We’ve all been there.  That moment of excitement when you realise you’re ready for a big trip.  Quickly followed by the babble of questions about how, what, where, when and possibly even why, that can put you into wheelspin.  Thinking how to plan a big trip can be stressful.  I’ve got several decades of trip planning under my belt now.  Let me talk you through how to plan a vacation trip. Grab your travel planning notebook, and we’ll take it step by step.

What Do I Mean By A Big Trip?

I’m calling a big trip one where you are away for at least two weeks, and visiting more than one destination.  If you’re doing something shorter but complicated (like a rail trip with many stopovers) you might still need to plan it out fully.  You might also need some of these steps if you’re away for a long time in one place (housesitting, for example) and need to make sure you sort out things at home before you leave.  Let’s get cracking.

Planning a big trip?  Why not pin this for later!

How To Plan A Big Trip - Without Your Head Exploding

1. Decide Where You’re Going

That sounds rather obvious, but you’ll need some consideration about the duration of your trip, destinations en route, and if you will need open jaw flights returning from a different airport.  What is your budget?  How are you going to fund your trip?  How long can you stay away from home?  Are there already commitments in your diary that you need to return to attend?

Once you’ve narrowed that down a bit, it’s time to start focusing on what you want to do at your destination.  If there’s a road trip involved, realistically how long will that take?  It’s neither fun nor safe to be loading up on caffeine to stick to schedule.  If you’ve got your heart set on something specific, is it possible to do that on any day of the week?  Of course, nothing’s set in stone at this time.  But it will give you a better idea of when you’ll want to fix your flights.

2. Book Your Flights

Now you have a fair idea of your dates, it’s time to research your flights.  Don’t forget to search incognito, so you’re not driving up the prices when you come to book.  It’s good to allow some flexibility in your dates if you can, as it might help to secure cheaper prices.  Also don’t forget to look at routes and connections.  We’re currently juggling around options to New Zealand from the UK, and choosing our preferred and/or cheapest layovers.  It might suit you well to explore a destination you’ve never visited.  Don’t forget to consider any internal flights you’ll need too.

If it’s feasible for you, this is also the time to consider taking out a credit card that gives you good benefits.  Don’t forget to check whether you have any alliance partners that can bump up your miles.

3. Travel Insurance

If you have an annual policy, see that it covers you for the destinations and activities you have planned.  You’ll also need to update if you’ve had any changes to your medical record.  If you’re taking out a trip-specific policy, consider when you’d like to bring it into effect.  You can choose to buy insurance just before travel, but if flights are costing you more than you’re prepared to lose, you might want to do so at an earlier stage.

When you buy your insurance, don’t forget to check it covers you for any activities you have planned.  If you’re unfortunate enough to need insurance, you really don’t want to find that it doesn’t cover what you were doing at the time you got injured.

4. Itinerary Planning

Now comes the fun bit!  You know when you’re arriving and going home.  In between lies the rest of the magic.  Particularly if this is a complicated trip, I’d suggest working out how many days you want to spend in each place, and how long it will take to travel between them.

When we planned our Deep South Blues Trip to the US, we started off knowing that we wanted to go to Nashville, Memphis and Clarksdale, Mississippi.  Having checked out the dates of a festival we wanted to hit in Clarksdale, it was best to fly into Nashville and out of Memphis.  We worked out how many days we wanted to spend in Nashville and Memphis at each end of the trip, the days in between becoming our road trip.

Out came the maps.  We found some stopovers that weren’t originally in our plan (lovely Brownsville, for example, and beautiful Natchez Trace) and rejected other stops after reading about them.  We found some YouTube vids of the routes we’d be driving to get a flavour of the conditions.  And we worked out the miles we could easily do in a day without feeling as though everything we wanted to see was flashing past our windows.

Our travel notebook ended up with a list of days.  Each had a note on where we’d be stopping that night, and if it was a driving day, how many miles we’d need to cover.  More detail was added later.

How To Plan A Big Trip - Without Your Head Exploding

5. Book Accommodation

Now you’ve got a rough idea of where you’ll be stopping over on your trip, it’s time to book accommodation.  Depending on your destination, you may want to leave some flexibility here.  But I’d certainly always suggest that you book your arrival night(s) and the days immediately before you depart.  Also think about where you’re headed.  If you’ll have good wifi and easy access, then it’s an easier decision to book a bed on the road.  But if you – like me – will end up stressing about finding somewhere last minute, book something with flexible terms so you can change your plans as you go if that suits you.

6. getting Around

There are all kinds of options as to how you might want to get around – hire car, long distance bus, rail or internal flights.  If you’ll want to hire a car, you’ll need to check out the local options against your budget, including insurance needed and any optional extras (satnav for our Deep South Trip, for example).  Budget in those and also your fuel.  Where suits you best to pick up and drop off the car?

For long distance buses and rail, check timetables and costs.  If you’re taking an overnight bus or train, don’t forget to factor that into your accommodation decisions.  You might prefer to book accommodation for the next night where you can shower and drop off your bags earlier after a night in transit.  Some buses in particular don’t run every day, so it’s time to make more notes in that travel notebook.  If you can get discounts by showing a student card or other form of ID, add that to your list of things to take.

7. Things To See And Do

By this point, I’m normally at the really excited stage of trip planning.  Here’s the chance to set up your Pinterest boards, read blogs and trip reports, and visit those websites for the places you want to see.  There’s a fine balance here between robbing the trip of spontaneity and having some idea of what you’ll want to see.  Don’t forget this is just a guide.  If you get there and are captivated by something entirely different, that’s cool.  My Adelaide stay ended up as an unscheduled road trip to Port Augusta, and that’s a fine memory.

From experience, I’d suggest making a particular note of any days on which venues such as museums and galleries are closed.  Boat trips may only run on certain days of the week.  Don’t forget to check public holidays and any religious festivals or other days on which attractions may be closed or exceptionally busy.

That list of dates and overnight stays you had earlier in your travel notebook?  Now’s the time to add the things you want to do.  For us, it looks something like this:

Memphis: Stax, National Civil Rights Museum (closed Tues), Sun Studio, Rock n Soul, Hall of Fame,  riverboat trip, Beale, overnight x 3 @ Overton Square, return hire car @ airport day 1, flight out via ORD day 4

It’s also good to think if there are any local restaurants or specialities that you want to try.  Add those to your list.  If, like me, you have food allergies, then it’s good to investigate what might be suitable locally.  I carry cards explaining the allergy in the language of the country in which I’m travelling, which definitely helps.

8. Manage Your Funds

Once the initial exciting bit of planning is over, it’s time to manage your money.  Your bank account may have taken a deep breath as your first payments went out.  Now it’s time to knuckle down and make sure you earn or earmark the rest of your trip funds.  Pre-trip planning is great to focus my mind wonderfully on what I want to save.  I’m much better at taking on contract work involving shivering in a muddy field when I know what travel treats lie ahead.  If I need more motivation, I’ll sometimes work out the rough cost per mile of the trip, so I can see how much of it I’ve already funded.  You can read more of my tips and tricks for funding your travels here.

9. Passports, Visas, Immunisations

Early on in your planning, it’s time to check out what you need in terms of travel documents.  Check that your passport has sufficient validity in its expiry date, or get it sent off for renewal.  Investigate if you need visas and how to obtain them.  If immunisations are required, check out how far in advance you should get them arranged, and find your local clinic.

Don’t forget your regular prescription medications, and any updates you might need while on the road.  Is your medication legal in the country you are visiting?  Carry a copy of your prescription too.

Not all of these documents are online, so I’d suggest you dedicate a plastic folder for all your trip information.

10. Staying In Touch On The Road

Next up is checking out how to keep in touch on the road.  Your phone provider may have an additional package you can purchase, or you can buy a sim for your destination.  If you want a mobile hub and data, now the time to investigate that too.  Buy your travel adaptor and check you have powerbanks, especially if you will be traveling for long periods of time during your trip.

How To Plan A Big Trip - Without Your Head Exploding

11. Keeping The Home Fires Burning

If you are going to be away for longer than a few nights, there’s merit in thinking about arrangements at home.  In no particular order, have you considered how:

  • to pay any bills that will arrive while you’re away
  • to ensure safety and security – can someone keep an eye on your place, or do you need a house sitter?  Do you need to leave the heating on low to avoid your place freezing up while you’re away?
  • to make arrangements for pets
  • to deal with any important post if you’re going to be away for a long time

Don’t forget to be mindful of your home security by not announcing too many plans on social media unless your place is occupied while you’re away.

12. Packing

Once I’ve got the trip sorted in my head, I also start making a list for packing.  While many things may seem obvious, there have been occasions when there have been significant omissions from packed bags.  Like underwear…

As you’ve made the list of the activities you want to try on the road, this will help to flag up any extras for your packing list.  Dive mask?  The one hat that’s guaranteed to stay on your head during a sunny boat trip?  Walking boots?

Don’t forget to adjust your list to allow for laundry on route.  We purposefully book a night in an airbnb with a washer, meaning we can pack less clothes.

13. Check In Online

Hug your loved ones.  Check you locked your door.  Make sure your bills are paid.  Head on out and have a wonderful time!

Want To Know More About Planning Your Trip?

We’ve got you covered for getting the most from your trip, road trip planning, packing carry on and flight essentials.  If you’re wondering about the best flight hacks around, I’d suggest exploring Flyer Talk, with a forum full of knowledgeable travelers to answer all kinds of questions.

If you’re planning a big trip, why not pin this for later!

How To Plan A Big Trip - Without Your Head Exploding



Author: Bernie

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4 thoughts on “How To Plan A Big Trip – Without Your Head Exploding

  1. Love this post. These steps will definitely help to reduce the chaos. Its almost how i do it as well.

    Posted on September 8, 2018 at 11:59 am
  2. I totally agree with you. Coincidentally these are the same steps I follow.

    Posted on September 8, 2018 at 3:35 pm
  3. What an amazing post it is! Planning a trip is fun but exhausting at the same time. This post contains all the major points that need to be followed while planning any major or small trip. Managing the finances is our major hurdle 🙁 Totally loved it!

    Posted on September 15, 2018 at 10:04 am
    1. Ah thank you! The funds are always hard work, but it is so worth it. I love the planning though – so much brilliant anticipation!

      Posted on September 15, 2018 at 9:02 pm