Walking in the Dolomites. Nice work if you can get it.

Does this sound like a job for you?

You go to Italy twice a year, in spring and autumn to avoid the main tourist season. On each trip you spend a week or two walking through attractive countryside with a jolly group of like-minded people, staying in boutique hotels, eating the best local food and sampling the local vintages.

You get paid to do this.

Simon Tancred and a cafe that bears his name, plus a bit.

At the end of the walk you say arrivederci to your friends and for a few weeks you head off on your own into unknown regions, researching some history and looking for new footpaths, food and lodgings. And deducting your expenses from your tax.

Lots of us aspire to converting our love of travel into a paying job or business.

Simon Tancred seems to have it nicely worked out.

Through his company, Hidden Italy, he’s been organising tours to that country for nearly twenty years.

In the 1980s, with an ancient history degree rolled up in the backpack, Simon set out from Australia to explore the world. He got as far as Milan. There was a woman of course.

For the first few years he lived there illegally, teaching English through a business college and becoming fluent in Italian. When an amnesty for aliens gave him a chance to go legit, he returned to Sydney, but by then Italy and walking had got to him.

A friend suggested he put together a guided walking tour and sell it through travel agent Mary Rossi. It sold out in a fortnight.

Taking tours to Italy became a regular hobby for Simon, but he always needed to keep a teaching day job to pay the bills.

Then a few years ago he began organising self-guided tours for independent walkers, and it became possible for him to run Hidden Italy full time.

On self-guided walks, shorter (and cheaper) than the guided ones, Hidden Italy provides the itinerary, bag transfers and accommodation, together with eating recommendations. A local contact is a phone call away to help sort out any problems. Simon can largely run this part of the business from his home in Sydney.

My normal hiking spaghetti doesn’t look this good, They do things differently in Sicily.

I’ve sometimes fantasized about doing something similar myself – maybe leading cycling tours in Holland and Belgium. I know the countries and the language. I love riding the bike…

There’d be difficulties of course. How would I handle the people, especially those less than gruntled with their rooms, meals or bike saddles, or finding the daily riding too hard, too long, too windy, too wet or too tame?

What about the annoying guy that nobody in the group likes? It would be my job to laugh politely at his awful jokes and keep him happy.

And what about insurance, medical emergencies and lost passports?

Bicerin – Turin’s caffe of choice.

Simon assures me that his clients pretty much select themselves as good travel companions.

They’re usually 55-65, physically active, well-educated, well-travelled, up for a challenge and, most important, patient and understanding when things unavoidably go wrong.

If a ferry is cancelled due to bad weather, they regard being stuck on an island eating an improvised meal in a private home as all part of the adventure. They sound like my sort of people.

Simon has very rarely had problems, though safety on the walks is a major priority. It’s a delicate balance, making them comfortable enough for everyone to do while being strenuous enough for those who like to challenge themselves.

The walking may not be as adventurous as treks Simon might do on his own, but the idea is that food, history and culture are as much a part of the tour as the walking.

‘It’s important to build in some variety and flexibility,’ he says. By arranging several nights in a larger town it’s possible for his clients to follow each walking day with a resting/exploring/shopping one.

Hidden Italy is always looking for new adventures, and Simon talks enthusiastically about a possible walk from the Friuli region on the Slovenian border to Switzerland, following a route taken by prisoners escaping from Fascist camps during WWII. Maybe he’ll explore it in detail next year.

It sounds as if Simon Tancred has arranged an enviable work/life balance.

And as he tells me more than once, he is fortunate to have a ‘very understanding wife’.

Has anyone else tried to make a business out of their travel bug? If not, what’s stopping you? What are the joys and pitfalls?

Dinner with a view.

Disclaimer: RT’s LOTR hasn’t done any of Simon’s tours personally. But he seems a very nice guy. He paid for the coffee. Thanks, grazie and good luck!

Photos on this post courtesy of Hidden Italy.


Filed under Hiking, Italy


  1. It sounds like heaven. I would love to do that myself.

  2. Caroline

    Mary has just done a similar trip organized by her sister in law.

  3. Friends have tried to get me to lead tours for a long time but I realized long ago that I couldn’t handle the disgruntled, the demanding, the snotty or especially the horrible one that nobody likes… Exploring hidden Italy sounds lovely though.

    • YL, in my (admittedly limited) experience as a tour group participant, the physical activity part of the adventure weeds out the worst of the demanding and snotty customers. Those who are prepared to sweat a bit will usually put up with other inconveniences as they crop up. They tend to be nice people who want to get on well with the group.

      That’s not to say it would be easy though – there’s a lot to organise and I’d still feel a great weight of responsibility for keeping people happy.

  4. Your bike tour idea sounds a good one. I’d be happy to sign up and be the difficult one to test your patience!

  5. I don’t think I would have the patience to deal with some people. I was with a group recently and one stupid woman wanted maple syrup on her porcini mushrooms and polenta. I wanted to stick a fork in her hand. So you can see that this job would not suit me.

    • It’s a pity you’ve ruled out this career choice, Debra. You’d be an excellent tour guide.

      And if I desperately needed to find maple syrup in Italy at short notice, (say, for a homesick Canadian) you’d be the first person I’d ask. Well, you and Heather.

  6. The spaghetti looked awesome!

  7. Ah, what a dream job! But, soon to be staring two sons’ college costs in the face, a less glamorous, but nonetheless enjoyable, career option remains reality :-). And, I am with Debra — not sure I’d have the patience for it! ~ Kat

  8. It sounds like a wonderful way to make a living, I regret not spending a year or two working in Europe after I finished Uni but my husband and I are hoping that we’ll be in a position to live in Italy for at least 12 months in the future. We often think that doing the B&B thing might be good, perhaps somewhere in Umbria or Le Marche 🙂

    • I did manage to work in Europe for a year post Uni, but only playing my fiddle in the streets and piano for a theatre company and dance classes. Fabulous fun for a while, but it didn’t lead to a real living.

      If you know Italian and know about B&Bs, I imagine it could be a great thing to do.

  9. Hey Richard! I am nominating you for The Inspiring Blog Award!! Love your post and thirst for adventure! You can see how it works on my link below!

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