7 golden rules of booking a holiday

Escape’s Doc Holiday has put together this simple seven-step guide to help you plan your next getaway.

Dilvin Yasa

less than 2 min read

May 28, 2025 - 10:52AM

Escape

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To book a holiday or not book a holiday should never be the question. Not only did you deserve that African safari, Great Wall of China excursion or transatlantic crossing of recent times, studies show taking time away from work can lead to spikes in happiness, energy and even productivity.

When it comes to the logistics of organising a life-changing getaway, however, things can become a little … overwhelming. Or it does until someone puts together the perfect seven-step guide. Don’t let travel stress hold you back. Follow these tips.

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Step 1: Choose your dates

True, the weather will play a key role in the time of year you travel (it’s a rare person who wants to ski Whistler in May), but you’ll also need to consider how much annual leave you have up your sleeve, the amount of time you can afford to take off, and how to maximise public holidays to extend your break. Wave cheerio to the office on December 19, for example, and you could return on January 5 having only taken seven of your allotted annual leave days for a glorious 17-day break.

Don’t forget to check in with colleagues to see if there is any leave crossover, as well as with your children’s school, not to mention investigating whether any events (Tour de France, Edinburgh Fringe Festival and the like) at your intended destination are likely to attract crowds, closures or eye-watering premiums.

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Step 2: Master the art of scheduling

Need to convince your boss? The most powerful tool in your pocket is an Ernst & Young study which shows that every additional 10 hours of holiday time an employee takes improves yearly performance by 8 per cent.

Once cleared for take-off, you’ll need to beat colleagues to the punch and block your dates in your calendar quickly. If in the course of action you find you need to reschedule appointments, it’s best to get in early, apologise sincerely and offer a couple of alternate times to reschedule.

This is also a good time to start managing everyone’s expectations of your inclinations during your time off. Do you plan to switch off entirely, or be open to important emails? There’s no time like the present to start communicating this information.

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Step 3: Set a budget

Unless you’ve got the balance sheet of a Vanderbilt, you’ll likely need to budget for your holiday. Happily, this is nowhere near as painful as your accountant (or partner) makes out and you can excel at this task in one of two ways.

You can either set yourself a total sum you know you can afford and then divide this figure by the number of days you’ll be away, or you can do your research on the cost of living at your destination, as well as the prices of attractions and restaurants you’re interested in (numbeo.com is a great site for this).

No matter which strategy you embrace, you’ll need to add in 30 per cent on top to arrive at your real figure. Remember, you’ll also need to factor the cost of travel insurance, visas, vaccinations and transfers when you’re doing your sums. Apps such as TravelSpend and Spendee help while you’re on the road.

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Step 4: Unleash your inner super sleuth

To avoid a potential “Is it really a water view if the water is coming from a burst pipe?” scenario, extensive research before booking a hotel, flight or even an attraction, is essential. While trusted recommendations remain the gold standard, search reviews on TripAdvisor, TrustPilot and Google Reviews. Travel forums such as Rick Steves and Flyertalk are a great place to ask a few questions of your own.

While Escape is always here for you (don’t forget to search our extensive backlog on this website), it’s also worth following a few discerning digital creators who specialise in a particular place or type of travel, such as Abroad in Japan or Eating with Tod.

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Step 5: Consider early bird discounts

Contrary to the idea of the early bird scoring the worm, fans of last-minute deals say it’s the second mouse who nabs the cheese. To us, nothing tastes better than a delicious serve of significant discounts, generous perks and better availability. And when it comes to cruising, these are typically aligned with early bird reservations.

Book a sailing as soon as it’s announced and you’ll find the lowest deposits, cheapest fares and some of the highest on-board credits advertised. It isn’t only cruise lines getting in on the early bird act. Club Med is currently offering up to 30 per cent off travel between November 2025 and June 2026.

Keep in front of the flock (or mischief of mice) by subscribing to email newsletters of travel providers you’re interested in. Don’t forget you can also follow them on social media to stay updated on promotions.

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Step 6: Book like a boss

Committing to the best week (or more) of your life doesn’t require much hand-holding, but this isn’t the time to hit the Book Now button with a devil-may-care attitude. First, take care to compare the cost of flights through Skyscanner, Expedia, Flight Centre, Kayak and Cheap Flights. Search functions within these sites such as Skyscanner’s “Whole month” or “Everywhere” tools can add value for money.

Online platforms like Booking.com and Agoda.com can offer competitive rates, but contact properties directly to see if they’ll offer a cheaper price for cutting out the middle man (some will). Book a rental car as soon as you can, but don’t forget to lock in some major attractions, too. Some, such as the Eiffel Tower, open for bookings two months in advance and are best secured as soon as possible.

Run your online searches using incognito mode, by using different browsers or clearing cookies for each one. This will help you avoid dynamic pricing increases.

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Step 7: Finalise the essentials

Insuring your legs for a staggering €750 million? Take a leaf out of Lionel Messi’s book and invest in insurance that will protect your bod (and your belongings) for future holiday goal kicking. It’s best to buy a policy as soon as you book your holiday, and policies can be compared through the website Compare Travel Insurance.

Any visas will need to be applied for at least four weeks before you go (smartraveller.gov.au has details on each destination), while a visit to your GP is required six to 12 weeks before any trips to a country that requires vaccinations. Sometimes several doses of a vaccine are needed to achieve full immunity before you go.

Now all that’s left to do is to turn on your out-of-office and exhale. This is your time to shine.

Original URL: https://www.heraldsun.com.au/lifestyle/7-golden-rules-of-booking-a-holiday/image-gallery/74e14cfda39946eb0df3cc21a820e851