A tough few years of the pandemic and business restructuring in Singapore had left me with a deep thirst to explore a new culture filled with art, ancient history, gastronomy and nature. Where in the world could I go for a fix of all that? Then, I remembered the ancient architectural marvels of Rome, the magnificent galleries and museums of Florence, the rolling hills of Tuscany, the sparkling azure waters of Amalfi, and, best of all, local food so delicious you could shed a tear. It had to be Italy.
My month-long love affair began in Florence. As the birthplace of the Italian Renaissance, the city is an art and architecture lover’s dream. Where most travellers spend two to three days, I allowed myself a full five to explore at a languid pace.
My next stop was a sojourn through the utopia of the Tuscan country. April and May are the best months to visit, and you’ll be greeted by vibrant poppies, yellow and white daisies and pink thistles. For cheese connoisseurs, the quaint town of Pienza is a necessary stop, even if only for a couple of hours on the way to Val d’Orcia. Known as the home of pecorino, you will find varieties of every maturity and flavour to sample within the towns cobblestoned stores, alongside the rustic local honey.
Bizarrely, despite having been in the travel industry for such a large part of my professional life, I had never been to Rome before this trip. So, it was only right that in my month-long Italian rendezvous, I carved out two weeks to explore the capital.
The last few days were spent further down the coast, with a glorious stop in Naples. Finally, I ended up in picture-perfect Amalfi, and it was exactly as I had imagined—with the sparkling Mediterranean Sea on one side and colourful townhouses jotted across steep cliffs on the other.
Below, find an insider’s guide to living la dolce vita—a curation of the chicest places to stay, the best restaurants to dine in and the most authentic activities to explore in each city I visited.
1 / 10
Florence: Stay at Portrait Firenze; Eat at Trattoria Cammillo
For a taste of true Florentine luxury and heritage, Portrait Firenze is seated on the perfect spot overlooking the River Arno. Incidentally, the hotel is owned by the Ferragamo family, who had once resided and built their fashion business in the city. Sunset hour at the La Terrazza Rooftop Bar next door is not to be missed, for it is the perfect cool down after a day of exploring.
On your days out, make sure to visit the world-famous Uffizi Gallery, home to incredible Botticelli’s such as Venus and Spring, along with exquisite ceiling murals that go on for as far as the eye can see. Michelangelo’s David at Galleria dell’Accademia is as impressive in real life as one may imagine. I recommend engaging a professional guide from Access Italy, who will be able to help you skip queues and get VIP access. Ask for Veronica or Leonardo if you can—they are extremely knowledgeable and fun locals who will show you a good time.
For glorious plates of pasta, a must-try is Trattoria Cammillo, an institution in Florence recommended by locals and the international jet-set alike. Order the pea spaghetti pasta if you’re in an adventurous mood.
2 / 10
Florence: Work out at The 22
To complement my love of wine and pasta, I checked in daily to The 22—a refined social wellness club offering not only a range of fitness and yoga classes, but also community events that connect you to friendly locals and expats. The space is owned and run by Singaporean Aparna Thadani, who really has her finger on the pulse of what’s happening in Florence, from art gallery openings to premium wine tasting events. She’ll be happy to give you a warm welcome to both The 22 and the city—and may even show you her husband’s famous violin shop, which incidentally makes some of the finest violins in the world.
3 / 10
Tuscany: Stay at Castello Di Vicarello
The family-run and owned Castello Di Vicarello was one of three countryside properties I visited in Tuscany—an intimate, romantic nine-suite castle hotel surrounded by acres of vineyards, olive groves and farmland. My Spa Suite was reminiscent of a log cabin, and included a generously sized steam room, sauna and hot tub overlooking the valley.
A peek into the other unique suites offered roll-top baths, artwork from the family collection and modern, cosy lounges equipped with fireplaces for the chillier months. With over 50 types of vegetables and 30 herbs grown on their farm, along with a family-run vineyard producing two varietals, the best thing to do here is to get sucked into their homegrown gastronomy. The family are warm and welcoming, so it feels less like a hotel and more like staying in the beautiful home of a friend.
4 / 10
Tuscany: Stay at Rosewood Castiglion Del Bosco
I also spent a night at Rosewood’s impressive Castiglion Del Bosco. This breathtaking property was once a small town—complete with castle ruins and a medieval church—which has now been converted into an expansive luxury hotel. A leading Brunello di Montalcino winery, two restaurants, an organic garden, cooking school, 18-hole private golf course and a full-spectrum spa means that one night here will not be enough to do it justice. The wine tasting was one of the best I have ever had—with the sommeliers more than willing to pop an extra cork and extend tastings beyond the standard set-up.
5 / 10
Tuscany: Stay at La Bandita Townhouse
Last but not least, I stayed at La Bandita’s Country House, which is a quirky guesthouse consisting of only 8 bedrooms, alongside communal dining, a pool overlooking the picturesque valley—and a stunning sister property in nearby Pienza known as La Bandita Townhouse. Both run by an ex-music producer, there have been a fair few bands visiting this secluded spot to write their next chart-topper. Staff happily wear multiple hats, and are on hand to assist with anything from laundering mud-splashed leggings to tasting a local wine with you at aperitivo hour.
Chef David Mangan, who trained with Gordon Ramsay back in the day (and who also oversees the Townhouse in Pienza), cooks up a storm with local produce. The Country House has since closed to plough all their efforts into the Townhouse. I stuck my head in when I was town, and with the same staff, management and chef, it seems like La Bandita Townhouse will tick all boxes as it did for my country stay—if not more.
6 / 10
Rome: Stay at Bulgari Hotel Roma
In Rome, I Airbnb-ed for the most part to live like a local, staying in a beautiful and not overly touristy neighbourhood to the west of Ponte and Piazza Navone. The piece de resistance of my time here, however, was my time in the stylish Bulgari Hotel. The Italian brand’s spanking new hotel is located in the heart of the Campo Marzio neighbourhood, a stone’s throw from the Spanish Steps. No expense was spared in this tribute to Bulgari’s hometown, with Italian design and craftsmanship imbued in every nook and cranny.
Like what you’d expect from an ultra-luxury hotel, the suites have all the bells and whistles. The in-room tech was next level, and there was even a set of premium makeup brushes in the vanity. The roof top bar Le Terrazza is beautifully designed and offers sweeping views of the city. On the ground floor, Il Caffe has a relaxed vibe with traditional Roman food—great for lunch or settling into a corner to catch up on emails with coffee.
7 / 10
Rome: Visit Borghese Gallery
The bucket list-worthy sights of the Colosseum and the Vatican are best seen with Access Italy’s top guides, who show the likes of Oprah around on her yearly visits, and are the only folks who can stop traffic in the Sistine Chapel if pre-requested.
One of my favourite sites and highlights, however, was the lesser-trodden Borghese Gallery. Best known for its magnificent collection of Bernini statues on the ground floor, which deserve time and explanation with a guide, there are also numerous paintings by Raphael and Caravaggio on other floors. Anyone who doesn’t do well with crowds will appreciate that only 360 visitors are allowed in at any one time, so you can browse at a peaceful pace.
8 / 10
Rome: Eat at Pier Luigi; Workout at Soho House
The best places I experienced in Rome for seafood were Assunta Madre and Pier Luigi. Don’t miss out on authentic carbonara at old-school institution Il Pompiere Ristorante Al Ghetto, and try Taverna Trillusa for the sublime Cacio e Pepe amongst many other phenomenal pastas—just remember to book at least two weeks ahead in high-season. Post-dinner ice-cream at Gelateria del Teatro also became a regular haunt since they have one of the best rum and raisin scoops in town. If you ask me, Rome is best explored by foot. Not only is it an open-air museum, there is sweet-smelling honeysuckle on every corner.
Soho House members will enjoy the Rome outlet’s roof-top terrace, pool, gym and cryotherapy chamber—perfect for decompressing from sightseeing and unlimited libation. They also offer exceptional manicure and pedicure services for a mid-trip tidy-up. For other wellbeing fixes, Pouchon-Jean is a brilliant, friendly personal trainer who will come and train you at a place of your choice.
9 / 10
Naples: Stay at Costantinopoli 104
Since there is a lack of big hotel chains in Naples, I’d recommend staying in charming, family-owned properties such as Costantinopoli 104. It was quaint, comfortable and perfectly located to explore the city. In terms of food, L’Antica Pizzeria da Michele is the spot that everyone flocks to, because of its Eat Pray Love fame. Many local friends recommended that I visit Concettina ai Tre Santi—and for good reason. A true Neapolitan pizza institution, the pizzas here are best enjoyed for their simplicity, with a tomato base and minimal toppings. The architecture of Naples is truly cinematic, taking you back nearly a century, so it’s worth a walk to the harbour and back to burn off that well-deserved pizza.
10 / 10
Amalfi: Stay at Residence Buonocore, Trek on Path of Gods and more
In Amalfi, I stayed at the ever-so-cute family guesthouse Residence Buonocore, which offered amazing views of the coastline and was a perfect spot to get to both Amalfi town and the rest of the Amalfi Peninsula. The interiors were immaculate—coastal blue hues against white-washed walls, with an expansive balcony that was a dream to lounge in at any time of the day. Nunzia, the owner, was incredibly helpful with giving advice and tips on cooking schools, transport and restaurants in the area.
I took up two cooking classes in my time there. The first was at Hotel Bucca Di Bacco, a very professional set-up with top chefs, takeaway recipes, gnocchi-making equipment and cookery linen all included. The other was La Vigna Degli Dei, a family-run operation in a rustic, hill-top farm where they make their own wine and olive oil. Here, classes are led by Papa Pasquale, whose dry sense of humour and generous wine pours will have you whipping up ravioli in no time.
For an active fix on Amalfi, a trek across the spectacular Path of Gods comes highly recommended, boasting incredible views before ending in Positano. Lovable guide Enzo Masullo will take you across, as well as on other Amalfi treks and waterfalls. For a post-hike libation once the dust has been brushed off, head to Le Sirenuse for a drink at Aldo’s. Dripping in style and curious art, it is obvious why the establishment is one of the buzziest hotels in town.
Lynda Williams is a global communications expert and coach who has worked for a multitude of leading brands in the travel industry for over 20 years. She now dedicates her time to teaching PR through Hack Your Own PR, coaching corporates and individuals, and in her spare time, writing about her travel adventures.