A Travel Insider’s Guide To An Off-The-Beaten-Track Holiday in Italy

GIACOMO GIAMBOI. The travel director with travel agency Trafalgar has 12 years of experience under his belt, leading guests on some 17 itineraries in Italy, and takes on occasional tours in Greece and Switzerland. But the Italian native, who calls the countryside of Umbria home these days, is all about sharing local secrets with guests, despite the fixed tour itineraries.

“My top travel tip would be to try to live like a local as quickly as possible — understand what they do, where they go and what they eat. It’s the same for me when I travel,” he says. Don’t know where to get started for your next Italian break? We’ve got your back.

SICILY: “It’s the island where I was born and raised in, in the south of Italy. For me, it is one of the most interesting regions. It has the right mix of food, wine and history. It’s not as recognised as it should be, but it’s so important in history. I love the area called Trapani where there are amazing islands right in front of it. I also like Syracuse which is a small, quaint 3,500-year-old city. The ancient Greeks built this city and you can still find traces of that civilisation here, such as the temples. I love the sea resort of Taormina, which is halfway between Sicily and Messina, and you have the volcano [Mount Etna] on one side and the sea on the other. It’s such a beautiful setting.”

UMBRIA: (above) “This is where I now live — it’s next to Tuscany and is known as the little sister of Tuscany. But Umbria is a little more rugged and undiscovered. It’s an amazing location for holidaymakers who love a bit of tranquility. It’s where [the UNESCO World Heritage-listed town of] Assisi and [tourist fave] Orvieto are. Be sure to also visit the cities of Spello and Montefalco.”

MARCHE (say ‘mar-ka’). “You get the countryside, the sea, a beautiful coastline and [the walled city of] Urbino here. It also has one of the most beautiful city centres in Italy. I also love the city of Ascoli, which is a beautiful small town of arts, history and culture.”

“In Tuscany, it’s all about food, wine and the slow life, which is what you want when you’re on holiday. You don’t want to be rushed or be in an overcrowded place, so I always tell people that you need more than three or four days. One of the itineraries we have is six nights in Tuscany, and every day we take day excursions in the most beautiful countryside in Italy.

"The Val d’Orcia area is one of the best spots in Tuscany and is one of the most beautiful pockets of countryside I’ve seen in my life. It’s more than just scenery — it’s romantic. It’s full of local small family-owned restaurants where they cook the best meats, prosciutto, and serve the best wines. It’s a great place to watch the sunset, and it’s not so crowded.”

“In the smaller [provinces] like Marche, Umbria and Val d’Orcia, shops are closed from about 1pm to about 4.30pm. Because it’s siesta — they go home to have a meal, sleep a couple of hours and then go back to work. [For tourists who don’t know], it may be a source of irritation. But at the same time, you admire it because the culture is unchanged. Life here is slower. If you’re in a restaurant and you rush, the service staff will ask you why you’re rushing. We also eat dinner really late, at about 8.30pm to 10.30pm. At 7pm, not many restaurants are open. It’s normal for kitchens to close only at midnight. A meal at a restaurant can take about three hours — you eat, sip your wine and admire everything around you.”

“They go to the Monti, one of the most beautiful neighbourhoods. The other area is Gianicolo (Janniculum Hill). There’s a big open space, a little park in the city and some bars, so you can have your evening coffee sitting there and see Rome at your feet. It’s a favourite among couples because it’s so romantic.”

For more info, go to https://www.trafalgar.com/en-sg.

Photos: Trafalgar