A friend once opined, “Don’t try to see all of NYC, because you never will. Go back.” After a week touring a relatively small part of Italy, this appears to be doubly true. You’ll never visit all the picturesque towns, see all the art, eat at all the burrata, nor drive all the spectacular roads. You’ll never shop all the shops and walk all the ancient alleyways nor take all the tours. You’ll never see it all. What you can do, however, is try these exceptional hotels, experiences, and stops along the way. You can take the slow road, in a fast car, benefit from a few insider tips, and learn from our experiences.
Our Ride: 2025 Maserati Gran Cabrio
As this is fundamentally a road trip, the most important component is the car; actually, the most important component is the road and the destinations, but an exceptionally flamboyant and fast car certainly enhances the experience. In choosing our ride, we wanted something powerful but elegant, dynamic but comfortable, enough space for two and luggage but still suitable to European roads. Something celebrated by locals, something with provenance, something Italian! A grand touring car is what we wanted and, as luck would have it, Maserati happens to make a car called exactly that: the Maserati GranTourismo. Given it was late summer, however, a convertible was especially appealing and, you guessed it, they have one of those too: the Maserati GranCabrio. Perfecto!
Two doors, four seats, sexy as Monica Bellucci in The Matrix, competing for la piu bella donna del mondo, but with over 500-hp and CarPlay. To say the GranCabrio sucks up miles is to do its engineering and design an incomparable disservice. This is simply one of the finest grand tourers ever conceived and executed. Unlike so many competitors, the GranCabrio is about grace, pace, and space. It’s compliant and comfortable but furiously fast and capable. It shows a deep understanding of what people really need if they actually plan on driving their car rapidly across continents. Comfort, practicality, elegance, and performance.
Our Route
Milan to Florence to Forte Dei Marmi to Portofino to Como and back to Milan. Perhaps unconventionally, for a road trip, we used Florence as a base from which to visit Forte as opposed to staying there… even though it’s on the way to Portofino. There was just too much to see and do in Florence to leave it and Forte makes for a lovely day trip but isn’t necessarily a place you need to stay unless you plan to do the beach day after day. From Portofino to Como for a palette cleansing couple of days of relaxation and back to Milan for shopping, art, ambiance, and the journey home.
Florence Day 1: Collegio alla Querce Auberge Collection, Forte Dei Marmi, and Bocelli
We used Florence as a jumping off point to experience not only the famed city but local attractions. There’s a wealth to see and do so close to the sea: Tuscany, Pisa, Cinque Terre, and more.
Our first two nights were at the newly reimagined Collegio Alla Querce, Auberge Collection college at the oaks in Inglese. Formerly a private school, Collegio Alla Querce, Auberge Collection is a refuge tucked away, out of sight and set above Florence, walled away in a lush garden. It’s private and comfortable, only a short ride to the most sought-after attractions. A welcome respite from the summer tourist crowds of Florence and a destination in its own right. The grounds, densely planted snaked with paths that meander to private nooks and enclaves, it has the feel of an estate as opposed to a hotel. This feeling of a grand residence is carried over when you enter the lobby, grand yet tasteful, private and warmly decorated not overly curated and planned. The staff were equally warm as the earth-toned interior palette but also attentive and charismatic. Charming.
Perhaps it was fate to start this journey with one of the most stunning rooms I’ve ever experienced, anywhere, or perhaps just good fortune. Our suite at Collegio Alla Querce, Auberge Collection was, simply put, spectacular. Immediately this exquisitely finished room (of roughly 2,000 sq. ft) further left the impression of a residence and not a hotel room. Oak is everywhere, and the joinery and millwork is simply beyond reproach. My grandfather was a furniture maker and refinisher and Collegio Alla Querce, Auberge Collection, I can assure you, is the finest lever of finishes there is. Everything you touch exudes quality, like the brass oak leaf cabinet pulls, the dove-tail joints of the drawers, the thick and wide oak flooring, the murals, the clay tiles and marble slabs in the bathroom. Every touchpoint, every piece of communication collateral, every décor item is charming and beautiful. There are great books on the coffee table, a fantastic bar stocked with local treats and libations, comfortable furniture, ample closet space, and a bathroom to put some hotel spas to shame.
It was dark by the time we arrived that first night, a travel delay and then a 4hr blast from Milan to Florence, the restaurant was minutes from closing, it was late. This made for two pleasant surprises, the exceptional room service food and presentation (food arranged and set on dining table without hesitation or request) and the view the next morning. Turned around in the twisting streets of Florence and arriving at night with curtains drawn it was only at sunrise, after throwing open the drapes and opening the shutters that the incredible view revealed itself. From Collegio Alla Querce, Auberge Collection’s elevated vantage point, a stunning panorama of leafy oaks, ancient rooftops and the legendary Duomo, all bathed in morning sun. The stuff of dreams.
Forte Dei Marmi
It’s about an hour-and-a-half from Florence to Forte dei Marmi (Fort of Marble) the quintessential luxury beach destination in Italy. A distance easily dispatched by the Maserati’s power and poise. We roared down the motorway with the well-insulated and cossetting fabric roof up and dropped it on the off-ramp to Forte. The beauty of a convertible roof that you can use up to 50 km/h is that you find more opportunities to put it up and down.
Forte is flip flops and LV, beach bags and Loro Piana. It’s beach clubs, sand and sun…and it’s complex cocktails and al fresco dinners. It’s charmingly simple and sophisticated all at the same time. A bit of a fashion show and entirely Instagrammable, but Forte beckons you to spend a month as much as an afternoon.
We arrived and had lunch at Remo Beach Club which is just steps from the heart of Forte. We spent a couple of hours by the shore under the tented beach chairs, soaking in the late summer heat and the powerful crashing waves of the Ligurian Sea. It’s all well-appointed and well presented with charming, historic change rooms (you get your own for the day) and plenty of space for 4-6 people in each cabana. It was equally worth it for two to luxuriate for a few hours before hitting the town.
You can easily spend an afternoon touring Forte for the luxury shops. Dior stole the show with their masionette, but all our favourite brands are present with special a Forte presence, products and pop-ups. LV ice cream bar? You go it. Paul and Shark bicycles to use? Of course. Loro Piana flower shop? Was there every any doubt? It’s such a charming and warm atmosphere, with more than a hint of whimsy. Everyone is relaxed, chill, enjoying beach life, the world’s most recognized brands included.
But an afternoon is what we had and more than a bit of driving in the GranCabrio was required to get to our next destination. Some brio would need to be added to arrive on time and some fuel, which brought us to the world’s most charming gas station. How many gas stations have you been at with a patio, let alone one cute enough to want to sit at? The kind of thing you can only discover if you drive.
Teatro Di Silenzio
Another hour and a half of top down motoring on winding country roads lined by sunflower fields and cypress trees saw us in Teatro Di Silenzio in Lajatico, where Andrea Bocelli is from, and where we would experience him that night. Teatro di Silenzio is a magical space set into a valley and the backdrop is a dramatic monolithic display that one might imagine in an ancient Greek amphitheatre. Bocelli’s performance is worthy of an entirely separate story, his magic filled the Italian night sky and rolled through the countryside captivating thousands.
By the end of his performance it was quite late and the Maserati was welcoming comfort. Roof up again, we blast to Florence, arriving I’m not sure when. Dinner was perhaps at 2am, but it was exquisite and exactly what we’d had the night prior: Burrata, focaccia, tomatoes, beef ragu, and a salad. All perfect, all carefully arranged on the dining table in our suite and all quintessentially Italian.
Our suite’s large and comfortable two-person tub made for welcome relaxion after possibly too-long a day. But why not live everyday like your last? Exhausted, full, relaxed by warm water and bath salts it was time to slip into the other world. Sweet dreams indeed.
Florence Day 2: Galleria Dell Academia and Uffizi Gallery
Our second day at Collegio treated us to the same splendid morning ritual. Languid wake up in the all-encompassing comfort of sumptuous sheets and pillows. Draw the blinds, open the windows to a landscape view of Florence’s rooftops and the Duomo. It could never get old.
Florence has an abundance of museums and galleries not to mention one very special brand museum. If you’re going to see one thing, however, see the David. As an art minor and art student my entire life, I can say, without a doubt, that it was a humbling experience, poignant in appreciation, and powerfully historic. You’ll want to allow for a couple of hours at Galleria Dell Academia to take in the serene beauty and gracefulness of the David, the other galleries in the museum and the gift shop.
Spend the afternoon at Uffizi. You’ll need at least four hours to do this incredible collection of ancient art justice. And when you leave Uffizi, Ponte Vecchio is inescapable in its significance, indelible on our collective imagining of Florence.
We, however, didn’t allocate enough time to Uffizi, however, as Collegio has resort-like amenities that also urgently required our attention. A serene and sophisticated pool area with restaurant, multiple al-fresco dining spaces, and exceptional restaurants.. It’s an ideal escape from the energy of summer Florence. A private and cossetting place from which to explore this vibrant, storied and seductive city.
Florence Day 3 – Four Seasons Firenze and Gucci Museum
After two nights at Collegio Alla Querce, Auberge Collection’s secluded sanctuary we spent an evening closer to the old town. The Four Seasons Firenze, like Collegio Alla Querce, Auberge Collection (a school), and Portrait Milano (a seminary), was a once a sprawling institution, a convent. It seems that repurposed institutions make for incredible hotels. With the second largest private park in Florence, the Four Seasons is a magical oasis in an area dense with ancient buildings and even denser in summer tourists. A short walk to everything, literally, the Four Seasons is a pied a terre par excellence for Florence.
The Four Seasons Firenze is resplendent with original frescos and isn’t that the ideal way to experience a stay in Florence? Surrounded by the art and craftsmanship of a bygone era? Imagine waking up each morning in a room crowned by an original fresco… it’s enough to give you chills. Naturally the Four Seasons has exceptional spa and pool facilities as well as multiple restaurants both indoors and al fresco. We dined at the casual restaurant by the pool, and it was one of the finest meals we had in Italy. Whole white-fish and sides, burrata and desert, the perfectly authentic Italian meal set amidst the calm, park-like sanctuary of the hotel’s expansive grounds with the warmest late-summer air whispering on the backs of our necks.
Beyond the history, the architecture, the food, and amenities there is something to the Four Seasons experience that’s hard to put into words. The robes are the softest you’ve ever touched or have touched you, the room has everything you need… nothing is missed, ever. It’s easy to feel comfortable, cossetted… you’d be forgiven for ignoring Florence, its history, galleries full priceless art and just enjoy the Four Seasons.
But when you do venture out the front door, you’re 10 minutes from the greatest depths of history. The density of traffic and people intensify as you wander closer into the city centre. The energy builds and, for these tired travellers, our energy does as well. Bathed in late-afternoon light, Florence is beautifully textured. Every street and façade is now a warmly lit canvas of ancient tales, the stories of the millions of lives over thousands of years that came before.
When you wander you discover and on our last night in Florence we discovered a truly impressive experience just before it closed for the night, the Gucci Museum. Not on our plans, and we had lunch just outside it and didn’t notice, the Gucci Museum is a fashion, culture and history afficionado’s dream. Immersive and engrossing exhibits of the brand’s history and creations, a restaurant, gift shop and Gucci boutique with unique pieces made this a true highlight of our Florence experience.
Day 4 – Portofino en route to Como
Two-and-a-half hours from Florence, Portofino might just be the most charming place on Earth. We use the Maserati’s power and poise to make short work of the motorway. The car excels at, um, elevated velocities and then, when you’re in town, drop the top and soak in the sun and scenery. Warm air swirling the cabin, our hair, scarves, linen shirts and light dress caught in the whirlwind… it’s the stuff of dreams, fantasies, and vintage films.
Portofino exceeded expectations. We cruised right in by telling the Carabinieri that we had hotel reservation at the Belmond, which was more or less true. Otherwise, the road was closed to traffic due to parking limitations. That said, when we arrived, there was indeed parking at the one garage, though it was a tight fit for the long, lurid lines of the Maserati. We managed to slip it in anyway.
Portofino is a charming, once fishing village, now luxury boutique and restaurant haven resplendent in colour and charm. It makes for a romantic afternoon and, though tempting us to stay overnight, was a perfect little break for. A couple of hours and no more. Drinks at Splendido Mare a Belmond Hotel are a must, metres from lapping waves. Boats undulating up and down, mottled light bathing the stylish crowds and the sounds of the sea. All our favourite brands are here too… Dior, Loro, Rolex, etc..etc. The finest luxury brands dot the Italian coastline with charming shops and whimsical activations. It’s another world.
As seductive as Portofino was, Como beckons.
Day 5 Como – Musa Lago di Como and Bellagio
Como is the stuff of dreams; one I’ve dreamed of my whole life, and you too, probably, if you’ve ever even heard of it. There are the principal towns of Como, Bellagio, Tremezo, and Menaggio to consider but, we elected for a quiet spot to stay and explored from. We chose Musa Lago di Como in Sala Comacina for this quiet village’s authentic Como energy. Ideally situated about 15 minutes South of the ferry to Bellagio. Musa is an intimate boutique hotel in an idyllic town with a wonderful walking path throughout it that extends along the waterfront. The hotel has fine dining and casual options, the most picturesque terrace on Como, a heated pool, sauna and charm. The ample charm that defined our Como getaway.
Arriving at Musa you have a great vantage point of the private pool area and the overall vantage point the hotel presents of Como from the elevated private parking area. There’s a walking path through the entire village and other coastal towns for several kilometres; it crosses the front of the hotel between it and the water. At the hotel’s doorstep is also a classic Como ferry and a charming outdoor dining area and lounge. I simply can’t do the charm and character of this location justice, you’ll just have to go.
Our room’s terrace, overlooking Como, had stirring views, the sound of Como’s waters lapping at the sea wall adds a level of romanticism befitting a Hollywood fairytale. The picture-perfect Como room with its French doors and windows opening to an iconic lake view populated by ferries old and new, classic wood water taxis and slick modern day-boats. It was a dream made real, or were we lucid dreaming? Hard to say…
While the dining at Musa is exceptional (perhaps the most satisfyingly sweet orange juice I’ve ever had, the pizza draws in locals and the tapas menu in the bar and lounge epitomized comfort food), we took their recommendation for a truly special and memorable experience at a local restaurant called Locanda la Tirlindana. Though they were booked for the evening, a little visit and chat with the owner’s father, in French no less, freed up some space. Or perhaps it was the charm of my companion that swayed him. We’ll never know. This courtyard restaurant set on the cobbled shore of Como, overlooks an armada of fishing boats from its iron bistro tables and canopied outdoor dining room. Simple, local, traditional fare is perfectly executed and entirely reasonable. A beautiful setting that made for a beautiful memory.
Villa Del Balbianello and Bellagio
On our way to Tremezzo (where we would take the ferry to Como) we spent the morning at Villa Del Balbianello in Lenno. As an architecture aficionado this was well worth the visit. This incredible property absolutely captures the charm of Como, Italian Villas, La Dolce Vita and bleeds romance and fantasy. And, in keeping with the theme of most of our hotels… it was once an ancient Franciscan monastery.
If there was one thing we wanted to see on Como, however, it was Bellagio — the jewel of Como. From Tremezzo it’s a short ferry ride and, as it would reveal itself later, Tremezzo is the ideal spot to ferry from. Bellagio is, as it turns out, the ideal spot to be surrounded by tourists. For all its charm and character, I enjoyed Sala Comacina, Tirlindana, Musa and the walking trail and Villa Balbianello more than the famed Bellagio.
Don’t get me wrong. It’s a charming spot and worth a day but, the serendipitous nature of Tirlindana, the relaxed and soothing elegance of Musa, the quiet ancient trail and the myriad details along the way left an indelible mark. These are warm memories whereas Bellagio, well, it delivered what was expected. And closing the loop on the ferries, Tremezzo was the ideal return destination because virtually nobody else was going there compared to other ferry destinations and the madness that naturally ensued at the terminal…
Day 6 Milan – Portrait Milano
Timing is everything, and on our departure day from Como, we not only woke up to torrential rains, but the road was washed out with a mud slide. As much as I like topless, warm, sunny drives, this was the perfect test of the Maserati. Roof up, comfortably ensconced in the leather-dipped interior, the AWD GranCabrio is as at homes in standing water and on slick mountain hairpins as dry motorways that stretch into the horizon. To get around the mud slide, we had to go up and over the mountain range surrounding Lake Como. Slippery wet hairpin after slippery wet hairpin we pushed the front-end turn-in and rear-end traction of the GranCabrio to its limit.
Our stay in Milan would be defined by the Portrait Milano hotel. This ancient seminary is a zen refuge in Milan and a short walk to the famed Duomo and Brera gallery as well as all the shopping you could possibly desire on Via Montanapoleone.
Abandoned for years, the Portrait Milano was rescued by Ferragamo family, yes that Ferragamo family. Reimagined and restored, they’ve bestowed it with touches of their famous leathers and fashions. Subtle details here and there, it’s finished and decorated like a home as opposed to a hotel. The lobby is a comforting and relaxing library living room with a large central table covered in architecture, design and fashion books. The rooms are like the rooms of a posh Italian home with lush decor and dense decoration provide a cosseting and intriguing space to discover the thoughtful details of its design. The lounge and restaurant warm and inviting. It’s a cosseting retreat within bustling Milan.
The central square is both a respite and a public meeting space as well as host to cultural and corporate events and activations. You’d be forgiven for not noticing the hotel at all as it’s nestled down a cobble lane. Similar to Collegio Alla Querce, Auberge Collection, Portrait immediately feels like you’ve entered a grand residence and it’s designed to soothe, relax, replenish and restore. But wander just past its immense walls and you’re in the thick of Milan. Scooters buzzing, sidewalks shoulder to shoulder with locals and tourists alike, hatchbacks trying to kill you at every intersection. Slip behind Portrait’s walls again and this all disappears. It’s a bit of a magic trick.
We shopped on Vi Montenapoleone, the Dolce and Gabbana home store was especially engrossing, the Duomo demands a visit, especially to the viewing terrace, and the Brera Gallery is enormous and soothingly, almost hauntingly, welcoming.
Returning to Portrait for dinner at Beef Bar we were treated to what was by far the best steak dinner we’ve had in Italy. Seated under the colonnade of the interior courtyard, it’s a magical and ethereal experience to dine outdoors at Portrait.
Why We Drive
Whether it’s high-speed touring, countryside exploring, seaside cruising or narrow-alley navigation it’s always better to drive. Especially so in a grand touring car like the Maserati GranCabrio. It’s not just transportation; it’s an integral part of the experience that also creates more opportunities for new experiences. The setting sun is soaked in over many miles, you see the whole show, the sunflower fields fill your peripheral vision when there’s no roof, you stop, turn around and go back anytime you like, and you should and will. True luxury is the luxury of time, and driving affords you the time to leave when you want, arrive when you want, take what you want and go where you want when you want. Whether you drive or not, the food and wine all tastes the same, the art won’t change, and the ancient, cobbled streets and weathered facades certainly won’t either, but the journey and the adventure you undertake can only be entirely written by you when you travel by motorcar. Write your own journey, preferably in Italian.
FEATURE PHOTO COURTESY OF FOUR SEASONS.
