From driving dramas and hotel horrors to booking mix-ups and missed flights, how do your holiday stories compare with these? They aren’t fun at the time, but we’ve found our holiday disasters often make for great dining out stories later on …

Eva Berg, founder The Secret Pilates
Moral: Check your destination isn’t swamped with students on Spring Break
I had always had very romantic notions of Costa Rica – of exotic sultry Hispanics with flowers in their hair, incredible jaw-dropping wildlife, beautiful white beaches with little shacks serving cocktails in coconut shells … you get the picture.
Well, we arrived after a long flight into a very busy Juan Santa Maria airport at the end of March one year and I couldn’t help but think how lively the place was with lots and lots of young Americans. When we arrived at our hotel, it was like a scene from the movie Frat House – there were huge blue fishbowl cocktails everywhere and drunk college students blasting appalling music and throwing each other into the pool. We renamed the island “Costa Shrieka.”
Trying to stay positive, we pottered hopefully down to the beach to be greeted by more hedonists, ‘making out’ or in a comatose state, drunk from the night before. To our horror we realised we had arrived during US college Spring Break – think 2017-era Magaluf on steroids, or better still; an Heironymous Bosch painting.
We stayed at our hotel for one (sleepless) night; the hotel very graciously refunded us the rest of our stay and we moved swiftly to an Airbnb high up a mountain and as far away from the beachfront hotels as we could get. This is where it became even more interesting, with 5am wake up calls from very loud macaws and packs of marauding monkeys stealing anything you left on the balcony. This was actually comical but the best entertainment was the pool activity. On the first morning, I claimed my sunbed in the shade and settled down with my book. Within seconds what I can only describe as a medium, dog-sized dinosaur barrelled out from the shrubbery straight for me! He proceeded to climb up onto my sun lounger and spread himself out. I was in a state of shock while my other half and the Airbnb host were falling around laughing. The dinosaur was, of course, just a huge and completely harmless 15kg iguana. We became pals and myself and Iggy would sun ourselves every afternoon. It was wasn’t exactly the exotic beach holiday I had imagined, but at least I got to experience the wildlife, a bit closer then I would have liked! @thesecretpilates
Sarah Halliwell, THE GLOSS Beauty Editor
Moral: You get what you pay for when it comes to budget hotels sometimes
There’s a particular teeth-grinding quality that comes with a fancy room in which you’re unable to sleep, due to either rampaging people next door/in the corridor, or something weird like a groaning water tank or whirring generator that leaves you lying there with drying eyeballs, your mind fixed on your hotel bill. First-world problems.
Worst ever was an overnight in a motel in my hometown, admittedly “budget”, but describing itself as a “perfect central hub with conference facilities”. Arriving late at night to the “chalet-style” rooms, we found it dark, deserted and seriously scary, not unlike something from a Coen brothers movie. This was the kind of room where you barricaded the door with furniture to be sure of not being murdered during the night. Bathroom ceilings were mottled with damp and mould, there were no charging points whatsoever and everything in sight was nailed to the wall. At 2am our next door neighbours returned from their night out on the town and played Ed Sheeran’s Shape of You incessantly for the next three hours at full volume, through paper-thin walls. That wasn’t even the worst of it; it seems that Sheeran is an aphrodisiac for some. We left as soon as it was light, pale and blinking yet relieved to be out of there.
Only too late did we read some TripAdvisor reviews, which made for hilarious reading. “Suspiciously sticky” is a recurring theme, as is “No redeeming features”. One mentioned the cleaner, who was “pleasant, but walking around the rooms smoking”. I especially enjoyed this unequivocal review: “Our room. OMG. We turned the light on and it was flashing and buzzing. The room stunk of damp and stale tobacco. The beds were dirty and the pillows were stained. Mattresses past their best. The floor had not been hoovered. Bottle left from previous visitor. Walls damp, stained and damaged. We went back to reception and they were not bothered. The bath looked like it had never been cleaned.” Any stay since has felt palatial. @sarahhalliwellbeauty
Helen James, designer
Moral: Sometimes Christmas at home is better
The only time we ever spent Christmas away from home was when we stayed with friends in the south of France. The kids hated being in someone else’s house so the whole trip was a bit of an anti-climax.
On the return journey, we arrived at the airport four hours before our flight was due to take off. We had four suitcases full of cheese which ended up being over our allowance. We had to remove said cheese. The flight was then delayed and with two small kids we eventually landed in Dublin at 11pm at night, having left our friend’s house at 8am.
I then realised I had no car keys and the car was in the long-term carpark – home was in Westmeath. I phoned our childminder who went to the house to get the spare keys. We paid for a taxi to deliver the keys to us at the airport and took the kids for a burger as we waited. The taxi eventually arrived at 1am with the keys. Obviously when we got the bus to the long-term carpark it was lashing with rain and pitch black. I put a milkshake on top of the car while I opened it and a gust of wind blew it over on top of me. When I got into the car I then discovered the battery was dead! At this point it was beyond a joke. I think we made it home around 5am, though nothing could beat waking up in our own beds the following morning. @helenjamesdesign
Emma Kelly, founder, Elevate PR
Moral: Always take local advice
Our biggest holiday disaster, about ten years ago, was not taking on board a friend’s advice that it would be a bad idea to hire a car to drive from New York to Cape Cod with three young kids. She insisted flying would be much better. Google maps said the journey was only four hours. It ended up taking twice that – eight hours with traffic and at one point, my three kids started vomiting and I joined them! It was a very large clean up job, thankfully the hire car had plastic seat covers. My husband somehow managed to not get sick. We got back on the road and loved the beaches of Cape Cod. @emmaelevate

Sarah Macken, THE GLOSS Contributing Editor
Moral: Check when the summer season begins in pretty, off-piste islands
We made the mistake of going to Ischia at the end of May last year, a month that saw a bout of intense flooding. The island, which was the shooting location for the film version of The Talented Mr Ripley, is renowned for its beauty, however we ended up spending a lot of time indoors. There was torrential rain, not a break of sun in the heavy clouds, and even reports of landslides! We got a good deal on a beautiful hotel because it was before the season officially kicked off, however the weather was so bad the hotel’s beach remained closed all week. Also, even though it was the end of May there were a lot of shops and restaurants not open yet for the season, which meant not a lot of diversion either. We made the best of it with card games, a glass of something bubbly and the occasional sit out by the pool (wearing a hotel robe, for warmth!). Not ideal! @ohegartysarah
Edel Coffey, THE GLOSS Contributing Editor
Moral: When booking a car rental, always check if your driving licence has expired
I do remember one holiday disaster which was probably more of a boyfriend disaster, but it’s too far in the past now for me to discern which it was. I was a very nervous driver when I first began driving and could never imagine driving on the “wrong side” of the road in a foreign country, so when a former boyfriend suggested we rent a remote villa and a car to get us there for our summer holiday, I laid down my one solitary condition – that he would do all the driving as I was too scared. He readily agreed and by the time we got to the car rental desk in the airport to collect our car, my thoughts were on which type of rosé wine I was going to drink with dinner that night, not how to navigate Spanish motorways. But as my boyfriend handed over his driver’s licence and the sales assistant frowned down at it, I knew my hopes of being chauffeured around in a two-glass haze were diminishing by the second. When she informed us that his license had expired, I handed over my licence and off we went in an atmosphere chilly enough to cool the Mediterranean. We survived the holiday but the relationship did not, alas. In time however, I came to be grateful for the experience as I now merrily drive on the wrong side of the road (in foreign countries I hasten to add). @edelcoffey

Suzanne Mullen, general manager, The Station House Hotel
Moral: Make the most of a missed connecting flight
My daughter and I were travelling back from the US one Christmas, from Denver via Houston and then Newark (NYC) on to Dublin. It was a circuitous journey to say the least.
Our flight from Houston to Newark was delayed in Houston, however we had no real concerns as the United Airlines crew knew we had a connecting flight to Dublin and were in constant contact with the ground staff at Newark. So far so good! However all of a sudden we couldn’t land and were held in the air circling Newark for around 30 minutes. That feeling of dread set in as I anticipated a night spent sleeping in the airport.
When we landed in Newark we were told that our flight had departed – when I investigated further, I was horrified to find out that it had departed from the same gate that we had landed into! In other words, the ground staff failed to tell our cabin crew that there was absolutely no way we would ever make the flight as we were arriving to the same gate they were leaving from.
Anyhow, I got to work trying to find our bags and arrange to get us on to the next flight to Dublin. But it was chaotic – the weekend before school started – pure chaos in the airport. After queuing for at least an hour for the bag claim, I was told that our bags were en route to Dublin the next evening. So I thought – let’s make a trip of it.
At this stage it was well after midnight – there was no help from United Airlines offered, so I decided to call The Whitby Hotel (part of the Firmdale group). I’d always wanted to stay in a Kit Kemp hotel (in particular, I really wanted to see her headboards and her technique for dressing the bed – which always looked so perfect in Instagram pictures). So I decided, now’s a great time to make that happen. Spoke with the night porter – rooms available! Woohoo!
We hopped into a taxi and off we went to Manhattan in the middle of the night. We were greeted warmly by the night porter – a lovely young gent – who very kindly ordered us food from his own personal delivery app. There we were – eating sushi in our room at 2.30am before hopping into the most lovely Lefroy Brooks shower and the most comfortable bed ever. Thankfully, I always travel with a change of clothes in my carry on whenever I go long haul – which came into good use on this trip. The following morning, we enjoyed a fabulous brunch at the hotel before heading out to meet friends in Central Park and then back to Newark for our Dublin flight later that day. A fun-filled and busy 24 hours was had and a memorable trip, made all the more enjoyable by the warm welcome and help from the very nice night porter in The Whitby Hotel. @stationhh
Aoife Dunican, Image Consultant, The Style Bob
Moral: Double check the hotel name and location
I am not sure how I am still married after this holiday disaster. The story began in LA back in 2017 when I met a German guy by our hotel pool and asked him for recommendations for ski resorts. Right away he said, Hotel Bergblick in Fiss, Austria. “Ski in, ski out – it’s the best area for good skiers,” were his words. I’m a real fan of meeting a local and getting recommendations, so I started researching immediately. My phone screen had a glare but I preceded to book the Hotel Bergblick (or so I thought). No time like the present to act on an impulse. Come the following March we were all excited about the ski holiday. Mr Bob is a serious skier and the kids were not bad at either. He was happy we were going to Fiss as the Ski Club gave it the thumbs up. The week before departure, there was a mini red flag. I rang the hotel to book ski lessons and they mentioned something about finding a bus to go to the next village where perhaps there might be lessons. Odd, I thought, but sure it’ll be grand.
We flew out Wednesday evening, driving straight from work, so we were all a bit stressed but excited to hit the slopes. I’d been communicating with the Hotel Bergblick to say we would be arriving late and I thought they were very kind as they said they would keep some sandwiches for us.
When we landed, we picked up the car rental and put Fiss in the Satnav. At midnight when we were just two miles from the hotel, we saw the road was blocked and the local police told us we would have to sleep in the car until the road opened in the morning. You can imagine the kids – I’d already staved off 20 “are we there yets” and it was now approaching midnight. So, we called the Hotel Bergblick and explained. They said, sorry we’ve no idea who you are. I was nonplussed and said I’m the girl who told you we’d be late and you are keeping me sandwiches. They said, sorry, we don’t know who you are, you must have the wrong hotel. Hubby asked me for my phone and looked at the emails. He then realised that the Hotel Bergblick that I had booked was a different one in a place called Gran – it wasn’t even a ski resort and was three hours drive away. Cue a lot of moaning from the kids, as for himself and I – well, need I say more!
We set off on the three-hour trip and were again stopped by local police asking us where we were going. We felt like the von Trapp family, but eventually got to the hotel at 3am. They were very nice, thankfully. I got up early the following morning and went to the reception to ask about the ski room. Blank stares. They had a boot room for hiking but no ski facilities. I was desperate at this stage and asked the receptionist to help me get out of the bad books. She said there was one slope half an hour away. So we went there and spent the day in silence going up and down the one ski slope. I was like Mrs Doyle on Father Ted saying “ah isn’t it lovely now, lovely little slope.” The next day we drove another hour to find one more slope. Relations were calmer by then.
When my husband speaks of the holiday now, it’s oddly with very fond memories. Our daughter met a very kind instructor who took her down the one slope ten times. My boys found a lovely local Irish bar on St Patrick’s Day were they watched the rugby with the staff. The hotel was lovely and the food was terrific. My husband did ask me last week if I wanted to go skiing in 2025, and where would I like to go? I said Fiss! I want to make sure I follow through on that recommendation from the German guy by the pool in LA! @thestylebob

Darina Slattery, founder bespoke travel company, Oomi Travel
More: Beware an early morning dip, and where you leave your clothes
I was in sunny Cascais in Portugal this summer. One morning, rather spontaneously I decided to do a bit of sunrise sea swimming after a night out. So, I stripped off (to my underwear), threw my brand new DeCastro dress on the sand, and ran in as quick as I could, to avoid anyone seeing me (I was top naked!). About ten minutes later I see hands waving from the beach. It looked like I was being called by some Portuguese policemen to get out of the water. I pretended not to see them and kept enjoying the lovely view of the sun rising.
Eventually, I felt I should get out. Only to find that my dress and sandals were gone! I believe they were washed up with the tide, or the police thought it to be a funny joke? Hoping not the latter. Thankfully, one of my friends ran to the rescue with a towel, and brought me to her hotel room to get changed. As I walked through the breakfast room of the hotel, where all our friends were enjoying a morning after debrief breakfast, I skipped by laughing my head off wrapped in a white sheet. It certainly topped the funny moments on our trip. @oomitravel

Penny McCormick, THE GLOSS Contributing Editor
Moral: Be wary of sending things to be ironed in Paris!
Several years ago, I was invited to a posh party in Paris for the launch of Hermès’ Rive Gauche boutique. The brand had taken over an old Art Deco swimming pool (Piscine Lutetia) on the rue de Sèvres and was making a huge splash (forgive the pun).
I was very excited about the trip and, as ever, immediately wondered what to wear. I was attending the party and interviewing the creative directors the following day. I brought two outfits – a never-worn cocktail dress and a new Armani suit – a splurge purchase which I was looking forward to wearing for many years to come.
Arriving in Paris, I hailed a taxi and told the driver to take me to L’Hôtel. Cue a comedic back and forth about which one. L’Hôtel, on rue des Beaux Arts, is famous as Oscar Wilde’s last abode, where he said of the decor, “This wallpaper and I are fighting a duel to death. Either it goes or I do.”
I got to L’Hôtel with very little time to spare and unpacked quickly. The room was dark and badly lit (Parisians seem to love this vibe, me not so much) and there were no ironing facilities. I immediately called housekeeping and asked if they could iron both outfits (repasser being to iron in French). Then I jumped in the shower. After freshening up, I called to ask where my clothes were – it had been a good 40 minutes by this stage. The receptionist said she would look into it. A short time later she called to say that my dress and suit could not be located. Comment? She thought they had been sent to Le Pressing (dry cleaners) which was now shut. Quel horreur! At this point, the manager sent up a large glass of wine as I surveyed my suitcase. I had the jeans I had travelled in, plus some shirts, which were much more casual than smart. I enquired about the staff member who had taken my clothes to be told he had clocked off for the evening. There was a lot of shrugging and not many profuse apologies, just the usual Parisian nonchalance, as if I was making an undue fuss.
Seeing my rising distress, the manager then offered to take me to Le Bon Marché to get a new outfit but there was no time – the party was starting and the store was also closing.
I ended up wearing jeans, a white shirt and a dash of red lipstick – to be honest, a passe partout for any occasion in Paris. I kept my coat on, like several other guests, as it was quite chilly in the store.
The next day I wore the same outfit – everyone I met was in butter soft Hermès leather pleated skirts or trousers I recall. When Le Pressing opened my clothes were nowhere to be found. I assumed they had been stolen by some of the hotel staff, though I received no logical explanation. The hotel did offer to reimburse me for my lost clothes (top marks to the staff at Harvey Nichols for being so helpful in tracking down receipts) and I was later offered a free stay at L’Hôtel but vowed never to return. Now, I don’t travel without my mini Steamery for any ironing emergencies and always make sure my travel jeans pass muster. @pennymccormicked