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Should you plan your own luxury holiday?

After my partner and I agreed that Thailand would be our next big holiday, I decided, perhaps somewhat over-enthusiastically, that despite working for a tour operator with two brilliant Thailand experts (Lynn & Alba) I’d actually give planning the whole 2 week luxury holiday a go myself.

For research purposes.

Because how better to understand what our clients might want from a luxury holiday, than to go on a luxury holiday?

(Don’t worry. It’s less LinkedIn post from hereon.)

Was planning my own luxury holiday a terrible idea?

Now, even my very patient partner would probably have imploded if I’d said something along the lines of ‘wahoo! Let’s rinse our holiday fund on a trip to Thailand & I’m actually gonna plan it myself so we can see how it goes, cause it’ll be a great case study for work!’

So I must confess that, longer ago than I care to admit, I lived and worked in Thailand teaching sailing.

The country is not a total unknown. I remember that it was fairly easy to figure stuff out then, and anticipated it would be similarly easy this time, too.

Plus, I didn’t tell him that it was, in part, an experiment.

*slaps own wrist*

What did we want from the trip?

Like many who worked overseas when they were younger and later return, I’m at a different stage of my life and have different priorities.

Mine and my partner’s non-negotiables include a comfy bed, fewer and shorter transfers, staying away from the crowds whenever possible, and eating really good food.

Past (but not gone!) are the days of scraping together every Baht from the bottom of the backpack to fund the next big adventure, or squeezing onto a bus for 12 hours to save £20.

We now prefer slower, more convenient trips. Trips where each day ends with relaxing into a well-appointed hotel room, sleeping soundly, and waking up early to head out diving, or to a cookery class, before ending with a sundowner on the beach, an easy dinner (no swanky food for me, I’m not grown up enough) and an early night…

So we wanted nice mid-range, comfy hotels with great amenities, that didn’t have hundreds of rooms, preferably had a pool or easy access to the beach, and that were close enough to the action that we could pop out when we wanted to – and far enough away that it was a peaceful escape later.

So with that in mind, how was the holiday?

It was great. Obviously.

Thai people are unfailingly wonderful, the food is unparalleled, the diving is gorgeous and even the monsoon (we went in late October) brings with it a sense of renewal and lushness – so of course, it was a completely delightful 2-and-a-half weeks.

I ate enough young coconuts to see me through the next 6 or 7 years, and replenished my soul with beautiful snorkelling and diving.

My partner fell in love with Thailand as much as I did. We dived, snorkelled, hiked, scooted, climbed waterfalls, learned how to make spring rolls, Pad Thai, curries and soups (& promised our cookery teacher we’d send her pictures of our efforts!) and, shock of all shocks, I took all emails off my phone and switched ‘do not disturb’ on. Liberating.

So on the whole, was planning my own trip to Thailand a resounding success? Yes and no.

What did I learn from planning my own luxury holiday to Thailand?

I should have used an expert.

While the holiday was great, and we loved every minute, I found the ‘before departure’ work of planning our dates, coordinating hotels, arranging transfers and endless googling what we should be doing in the 3 places we visited totally exhausting.

I made my own Vamoos, which was incredibly useful (I can’t imagine ever travelling using the same email/app shuffle of before!) but again, this was work that I was doing, in my evenings and over weekends, when actually all I wanted to be doing was getting excited about going back to somewhere I loved.

The planning fatigue won the battle about 2 weeks before we departed and, I’ll confess, I lost my motivation.

I called Lynn and Alba and asked for suggestions. They reassured me that while it was monsoon season, we would actually see the sunshine (did you know if you read the entire internet, you still won’t find the answer you’re looking for?!)

They also immediately sent me through a list of suggestions, half of which I’d never have found by googling.

What will I do differently next time?

I’ll use a tour operator to plan my holiday.

I didn’t think that I was ‘Fleewinter’s typical client.’ But, it turns out, I am.

I’m increasingly precious about my non-work time being ‘offline,’ so I found the hours spent organising the trip ate away at my excitement and eventually became just another job on my long list of jobs to be done.

And that’s really, really not how I wanted to feel about my holiday.

Frankly, all I wanted to do was giggle about how lucky we were to be going back to one of my favourite countries.

To the reader who’s eyebrows are currently somewhere near the clouds (because obviously I would say use a tour operator la la la, I work for one…) rest assured, this is my hand-on-heart, honest-to-Mother-Nature experience.

What are the lessons I learned from planning my own luxury holiday?

1. I did not want to open my emails. This will come as a great shock to anyone who knows me; but while we were there, I really, really didn’t want to open my email inbox to look at stuff. It was a connection to home that I didn’t want to tap into while we were relaxing and having fun. So now, I am even more obsessed with Vamoos than I was before: it had everything I needed for our trip, without opening the dreaded Mail app and accidentally seeing what was happening in the ‘real world.’
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2. Planning fatigue is real, and I wish I’d only given myself the job of getting excited. While it was lovely to look at endless pictures of beaches, on more than one occasion I caught myself stressing that maybe I hadn’t earmarked ‘the best beach.’ Which would leave me googling every beach on an island to make sure I know which was ‘the best.’ They’re all good. And I needed someone to tell me that I didn’t have to worry about whether we’d end up on the best beach, and that they’d send me a list of places to take daytrips too, each of which would be as beautiful as the rest.
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3. I was going to the same places as everyone else, but I was in the queue for tickets. Everyone who used a tour operator just waltzed right past us, tickets in hand. I love a queue as much as the next person, but this was a no brainer.
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4. Using a tour operator wouldn’t have meant I had less control over my holiday. The day trips, excursions, sites visited – they’re all the same ones Fleewinter sends their clients to. But I was the one organising the tickets, transfers, timings and everything else. If I’d let someone like Fleewinter organise it, I’d still have gone to the same places: but I would have had more time to read a book when I was there.

Overall takeaway from planning my own luxury holiday?

When we go on holiday again, we’ll decide on a budget per head early, book some flights (because then there’s a lovely feeling of certainty!) and then I’ll call a specialist and ask someone else to be a travel expert, because my job is running a business. Not being a travel expert.

Next time I’ll hire the right person for the job straight away.

Coming up on the travel wish list is Brazil, so you can bet your trans-Atlantic flight that I’ll be calling Val.

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