Planning A Road Trip Alaska

Who’s Up For Planning A Road Trip? Me…Me..!!

Ah travel, how I miss thee….It may not be Shakespeare and it’s certainly not up there as one of life’s great problems. But without a doubt, being unable to leave the UK leaves me struggling to contain my travel lust.

Being able to travel more was one of our big drivers for financial independence. In the ultimate British understatement, it’s been odd having that freedom taken away. Like said, it’s not a big deal in the grand scheme of things. But I miss it.

The sense of exploration, the new and unknown. The food, the culture, the stories shared. Connections made. Travel for me is how I continue to get out of my comfort zone, try new things. Learn, grow. Practise patience 😉

Even before retiring travel was a big part of our lives. Maxing out that holiday allowance each year. From short breaks to month-long “use it all at once” adventures, we made the most of our time.

And now, as the world slowly, slowly starts thinking about opening back up – I can’t help but start to tinker with ideas for our next trip. Thinking and planning a trip is practically a hobby for me and I’ve learnt a lot over the years.

So, for those who may be wondering – just how do I go about planning out a road trip? 

How Do I Define 'Road Trip'?

First up – let’s get clear on what I mean by a road trip. Since I suspect it’s slightly different to what most people imagine. 

A road trip to me is simply some time away from home, travelling around and  staying in more than one place.

It doesn’t have to be an epic journey of thousands of miles. Although we have done those and loved them. It doesn’t even have to be in an RV or motorhome. Though we’ve done those too and funnily enough loved them too.

Whether by foot, bus, bike, car, whatever –  to me, a road trip is simply a way of experiencing a wider selection of locations in one country. Getting a taster (usually literally) for the different places and characters.

It’s the best way I know to really start to get to know a country.  It always makes me smile when people say;

Sure, I’ve been to the UK. Well, I mean London. It sure was a bit hectic and pricy but that’s the UK for you.

I mean, some places are huge and every country I know is way more than a few days spent in it’s capital city. Well, Vatican City excepted maybe but I’ve not been there!

It’s impossible to compare something like a hike up Tryfan in Snowdonia or a slow river meander down the Norfolk Broads to seeing the sights of London City. They’re just different things.

Snowdonia in June. Tryfan
Snowdonia in June. Yeah, British weather...

So when I’m planning out a road trip to a new country, I employ the same thinking. The capital is often the easiest point to fly into and we’ll stay 3 or so days. But then we’ll move on and explore deeper.

But when faced with a blank piece of paper saying “explore xxx” – where do you start? It can seem overwhelming and the temptation can be to pay over the odds and let an expert handle it all for you. Take the cookie cutter option, see the same sights with the crowds, eat at carefully found locations.

It’s safe, easy – but it’s not exactly really getting to know the place. Let alone ensuring your tourist dollar goes towards the local economy.

So unsurprisingly, that’s not how I do it. Besides the obvious opportunity to get a better value experience for both us and the locals – I just find it much more fun to organise our own trip. 

But where do I start?

How To Start Planning A Road Trip

Ok, so you’re intrigued enough to decide you’d like to do more than a traditional ‘fly & flop’ (and who hasn’t done one of those?!) style holiday. Now how the hell do you actually start when planning a road trip to somewhere you have never been?

First up, you will want to be able to answer some basic questions about your trip, like these;

  • How long can you go for?
  • When can you go / anything specific to see or do?
  • What’s your ‘holiday style’?

The answers to these will help to start to shape your road trip, giving you a framework to then play around with.

So let’s work through them…ooh…I feel a spreadsheet coming up…

How Long Is Your Road Trip?

If you think about the length of time you have, it becomes obvious that a two week road trip is going to look a lot different to a three month extravaganza.

After discovering our love of slow travel, our rule of thumb is to give any place we stay at least three nights. We’ve RV’d across Alaska and driven more than two thousand miles across South Africa staying a night at a time. 

Alaska Motorhome RV Road Trip
Alaska. Even the laybys are stupidly stunning.

They were still fantastic trips but after a while you realise you’ve spent more time driving than anything else. Sometimes that’s ok – but it can be more tiring than you expect. Especially if you are packing and unpacking every day. 

It’s really (really!) easy to want to cram in everything a country has to offer. But experience has definitely taught us that less is often more, even when trying to get a taste of everything.

Staying at least three nights in each place gives us at minimum two clear days to explore. Enough time to get a feel for the place. To know if it’s somewhere we want to return and spend longer another time. Not long enough to regret trying it out at the cost of somewhere else. 

Plus it gives you time to actually relax. If we feel like taking a day to go hiking, we can. If we just want to sit around in a sunny courtyard with beer and tapas – we’re there.

To us – a road trip is at it’s best when you can savour a string of new experiences without feeling like you need a holiday when you get back

Ofcourse, it’s only a rule of thumb and you need to make your own judgement as to what suits you best. But as a starter for ten – take the number of days you can be away for and divide it through by three.

That’s now the number of places you can likely easily fit into a good road trip. A rough guide only but it’s a start.

So now let’s take a look at how when you can go makes a difference.

When & What On Your Road Trip?

For us, with no kids and S’s digital nomad work – we have no limitations on the when. But I recognise that’s not the normal yet, even if remote work is increasing for a lot of people through the lockdown.

We can look to time our roadtrip to work with either the local weather or events that we want to participate in.

E.g. if we want a hiking holiday, there’s not a lot of point in visiting a part of the country that will be enjoying/enduring constant downpours at that point in time.

Likewise, you may really really want to watch the awesome display of whales from one of the few land-based whale watching spots in the world, Hermanus, South Africa. But that pesky Mother Nature dictates you need to be there Oct/Nov for your best chance. It’s not really up for debate.  

Hermanu whale watching
Picnic whilst whale watching - it's a tough life..

In a similar way,  if you are tied to the joys of the school holiday schedule, then you just recognise that’s what you work with as your fixed element.

It’s not that different to the whole FIRE approach of balancing scope, time and money. You have three different elements of weather, events and your own flexibility with which you figure out the right balance for you.

In terms of planning out your road trip, if there’s something specific you want to see or do, pencil that in first and work back from there.

Our top tip though?

Pick one or two specific things max from the guide books/blogs. One of the biggest joys of a road-trip exploring a country is discovering things yourself.

For example – on our first trip to South Africa we wanted to hike up Table Mountain and go on a safari. We were intrigued by a whole bunch of other things but those two were what started it all.

So our road trip started in Cape Town, where we duly had one of our best day hikes ever climbing Table Mountain. And it ended flying back from Johannesburg after trying out three different kinds of safari style in Kruger Park.

Kruger Park Elephant
There is such a thing as too close...

That left three weeks and just the two thousand miles drive across country to plan out. But having those two “really want to do’s” gave us a basic start/end framework to work with.

Now, South Africa is a big country with an awful lot to offer and experience. So just how do I go about narrowing down the myriad of options into something that looks like a plan for a road trip?

Well, that neatly leads on to knowing and using your own “holiday style”…

How To Use Your Holiday Style In A Road Trip

First up – what even is “holiday style”? Is this going to be some dive into recommended brands of flip flops and sun hats? Unsurprisingly, no….it’s not. What I mean by ‘holiday style’ is simply this;

When free to do whatever you choose – what do you choose to do?

Are you a culture vulture or an outdoors lover? Thrive on the buzz of a city or prefer a more local feel? Shopper? Snacker? Drinker? 

You get the idea. The more you know what you enjoy, the easier it is to understand where and what you are likely to enjoy most when looking at what a new country has to offer.

This is the fun part for me. Reading up about a new place, getting to understand the vibe of the different places. Finding gems like a brewery in the middle of nowhere. A hike through a canyon in a day. A local market with a thriving food/drink/entertainment thing going on.

Before I know it, I’ll have a ton of ideas about what sounds interesting to us. And that’s the key here – interesting to us.

Beer tasting Saggy Stone brewery
Beer tasting in the middle of nowhere - love it...

FOMO, or the “Fear Of Missing Out” is an oft-discussed phenomenon. I understand it. When page after page of either blog or guide book refers to the same thing, you can start to feel like you would be crazy not to check it out. E.g.

Why yes, despite having zero interest in shopping, I should immediately schedule in an afternoon of hell by browsing every single one of those famous designer shops. Awesome.

This is why knowing your holiday style is so helpful. I rarely use ‘Top 10’ guides beyond the first quick glance. Funnily enough, they are often more useful as a “where to avoid as it will be overpriced and crowded”. Pre-Covid days clearly.

I also often find blogs more useful than official guides too. Especially if the blogger has similar interests/outlook. You can quickly tell if if someone is selling something or just genuinely loved it.

And so I’ll spend my time happily learning and reading about this new land. The joy of the internet makes this a far cry from when we planned our first long road trip over fifteen years ago! I can at times be mildly obsessive in this stage (you can probably hear S laughing at this point). So if it ever starts feeling like “work” I stop. That’s enough.

In this way I’ll end up with a string of places I can tell we’re likely to enjoy. More than enough to fill the time we will have already.

But to me, especially now we have more time, travelling is about more than just a string of things to enjoy. It’s about getting out my comfort zone and stretching myself. 

Travelling is different to a holiday. So this next tip is for those who aren’t stressed out to the eyeballs and ready to drop. Sometimes you really do just need a simple break. Been there, done that. Didn’t get a t-shirt.

So often our best memories have come from the unexpected, the unplanned. The different to what we know already. And you know what, it’s happened enough that now I purposely include places and things I know will stretch me.

Adding The Unexpected To A Road Trip

It may sound impossible or crazy but I’ve learned it’s not only possible but also actually incredibly positive to add locations or events I’m not sure about.

After all, one of the whole points of travelling for me is to really get to know a country. What makes it different to what I know already.

If I spend the whole trip doing things I already know I will enjoy, staying in luxury places, talking to people similar to me – what do I learn? That’s just a comfortable bubble in a different location.

And that’s why as crazy as it might sound to some, we now look to include a few things in each trip that don’t fit our normal style. 

One of the best recent examples was probably Ho Chi Minh City. Neither of us enjoys cities in particular and this one was well out of our comfort zone. But it’s kinda impossible to avoid when travelling through Vietnam one way or another. 

And so rather than just glide in/out of the airport and onwards, we booked ourselves in for three nights and set out to explore. And you know what – we both ended up having a great time!

I think it’s possible to find something you enjoy about pretty much anywhere you go if that’s the mind-set you have.

When you have plenty of time, this is much easier, clearly. But it holds true anyway I think. And now we have a bunch of fond memories of new friends found, craft breweries explored, hidden temples down back streets and oh the food, the food…

Some new friends in Ho Chi Minh City

This has happened enough now that I think of it like diversifying your portfolio. The ‘top tens’ and ‘sure bets’ are like your global trackers but you want to tinker and mix in a few surprises.

And surprise is another often underrated element of a great road trip..

Planning For The Unexpected

It  can be tempting, especially if you are analytically minded, to want to plan out the entire trip.

Certainly for me, I can relax a lot more when away if I don’t have to be constantly thinking about where next. How do I get there, where will I stay. I’m not a big fan of the ‘turn up somewhere and knock on a door’ approach.

Travelling is often tiring, especially in a strange place where you don’t speak the language. I like to know I have a bed for the night.

And I’ve found it’s much cheaper to sort out ahead of time too. Plus all the best places are booked ahead for a reason.

Best is clearly subjective – you will always find somewhere nice if you flash the cash. And you will pretty much always find a bed for the night. But I’ve defn learned that a bit of time and effort upfront pays off big time when out exploring.

At the same time – I don’t want my road trip to feel like a route march. Do this, eat here, try that. So my top tip is this;

Find your personal balance between known and unknown

For me, so long as I know where I am staying and how I am getting there. That’s enough. 

The time there is then my unknown. And that’s the fun part – exploring. Finding those unresearched corners of the world. Surprising yourself. Saying yes instead of no. Appreciating what is there already, not looking for something specific.

So leave time in your road trip planning for surprises – they are so often the best part.

Pulling It All Together

At this point, assuming you are still with me, I start to pull it all together into an actual plan for our road trip. Sometimes breaking out that spreadsheet to work it all through.

It helps to make sure I don’t accidentally book the wrong nights. Yep, done that. Turned up late at night in Warsaw and was only saved by the generosity of the owner letting us stay in their ‘spare’ penthouse flat instead. It was my mistake but they looked after us still. Huge thanks to you, stranger. 

I’ll just start playing around with what fits where, minimising back-tracking. Keeping travel distances manageable. Finding out how the country works best – they often have a natural ‘flow’ to them which can make transport easier. 

At some point I’ll write about all the various tips, tricks and tools I’ve learned over the years. Clearly I love doing this – if I ever needed to work again it’s something I’d look to get into.

For me – it isn’t work. I love everything about it. Best of all, we end up with a truly unique trip – tailored for us.

I find it difficult to imagine a time when travel would not be a big part of our lives. From a personal perspective, all travel – hell – all life – has a risk. You choose the ones you take. But with travel, it’s not just my risk and I’m conscious I don’t want to increase risk to others.

So I’m hoping and tinkering with plans in the meantime to stay sane. And as and when it becomes safe for others and travel outside the UK opens up again – you can bet we’ll be out there somewhere 😉

How about you?

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6 thoughts on “Who’s Up For Planning A Road Trip? Me…Me..!!”

  1. Great advice not to take the guide book is gospel. Good for a reference point, but there is value lost in going too much by the book and not enjoying the experience for what it is. Now I want to go on a road trip!

    1. Hey, thanks for stopping by. Exactly right about enjoying it for what it is – some of our best memories are of things you’d never have found in any guide book. Glad it inspired you to want to go travel now – me too! Just waiting in readiness…..

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