The Hive Minds Checklist For Going on Holiday
From leaving work, to packing up and everything in between – a virtual assistant’s guide to jetting off
You’re sitting on a sun lounger, with a book you’ve been wanting to read for ages in one hand, and your third Mai Tai of the day in the other. The breeze gently tickles your sun-kissed face as you hear the waves rolling onto warm, soft sand.
Then, the printer starts jamming and makes that high-pitched beeping sound that no-one, except Barry from IT who’s away on his honeymoon, quite knows how to fix.
Daydreaming is a perfectly natural part of the holiday countdown and a very welcome form of procrastination.
But why is it that even though you’ve had a holiday planned for months, it hits the 1-month-to-go mark and there’s a mountain of things to do?
Sometimes it feels like you need a holiday just from running around and trying to get ready for going away (just as well you have one booked, right?).
As Virtual Assistants (or, more accurately, on-demand executive assistants), we organise holidays all the time—from city breaks and family catch-ups to birthday parties in Ibiza—so we know how much it takes to get organised.
Sometimes an extra pair of experienced hands—or flexible admin support—can be a welcome addition to the fold.
As big fans of checklists (it sort of comes with the job), we have a list for everything. Here, we’re sharing our ultimate checklist to get you from desk chair to deckchair in no time…
Out-Of-Office
Ahh, pre-holiday work stress – the storm before the calm of going away.
It’s something that a lot of us have experienced, but with some planning, it can be a ghost of holidays past. Here’s how to make it happen…
Plan out your time and tasks and make sure to leave some wriggle room (we’d recommend planning to finish everything 2–3 days before, so you have a little bit of extra time if everything doesn’t go to plan). And hey, if you do finish everything early, you can get ahead for when you come back.
Let people know you’re going on holiday as soon as possible, including others in your team and your clients. Make it visible in a shared calendar and feel free to drop it into conversation when project planning is taking place.
If you’ve tried to plan everything out and the only way to get everything done would be to bring your laptop to the pool, then you could do with an extra pair of hands. On-demand executive assistant support or temporary executive assistant cover can keep things ticking over while you get some well-deserved time off.
Sometimes you can’t get everything done—and hey, that’s okay. Other people in your team can help take care of things, but you need to give them the information to do that.
Writing a handover—a good handover—is like a pre-holiday present to yourself and 100% worth the time.
If you don’t have time to write one, a virtual assistant or project-based EA support can step in and help pull everything together for you.
Now for the satisfying part. Set your out-of-office message and include the details of someone they can contact while you’re away, so you can switch off completely.
A recent study showed that 65% admit to checking work emails on holiday even though 96% of bosses don’t expect it. In fact, 64% actively encourage switching off.
With the right prep—or the right reliable admin support service behind you—you won’t have to disturb your holiday with work.
Get Holiday Ready
From travel insurance to having nightmares about leaving your passport at home—there are a lot of things to remember before jetting off.
Here’s our go-to list to make sure you don’t forget anything:
Passport – a few months before you go, double check your passport and expiry date. Once you’ve checked it, put it somewhere safe. Then set a reminder in your phone a week before with details on where it is (because you could’ve sworn it was in your desk drawer, right?)
If you need them, apply for visas as soon as you can and print copies
Get travel insurance – quick, inexpensive and always worth it
Check if you need vaccinations via the NHS or your GP
Book airport transfers early (both ends of the journey)
Bring proof of bookings – apps are great, but we’d always recommend printing copies just in case
And if even reading this list makes you feel overwhelmed, this is exactly the kind of thing personal and business assistant support or ad hoc business support in the UK can take off your plate.
Pack, Pack, Pack it Up
Have you ever opened your case on holiday to realise you’ve left something at home?
With this list, you’ll be packing like a pro in no time:
First of all, check your suitcase – ideally a few months before. If it’s been a while, pull it down and make sure it’s still in good shape. Trust us, there’s nothing worse than a wonky wheel.
Next up, outfit planning – a Friday night well-spent, or the exact idea of hell depending on who you are. Think about how many days you’ll be away and plan outfits accordingly. If you want to be savvy, bring separates so you can mix and match.
Oh—and always bring extra pants.
Check the amenities in your hotel or Airbnb – do they have an iron, hairdryer, towels? This can save space in your case.
If you’re travelling by plane and have cabin luggage, make the most of it for some in-flight me-time:
Earphones
Chargers (and adapters)
Passport and documents
Snacks
Entertainment (books, playlists, podcasts)
Skincare if you’re that way inclined
A change of clothes (in case your main bag goes missing)
Neck pillow
A big scarf for warmth
Remember – liquids under 100ml.
Phew! That’s a lot to organise—and that doesn’t even include deciding where to go, finding hotels, and booking flights.
Whether you have extra help or decide to do it all yourself, if there’s one thing we’d recommend, it would be to use this checklist as a guide to create your own a few months before you go.
Or better yet, outsource the admin and planning altogether.
Using a flexible, no contract virtual assistant or on-demand executive assistant means you can get all of this handled for you—without hiring, without stress, and without it taking over your evenings and weekends.
Either way, getting organised will make your holiday feel like a balmy breeze, even before you’ve left for the airport.
Need a hand to do all of this?
If you’re short on time, overwhelmed, or just want someone else to handle it, we can help.
From travel planning to inbox management and everything in between, our flexible admin support and pay-as-you-go EA services are designed to fit around you.
Get in touch to book a Virtual Assistant and get from desk to deckchair—without the chaos.