Four Days, Four Worlds: An Italian Autumn
- Nov 8, 2025
- 11 min read
Some destinations linger on our bucket lists longer than others – the romantic ones especially on mine. However, there’s something timeless about Northern Italy – a region where style, natural serenity, and centuries of artistry coexist in perfect harmony – that felt too special to continue waiting for! This autumn, whilst based in London, I decided to take advantage of Europe’s cheap air-travel and set out to experience it for myself: five days tracing a route from Milan’s fashionable pulse to Venice’s dreamy canals, through the glassy calm of Lake Como, and across the border for a Swiss Alpine adventure.
This trip was not about ticking cities off a list. It was about feeling Northern Italy’s many textures. Northern Italy is a treasure trove of experiences, from the sharp, snow-dusted peaks to the layered, colourful charm of coastal towns, each destination offering something entirely different and all within proximity. Thereby, any itinerary is inherently subjective, and shaped by what travellers individually seek, the time they travel with, and the season of the visit. There’s no perfect route; this blog simply chronicles the highlights that made my five-day journey unforgettable, alongside nearby destinations that lingered on my open tabs for weeks, which I will surely return to visit in the future.
PAGE CONTENT:
Milan
Venice
Lake Como
The Bernina Express ~ St. Moritz to Tirano
BEFORE YOU GO:
Tourism. Tours can be pre-booked via sites including GetYourGuide and Booking.com. If contemplating on either independent or guided explorations, I highly recommend a combination of both. While I travelled independently to Venice and Lake Como, I booked a full day Bernina Express excursion.
Travel. All train tickets departing from Milano Centrale can be pre-booked on Trainline and easily accessed via the app. Train tickets can also be purchased at the station kiosks on the days of travel, if feeling spontaneous. Transport around Milan via public busses and trams is also convenient, accepting card payments by simply tapping.
Safety. Unfortunately, pickpockets and robberies are common in busy Italian cities like Milan. To minimize this risk, consider cable locks, money belts, portable safes, and anti-theft bags, and simply remain vigilant.
Set your Italian Playlist and don't forget your camera!
Where Energy Meets Elegance
~ Milan ~
Milan buzzes in elegance. It’s a city that balances art and ambition, where centuries-old cathedrals share skylines with cutting-edge fashion houses; Italy’s modern heart.
When I last visited Milan years ago with my family, the city felt rough and rushed, making me hesitant to return. This round, I chose Milan out of practicality – considering the affordable flights and the city’s proximity to desired destinations making it the perfect base for day trips. Whether it was the season, the people, or simply time, Milan redeemed itself, surprising me with warmth, humility, and curiosity.
Listed below are top attractions and things to do to make most of your time in Milan.
Discover Duomo di Milano – a Gothic Masterpiece
No trip to Milan is complete without standing before the Duomo, its intricate spires and marble façade. Rising above the heart of the city, the Duomo di Milano’s construction began in 1386 and took nearly six centuries to complete, resulting in a Gothic masterpiece of spires, statues, and stained glass that glows golden at sunset.
Galleria Vittorio Emanuele II – Shop at the World’s Most Glamorous Galleria
Just steps from Duomo, is one of the world’s oldest shopping arcades. Even if designer shopping is not your thing, the evocative architecture alone – glass ceilings, mosaics, marble floors – is worth taking a stroll under.
Built in 1867 and named after Italy’s first king, the Galleria Vittorio Emanuele II was one of the first iron-and-glass arcades in the world, and remains the city’s beating heart of luxury.
Whilst there, don’t forget to take a moment to spin on your heel over the bull mosaic in the central floor. Full disclosure, I saw this on TikTok and am not entirely sure whether it’s a genuinely quirky Milanese tradition said to bring good luck or a local joke on tourists.
See The Last Supper at Santa Maria delle Grazie or at Leonardo3
A short stroll from the city centre and inside the modest walls of Santa Maria delle Grazie hides one of world’s extraordinary works of art – Leonardo da Vinci’s The Last Supper. Painted between 1495 and 1498, it captures not just a biblical scene, but the emotion of betrayal and faith frozen in time.
Alternatively, just along the Galleria is Leonardo3, a unique interactive museum dedicated to the Renaissance inventor, and featuring a virtual set of The Last Supper. I visited Leonardo3, hence didn't visit Santa Maria.
Wander Through Sforza Castle & Rest in the Renaissance
The 15th-century Castello Sforzesco, once a fortress and ducal residence, now houses some of Milan’s most important museums and art collections, including Michelangelo’s unfinished Pietà Rondanini, ancient musical instruments, and frescoes by Leonardo da Vinci.
Catch a Train (or a few) at Dawn from Milano Centrale
With its effortless train connections, Milan makes the perfect base for exploring Northern Italy and neighbouring countries. Destinations from Milano Centrale that sat on my open tabs for weeks leaving me in a conundrum include Cinque Terre, Portofino, Genoa, Bologna, Florence, Lugano, and the Dolomites – all within two to four hours from Milan by train and offering entirely unique experiences.
From here, I finally chose to explore Venice, a little over two hours away, and Lake Como, less than an hour – making Milan not just a destination, but a gateway.
Falling for a Floating City
~ Venice ~
Venetian Visage & a Summoning to Venice
For someone who lives by their calendar, depends religiously on Google Maps, and is always in a hurry to tick things off a list, there is something unexpectedly liberating about arriving in Venice with no agenda (apart from riding a Gondola, obviously) – and just a willingness to let a city lead me for a change. In Venice, getting lost isn’t just inevitable; it’s the point.
Why Venice? Perhaps because it never really asks to be chosen – it summons you. Like most dreamers, I’ve long imagined this city of water, and reflection: an elusive place that exists between dream and memory, as if you’ve known it long before arriving.
Venice has been painted, sung about, and written into legend, but still, she holds mystery. Built across more than 100 small islands, Venice has no cars or roads – only canals, bridges, and alleys that seem to twist with a secret purpose.
Arrival & Departure ~ Santa Lucia Station
The arrival into Santa Lucia Station from Milan was an invitation into a curated world with the Grand Canal metres away. From here, travellers can step directly onto vaporetti (water busses), cross one of the arched bridges, or take the longer route turning left to wander into the labyrinth of narrow streets.
I realized Venice is a main character – a thespian, an enchanter, whimsical in nature, and embodying a sense of humour-combined-romance that sparks love and curiosity at first and fleeting glance.
Through the Arch of Aquila Nera ~ Venice’s Hidden Frame
Some photos find you, and this one quite literally appeared at the end of an alley that I ran into escaping the rain. Tucked near Calle dell’Aquila Nera, just minutes from Rialto Bridge, lies a quiet photogenic corner with a soft yellow arch framing the canal with its passing vaporetti and gondolas, rewarding curiosity and awaiting those wandering without hurry.
This was one the serendipitous moments where my £6 Amazon tripod proved its worth; highly recommend for solo travellers, even though he’s a short king.
Strolling through St Mark’s Square
No matter how many photos, paintings, or cinemas you’ve seen, nothing prepares you for Piazza San Marco – a grand stage of history framed by Byzantine domes and Renaissance facades. Once the political and spiritual heart of the Venetian Republic, the square continues to feel larger than life, even in the rain.
Drifting Through a Dream ~ the Gondola
No, I did not pay €100 for boat… Platforms like GetYourGuide offer shared tours for about half the price (in CAD, no less), and it is so worth it. Venice is best understood from the water, and a gondola experience is far more than just the click.
The gondola itself is a masterpiece – each one handmade from eight different types of wood, carefully balanced to keep its single oar steady on the water. Once the main mode of transport across the Venetian lagoon, today it’s more of a cultural symbol – a living relic of elegance and craftsmanship. Watching the gondolier navigate the narrow canals with effortless grace feels almost choreographed. A truly authentic Venetian experience that cannot be replicated.
Alternatively, of course, there are vaporetti (water buses) along the Grand Canal for those seeking to explore Venice by water. For those keen on capturing at least a Gondola photo without the splurge – Libreria Acqua Alta, Venice’s famously quirky bookshop, offers free photos on a parked gondola surrounded by stacks of books.
Pages & Puddles ~ Libreria Acqua Alta
Libreria Acqua Alta is a charming chaos of books piled into bathtubs, boats, and even a full-sized gondola right in the middle of the store. The name literally means “High Water Bookstore,” a reference to the city’s seasonal floods. Instead of fighting water damage, the owner embraced it, turning potential disaster into one of the most whimsical bookstores in the world.
The bookstore features a popular staircase built entirely out of water-damaged books and a parked gondola.
The Venetian Food Scene ~ Sips, Spritz & Ciccetti
If Milan is all espresso and elegance, Venice is a glass of Aperol Spritz! The city’s food scene isn’t about Michelin stars or fine dining (though those exist); it’s about bacari, small, standing-room-only wine bars serving cicchetti – Venetian tapas.
And for dessert? Gelato at Suso Gelatoteca and tiramisu at I Tre Mercanti (although mine is better)! I went traditionally wild on my carb intake during my time, and enjoyed every bit. The Venetian atmosphere is wonderfully casual, a reminder that good food doesn’t need a reservation or a white tablecloth, just an open mind and a hungry heart.
With Love from Venice to Varenna
~ Lake Como ~
While most romantic destinations are celebrated for flings or honeymoons, Lake Como has always represented promise to me, carrying a certain weight and a sense of forever. Hence, naturally, it was never on my list of solo travel destinations.
But as I mapped out my Northern Italy route, I realized how foolish it would be to let this opportunity slip by while time, proximity, and travel, were on my side. So, I planned my trip, woke up at dawn, and boarded a train from Milan to Varenna.
And I’m so glad that I did. The Lake didn’t just exceed my expectations; it kept me company. Every moment – from the ferry cutting through mirrored waters to getting lost in Monastero’s vast garden estate – felt unexpectedly complete. For a place known for shared sunsets and princess cut proposals, Lake Como reminded me that wonder and connection can exist just as effortlessly in solitude.
Note: Although comprising a Mediterranean climate, the best time to visit is between March to October. The villas are also closed during winter months.
Milan to Varenna: The Journey
Varenna is a picturesque village that connects seamlessly to Bellagio by ferry and happens to be the most direct gateway from Milan. The regular trains to Varenna-Esino from Milano Centrale cost around €7 each way. Sit on the left-hand side for the best lake views!
Varenna
If Bellagio is the showstopper, Varenna is the the quieter beauty that steals your heart without trying. There’s something magnetic about its serenity, the pastel houses stacked along the cliffs, boats bobbing in rhythm with the lake, and a pace that is deeply grounding.
Villa Monastero ~ Lost Between Architecture & Botany
Varenna opens into its most celebrated treasure – Villa Monastero. Once a Cistercian convent, later a noble villa, and now a museum and botanical garden, it’s a place where history and horticulture blur into something dreamlike.
A few moments matching the Lake captured by my £6 Amazon tripod.
Villa Monastero was my first stop and unexpectedly took a few hours of my time, leaving me in awe. Entering the two kilometre garden estate felt like stepping into a painting: marble balustrades tracing the lake’s edge, and statues peeking through cypress trees.
Inside, the House Museum preserves the villa’s aristocratic past, with its frescoed ceilings, antique furniture, and panoramic windows framing the lake in every room. The estate is open until early November, with entry for about €10, or €22 including Villa Cipressi.
Villa Cipressi ~ Terraces that Touch the Lake
Right next to Monastero, is Villa Cipressi. Originally built in the 15th century and lovingly restored, Cipressi hosts both a luxury hotel and gardens that remain open until November.
The Lake is Your Lover ~ Lover’s Walk
Passeggiata degli Innamorati, or the Lovers’ Walk is a crimson-railed pathway clinging to cliffs and tracing the waterline. The walkway leads you straight from the ferry terminal into the heart of Varenna, an impossibly scenic route.
Ripples of Romance ~ Between Varenna & Bellagio
The 15-minute ferry ride between Varenna and Bellagio is less transport and more mini adventure. This is the moment you come to finally step into those breathtaking 20-second reels that inspired your first journey, only to realize that videos simply don’t do the sight justice! The lake unfolds like a living painting against the villas clinging to cliffs, and mountains reflected in every ripple.
I was utterly in awe of Como – even in its storm-like clouds, it presented grace and layered resilient beauty that I hoped to return to.
You can pre-book your ferry tickets here, simply purchase them onsite, or book private transfers. Pre-booking is recommended for summer months or peak tourist seasons but was not necessary during my visit in early November.
Bellagio
Situated right at the intersection where the three branches of Lake Como meet, Bellagio is regarded as the Lake’s crown jewel.
Climbing the Coloured Cobbled Stairways
I stepped into Bellagio, with no itinerary. The narrow stone steps are lined with boutique shops, gelaterias, and cozy trattorias inviting exploration. I took my time and stumbled across Salita Serbelloni, Bellagio’s most photographed lane.
Bellagio’s Gardens ~ Villa Melzi d’Eril
Villa Melzi’s Gardens, built in the early 19th century for Duke Francesco Melzi d’Eril, offers English-style gardens. I didn’t go, because I can only explore so many gardens in one day, and Monastero had already exceeded my expectations and fulfilled my daily nature quota!
The Lakefront Promenade
Bellagio’s promenade offers high-end boutiques, family-run cafés, and gelaterias. Whilst waiting for the return ferry, I looped along the lungolago, Bellagio’s lakefront, where every bench seemed to have been placed perfectly for reflection.
An Adventure into the Alps
~ Switzerland & the Bernina Express ~
After weeks of debating on how to spend my final day – whether to unlock a new neighbouring country or to explore one more of Italy’s endless gems – I finally settled for adventure over romance. I finally booked the Bernina Express just four days before the flight!
While Northern Italy felt like a painting in every step, venturing to the Swiss Alps, 7,400 feet above sea-level, felt like a moving masterpiece.
Note: While travelling to one of Bernina’s bases independently is an option, I found that an immersive, all-inclusive tour can be both more convenient and cost-effective. I booked my full-day journey with City Wonders via Booking.com. During the excursion, I also made a friend who I spent my last day with, making the Swiss experience infinitely more memorable!
St. Moritz ~ Meeting the Alps
Every great journey begins somewhere unassuming, and for the Bernina Express, that place was St. Moritz. Driving up the winding mountainous road, and arriving in St. Moritz felt like stepping into a winter wonderland curated for both nature and glamour. The town itself is lined with luxury boutiques and castles-turned-hotels against snow-dusted peaks. The natural beauty truly is undeniable.
The Bernina Express ~ Windows into Another World
The Bernina Express invites travellers aboard the iconic Swiss-red train and onto a world-class Alpine adventure celebrated for its UNESCO World Heritage route connecting St. Moritz, Switzerland, and Tirano, Italy.
Wild. Natural. Transcendent. The Bernina route – famous for its alpine landscapes, glaciers, and spiral viaducts that all seem impossibly close – delivered its promise beyond expectations.
The journey, from over 7,400 feet at its highest point, was a surreal revelation of autumn vineyards, stone cottages, animals, and entire lakes juxtaposed against snow-capped alpine peaks and glaciers. This Swiss-engineered route is a masterpiece suspended between earth and the sky – a breathtaking finale and perfect close to the trip.
Tirano ~ Back on the Grid
After a day suspended in the Alps, we finally rejoined civilization in Tirano, a quiet Italian border town and our last stop before the landscape surrendered to structural Milan. The town comprises Basilica di Madonna di Tirano at its heart surrounded by stunning hilly vineyards, a fitting farewell to the Alps and the mountainous region.
Gallery
~ The Italian Escape ~
More of Northern Italy? Visit Cinque Terre, Portofino, Bologna, Verona, Bergamo, Dolomites, and more!
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