ITS ITALY, The Grand Tour - A Week in Salento
Una settimana salentina, com'è andata la prima tappa del nostro Grand Tour
Originally published in Italian on “Esco quando voglio #81” by Matteo Cerri – June 26, 2025
Per la versione italiana clicca qui sotto 👇🏻 otherwise… enjoy it in English!
Things I saw and did during one of the most intense work weeks I’ve had in recent months — and why I can’t wait to do it all over again (as soon as the weather allows).
In the end, it was meant to be a kind of test — the first stop of what we, together with
/ ITS ITALY and , decided to call The Grand Tour. An ambitious name, sure, but one that perfectly captures the idea of a weekly journey through the towns across Italy where ITS ITALY is active (more than 20 to date), with the ambition of doing things differently: starting from the needs of our guests (future international residents), with a digital nomad spirit, in places that truly match their lifestyle.The goal was to work from a place, but not in some abstract or superficial way — to actually live it. To enjoy the local area, yes, but also to work, to meet entrepreneurs and changemakers, to connect with other international nomads — even if it often seems like there’s little to share, since everyone travels with different intentions. But above all, to engage with those leading innovation, entrepreneurship, and regeneration at a local level.
All of that, packed into a single week. A kind of teaser for what could become a long-term model, lasting several months, with deeper engagement in the places that host us.
We chose to start in Salento — more precisely, in Lecce. In July we’ll be in Sicily (though we’ll see how we cope with the heat), then Cilento and Irpinia in September, back to Puglia, and then up to Le Marche, Tuscany, and Sardinia before autumn. We’re also keeping the Veneto region as a wildcard — somewhere between Prosecco and Cadore we’d love to launch something. The ideal ending? For me, it would be Bressanone — where there’s little to regenerate and so much to admire (both naturally and entrepreneurially), among “my” Plose mountains and the friends who work in the area.
Anyone interested in following this journey can check out Nomag Media and ITS Journal, where we share updates on upcoming stops and collect interest from those who’d like to join.
Now, back to this past week’s adventure. I have to confess upfront: I made two big personal mistakes.
First: traveling alone. Those who know me know that I share 99.99% of my days (and entrepreneurial journey) with my wife. Going solo just doesn’t work as well anymore. I probably miss out on insights and on the beauty of the people and places I encounter. But for personal reasons, I had to do this trip on my own. And even if it was a 9 out of 10… with her, it might’ve been a 10.
Second (and worse): overestimating my physical endurance. Too many hours of driving solo, nearly zero hours of sleep, and extreme temperatures my body isn’t used to. If you live where 20–22°C is a summer average, don’t expect to survive 30–35°C without consequences.
My small odyssey began in London. Wake-up at 2 AM on a Sunday to catch a 3:30 train for a 5:30 flight. Only a sadist would schedule a flight at that hour with no decent train options. After a hellish ride on a British commuter train packed with tourists (who clearly hadn’t discovered showers) and some homeless people who seemingly live on that train, I caught my British Airways flight to Bari.
My ultra-compact packing strategy (30kg carry-on + 20kg backpack — thanks vacuum bags!) let me travel light-ish. Upon landing, the first surprise: my rental agency (Drivalia) had a queue of at least 50 people. One poor agent, clearly not having a good day. After 70+ minutes in line, hungry, thirsty, but too stubborn to give up, I finally get to the desk — and no Fiat 500 for me.
Okay, what do you have? “Something small please, I’ll be driving through tiny villages.”
Instead, they offer me a huge car (with an extra fee — why?), and to top it off, my credit card isn’t accepted because it’s electronic. Debit card? Nope. Apparently, buried in the fine print of the medieval contract I’d blindly clicked through, it says you need a “real” card. No flexibility, no empathy. Cash deposit or walk away.
So I walked — literally one step to the right — to Autovia. Kind, fast, efficient. 15 minutes later I had my keys.
It was an ugly, large, overpriced compact SUV (a MG), but at least I had wheels. Goodbye to my dream of cruising through Salento in a stylish 500. Hello awkward MG.
Next stop: Irpinia, where Nicholas Verderosa — founder of Ruralis — awaited me in his countryside office near Sant’Angelo dei Lombardi. Among rolling hills and the kind of light only certain places can offer, we had one of the most honest conversations of the whole trip. Nicholas welcomed me with genuine enthusiasm, and his family was just as warm. Ruralis isn’t just a project in an unexpected place — it’s a vision. And as Nicholas knew, I arrived with plenty of questions and a few assumptions.
In his white Tesla (which looks surreal on village roads), we toured the countryside, talking about regeneration, real estate, and storytelling. That’s where it clicked: Irpinia — like Cilento — is not off-route for ITS ITALY. These are vibrant, welcoming, well-maintained areas, surprisingly well-connected. From Bari I arrived easily; from Naples or Salerno, it’s even faster. With Nicholas’s infectious energy, we already started planting the seeds for something together — perhaps also with the Sei Ventures crew (Vincenzo Vitale & co.).
Then came the drive to Lecce. Tired, melted, but greeted by the timeless charm of Masseria Torre Luciana. A rural yet modern oasis, run by local entrepreneur Stefano Ingrosso, who has turned his Sew HandPan business into a beautiful retreat space. Coworking, temporary residency, or just an escape filled with the sounds of his otherworldly ‘Sound Trees’.
The masseria welcomed us with simplicity and elegance: incredible food, spaces to work, reflect, and be still. A place where time expands but ideas accelerate. And that’s where the real week began.
Over 30 meetings in 5 days. A marathon that included property visits, meetings with local officials, entrepreneurs, startups, artisans, media — and above all, with foreign visitors genuinely looking to make Salento their home. Not as tourists, but as residents.
We met people who are making a real difference. Like Paolo Greco, mayor of Caprarica di Lecce, who is turning his town into a hub of urban, social, and entrepreneurial regeneration. One of many projects we’re exploring with him? Reopening an old school as a youth entrepreneurship center.
This ties naturally with the work of Prof. Daniele Manni — teacher at Istituto Costa and founder of WeDo! Academy. Daniele is a local legend with an educational approach to entrepreneurship that has inspired generations. In his office, we also met Mirko Cazzato, founder of the anti-bullying movement MaBasta, now leading a national social cooperative.
We also crossed paths with Elisa Pogliano and Claudia Sviluppo (Unlock Puglia — a community of nearly 2000 expats), rediscovered the work of Olivami (replanting olive trees where Xylella struck), and engaged with folks from Puglia Sviluppo, ARTI, Officine Cantelmo, and Puglia Techs. A network ready to grow new ideas together.
Possibly the most pivotal moment of the week? The Sud Up event at Castello Carlo V, hosted by Over Ventures (the Vergine brothers), where we discussed alternative finance and crowdfunding. A powerful reminder that you can attract capital and build strong projects — even from the South, even from places many consider “remote.”
And then came the side reflections. Like the one with Floridiana Ventrella and her project Lavoro al Sud. Jobs are emerging. What’s still missing? Stable, non-touristic housing for newcomers. That’s exactly what ITS ITALY is working on: year-round liveable spaces for those staying from September to April. Not for vacation — for real life.
This week was, ultimately, just a taste. But a real, vivid, energizing taste. Proof that it’s not only possible, but desirable to bring life, energy, and enterprise into places often seen as peripheral — but which are, in fact, central.
Would I do it all again? Absolutely. Even the exhausting parts. With a few lessons in hand, a lighter suitcase, and my wife beside me. Maybe with a smaller car. But yes — I’d do it all again.
Actually, we’ve already planned the next stops. Can’t wait to tell you about them.
This Salento week was more than a test.
It was a promise.
And this is just the beginning.
Next stop: Sicily!
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