My £99 ‘mystery holiday’ ended up costing over £500

Jack Rear exploring his mystery city on his two-day break
Jack Rear exploring his mystery city on his two-day break

Nothing gets me pinching pennies quite like booking a holiday. Dropping large sums of money on projects with so many moving parts makes me nervous. I could spend the same amount on a day at the shops without a thought, but on a travel website it takes me at least a few days of anxious consideration before I can work myself up to paying.

In short, I’m exactly the type of person for whom the offer of a two-night mini-break for £99 was made. It’s a respectable figure, not quite hitting the “too good to be true” threshold, but not (in my case anyway) totally ruinous if it didn’t come together.

Having launched its “£99 mystery holiday” offer in early January, discount website Wowcher says it has sold more than 4,000 trips to destinations from the Maldives to Ibiza, Paris to Berlin, New York to Las Vegas.

While the chance of being assigned a headline-grabbing destination like New York or the Maldives is extremely small, it promises that for £99 you will get a minimum of a two-night stay in a three-star hotel. The majority of the potential destinations were in Europe, primarily France and Italy, but also Germany, Poland, Spain, Sweden and Austria.

But of course there are catches. You get to choose your dates, sort of. The company reserves the right to ask you to change if you pick a weekend at the start of half-term, for example, but you don’t get to pick your destination. This is the “mystery”. Once you’ve paid your money, all is revealed.

Furthermore, the £99 price is per person, based on two people sharing a room. You’re not allowed to pay £99 for a single room. There are a few optional extras too. If you don’t like the location you’re given, you can pay £30 for something different. If you want to go in April, June or July, the price is £129 per person. Plus there’s a £6.99 administration fee.

A two-night break for £204.99 still sounded like a bargain, however, so I took a deep breath and paid up.

My destination would be… Milan; not a bad place to go in late February, I decided, so I confirmed. An agent would be in touch in three to four business days to organise the particulars, then I was unceremoniously ejected from the website.

As I waited to hear back, I began feeling convinced I’d been scammed. When I heard nothing for a week, I fired off a nervous email requesting more information. No response.

Ten days later, an automated email explained that due to high uptake of the Wowcher offer, they were very busy and would be in touch nearer departure. I began drafting my email to Telegraph consumer champion, Katie Morley, ready for when the scam became clear.

Yet at 9.30pm on a Monday night, less than a month before I was due to fly, my phone rang.  “Hi, this is Kanika from WeekenderBreaks [a third party acting on behalf of Wowcher] – I’m calling to organise your trip to Milan.”

Given the late hour, I remained suspicious, but Kanika shared a list of potential hotels and flight times. She offered the opportunity to swap Milan for Lake Garda, which I declined, and took my passport details, promising an email confirmation once it was booked. A few moments later, my phone pinged.

It wasn’t luxurious: I’d be flying with Ryanair at 9.35am from London Stansted to Milan Bergamo on a Wednesday, then back at 10.30pm on Friday night – but it looked genuine. My digs? An outpost of the B&B Hotels chain, next door to the AC Milan’s San Siro stadium on the city’s outskirts, it looked unglamorous but fine.

The B&B Hotels room included in the deal
The B&B Hotels room included in the deal - Jack Rear

But I remained nervous as my holiday drew closer. Maybe I’d arrive at the airport to be told the flights didn’t exist. Or I’d arrive at the hotel to find it under construction.

In fact, nothing of the sort transpired. It was all rather uneventful. The £204.99 bill soon started creeping up, however. I paid £11.15 to reach Stansted from London and €12 to get to Milan from Bergamo. The hotel itself was a slightly laborious half-hour journey from the city centre on public transport, so I paid €15.50 for a Metro pass, which offered three days of unlimited travel.

Jack paid a visit to Milan's Galleria Vittorio Emanuele II during his trip
Jack paid a visit to Milan's Galleria Vittorio Emanuele II during his trip - Jack Rear

B&B Hotels proved to be the Continent’s version of Travelodge: cheap and forgettable, but clean, modern and with free Wi-Fi. I parted with €7.90 per day for access to the breakfast buffet, and €9 on the “city tax”, paid by all hotel guests.

There were downsides to the “mystery” element of the trip. To see one of Leonardo da Vinci’s The Last Supper, one of the highlights of Milan, one has to book over a month in advance – so I hadn’t been given enough time to get tickets. The same went for a show at the La Scala opera house – even the backstage tours were long since sold out.

Milan's celebrated QC Termemilano spa
Milan's celebrated QC Termemilano spa

Even so, I managed to book tickets to the remarkable Duomo and its roof terraces the day before, and got into the TikTok-famous QC Termemilano spa.

I also didn’t have any trouble finding a table at the city’s restaurants, and indulged in the city’s renowned aperitivo scene like a prince.

It’s easy to get caught up in the hype of a “£99 holiday” and forget how expensive travelling can be. Factoring in food and drink, transport and sight-seeing, along with the initial £204.99 booking price, soon topped £500 for my two-night mini-break.

Jack enjoyed pasta for dinner at Montalcino Restaurant in Milan
Jack enjoyed pasta for dinner at Montalcino Restaurant in Milan - Jack Rear

Even so, I have no regrets. That low-level initial cost allayed my usual booking anxiety and ultimately took me to a city I might have never bothered visiting if I was fully in the driving seat. The mystery element won’t suit everyone, particularly the planners who like to curate their holidays in advance. Still, for those at peace with spontaneity, evviva la vacanza da £99!