow kind of attitude to your trip.

If you are planning to go to somewhere that requires tickets, you really should book ahead.

Even if your travel partner does not want to plan much before the trip, this is a must. In many cases, tickets are more expensive when you buy on the door, and you could even end up being sent away because the place has reached full capacity for the day. What a waste of time! To avoid this, choose the day(s) on your trip that you would like to visit places such as a theme park, water park or zoo, and get it out of the way. Your spontaneous partner will thank you later.

Write down, and research the bars, restaurants and clubs nearby.

While this is still pretty compulsive planning, to compromise, write down a list of the places you’d like to go, and instead of allocating one to each day, just pick one together at the time. Maybe that Saturday night at a Mexican buffet restauraunt seems less appealing if you over-ate at lunch. Again, if it is somewhere that needs to be booked, this could be a problem, so perhaps avoid places such as these, unless again, you choose the specific day you’d like to go. Try using Open Table if you are booking from another country. One other thing, if you are planning to visit quite a few different towns or cities on your trip, separate the list as such, and then choose together when you visit that specific place. Then, you are maintaining a free-spirited mindset, while still being fully aware of all your options.

Don’t put all of your eggs in one basket with a travel itinerary.

Things go wrong. If you’ve spent hours planning the perfect itinerary, and something happens which throws you off, you’ll be stressed and feel disorganised. To avoid this, create 3 or 4 different options, so you can always refer to another one if things do not go to plan. For example, if on a Tuesday, you wanted to spend the whole day by the hotel pool, but you didn’t quite have enough time to do everything you wanted the day before, moving the pool day to another day might be the best option. You’re on holiday, so you shouldn’t always feel like you’re working on a tight schedule. So, either have a more relaxed approach to your itinerary, or make multiple different ones. Tip: have a ‘busy day, quiet day’ schedule. 

Don’t over-pack your suitcase.


Research nearby supermarkets, and only take what you definitely know will be hard to find on your travels. That huge bottle of shampoo that you definitely need? Consider leaving it at home, you’ll be surprised at what is available when you get there. A fun part of your holiday will be what you buy and bring back. Another tip is to wear your heaviest things on the plane, to maximise packing space.

Work out a realistic budget.

Even if that means taking more money that you think you’ll need. It is much better to have too much money than not enough, so always take more. Most currency exchanges have deals now so you won’t get ripped off if you come back with more money than you thought you would.

Let your partner take the lead.

There’s a reason why your partner didn’t want to plan. If they see something that’s not on your list of things to do, let them do it, even if that means compromising something from your list. The important thing to remember is that everyone is different, and by your partner not planning, while it may seem like a burden to you at the time, who knows? Maybe it will surprise you. It’s their holiday too, so let them have a little adventure of their own, in their own way.

The overall tip: plan, but have options…


Don’t be afraid to completely scrap your itinerary altogether if when you get there you discover a million more things do to that you missed during your planning. Make your holiday your own, do all of the things you want to do, and if you want to stay organised, make sure you have alternatives just in case. Sometimes you will encounter unavoidable situations, so be prepared for them. The main point is to have a great time on your trip and not stress too much about the little details.

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Do you have any other tips for planning do’s and don’ts? What experiences have you had travelling with others? Let me know in the comments.

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6 thoughts on “To Plan or Not to Plan? Compromising Your Travel Style

  1. I plan trips and take people on them, so planning is very important, especially when you’re spending over $1000 to get there and back. But, I do think it’s fun to take a day trip some where and just go with the flow! Perhaps your boyfriend is like that because planning takes work. 🙂 ~Sherry

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  2. We think the planning is part of the fun! People think we’re quite chaotic and just fly by the seat of our pants but actually we’ve spent months putting together spreadsheets and itineraries (we’re an accountant and business analyst so we get very carried away with our spreadsheets!) and building in a few contingency plans just in case things don’t go smoothly.

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