It was 2009 when I last set foot in Italy. Seven years later, I find myself back here, this time without my backpack or student card. Gone are the crumpled maps or dog-earred guidebooks sitting in my bag, the best laid plans have been tried and tested long before my arrival. Thanks to the travel maestros at Insight Vacations, my week-long discovery of Italy's crown jewels begins without the need to poll friends or Google for recommendations. 

My whistle-stop tour of Italy's crown jewels begins right here in Rome and takes me through the Tuscan countryside, historic port-of-call that is Florence, and up to the enigmatic city of Venice. Those familiar with Insight Vacations might already associate the brand with all the hallmarks of a luxe experience, but this being their Luxury Gold itinerary, I'm told to expect privileges that few are privy to. Think private tours of the Sistine Chapel before it opens for the day, stays in villas once owned by the Medici family, and even the chance to meet the pope himself. 

Day 1 & 2: A ROMAN HOLIDAY

Fellini's Rome might be one awash with romance at every turn, but the Rome that strikes you at first glance is one that echoes the majesty of its past. Here, it's easy to imagine the scale and magnificence of the Roman Empire. Efforts to expand the metro system are repeatedly halted by excavations that bring to light relics from the past.

The Colosseum

Led by Amelia Grazia, a local expert who has been dispensing her knowledge of Rome since 1974, we visit one of the city's most enduring monuments — the colosseum. The bona fide landmark is both a ruin and monument of Roman glory. It's a stage for ferocious battles and adrenaline fuelled by plenty of gore. Riding on special privileges afforded to Insight Vacations, we slide into the behemoth structure without having to join the snaking queue. Given that the ground we're standing on is over 1,900 years old, it's clear the Romans meant for everything to last forever. Here, the hollowed arches, once fitted with golden copper shields, continue to exhibit its geometric perfection. Besides setting the backdrop for gladiator battles, a sophisticated hydraulic system enabled the colosseum to be flooded with water to stage mock naval battles.  

St. Peter's Square

We also rise early to discover the Vatican Museums, entering the grounds even before its doors open to the general public. The museum sees over 25,000 visitors — both devout Catholics and curious pagans alike — daily, and getting a head start before the madding crowd gives us time to contemplate the artworks without battling a sea of selfie sticks. A pilgrimage to the Vatican City isn't complete without a stop at The Sistine Chapel, where Michelangelo's labour of love resides. Our visit is also timed to coincide with the weekly papal audience session on Wednesday mornings, where he holds court at St. Peter's Square, addressing a flock so massive that it'll put a Justin Bieber concert to shame. 

Baglioni Hotel Regina

The royal treatment extends to our home in Rome — the Baglioni Hotel Regina. From the white-gloved doorman to ornate decor in the rooms, stately elegance comes easy for this five-star abode. Occupying an enviable location on Via Vittorio Veneto, the hotel sits on one of the city's most expensive real estate, made even more precious by the fact that Federico Fellini's classic 1960s film, La Dolce Vita, immortalised this very street in cinematic history. 

We are also given a taste of Rome's culinary prowess at Le Volte, a homely restaurant that turns out Italian classics driven by seasonal produce. Sharing the spotlight with the meal was a duo of opera singers who filled the restaurant with arias from Puccini and Verdi — all firm nods to the unwavering charms of the Eternal City. 

DAY 3: EN ROUTE TO TUSCANY

Wild hazelnut trees and white cassia flowers in bloom flank our path as we depart Rome for Calcata, a 3000-year-old medieval village perched high on a volcanic cliff. Abandoned in the 1960s due to fears of an increasingly unstable foundation, the village is now home to artists seeking affordable housing and plenty of quietude. Walking through the village, we encounter more languid cats and gurgling pigeons than we do people. Come weekends, artist markets breathe life into this sleepy alcove while numerous cafes fire up their coffee machines and set up tables on the terrace — backed by sweeping views of the valley, no less. 

Calcata

We forge North, this time crossing into Umbria, where a population of 900,000 is dwarfed by 7.5 million olive trees. Unsurprisingly, it's home to some of the country's best olive oil — liquid gold that's rubbed onto bread and drizzled into salads. Marco Bellanca, a local expert with a predilection for all things dramatic, leads us through Perugia, famed for staging the biggest chocolate festival in Europe and the Umbria Jazz Festival, a mandatory port of call for jazz cats the world over. Drop by Gelateria Veneta to grab a cone of what the locals dub the best gelato in town (made with organic fruit, no less) before heading up to Palazzo Della Provincia for spectacular views of Assisi and beyond. 

Perugia

Perugia's great weaving tradition continues to endure, thanks in no small part to Giuditta Brozzetti, a workshop that uses eighteenth- and nineteenth-century looms to produce historic textiles ranging from Perugian tablecloths to more imposing works of tapestry.  

Giuditta Brozzetti Museum and Workshop of Hand Weaving
DAY 4: FAIR FLORENCE 

With 72 museums fanned out across the city, Florence has the cultural heft to bring any art lover to their knees. It's also here you'll find a man called David, standing tall at five metres in the Galleria dell'Accademia. Carved from a single block of marble, Michelangelo's Renaissance masterpiece captures every inch of the human anatomy with grace and precision. No one puts it better than Giorgio Vasari, who said: "Nor has there ever been seen a pose so easy, or any grace to equal that in this work, or feet, hands and head so well in accord, one member with another, in harmony, design, and excellence of artistry."  

Michelangelo's David 
Then there's the Uffizi Gallery, the most visited museum in Italy and second most in Europe after the Louvre. One could knock back a few cups of espresso while standing in line to get in and still find time to lick down a few gelatos. It's possible to bypass the excruciating queues, but arrangements have to be made months in advanced. Even then, only limited slots for priority entry are available. Once again, Insight Vacations has taken care of all that; We head straight in and find ourselves amongst artworks spanning the 13th to 18th centuries. It takes over three hours just to view the key highlights of the entire collection, including Sandro Botticelli's The Birth of Venus, Filippo Lippi's Madonna and Child with Two Angel, and Titian's Venus of Urbino.

Vasari Corridor
We're also given access to the museum's elusive Vasari Corridor, a meandering one-kilometre-long passage flanked with paintings dating from 1500s to 2000s. Here, the artworks are not distanced by velvet ropes or glass panels. One can get so close to these masterpieces that the earthy smell the paint touches your nose. It's ours to explore for an hour without other visitors in sight — an exclusive viewing which would cost others over 400 Euros to experience.

Cathedral of Santa Maria del Fiore

Our visit to Florence also slips in a stop at the Cathedral of Santa Maria del Fiore. The iconic Gothic structure impresses with a 106m tower and facade layered with marble in pink, white, and green. 

Day 5 & 6: UNDER THE TUSCAN SUN

While Rome might be supercharged with operatic grandeur, Tuscany's charm moves at a tectonic level: Gentle rolling hills, swathes of green pregnant with vines, and sand-coloured houses shaded by tall cypress trees. Under the Tuscan sun, everything is illuminated. 

A rich bounty from the Tuscan countryside

Hidden within forgotten hills is Villa le Maschere, our historic home in Tuscany. Built in the second half of the sixteenth century, these storied walls have played host to popes and noblemen, boasting Venetian-style floors and elegant frescoes crafted by artists such as Francesco Furini.

Villa le Maschere, our hotel in Tuscany

We stay here for three nights, which gives us plenty of time to discover the villa's soaring chapel, enjoy breakfast on a sun-lit terrace, take a stroll in the property's sprawling grounds, and have our first taste Tuscany's famed wines over dinner. 

A suite at Villa le Maschere

Where Florence is rich in art, Tuscany's bounty spills forth from the land. Here, we partake in some of the most spectacular meals of the trip — all of which don't require Michelin stars to prove their worth. There's Rivasud, a family-run restaurant frequented by locals that turns out excellent homemade pappardelle with tender slivers of duck; and Ristorante Le Maschere Enoteca — located just across the road from our hotel — where we taste a flight of wines on the terrace, with the sun warming our bodies by degrees. Nonna brings everything out to the table — creamy discs of caprino, pots of ricotta, omelets topped with shaved truffles, pheasant pâté on toast, and sfogliatelle — Italian-style filo pastry — stuffed with prosciutto and asparagus. Our vocabulary in Tuscan wines expands with glassfuls of rosés, whites, and of course, the famed Tuscan Chianti, which in our case is a deep, inky 2013 vintage from I Veroni. 

Tuscan wine tasting at Ristorante Le Maschere Enoteca

We also work hard for our dinner at Villa Dianella, which lies 40km west of Florence. Once upon a hunting pit stop for the Medici family, this well-appointed Tuscan villa anchors a 90-hectare land that produces wine and olive oil. Owner Francesco Passerin d'Entrèves shows us around the cellar, which sees over 100,000 bottles of wine — a mix of Chianti and Super Tuscans — that passes through each year. We're told that dinner will be served shortly. The catch? We have to make it ourselves. We roll up our sleeves to prepare pasta from scratch (tedious, but greatly satisfying), fried zucchini flowers, and chocolate dessert which resembles a salami in form.  

Rolling up our sleeves to prepare dinner at Villa Dianella
Day 7 & 8: VENICE CALLING

Venice is a favourite port of call for honeymooners, but the city itself can be far from romantic. St. Mark's Square is as over-run with tourists as it is with pigeons, and the endless stretch of fluorescent-lit shops pandering everything from twee magnets to faux leather bags can get tiresome after awhile. Looking to avoid all of that? Stay off the well-trodden tourist path. Take your time to wander off the main thoroughfare and into the quieter arteries of the city, where you'll find a wealth of galleries, antique shops, and local eateries serving up squid ink pasta the city is famed for.

Venice

We count ourselves lucky to be whisked into a gondola and serenaded by a singer and guitarist as we weave our way through Venice's complex network of canals. It's one thing to discover Venice on foot, but another to see it from a gondola — in itself the sum of 280 parts crafted from nine different kinds of wood. In this quiet voyage, you finally comprehend the mystique and marvel of an entire kingdom rising out of the water, where boats are used to ferry not only humans, but also fresh produce, furniture, and even garbage.

Anna Pietrobon, our local guide and resident Venetian, leads us to the Doge's Palace, where vestiges of Venice's glory days still remain. The palatial building was once the seat of power from which the Venetian Republic was ruled. Today, it has been beautifully restored, its Venetian Gothic façade harbouring a wealth of elaborate frescoes by Tintoretto and Paolo Veronese. 

Doge's Palace in Venice

The charms of Venice doesn't end at the historic center. A constellation of islands scattered in the lagoon are worth a boat ride out, one of which is Murano, the birthplace of the famed Murano glass. Here, we visit Arti Veneziane alla Giudecca, a glass factory turning out everything from delicate wine glasses to stately chandeliers. Enrico Deirossi, an eighth generation glassmaker demonstrates the art of glassmaking. He works swiftly, shaping and blowing molten glass till it solidifies into a solid glass horse. The entire process takes him no more than three minutes, underscoring his decades of training as a glassmaker.

Further afield, we discover the bucolic charms of Burano, and are greeted at mooring by rows of colourful houses. It is evening and all is quiet, save for two bars bustling with life as the townsfolk gather for apéritifs. We settle down for dinner at Ai Pescatori, a little restaurant with pink pastel coloured walls and an excellent seafood menu. As we make our way through perfectly al dente risotto, grilled fish simply marinated with olive oil and herbs, and spaghetti punctuated with sweet clams hand-picked earlier in the day, we're presented with the very fisherman who brought us these treasures from the sea. The 78-year-old doesn't look a day older than 50 and speaks of the sea as a dear friend, one whom he's known since he was nine years old.

Burano, an island in the Venetian Lagoon

Italy, for all its charms, can't quite hold a candle to Daniele Nannetti, our Travelling Concierge for this trip. He has the patience of a priest, organisational skills of a German engineer, poise of a seasoned maître d', and warmth of a hundred (kindly) Italian grandpas rolled into one. He's pointed me towards Rome's finest perfume boutiques, ensured my luggage was cared for from arrival to departure, and dealt with numerous mishaps  encountered by my travelling companions - all the while keeping his cool. I wish I could bring him back to Singapore — life is just easier with Daniele — but alas, he is now in Rome, preparing to give another group of travellers from Insight Vacations the tour of their life.

Our trip with Insight Vacations was based on their Ultimate Italy itinerary. Discover more journeys with Insight Vacations.


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