Get creative and take risks: Tips for a cheap holiday this summer from a viral budget travel expert

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Despite the cost of living crisis, holidaymakers are still planning on jet-setting to popular holiday destinations this year. But, as we saw last summer, travel disruption could play havoc with the approaching school holidays – and it’s not unthinkable that travel plans could go awry.

That’s where Chelsea Dickenson, founder of CheapHolidayExpert.com, comes in. The budget travel expert has gained a following online by helping people to get as prepared as possible for booking trips, flying and – the worst case scenario – figuring out next steps when holidays go horribly wrong.

The 33-year-old, based in North London, has become an expert in maximising your money with minimalist packing techniques and tried and tested travel hacks. At the heart of everything she does is finding realistic ways to travel for less without sacrificing the quality of your holiday.

“We truly do see holidays as being this additional human right,” says Chelsea, “But the bones of really affordable travel are taking risks, being flexible and also accommodating people who are just doing their jobs.”

From free hotel upgrades to luxury housesits and bargain flights, Chelsea shares her story – plus budget travel secrets and how to escape hidden baggage costs – with The Independent.

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How it started

While studying at Manchester University, Chelsea landed a role in student radio and went on to become a production coordinator for documentaries and TV shows, booking hotels, trains and flights for crew members. “I got such a buzz from it, it reminded me of getting the Eurocamp catalogues growing up and seeing the insane price differences between August and September holidays,” she says.

In December 2016, she decided to start her own YouTube channel. She saw a study claiming that the average British person spends £3,418 a year on holidays, which triggered the inspiration for her first video series: “I started thinking if I was to half that amount of money, what could I do with it, how many holidays could I go on? And that’s exactly what I did.”

Chelsea had five rules for the £1,709 challenge: she could only travel using 28 annual leave days, two of the trips had to be longer than five days, she had to travel to at least three continents, go on at least 10 holidays and fly business class at least once (a rule she followed on a flight to Benidorm).

At the end of the series she had travelled to 10 holiday destinations, including Valencia in Spain and Gdansk in Poland – a budget favourite of Chelsea’s – plus Dubai, spending an average of £170 on each. After a press release was picked up by the media, her 1,000 subscribers grew significantly.

“That’s when I realised that there is this appetite for travelling cheaply, obviously, but also for somebody actually trying out the hacks,” she says. “There’s a real difference between reading about it, and then actually doing it.”

In the year that followed she tried house-sitting, house-swapping, and making the most of every hack she heard about. With arrival of the pandemic, her travel project only got more serious.

Although the launch of her website CheapHolidayExpert.com was postponed from April 2020 to August that year, as a lot of experts pivoted away from travel content, Chelsea “really went all in, initially on consumer advice – it was about helping people get their money back.”

When Portugal opened its borders to tourists in May 2021, Chelsea flew out on the first day possible to test every step of post-pandemic travel for her followers: “It was all about explaining the traffic-light system. My followers came on social media because people just wanted to know what was going on. I was putting in layman’s terms what you actually had to do.”

How to get the best deals

Unsurprisingly, there’s no magic wand when it comes to securing the best holiday deals, and it’s the classic move of travelling during shoulder season that Chelsea most often recommends to bargain hunters: “Off-peak, you’re going to get so much more for your money, simply because prices are due to demand and not because of an increase in quality.”

Of course, switching to self-catering can also help reduce prices, and Chelsea is keen to encourage people away from the allure of package holidays to “trips that actually explore the local area”.

“I think you can make most places affordable. Even London in this climate,” Chelsea says; but you don’t always have the luxury of location choice when trying to secure the cheapest prices.

As for the best deals Chelsea has ever found, a £250 return flight to Japan via Moscow with Aeroflot – which she describes as “an experience” – and taking a risk on a week house-sitting an architectural award-winning home in Germany both paid off.

Ever dreamed of arriving to champagne at reception and the surprise of a free hotel upgrade – no fake proposal necessary? Chelsea has a hack for that, and it couldn’t be more simple: just ask. She suggests travellers get proactive about a stay in their fantasy room by copying the hotel upgrade email template on her website.

“If you’re staying in a hotel which has customer service at the centre of what they do and they have the availability, they will try to make it a memorable stay for people,” she says, adding that, while nobody owes you anything, it will be a “lovely surprise” if it does happen.

The popular template sees high success rates, according to Chelsea. “I get an email or message from someone at least once every other day saying that my hotel upgrade email has worked for them; I screenshot all of them because they make me so happy.”

Avid Airbnb users on a budget should also take note: your host may be open to some last-minute haggling.

Chelsea explains that the platform was built around the idea that you could send offers to hosts, so “you can ask for last-minute offers within your price range on the basis that it’s a win-win for two people because you are actually doing them a favour by providing an income.”

As with asking for most travel deals, the worst thing that can happen is that they say no.

Hacking packing

From stuffing her neck pillow and bra to the classic collection of a duty-free bag post-security, Chelsea’s tried, tested and usually ridiculous packing hacks ensure travellers won’t have to splash the cash on checked luggage.

Take wearing a £10 fishing vest to the airport for example, inspired by a travel vest that retailed for £80, negating the whole point of cutting costs. With 26 pockets, including a “gamechanger” back zip large enough to store a laptop, this seriously storage heavy fashion statement has helped Chelsea breeze through security.

The viral TikTok hacks are undoubtedly “silly” and risky, but they haven’t failed Chelsea yet. And the soaring price of checked luggage when flying on low-cost airlines has made the videos ever-more popular on social media.

“Packing hacks have been around for so long – the stuffing my bra hack was inspired by my boyfriend’s family friend who packed too much about 15 years ago, but the standard has completely changed,” she says. “There are no longer set values for checked baggage and people are forced to get creative.”

Chelsea is a fan of taking the minimalist approach to her compactly rolled travel wardrobe, often using hand-squeezed vacuum packs where you can force the air out. She’s keen to crack down on overpackers: “You always overestimate what you’re going to wear, so plan some hero pieces you can mix and match and a jacket that goes with everything.”

For hand luggage, her top tip is to “be a bit cheeky by a few centimetres with bags for hand luggage and take the risk – just make sure if you’re packing them full of clothes you could take them out and put them on to make it fit.”

What to do when things go wrong

Often inundated with messages from distressed travellers navigating flight delays and cancellations, Chelsea recommends knowing your travel rights and finding a person to speak to to take back control when things go wrong.

“It’s powerful to be able to go up to an individual and say, ‘this is what I want from the situation’, as you may not be presented with all the options,” Chelsea explains.

“Last year, when people were getting their cancellations through, airlines did not mention that you could fly on another airline or even travel on a different transport mode.” Yes, that means an airline would technically be obliged to book you an available Eurostar seat in the event of a cancelled Paris flight, if they had no alternative same-day flights available.

Chelsea is regularly frustrated at airlines that simply refund cancelled flights – the nail in the coffin for most people’s summer holidays – and insists people remember that the rules are there to protect them, not to catch them out.

“Bad travel experiences happen to everyone from every budget,” she says. “It’s easy to tarnish something from just one bad experience, but to expect a perfect trip every time is just completely unrealistic. There’s also a lot of fun that can come out of something you perhaps weren’t planning.”

Chelsea’s top five cheap travel hacks