The life of a Tour Leader in Italy

Imagine. You create a business from a tiny idea one day to take a small group of people on a travel adventure to Italy, a country you have never visited. Life is about being adventurous and Italy looked amazing! Fast forward fifteen years and the passion, excitement, enthusiasm and love for Italy has only become more intense through discovery, knowledge and experience.

Here is a job that evolved from a single thought that allows me to travel throughout Italy and share the best of all that I have learnt with like-minded intrepid travellers. Every single year. Does it get any better than that? Nope.

Is it an easy job?

Not always. Believe it or not, some people don’t make good travellers, but are often completely oblivious to this fact. Travel puts you out of your comfort zone; can be unpredictable due to weather; is not the same as home and can be tiring. Accept that your pillow may be too soft, too hard; coffee not hot enough; too many tourists; pastries for breakfast; pizza isn’t cut into slices! Seriously, it’s always the little things that cause angst.

What makes a good traveller?

One who is open to spontaneity, adventurous, enthusiastic to embrace a different culture, keen to engage with locals by learning a few basic phrases of the local language, willing to try new experiences and is flexible.

My top three challenges

• My enthusiasm and energy run high . . . everywhere we go. Be it Rome, my favourite city in the world, or a tiny hamlet perched on top of a mountain with fifteen locals, I want to show you all my secret alleyways, favourite artisan shops, introduce you to beautiful Italian people I have come to know and eat the most delicious food in authentic trattorie. I want to take you on spectacular walks that reveal breathtaking landscapes.

  Herein lies the challenge. Everyone has a different energy, a different pace and different priorities. It is therefore important to find a balance and offer appealing choices and options for individual interests, but at the same time recognise when I can push people a little out of their comfort zone so that they do not miss out on an unforgettable experience.

• Always have a plan B. I have a great love of spreadsheets (just ask Vassili, Manager of our Hotel Gregoriana in Rome) and am fanatical about attention to detail. However, there are some things one cannot control. The weather. Train strikes. A G7 meeting in Matera on the same three days we are there. High seas, no ferries. I have learnt to love Plan B!

• Within any group of people who don’t all know each other, there will be different personalities, different expectations and circumstances that may have an impact on how people are feeling on any given day. A natural reaction is to take it out on the person leading the tour. My biggest lesson here has been that I cannot please everyone every day, but I try!

What happens when I return to Australia?

The first few days, I’m adjusting to getting my head space out of Italy, having been completely and utterly immersed in the Italian way of life every day and night of the tours.

Once luggage is unpacked, clothes washed and the fridge has food in it, it’s time to jump into a new year of tours. Although accommodation has been booked for seven tours so far in 2025 and most of these tours have only a few spots left, Italy is a never-ending journey of learning. I have a notebook of new things discovered this year, all of which will be included next year; hidden paths to walk without tourists; incredible cultural experiences; wonderful Italian families to meet; more great places to eat where the locals eat; shopping experiences where you can meet the artisan and learn the extraordinary history behind the family business. And 2025 brings a new itinerary exploring Puglia.

My luggage is unashamedly heavier when I return home because of the purchase of new books (maybe a couple of new dresses too!) about the history of places visited. It is a life of continual research and ideas for new itineraries. A lifetime would not be enough to discover Italy. This is the beauty of a country with twenty regions that are so diverse in landscape, food, festivals and people. My gosh, I’ve only covered twelve regions so far!

It is also a time of talking to everyone planning on travelling with me next year; booking private transfers; booking local experiences; finetuning 101 details on every tour; rooming lists; building new collaborations and continuing the wonderful working relationships I have with people in Italy, not to mention reconciliation of budgets and the tedious administrative side of running a business. And the weekly newsletter!

A huge thank you to everyone who has travelled with me in 2024 and made it possible for me to have the best job in the world, a job that continues to inspire me every single day and allows me to meet fantastic, interesting people who also have a love of Italy.

Simply cannot wait for 2025!

Ci vediamo la prossima settimana.

Deb