The type of holiday you’re currently planning is so indicative of where you’re at in life. Where you go, who you go with and the reason why, reveal a moment in time you might never live again. It’s funny to think that now we go through a cycle of holidays from child to OAP, as symbolic as the life stages we know and celebrate.
I can measure my life by the trips I’ve taken, but there are still a few trips below I’m still looking forward to hopefully doing one day – keep scrolling to the end. And I’d love to know, how many have you done?
28 Types of Holiday to Take in a Lifetime
1. Childhood family holiday
My childhood family holidays were spent at River Dart Country Park in Devon. I don’t even know how many times we went there, and it never got boring. We’d camp, swim, play in the forest and eat from the BBQ. There were a few times when we were allowed to bring friends along, we’d go with our neighbours, and my Easters and summers spent there are full of fond memories.
It was either there, or the ‘Upside Down House’ in Cornwall. It seemed so exotic at the time, that the bedrooms were downstairs and the kitchen and lounge up. I’d love to go back to the area again and relive where we walked, the snail races we used to have and visiting Sennen Cove on those rare sunny day.
2. Going away with someone else’s family
I went to Devon with a school friend, to Butlins with another one and to Weston Super Mare with my next door neighbour. Questionable and variable levels of enjoyment ensued.
In Devon her and her brother would physically fight so viciously people would stare at us and her mum would cry.
On the way to Butlins, five hours away, her dad chain smoked the entire way with the window closed and me sat behind, dying. She went off to snog her cousin every night while I just sat on a picnic bench waiting for her to return. It was a weird trip. We didn’t stay friends for long after that.
Weston was great, we went twice, maybe thrice.
Be careful who you holiday with.
3. School trip
I went to France with school when I was in Year 8, I think it was, so about 13. God we had so much fun. All the way from Derbyshire to Paris on a bus – seems slightly insane now. Definitely wouldn’t’ve wanted to be a teacher on that trip but I have some great memories.
And then when I was about 15 a few friends and I went to Turkey on a school trip – again, fun. As well as checking out all those important religious sites – it was a Religious Studies trip after all – we managed to fit in a few drinks, and lots of laughs. Again, driving the teacher’s crazy.
Then there was that school trip to London where our teacher bobbed out of the museum we were visiting, went to Soho, got absolutely annihilated and then shouted abuse at us on the bus on the way back while being held back by the other teachers. Oh John Taylor High School, you were FUN.
4. Caravan holiday
I’ve been on caravan holidays to Weston Super Mare (see point number 1), Newquay with the girls at 17, and Hoburne Bashley in the New Forest just a few years ago.
One of my friends actually met her husband at Sunnyside Holiday Park when we were 17, on the bus on the way back to the caravan from a night out. Honestly it was one of the rankest, skankiest places ever and I think it got shut down a few years later. But at least they’re going strong with two beautiful children.
Anyway, love a good caravan holiday.
5. Girlie / lads party trip
Gather your girls (/lads), book your flight, and get ready for a week in the sun.
I love a good girlie trip where you can just sit back and relax and get those cocktails on ice. Nothing to do but tan and party without a care. When I was 18 I went to Kavos with the girls I worked with at Boots (see life changing trips), at 19 it was Kos with 5 school friends, 21 Cancun after summer camp and at 22, I went to Ibiza.
The teenage ones we’d pretty much all fallen out by the end, as is the way with teenage girls – too much sun and too many fishbowls – but the memories hold strong. In fact, I think I’m due another one.
READ MORE: A Survivor’s Guide to the Girlie Holiday
How about booking a villa for your girlie holiday?
Check out the great properties on Airbnb for some inspo. They have villas, chalets and apartments for all budgets.
6. Best school friend trip
When we finished school, and just before university, my high school bezza and I went to America for two weeks. It was my first time flying long haul and we went to New York and California. SO exciting. We both worked all summer to afford it and just had the best time in NYC.
At that time we were both really into theatre – Kirsty was off to go drama at uni.
We went to shows, drank cosmopolitans a la Sex and the City – our favourite show – and shopped till we dropped.
California wasn’t quite so successful seeing as we were 18 and couldn’t hire a car. Getting round by public transport is pretty sketchy and difficult in LA. I can always remember a bus driver telling us about all the gun crime in Inglewood, where we were staying, and the two of us, innocent village girls, were wide eyed and paranoid as we realised we were staying in one of the most dangerous neighbourhoods in the US.
That was the days before we had travel bloggers like me to tell you where’s dangerous or not.
7. Girlie zen trip
Seeing as I’m now 30+ and the idea of partying the night away in the likes of Kavo, Kos and Ibiza is just far too disturbing, my girlie party trips have turned into foodie, zen trips – though alcohol is still very much welcome and involved.
I went to Lake Garda in Italy and Rovinj in Croatia with Chloe, to the Sporades Islands in Greece with Jayne, Lisbon with Helen and to Saas Fee in Switzerland with Fiona. Just to get away, somewhere new, and enjoy being outside, exploring and hanging out with your friend is definitely my favourite way to travel now.
8. The fly and flop beach holiday
Ooo you can’t beat a beach holiday, can you?
Some travel snobs would turn their nose up at these type of holidays, but when you work hard for the other 50/1 weeks of the year, you deserve it. Jayne and I had a great time relaxing in Antigua, and I have two Greece holidays coming up this year that I can’t wait for. I’ve laid on the beach in the Philippines with a good book, and in Vietnam, instead of going off exploring.
There’s nothing wrong with taking time out to relax and enjoy your surroundings.
9. Island hopping
Pick a group of islands and go explore. One of my favourite trips I’ve ever done was the Tao Experience out in the Philippines. Being on the water, around a good group of people and seeing such beautiful islands was just incredible. Knowing that the payment was all going back into making the islands we went to better also made it all the more enjoyable.
I loved being away from land, WiFi and our commercial world.
I’ve also done ferry hopping in the Sporades and the Cyclades in Greece, and a Medsailors trip in Croatia. I just love being out on the water and getting a different view on life. I’d totally recommend you do too.
Next up I’d like to sail round the Azores, in Portugal. Dream trip.
READ MORE: The Tao Experience: The Best Week of My Life
10. The heart break trip
Oh it’s a tough one to take but also one of those that could morph into a life changing trip too. My break up trip actually lasted a few years but sometimes, even just to get away for a few weeks after you’ve been through some emotional trauma is a good idea.
Get away, get some perspective and you’ll soon work out what to do next with your life. Great idea to do that in the luxury of a tropical destination, trust me.
11. Ski trip
It was silent, the trees were huge, the views amazing and I couldn’t believe that little old me was there to enjoy and experience.
I didn’t learn to ski till I was 25, my friend’s mum, till she was 58. You’re not too old and it’s a great way to have a healthy holiday where the copious amounts of gluhwein drunk are justified. Coming together after a physically tough morning on the slopes for a schnapps and mulled wine is all part of the fun for me.
And, you can eat totally guilt free knowing you’ll just burn it off.
12. Life changing trip
It’s hard to predict that a trip will change your life, even the most awesome of adventures might not have a lasting effect. There are three trips that I think really changed me though:
Kavos at 19: this was the first time I met people who were really happy in their careers. It sounds weird but chatting to the holiday reps here changed my life. One in particular told me how he worked all summer in Greece and then went to the mountains for the winter. Honestly, I’d never me anyone like that before and it really got me thinking. I thought it sounded like the coolest life ever.
Camp America at 20: my summer at camp was incredible. Meeting people from all over the world, going to New York on days off and making friends I still have to this day. This trip totally fuelled my wanderlust.
San Francisco, Coachella and New York: this had been a dream trip for years. And then second night in, my boyfriend and I split up. I had a lot of time to think on this trip, to sort my life and have the opportunity to reset it at 29. The other guys we went with were great, kept me sane and ensured I still had a brilliant time at Coachella. I’d even go so far as to describe the trip as ‘fun’ when I look back, although the Golden Gate Bridge is totally ruined for me forever now. Memories of crying all the way across it would do that to someone.
Onwards and upwards!
READ MORE: Best Places to Stop on a Coachella Road Trip
13. Travelling with boyfriend
Travelling with someone is the best way to really get to know them, to know whether you ever want to continue on this crazy adventure called life together.
I travelled with my ex for four months throughout Europe and had an absolutely brilliant time. Although it obviously didn’t work out for us, I still cherish those four months we spent exploring the world just me and him.
Remember what the almighty Bill Murray said:
“If you have someone you think is the one, take them and travel around the world. Buy a plane ticket for the two of you to travel all over the world, to places that are hard to reach and hard to get out of. And when you land at JFK and you’re still in love with that person, get married.”
14. Travelling with mum
Being able to take my mum on holiday abroad was a big thing for me – granted I’d won one of the competitions I talked about, not quite ballin in the big time enough to pay for her. I can clearly remember the moment I asked her if she’d like to come to Sharm el Sheikh with me. She grabbed a pillow of the sofa and screamed into it with excitement, almost crying with excitement. It was lovely.
We had such a good week, doing things both mum and I had never done before. We went stargazing, snorkelling, riding camels and quad biking and had massages at the Savoy Hotel.
We also both got the shits like never before – gotta take the rough with the smooth.
15. Grown up family trip
My family is very lucky in that we get on. During the teenage years and the 20s we didn’t really go away that much together – all living our own lives. But since then we’ve been to Iceland, Barcelona (numerous times), Tenerife and we had a big trip to Samos in Greece for my brother’s wedding too.
Unfortunately you have to start paying for things when you’re older but apart from that, it’s lovely to go away with your family as friends, as well as close relatives.
READ MORE: What to Do With Your Parents in Barcelona
16. Your ultimate dream trip
Still got Patagonia, the Azores and Hawaii left, among many, many others.
Work out where you’re number one travel destination is, make a plan to save for it, and go for it. You deserve it.
17. Free trip
For a period of time in my life I was obsessed with entering travel competitions. I must’ve entered hundreds. I got lucky though.
I won a safari from Zanzibar to Nairobi, two flights to Amsterdam and a week for two in Cuba. None of those were related to me having a blog, I just entered and lucked out.
Free trips are great, trust me.
18. The solo trip
I’ve probably overdone it on the solo trips after spending over two years of my life travelling alone, but I’d definitely recommend you give solo travel a try, even if just for a weekend.
There’s just something about experiencing the world solo and doing exactly as you please every day that’s kind of addictive.
READ MORE: Am I Lonely, Travelling Solo?
19. Sibling trip
I did not get on with my brother growing up. If you’d’ve told me when I was 14 that I’d actually want to go on holiday with him, I never would’ve believed you. And look at us now – we’ve been to Ibiza together, twice, and Tromso in Norway. And many, many trips to Barcelona.
My brother is cool, we have a lot in common and I like hanging out with him.
Go on holiday with your sibling when you’re older, you might change your mind about them.
20. The road trip
There are so many good road trips around. My ultimate was the Pacific Coast Highway in the USA, which has now been ticked, twice. I really want to do the Garden Route in South Africa, I think that’s my next big dream road trip, although I quite fancy road tripping Ireland and Scotland too.
Get out there and start your engines!
READ MORE: How to Plan an Emerald Coast Road Trip
21. Physical challenge
Climbing Everest or Kilimanjaro usually tops people’s bucket lists. I don’t particularly want to do either to be honest.
I did cycle from Hanoi to Ho Chi Minh City in Vietnam though, and loved it. I’d like to do another physical challenge sometime, somewhere. I’m also really interested in doing one of those charity tuk tuk rides across somewhere – Sri Lanka or Cambodia are definitely calling. It may not be physical but it’d definitely be an exciting mental challenge, and one to remember.
The sense of reward you get is amazing, after completing something you never thought possible. And they’re a really good way to see a destination differently from everyone else too.
Left for me
Despite having a pretty good travel repertoire, as you see above, I still have so much to look forward to…
22. Weddings abroad
You get to that point in life where all your mates start getting married. And at least one of them will go for a ‘destination wedding’ in some far off land, usually Greece. I’ve been invited to two destination weddings before and unfortunately couldn’t afford either of them, but this September is the big one: my brother’s in Samos.
Literally just booked my flight. Well excited.
23. The honeymoon
Sri Lanka and the Maldives sounds like a pretty popular choice for the honeymoon, according to where my friends go anyway. I think I’d like the idea of lounging about for a few days, and then getting up and actually doing something, somewhere.
Dunno where I’d go for honeymoon – Patagonia?
Yeah, that sounds fun, that’ll do.
24. The babymoon
So in the UK it’s popular to go away just before the baby arrives, to celebrate one of your last weekends of freedom. It’s usually pretty tame and a chance to be at one with yourself and your partner before the craziness begins. Think: Lake District, or Cornwall, or maybe Brighton.
25. The first family holiday
And so the cycle starts again, with you at the helm. Your first holiday as a family will be errr, fun, especially if you take your little one on the plane. Good test of patience anyways.
26. Holidaying vicariously through your children
It must be so much fun to take your kids on holiday the first few times. To see their faces light up when they experience things for the first time, it’s a new chance for you to see the world through your kids eyes. This time though, you have to do all the worrying and paying for everything.
Not so much fun.
What do I want to do when I’m retired? Hmmm, travel the world and write about it…?
Where do I want to go? Camper van round the Arctic Circle, if I don’t get round to it before, backpack through South America, go and work on some worthwhile project in Africa – one of these will do.
Retirement travel is a huge thing now, your big chance to see the world while you have the money and the health.
28. Your kids take you on holiday
And after all the dramas of bringing a child up, I think you’re totally within your rights to expect them to take you on holiday. Whether it’s a UK city break or a full on family trip to the Bahamas, they owe you.
How many holiday types have you done?
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