The Eternal Holiday: Guest Post By Jenni Midgley

I read an article in a popular British magazine the other day. It was about a girl who had been on holiday for three years.

They mean holiday as in, she had quit her draining 9-5 job and decided to travel the world. She has now been on the road for a substantial period of time..

I refute calling this a holiday, it’s simply a new option, a new lifestyle that many people make a life out of. I’m someone who’s  doing the same. It’s not a holiday, holiday suggests its lesser somehow to staying put, to doing the same job for 25 years, buying a house, getting married and churning out babies.

It’s enviable yeah, which is probably why those in the ‘real world’ need to call it a holiday.

What I call it is challenging yourself to work out what really makes you happy.

For me London wasn’t making me happy. I don’t have some demon that I’m running away from (wait, do I? DO I?), I do have wonderful friends in England, London especially. I had a lovely job. But I knew there was something I needed to explore. Living somewhere warmer, meeting new, open-minded people, learning another language, seeing beautiful things every single day.

So, I saved some money – not loads, but enough. I stayed on friends’ couches for as long as I could get away wIth, saving three months rent, which in London is a sizeable amount and then I flew to Rome.

I mainly travel to find door porn

I mainly travel to find door porn

The main roadblock for people is the money thing. Relax, it really is different once you start your adventure. You will be amazed at how easy it is to get about now for a lowly sum. You don’t have to eat out at fancy restaurants – in fact, make it your mission to meet locals. Work out how they live their life and see if you enjoy doing the same.

I knew I wasn’t up for trekking about with a big old backpack for two years, so i started with Italy. Knowing I wanted to see it properly, be immersed in the culture, learn the language and see a lot of it, that was the extent of my plan.

I started with a few weeks WWOOFING, which cost me next to nothing. By the time I was done, I was ready for the cultural stuff – ie. I learned so much from living and breathing my hosts lives that I knew I’d be able to hold my own alone.

I also made friends this way. You’ll be amazed the huge difference that travel friends make. They are intense relationships and they really pay dividends, the kindness of ‘strangers’ never ceases to amaze me.

Opportunities continually arise because of those I’ve met on the road. That’s how I ended up house-sitting in Imola for two weeks (cost: nothing), that’s how I ended up in an Air BnB apartment with an American I met the day before (experience: FUN , cost:little, privacy: lovely).

Imola - cleaner than a clean thing

Imola – cleaner than a clean thing

Sharing Air BnB's-Local Style

Sharing Air BnB’s-Local Style

If you want to get from one place to another, don’t panic. Use Blah Blah Car, look at train prices – there are simply hundreds of ways to save money these days. Every time I use Blah Blah Car in Italy, I meet lovely good-spirited Italians who know stuff. Ask your co-passengers questions, you never know where it might lead. I also love BBC as you get to see the country you’re staying in.

Of course, all of this is a little bit of a headache sometimes. I like to have bases when I’m travelling – they make me feel more calm. But, if you’re in a city for a couple of days. Book a hostel for a couple of nights and see what happens.

Perks of housesitting - Ravenna

Perks of housesitting – Ravenna

Hostels – of course read reviews, if you’re 30 don’t go for some monster raving loony 18-year old party hostel. There’s something for everyone out there now and people who are backpacking want to talk to other people who are backpacking, it’s as simple as that.

I guess the main thing I should address is the idea of loneliness. Travelling solo, travelling as a girl solo, has a few alarm-bell type strings attached to it. Please believe me when I say, you won’t feel alone. You may physically spend time alone. But isn’t that great? It only takes one person in one place, to make you feel like someone’s got your back.

I sometimes crave more time alone! I like to wander the streets of another country, people looking at you not knowing why this old pasty non-Italian is in Imola. Being the local freak is great and then, guess what? You’re not alone. Local inhabitants of any non-tourist spot the world over are desperate to know what you’re up to and ask you questions.

Obviously, don’t be yelling English at all the locals, telling them what you’re doing there, what I’m saying is some people will be attracted to you and want to know what you’re doing.

Right now I’m a little more static, to people back home it’s exotic, I’m off to live in an apartment in Bologna and go on adventures (it’s a great place to get to other places in Italy) while writing and desperately trying to make more friends. For me, almost three months into my life ‘abroad’ it’s become a little less exotic, a little more just-my-life. I find that the anxieties I might have had in England don’t raise their little heads so much here. I don’t panic about money, I see each day as an opportunity instead. I don’t worry about relationships (friend, male, female, love, animal) as I have an Italian phone now which (surprise, surprise) helps with that stuff. I just try and go with the flow while still keeping hold of my identity.

The author- On Top Of A Mountain

The author- On Top Of A Mountain

It’s not always La Dolce Vita but, so far, it sometimes feels damn close. Yes, that may because I’m comparing it to commuting from Peckham to Oxford Street every morning (I resent all phrases such as HappyHumpDay, HappyFriday, SundayBlues – every day should be as good as the one before or after!) but trust me, you just need to be brave and see what happens.

If everything goes tits up, we can all return from whence we came. God I hope not.



Jenni Midgley is a 20-something writer. She left her 9-5 editorial role in London to reinvigorate her lost sense of adventure and to take more naps by the sea. She currently resides in Bologna, enjoying good food, better wine and writing about what happens whenever she leaves her apartment at She loves Instagram.

4 thoughts on “The Eternal Holiday: Guest Post By Jenni Midgley

  1. “Seeing beautiful things ever single day.” This is soooo true, and even though I live where the scenery is gorgeous, I MISS the architecture, people stylishly dressed, art, and flowers of Italia!!! In Italy I can walk down the same street every day and see something different. Simply having your package of cookies beautifully wrapped at the pasticceria makes me smile. By the way, while you are in Bologna be sure to eat at Trattoria da Gianni and Officine degli Puglia (tell Emilio Bonnie and Michael Melielo from Alaska say hi and hope to see him again soon). We love Bologna!!

  2. This took me back when I first moved to Italy! It is so scary to make that move by yourself. And there will be some very challenging times ahead for you. But you will gain so much. If I hadn’t left my friends in London (we were on a working holiday, I’m Australian) to move to Italy 14 years ago I wouldn’t be married to my wonderful Italian husband today and have my darling little daughter. Thanks for sharing and good luck with everything!

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