Inside the storied lobby of the Uffizi Gallery in Florence my travelling concierge Daniele is busy dialling a local phone number I’m dictating. He then passes his phone and suddenly I hear an old friend I haven’t seen in a decade say, “Ciao Ilona.”

This dream-come-true happens in seconds, as so many other memorable moments on my latest Luxury Gold by Insight Vacations trip to Italy.
Insight Vacations has been curating itineraries for over 35 years and has emphasized quality, authentic engaging experiences, and learning, in its offerings. “If you travel with us you won’t be herded around. You will feel like an individual. You can enjoy things your own way. Your own personal aspirations can be realized and the travelling concierge is there to help you fulfill your dreams. That’s the big thing. You have this independence yet the advantage of the group at the same time. It’s a cracking dynamic,” says John Boulding, CEO of Insight Vacations joining us on this ultimate quest of Italy.
Indeed the luxury experience was all that and more. When I lived in Tuscany in the nineties, I had a tiny attic flat in Florence but despite the piccolo (small) place I lived la dolce vita in surrounds once inhabited by the great Renaissance artists. Yes, I was once one of the pesky turistas who lined up for hours to enter the art temples of the Accademia to see Michelangelo’s David as well as the Uffizi Gallery to see Botticelli’s The Birth of Venus.
But on this return visit I lived like a modern-day Medici as the luxury tour operator selects only the finest accommodations in the most scenic locations in a road trip that has guests of this escorted land tour dine at local establishments and a Michelin-star restaurant. You get to go where the masses don’t in exclusive VIP tours and have the finesse of a seasoned travelling concierge whose local expertise manages to move mountains it seemed at times. In my case it was to reconnect with an old friend.
You’d also think this trip would cost an arm and leg. Well think again.
“I think we are the most perfectly positioned product out there for this market. We are premium so we appeal to people with aspirations to do things more comfortably, but we also have the opportunity,” says John on the breadth of the Luxury Gold programmes, and recognizes today’s traveller is so much different than our parents’ generation who enjoyed being ‘carted around’ and shown things.
“The core customer today is a baby boomer,” he says of the new 13-day Ultimate Italy itinerary which includes a Tuscan cooking class in an Italian villa, and a private tour of the Vasari Corridor in Florence as some of the company’s Signature experiences.
All Roads Lead to Rome
My dream-come-true trip starts in Rome when a personal greeter welcomes me at the Fiumicino (Leonardo da Vinci) Airport for a private transfer to the iconic Baglioni Hotel Regina. Located on the legendary Via Veneto immortalized in the Federico Fellini film La Dolce Vita, the tree-lined street is ideally situated for easy walking tours. You can smell the flowers at the nearby Villa Borghese, shop along the fashionable Via Condotti, tour the Trevi Fountain and see the Spanish Steps.
On my first day with free time that is regularly scheduled in the itinerary, I was off to see the nearby landmarks. A crowd of tourists aim selfie-sticks at the newly renovated Trevi Fountain and over by the Spanish Steps tourists ascend a side staircase as the iconic steps currently are under renovation. For me, I dive into the rich English love affair the early Brits had with Rome.
By the Spanish Steps, I tour the apartment of the poets John Keats and Percy Shelley now a museum and complete the British romp at the fabled Babington’s Tea Rooms with its vintage interior, a complete throwback to yesteryear. As soon as you shut the entrance door it felt like the days of Mary Poppins, dainty china, pretty table settings, floral vases, and original shelves stacked with tea of every variety.
I did, however, tag along on every organized Luxury Gold tour. How could you not?
In Rome my personal highlights are a visit to St. Peter’s Square for a Papal Audience to see Pope Francis, a private VIP tour of the Vatican Museums and the Sistine Chapel before the regular public opening and a tour of the Roman Colosseum with a local expert. Our group managed to slink past the snaking line-ups as we slithered by the hordes at both locations.
Florence
“Ilona I am so sad you do not like Florence,” Daniele teases me.
I can’t stop oohing and ahhing. The impossibly long Vasari Corridor used to be the private world of the Medici’s, and there I am on a grand arts walk over the Arno River in the presence of rarely seen masterpieces. (For personal reservations to unlock the secret door of the Vasari Corridor would cost you €450).
I keep gasping and pinching myself all at the same time at the endless portraits but the one that totally catches my eye is the self-portrait of a particular Florentine artist. Pietro Annigoni is considered one of the world’s finest 20th century portraitists. I know this artist’s life well, having been an Associate Producer on the film, Annigoni: Portrait of an Artist (Watch a movie clip )
In Florence, my personal highlights are too many to count. Still, among the many memorable moments, it was seeing a side to Italy that was previously off-limits to my meager pocketbook, and of course, catching up with a dear old friend.
The city and its surrounds are indeed captivating and inspiring but there’s a sadness attached to these magical moments as well. Later that evening back at our luxury villa in the Mugello that overlooks Tuscany’s storied countryside my friend’s sentiments come back to me again.
“Florence is like a woman who always stays the same. But we are the one who changes, and always, in the end must leave.”
And that is how I now feel about all of Italy.

Staying awhile? How to get a job in Rome
If you want to work ask around at the hostels, hotels and restaurants. There are differing views on how easy it is to get a job in Rome, however. There is high unemployment and most jobs seem to go on a family – friends – other Romans – other Italians – white EU – other foreigners pecking order. Knowing Italian helps. And be wary about making any financial commitments before you’ve actually been paid — late and non-payment is common
here, and you may find as a non-Roman you are more likely to be seen as an easy target for this. You will also need a permesso di soggiorno, whether or not you are an EU resident. Legally, you are required to have a working visa, although it is very easy to work and live without one. There are numerous schools to teach the English language in Rome and if you are a mother-tongue this may be the best opportunity of picking up part-time work.