From Milan Rooftops to Swiss Lakes: A Soul-Filling Summer by Train

Milan: Rooftops, Aperitivo and Big-City Buzz

The trip began with a night in Milan, the perfect urban prologue before the lakes and mountains.  We flew into Linate Airport, just 7 km outside Milan and much easier than Bergamo (45 km away), often used by the low-cost carriers.  Rather than a transfer, we got the Metro to our hotel.  It is simple to use with a contactless card and has a maximum charge of 7.60 euros per day.  After checking into our hotel, we headed straight for a rooftop bar overlooking the Duomo.  As the sun began to set, the city turned gold.  Terracotta roofs, church spires and the incredible detail of the cathedral were all wrapped in a warm evening glow.  With chilled wine in hand and music in the background, it was the kind of view that invites you to exhale and slow down.  Milan is made for aimless wandering.   We spent time simply mooching and people-watching, letting the city reveal itself in little moments: impeccably dressed locals, café chatter drifting out onto the pavements, elegant shop windows and that unmistakable sense of Italian style.  The next morning was just enough for a taste of sightseeing: a gentle stroll through the historic centre, a coffee stop (or two), and a promise to ourselves that we would return when the weather was cooler and we could linger longer.

Lake Como & Bellagio: Pastel Lanes and Lake-Light Magic

From Milan, the train ride to Lake Como is short, easy and wonderfully scenic. Before long, the urban landscape gave way to glimpses of water and mountains, and we were stepping onto the ferry bound for Bellagio.  We headed to the station for the next chapter. Tickets were all pre-purchased so all we had to do was find a seat.  It was 15 August and, unknown to us, Ferragosto: an official national public holiday marking the peak of the summer.  Every station brought more passengers ready to spend their day at Como on one of the many beaches.  Brollies, coolers, you name it, were brought onto the train.  The views out of the window went from flat plains to mountains to lakes and mountains and in just over an hour we were there.  You have several options but I would opt to get off at Lierna, walk down the hill, grab a wine and pizza in the square ready for the boat to take you to Bellagio.  Ferries go pretty irregularly from here but it is much quieter and the walk is shorter.  If you do not go through me, please make sure you check the times before. 

Bellagio is every bit as beautiful as you imagine: cobbled lanes that twist and climb, pastel facades with shuttered windows, and boats gliding across the lake like little brushstrokes.  It is the kind of place where you do not need an itinerary.  You simply wander, discover and let the day unfold.  Yes, it was busy, but this was mid-August and it did not stop our enjoyment of discovering the town.  We spent our time: Enjoying a long, lazy lunch right at the water’s edge at the newly opened Palazzo Genazzini, then on to Grand Hotel Villa Serbelloni for an Aperol Spritz with the most delicious olives and almonds anyone could wish for.  Ducking in and out of narrow side streets, discovering tiny boutiques and cafés.  Pausing often, just to look out across the lake at the shifting light and distant villages.  Evenings on Lake Como are where the magic really happens. That soft, silvery light on the water makes you want to press pause and stay forever.  As the sun drops, the mountains turn deep blue, the restaurants fill with candlelight and conversation, and there is a wonderful sense of being cocooned in your own little lakeside world.   Unfortunately, the day we visited the late afternoon brought a storm which meant all the ferries were cancelled!  Tourists dressed for 30+ degrees were now soaked to the skin and cold!  It did take a while, and I did wander if we'd ever get home but we did and it was worth it.  Somehow the hundreds of people waiting for a ferry all managed to get on and we were off.  A ride to Varenna and we were picked up be our fabulous hosts. 

Tirano & The Bernina Express: A Moving Alpine Panorama

From Lake Como, the journey continued north to Tirano, the Italian gateway to one of the world’s most iconic rail experiences: the Bernina Express to St Moritz.  Boarding the Bernina Express feels like stepping into a moving cinema.  Huge panoramic windows wrap around the carriage, so nothing comes between you and the landscape.  Once the train pulls out of Tirano, the views just keep building: dramatic mountain passes, tumbling waterfalls, glittering glaciers and high alpine lakes that look almost unreal.  This is not a journey for multitasking. It is one of those rare travel experiences where the entire carriage falls quiet because everyone is simply absorbed in what is unfolding outside.  You find yourself pressing your forehead to the glass, pointing out details, and then falling silent again as the scenery keeps surpassing itself.  It is a wonderful way to transition from Italy to Switzerland, the gradual shift in architecture and landscape mirroring the shift in pace and atmosphere.

St Moritz: Mountain Reflections and Swiss Comfort

Arriving into St Moritz, you immediately feel the change in air: crisp, clear and full of that invigorating alpine freshness, even in August.  St Moritz has a reputation for glamour, but in summer it also has a tranquil, laid-back side that is perfect after a day on the rails.  The lake is the heart of it all, framed by mountains and perfectly still on a calm day, so the peaks are mirrored on the water like a painting.   We spent time: Walking the lakeside path, stopping often just to drink in the views. Sitting at a café terrace watching the world go by. Indulging in wonderfully carb-heavy Swiss comfort food and then sleeping like babies.  There is something deeply restorative about time in the mountains.  The combination of fresh air, gentle walks and hearty food leaves you feeling reset and grounded, but without the need to be constantly on the go.

Lake Zurich: Morning Dips & Waterfront Wanders

The final chapter of the journey took us to Lake Zurich, a softer, more urban kind of lakeside escape that still feels wonderfully relaxed.  Mornings began with dips in the lake, that bracing first plunge giving way to the most refreshing, silky-cool swim. There is something special about starting the day in open water and the mountains sitting softly on the horizon.  Afternoons were for strolling along the waterfront and meandering through the streets.  Zurich’s old town has a charming jumble of lanes and squares, and the lakeside promenades are full of life: paddleboarders, families, friends gathering at the water’s edge.  Evenings were simple and perfect: sitting by the lake, watching the boats come and go, and soaking up that final blend of city buzz and waterside calm.

Why This Journey Works So Beautifully

This itinerary feels so special because it balances contrast and continuity. Contrast: Big-city energy in Milan, storybook charm on Lake Como, dramatic alpine scenery on the Bernina route, stylish mountain calm in St Moritz and relaxed lakeside city life in Zurich.  Continuity: Water and mountains form a thread throughout, with every stop offering its own way to slow down and enjoy them, whether from a rooftop bar, a lakeside promenade or a panoramic train window. Travelling by train adds another layer. Instead of airports and security queues, you move smoothly from centre to centre. Scenic routes become part of the holiday, not just a means to an end. Your journey days still feel like holiday days. Crafting Your Own Version.

The beauty of this trip is how easily it can be tailored to you.

You might want:

• More time on the lakes: Add an extra night or two in Bellagio or swap in another town on Lake Como or Lake Zurich.
• More mountains: Extend your stay in St Moritz or combine with another Swiss alpine resort.
• A different season: Try autumn for cooler city sightseeing and beautifully coloured mountain landscapes.
• A touch more luxury: Upgrade to five-star lakeside or mountain-view hotels and add private transfers where you prefer not to use local transport.
• A slower pace: Add extra nights so there is always time for a leisurely breakfast, an afternoon swim and an unhurried dinner.

Every element of this journey can be adjusted: the number of nights, the style of hotels, the balance between city, lake and mountain, and even the exact rail route.

How I Can Help:

If this sounds like your kind of trip, I can design a bespoke version that feels like it was created just for you.  I can:

• Suggest the best order and number of nights for each stop based on what you enjoy most.
• Handpick hotels that match your style, whether you love intimate boutique stays, lakeside luxury or grand alpine classics.
• Arrange all trains and transfers before you leave home, so tickets and timings are taken care of and everything flows.
• Add special touches such as rooftop drinks reservations, lake cruises, private walking tours or restaurant recommendations at every stop.

All you have to do is sit back, watch the scenery unfold and enjoy the view, knowing that the logistics are already taken care of.

If you would love your own Italy–Switzerland rail adventure, tailored to your pace, your wishlist and your budget, contact me today and I will help you bring it to life.