My ‘secret holiday’ cost £99 over £500

Jack Rear exploring his secret city on his two day break

Nothing makes me pinch pennies like booking a holiday. It worries me if large sums of money are put into projects with so many moving parts. I could spend the same amount in a day at the shops without thinking, but on a travel website it takes at least a few anxious days before I can work up to the payment.

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

After launching a “mystery £99 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.

Although the chances of you being assigned a destination like New York or the Maldives are slim, it promises to get you at least two nights’ stay in a three-star hotel for £99. Most of the potential destinations were in Europe, mainly 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 choose a weekend at the start of half term, for example, but you cannot choose your destination. This is the “secret”. Once you’ve paid your money, everything is revealed.

In addition, the price is £99 per person, based on two people sharing a room. You are not allowed to pay £99 for a single room. There are also a few optional extras. If you don’t like the site 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. There is also an administration fee of £6.99.

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

My destination is… 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 organize the details, then I was unceremoniously kicked off the website.

As I waited to hear back, I began to feel certain that I had been scammed. After hearing nothing for a week, I fired off a nervous email asking for more information. No answer.

Ten days later, an automated email explained that they were very busy due to the high number of takers on Wowcher’s offer and that they would be in touch closer to the event. I started drafting my email to the Telegraph’s consumer champion, Katie Morley, ready for when the scam became clear.

But at 9.30pm on 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 am trying to organize your trip to Milan.”

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

It wasn’t luxurious: I would fly with Ryanair at 9.35am from London Stansted to Milan Bergamo on Wednesday, then back at 10.30pm on Friday night – but it seemed real. My dig? An outpost of the B&B Hotel chain, next door to the San Siro stadium of AC Milan on the outskirts of the city, it looked unglamorous but fine.

The B&B Hotels room included in the dealThe B&B Hotels room included in the deal

The B&B Hotel room included in the deal – Jack Rear

But I remained nervous as my holidays drew closer. I might arrive at the airport only to be told that the flights were not there. Or I would arrive at the hotel to find it being built.

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

Jack visited Milan's Galleria Vittorio Emanuele II during his tripJack visited Milan's Galleria Vittorio Emanuele II during his trip

Jack visited Milan’s Galleria Vittorio Emanuele II during his trip – Jack Rear

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

The “secret” aspect of the trip had its drawbacks. To see Leonardo da Vinci’s Last Supper, one of the highlights of Milan, a place must be booked more than a month in advance – so I hadn’t been given enough time to get tickets. The same was true of a show at the opera house La Scala – even the backstage tours were long sold out.

Spa celebration QC Termemilano in MilanSpa celebration QC Termemilano in Milan

Spa celebration QC Termemilano in Milan

However, I managed to book tickets to the magnificent Duomo and its roof terraces the day before, and entered the TikTok-famous Spa Termemilano QC.

I also had no trouble getting a table in the city’s restaurants, and enjoyed the city’s famous aperitivo scene like a prince.

It’s easy to get caught up in a “£99 holiday” and forget just how expensive travel can be. Food and drink, transport and sight-seeing, together with the initial booking price of £204.99, quickly added up to more than £500 for my two-night mini-break.

Jack enjoyed pasta for dinner at the Montalcino Restaurant in MilanJack enjoyed pasta for dinner at the Montalcino Restaurant in Milan

Jack enjoyed pasta for dinner at the Montalcino Restaurant in Milan – Jack Rear

However, I have no regrets. That low-level upfront cost eased my usual booking anxiety and I ended up going to a city I wouldn’t mind visiting if I was completely in the driver’s seat. The mystery aspect is not for everyone, especially the planners who like to book their holidays in advance. Still, for those who are at ease with spontaneity, evviva la vacanza and £99!

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