In 2016 I had the privilege of being invited to speak at a conference in Milan. The professional reason got me on the plane. What I didn’t anticipate was how much the trip itself would shift my relationship with Italy. I’d been to Italy briefly before, on the kind of fast tour that hits Rome and Florence and doesn’t really sit anywhere long enough to learn anything. This trip was different. Milan for the conference, then a train up to Lake Como for a few days, and the kind of meals that make you realize you’ve been getting Italian food slightly wrong your whole life.
I left wanting more of Italy. I haven’t been back yet for the deep dive I keep promising myself. Until I do, this is the trip.
Milan: The Underrated Italian Capital
Milan doesn’t get the romantic press that Rome and Florence and Venice do. The standard travel narrative treats it as a business city, an industrial city, a fashion city, but rarely as a place to actually visit for its own sake. Having spent some time there, I think this is wrong. Milan is one of the most interesting Italian cities, precisely because it doesn’t perform for tourists in the same way the marquee destinations do.
The center is anchored by the Duomo di Milano, the cathedral that took nearly six centuries to complete and is one of the largest Gothic churches in the world. The exterior is a forest of marble spires and statues. The interior, vast and dim, is dotted with stained glass that catches the light. And the rooftop, accessible by elevator or stairs, gives you a 360-degree view of the city with the Alps visible to the north on clear days.
The Duomo was the highlight of the architectural side of the trip, but I want to be specific about why. It’s not just the scale, which is real. It’s the patience embedded in the building itself. People worked on this church across generations who knew they wouldn’t live to see it finished. There’s something about that level of long-term thinking that puts modern construction projects, my own included, in perspective.
Adjacent to the Duomo is the Galleria Vittorio Emanuele II, the 19th-century glass-roofed shopping arcade that’s one of the oldest in the world and still functions as the city’s main shopping hub. It’s photogenic to a slightly absurd degree. Iron and glass, marble floors, the famous mosaic of the bull at the entrance that you’re supposed to spin your heel on for good luck. The locals do it. The tile under the bull’s testicle has worn through to the substrate from decades of foot-spinning. Tradition’s evidence in concrete form.
The Last Supper and the Other Stuff
I made it to see The Last Supper at Santa Maria delle Grazie. This requires a separate booking, often months in advance, and you’re admitted in small groups for a strictly limited viewing window. The painting itself, you’ll know already, is in fragile condition. What surprised me was the size of it. It’s bigger than the reproductions suggest, and the room is set up so you stand at a distance that feels appropriate. The whole experience is about fifteen minutes long. It’s plenty.
The other thing about Milan that I want to flag is the Brera district, the old artists’ quarter that’s now full of art galleries, antique shops, and small restaurants. I had several of my best meals in Milan in Brera, in places I wandered into without much research. The trick to eating well in Milan, I discovered, is to walk away from the obvious tourist zones and find the neighborhoods where Milanese actually go for lunch. Two blocks off the Duomo, the food gets significantly better and significantly cheaper.
The Train North to Como
The train from Milano Centrale to Como takes about an hour and is one of the easier travel logistics in Northern Italy. You leave the Milan train station, watch the city give way to suburbs, then to countryside, then to the foothills of the Alps, and you arrive in Como with the lake spread out in front of you. The shift in scenery is dramatic. The shift in pace is even more so.
Lake Como is shaped like an upside-down Y, with three branches stretching into the foothills of the Alps. The town of Como sits at the southern end of the western branch. The town of Lecco sits at the southern end of the eastern branch. The famous villages, Bellagio, Varenna, Menaggio, are scattered along the shores in the northern half of the lake.
The thing about Lake Como is that the photos don’t lie. The mountains plunge directly into the water. The villas with their formal gardens line the shores. The light on the lake at golden hour is the kind that makes you put down whatever you were doing and just look. I shot a lot on this trip and I think a few of those frames are still some of my best lake-and-mountain compositions. The same approach I write about in my outdoor photography fundamentals, translated to a softer European context.
The Boats and the Villages
The way to actually experience Lake Como is by boat. The public ferry system connects all the major villages and lets you island-hop, or rather village-hop, around the lake at a leisurely pace. A day pass gets you on and off as many ferries as you want. I’d recommend giving yourself two full days for this. One day to do the central lake villages (Bellagio, Varenna, Menaggio), and a second day to do the southern stretch including the Villa del Balbianello at Lenno.
Bellagio is the village everyone has heard of, and it earns the reputation. The town sits on the promontory where the lake forks into its three branches, with cobblestone streets climbing up from the water and views in every direction. Yes, it’s touristy. Yes, the prices reflect that. The setting still makes it worth it.
Varenna on the eastern shore is my preferred village. Smaller than Bellagio, less crowded, with a beautiful waterfront promenade and a couple of botanical gardens that are worth an afternoon. The walk along the lakefront from the ferry dock to the village center is one of those routes that justifies its own trip.
Villa del Balbianello is the villa from the Star Wars and James Bond films, sitting on a small wooded peninsula. The grounds are a working botanical garden, and the views from the loggia are some of the best on the lake. Boat access only or a hike along a footpath. Either is worth it.
The Food and the Wine
I want to be specific about the food, because it’s the part of the trip that changed my relationship with Italian cuisine.
I had been eating Italian food in the US for thirty-something years and thought I understood it. I did not understand it. The bread is different. The olive oil is different. The way the dishes are constructed, with three or four ingredients chosen for quality and combined simply, is fundamentally different from the heavy, overstuffed Italian-American versions I’d grown up with.
The standout meal of the trip was at a small restaurant in Bellagio overlooking the lake, where the owner brought us a tasting of local wines from the Lombardy and Piedmont regions and walked us through each one. The wines from this corner of Italy don’t get the international attention that Tuscany and the Veneto do, and they’re often a better value as a result. The reds from Valtellina, the alpine valley north of the lake, were a revelation. The sparkling Franciacorta wines from the area south of the lake are some of the best Italian sparkling wines and are consistently underrated compared to Champagne.
I left that meal with a list of wines to look for back home. I’ve been adding to the list ever since. Italy did this to me.
What I Want From Italy Next
The lesson of this trip is that I haven’t been to Italy properly. I’ve been to the famous cities. I’ve been to one corner of the Lake District. I haven’t been to Tuscany for any meaningful time. I haven’t been to Puglia or Sicily. I haven’t been to the Cinque Terre. I haven’t done the food tours through Bologna and Modena that everyone tells me are essential.
The next Italian trip is going to be a long one. Three weeks minimum. A car. A loose plan. The kind of trip where you stay in a small village for three days, find one restaurant, eat there every night, and let the rest of the trip be flexible. The way Peru and Panama rewarded slowing down and Patagonia rewarded patience, I think Italy rewards staying put.
Final Frame
The conference paid for the trip. The trip paid me back in ways that haven’t really stopped. I think about the meal in Bellagio more than I should. I think about the light on the lake at sunset. I think about the patience of the Duomo, and what it means to build something across centuries. Some trips give you photos. The best ones give you a slightly different way of moving through the world afterward.
Italy gave me both. I’m overdue for the second visit.
Milan and Lake Como in 2016: A Conference, a Train, and an Italian Education
In 2016 I had the privilege of being invited to speak at a conference in Milan. The professional reason got me on the plane. What I didn’t anticipate was how much the trip itself would shift my relationship with Italy. I’d been to Italy briefly before, on the kind of fast tour that hits Rome and Florence and doesn’t really sit anywhere long enough to learn anything. This trip was different. Milan for the conference, then a train up to Lake Como for a few days, and the kind of meals that make you realize you’ve been getting Italian food slightly wrong your whole life.
I left wanting more of Italy. I haven’t been back yet for the deep dive I keep promising myself. Until I do, this is the trip.
Milan: The Underrated Italian Capital
Milan doesn’t get the romantic press that Rome and Florence and Venice do. The standard travel narrative treats it as a business city, an industrial city, a fashion city, but rarely as a place to actually visit for its own sake. Having spent some time there, I think this is wrong. Milan is one of the most interesting Italian cities, precisely because it doesn’t perform for tourists in the same way the marquee destinations do.
The center is anchored by the Duomo di Milano, the cathedral that took nearly six centuries to complete and is one of the largest Gothic churches in the world. The exterior is a forest of marble spires and statues. The interior, vast and dim, is dotted with stained glass that catches the light. And the rooftop, accessible by elevator or stairs, gives you a 360-degree view of the city with the Alps visible to the north on clear days.
The Duomo was the highlight of the architectural side of the trip, but I want to be specific about why. It’s not just the scale, which is real. It’s the patience embedded in the building itself. People worked on this church across generations who knew they wouldn’t live to see it finished. There’s something about that level of long-term thinking that puts modern construction projects, my own included, in perspective.
Adjacent to the Duomo is the Galleria Vittorio Emanuele II, the 19th-century glass-roofed shopping arcade that’s one of the oldest in the world and still functions as the city’s main shopping hub. It’s photogenic to a slightly absurd degree. Iron and glass, marble floors, the famous mosaic of the bull at the entrance that you’re supposed to spin your heel on for good luck. The locals do it. The tile under the bull’s testicle has worn through to the substrate from decades of foot-spinning. Tradition’s evidence in concrete form.
The Last Supper and the Other Stuff
I made it to see The Last Supper at Santa Maria delle Grazie. This requires a separate booking, often months in advance, and you’re admitted in small groups for a strictly limited viewing window. The painting itself, you’ll know already, is in fragile condition. What surprised me was the size of it. It’s bigger than the reproductions suggest, and the room is set up so you stand at a distance that feels appropriate. The whole experience is about fifteen minutes long. It’s plenty.
The other thing about Milan that I want to flag is the Brera district, the old artists’ quarter that’s now full of art galleries, antique shops, and small restaurants. I had several of my best meals in Milan in Brera, in places I wandered into without much research. The trick to eating well in Milan, I discovered, is to walk away from the obvious tourist zones and find the neighborhoods where Milanese actually go for lunch. Two blocks off the Duomo, the food gets significantly better and significantly cheaper.
The Train North to Como
The train from Milano Centrale to Como takes about an hour and is one of the easier travel logistics in Northern Italy. You leave the Milan train station, watch the city give way to suburbs, then to countryside, then to the foothills of the Alps, and you arrive in Como with the lake spread out in front of you. The shift in scenery is dramatic. The shift in pace is even more so.
Lake Como is shaped like an upside-down Y, with three branches stretching into the foothills of the Alps. The town of Como sits at the southern end of the western branch. The town of Lecco sits at the southern end of the eastern branch. The famous villages, Bellagio, Varenna, Menaggio, are scattered along the shores in the northern half of the lake.
The thing about Lake Como is that the photos don’t lie. The mountains plunge directly into the water. The villas with their formal gardens line the shores. The light on the lake at golden hour is the kind that makes you put down whatever you were doing and just look. I shot a lot on this trip and I think a few of those frames are still some of my best lake-and-mountain compositions. The same approach I write about in my outdoor photography fundamentals, translated to a softer European context.
The Boats and the Villages
The way to actually experience Lake Como is by boat. The public ferry system connects all the major villages and lets you island-hop, or rather village-hop, around the lake at a leisurely pace. A day pass gets you on and off as many ferries as you want. I’d recommend giving yourself two full days for this. One day to do the central lake villages (Bellagio, Varenna, Menaggio), and a second day to do the southern stretch including the Villa del Balbianello at Lenno.
Bellagio is the village everyone has heard of, and it earns the reputation. The town sits on the promontory where the lake forks into its three branches, with cobblestone streets climbing up from the water and views in every direction. Yes, it’s touristy. Yes, the prices reflect that. The setting still makes it worth it.
Varenna on the eastern shore is my preferred village. Smaller than Bellagio, less crowded, with a beautiful waterfront promenade and a couple of botanical gardens that are worth an afternoon. The walk along the lakefront from the ferry dock to the village center is one of those routes that justifies its own trip.
Villa del Balbianello is the villa from the Star Wars and James Bond films, sitting on a small wooded peninsula. The grounds are a working botanical garden, and the views from the loggia are some of the best on the lake. Boat access only or a hike along a footpath. Either is worth it.
The Food and the Wine
I want to be specific about the food, because it’s the part of the trip that changed my relationship with Italian cuisine.
I had been eating Italian food in the US for thirty-something years and thought I understood it. I did not understand it. The bread is different. The olive oil is different. The way the dishes are constructed, with three or four ingredients chosen for quality and combined simply, is fundamentally different from the heavy, overstuffed Italian-American versions I’d grown up with.
The standout meal of the trip was at a small restaurant in Bellagio overlooking the lake, where the owner brought us a tasting of local wines from the Lombardy and Piedmont regions and walked us through each one. The wines from this corner of Italy don’t get the international attention that Tuscany and the Veneto do, and they’re often a better value as a result. The reds from Valtellina, the alpine valley north of the lake, were a revelation. The sparkling Franciacorta wines from the area south of the lake are some of the best Italian sparkling wines and are consistently underrated compared to Champagne.
I left that meal with a list of wines to look for back home. I’ve been adding to the list ever since. Italy did this to me.
What I Want From Italy Next
The lesson of this trip is that I haven’t been to Italy properly. I’ve been to the famous cities. I’ve been to one corner of the Lake District. I haven’t been to Tuscany for any meaningful time. I haven’t been to Puglia or Sicily. I haven’t been to the Cinque Terre. I haven’t done the food tours through Bologna and Modena that everyone tells me are essential.
The next Italian trip is going to be a long one. Three weeks minimum. A car. A loose plan. The kind of trip where you stay in a small village for three days, find one restaurant, eat there every night, and let the rest of the trip be flexible. The way Peru and Panama rewarded slowing down and Patagonia rewarded patience, I think Italy rewards staying put.
Final Frame
The conference paid for the trip. The trip paid me back in ways that haven’t really stopped. I think about the meal in Bellagio more than I should. I think about the light on the lake at sunset. I think about the patience of the Duomo, and what it means to build something across centuries. Some trips give you photos. The best ones give you a slightly different way of moving through the world afterward.
Italy gave me both. I’m overdue for the second visit.
dhavalilama