This post shows you: Italy Itinerary 5 Days by Train: Milan, Florence & Venice Guide
Planning an Italy itinerary 5 days by train can feel overwhelming — there’s so much to see and so many decisions to make. Italy is, after all, a living museum: art, history, landscapes, food, trains, museums, and accommodations all come into play.
But after living in Italy for several years, I’ve learned how to move around easily, and that experience helped me design this trip in a way that was both efficient and meaningful.
If you’re planning something similar, this guide includes real insights, personal tips, and practical advice — everything we did, step by step. I hope it serves as a helpful reference or even a bit of inspiration for your Italian adventure.
Day 1 – Arrival in Milan: Duomo, Rooftops & Aperitivo Vibes
Getting to Milan: A Smooth Start
We flew from Amsterdam to Milan in the morning and landed at Linate Airport around 11:15 AM. From there, we took the M4 blue metro line, which connects Linate directly to the city center in about 12 minutes. We got off at San Babila and then took a quick metro connection to Milano Centrale, where our hotel, Canova Hotel, was located.
The metro was quick, clean, and a really easy way to start our italy itinerary 5 days adventure.
First Impressions: The Duomo & Rooftop Views
After checking in and resting, we headed straight to Milan’s beating heart: the Duomo. This grand Gothic cathedral is even more impressive in person. We walked around and then went up to the rooftop terraces (definitely worth it if there’s no long line).
The views were stunning — a sea of rooftops glowing in the afternoon sun.
Slow Wanderings & Espresso Moments
We passed through the Galleria Vittorio Emanuele II, which is beautiful, though admittedly crowded. Afterward, we wandered into some quieter streets nearby to take a breather.
We made two coffee stops — because why not? First, we went to a small local café for our first Italian espresso, a tiny but perfect shot that set the tone. Then, out of curiosity (and caffeine love), we also visited the Starbucks Reserve. It’s housed in a beautifully restored post office and feels more like a cathedral to coffee than your average Starbucks. It is big, stylish, and worth stepping into if you’re into design or specialty brews.
Evening in Navigli: Canals, Aperitivo & String Lights
As the sun set, we walked about half an hour to the Navigli district — one of Milan’s most vibrant areas — but you can also take a tram and get off at Porta Genova. Famous for its canals, small bars, and aperitivo culture, it was the perfect place to celebrate our arrival.
We found a cozy spot along Naviglio Grande, where people were sipping wine, chatting under string lights, and watching the reflections dance on the water. We shared a relaxed dinner and toasted to the beginning of our Italy itinerary 5 days — tired, happy, and already feeling the magic of slow travel in Italy.
Day 2 – Florence: A Day of Art, Light & Renaissance Beauty
From Milan to Florence: A Scenic Start
We left Milan early in the morning, catching the 06:40 AM train from Milano Centrale to Firenze Santa Maria Novella. The ride was just under two hours, peaceful and scenic, offering a quiet window into the Tuscan countryside as it woke up.
We arrived at 08:35 AM and walked to our guesthouse, Hotel Nella, on Via Faenza. It’s a small, friendly place in a central yet calm area. Even though check-in wasn’t until later, they kindly let us leave our bags so we could start exploring right away.
Breakfast at Antica Pasticceria Sieni: Starting the Day Like a Local
What better way to explore Florence than with a classic Italian breakfast at Antica Pasticceria Sieni? Our hotel had recommended it as one of the few places in the city where they still make their cornetti — and they were right.
We enjoyed a simple cornetto vuoto, but they had every flavor imaginable, from jam to luscious custard-filled varieties. Watching the barista work was a show — remembering everyone’s order by heart, juggling requests for espresso, macchiato, macchiato in vetro, with or without milk… It was truly a performance.
Italian coffee culture is a real art form; this was the perfect place to experience it.
Immersed in Art: Galleria degli Uffizi
Our first stop was the Galleria degli Uffizi, where we had pre-booked tickets for 10:30 AM. Stepping into this iconic gallery felt like entering a dream, surrounded by Renaissance masterpieces like Botticelli’s Birth of Venus and works by Leonardo, Michelangelo, and others.
It was crowded, so keep that in mind. The place’s energy was intense, but so was its beauty. We stayed for over two hours, slowly weaving through the halls and pausing often to take it all in.
It’s worth the visit — just come prepared with patience.
A Literary Lunch at Libreria Brac
After the museum, we walked just a few minutes to Libreria Brac, a cozy vegetarian café on Via dei Vagellai. It’s part bookshop, restaurant, and art space — and 100% peaceful. The food was fresh, beautifully presented, and creatively put together.
We had a lovely chat with the woman who served us, and the whole experience felt unhurried and nourishing, precisely what we needed after a morning of intense visual inspiration.
Afternoon Strolls & Ponte Vecchio
Feeling refreshed, we continued toward the Ponte Vecchio, crossing the Arno River under soft afternoon light. We lingered on the bridge, taking in the atmosphere, then wandered through Piazza della Signoria, admiring the outdoor sculptures and the bold façade of Palazzo Vecchio.
Walk to Piazzale Michelangelo: River Views & Quiet Streets
By late afternoon, we decided to walk up to Piazzale Michelangelo—honestly, it was the best choice. Taking the route along the river and through the small backstreets gave us a different perspective of Florence. It was quiet, charming, and full of details we would have missed otherwise.
We didn’t stay for sunset, but the view from the top was breathtaking even in the afternoon light. The entire city lay before us — the Duomo, the rooftops, the Arno — glowing softly, like a painting just before it’s finished.
It was peaceful, expansive, and completely worth the climb.
Evening in Oltrarno & Dinner at the Market
Before dinner, we took a short walk into the Oltrarno neighborhood, known for its artisan workshops, quiet churches, and authentic Florentine life. We visited the peaceful Basilica di Santo Spirito, a soulful but straightforward contrast to the city’s grander sights.
After that, we wandered slowly back toward the city center. We paused at Giunti Odeon, a stunning cinema-bookstore hybrid in Piazza degli Strozzi. Here, you can flip through books, sip an espresso, or admire the elegant architecture—a calm and cultured break between activities.
We ended the day with a casual dinner at Il Mercato Centrale, which was lively and full of options—perfect after a long day of walking. From handmade pasta to local street food favorites, there was something for every taste, and the relaxed vibe makes it easy to wind down.
After dinner, we returned to the hotel to rest, looking forward to another full day in Florence.
Day 3 – Florence: Gardens, Local Flavor & Quiet Masterpieces
A Different Kind of Monday
We planned this day to be slower and more local, not rushing between famous landmarks, but rather soaking up the everyday beauty of Florence. After days filled with art and history, this was our moment to breathe, wander, and discover a more intimate side of the city.
Most museums are closed on Mondays, so we explored open-air beauty instead of indoor galleries, which was the perfect choice.
Morning in the Bardini Gardens
We started the day at the Giardino Bardini, a peaceful garden filled with olive trees, statues, and quiet corners. The path winds gently uphill and rewards you with a stunning panoramic view over Florence, including a direct line to the Duomo. The garden felt serene and uncrowded, a welcome contrast to the busy streets below.
We also explored the interior of the Bardini Villa, which added another layer to the experience—elegant rooms, quiet exhibitions, and the feeling of stepping into another time.
Lunch at Il Vegetariano
After the gardens, we walked across town to have lunch at Il Vegetariano, a spot slightly off the tourist path — and it showed. The place was filled with locals, the portions were generous, and the dishes were nourishing and flavorful. Everything was Italian, vegetarian (or vegan), and full of care. We sat outside in the peaceful courtyard, enjoying a slow meal that felt like a real break.
Rooftop Calm at Biblioteca delle Oblate
Later in the afternoon, we went to one of Florence’s most underrated gems: the Biblioteca delle Oblate. Tucked away behind the Duomo, this public library has a rooftop café with stunning views of Brunelleschi’s dome. Locals sat reading, working, and chatting softly over coffee. We joined them, sitting quietly, watching the light change across the rooftops.
It was one of those rare moments when the city slowed down, and you could exist in it.
Artisan Traditions at Lastrucci
Our next stop was the Lastrucci Mosaic Atelier, where tradition lives on in every detail. We were welcomed inside and met a gentleman who had lived there. He explained the ancient mosaic techniques, step by step, with passion and warmth. This family-run workshop has passed down its craft for generations; you can feel that legacy in every piece.
Final Stop: Basilica di San Lorenzo
To wrap up the day, we visited the Basilica di San Lorenzo, one of Florence’s oldest churches and the resting place of the Medici family. It was open (luckily, since many museums close on Mondays), and we had the chance to admire its impressive mosaics, just as the artisan at Lastrucci had described. The grandeur, the details, the Medici opulence — all came together in a space that felt both historical and alive.
Day 4 – Venice: Quiet Canals, Art Bridges & Sunset by the Lagoon
Arrival in Venice: Water, Rules & First Impressions
We left Florence early and caught the 08:39 AM train to Venice. The journey took just over two hours, and we arrived at Venezia Santa Lucia Station ready to embrace a completely different rhythm.
We took Vaporetto line 5.1 from the station to Zattere, just a short walk from our accommodation. The Vaporetto (public water bus) costs €9 per person for non-residents—a bit steep for public transport, in our opinion.
When you exit the train station, city officials check QR codes to verify if visitors have registered and paid the city access fee. If you’re staying at a hotel at least one night, you’re exempt, but you still need to register online and show your permit if asked.
Staying in Dorsoduro: A Calmer Side of the City
Our base was Casa Accademia, a guesthouse tucked into the Dorsoduro district — one of Venice’s most authentic and relaxed corners. We dropped off our bags and stepped into the city without a plan, just curiosity.
Instead of heading into the packed tourist zones like San Marco or Rialto, we wandered toward quieter paths, letting Venice reveal itself slowly.
Midday Walk: Bridges, Piazzas & Neighborhoods
Our walk led us through some of the city’s most atmospheric and often overlooked gems:
- Accademia Bridge – with its sweeping views of the Grand Canal.
- Campo Santa Margherita – a lively square filled with student life, cafés, and casual local energy.
- The Castello district – with its noble houses, hidden palaces, and laundry-lined alleys that feel cinematic.
- Basilica dei Santi Giovanni e Paolo – a massive, solemn church that few tourists seem to find, despite its grandeur.
- Santa Maria dei Miracoli – a small but breathtaking Renaissance gem, full of light and perfect proportions.
A Sunset to Remember at Punta della Dogana
In the late afternoon, we returned toward Dorsoduro and walked to Punta della Dogana, just a few steps from our accommodation. This spot, where the Grand Canal meets the lagoon, offered one of the most beautiful scenes of our entire trip.
Of course, before that, we had to stop for gelato at Venchi—rich, creamy, and worth the indulgence. I especially loved the ” Azteca ” vegan chocolate flavor—intense, smooth, and unforgettable. Their chocolate is famous, but every flavor we tried was a hit.
We noticed a change in the city’s rhythm as we approached the golden hour. After 5:00 PM, many day-trippers return to the mainland by train, and Venice quietens. The canals feel more still, the alleys more empty — and suddenly, the city feels like it’s yours.
Standing at the island’s tip, facing San Marco across the water, with the light turning golden over the lagoon, was one moment where everything felt exactly right.
Day 5 – From Venice to Milan: A Half Day of Quiet Canals, Fashion & Jazz
Early Morning in Piazza San Marco
We wanted to make the most of our final morning in Venice. After an Italian-style breakfast at Casa Accademia — espresso with a cornetto (and a pleasant surprise: they had soy milk) — we headed out early to enjoy the city before the crowds returned.
We wandered through a nearly empty Piazza San Marco, bathed in soft morning light, and took the opportunity to visit the Basilica of St. Mark. Its golden mosaics and majestic domes were even more impressive in person.
There’s an entrance fee for regular visitors, but if you’re going to pray or attend Mass, you can enter for free through the side door, as long as you’re respectful. Photography is not allowed during the service, which makes sense. It’s not a photo op — it’s a moment of reverence.
Discovering Venice’s Quirkiest Bookshop: Libreria Acqua Alta
While wandering through Venice, we stopped at one of the city’s most iconic and unusual bookstores: Libreria Acqua Alta. Tucked into a side street and opening directly onto a canal, the shop is dimly lit, chaotic in the best way, and overflowing with second-hand books stacked in every corner — even in a gondola right in the middle of the store.
We casually flipped through vintage titles and foreign editions, surrounded by paper towers, cats lounging between shelves, and the gentle sound of water just outside. The fact that part of the shop opens directly onto the canal makes it feel surreal, like the books are floating with the city.
It’s not a quiet, orderly bookstore — messy, intimate, and wonderfully alive. If you love books or want a break from the tourist rush, this little stop is worth slipping into.
One Last Walk Through Venice
After that meaningful visit, we returned to Dorsoduro, had a simple lunch near our hotel, and packed up slowly. Rather than retaking the Vaporetto, we decided to walk back to Santa Lucia Station—about 40 minutes on foot, crossing bridge after bridge. It was a bit of a workout with our bags, but doable, and a final chance to experience the city at street level.
Afternoon Arrival in Milan
At 13:57, we boarded our train to Milan, arriving just after 16:25. We checked back into Canova Hotel, conveniently located near the station. After settling in, we headed out to enjoy the last few hours of our trip.
We visited Via Montenapoleone and Via della Spiga, two of the city’s most elegant shopping streets. Even if you’re not buying anything, it’s worth walking through historic buildings, designer windows, and the undeniable sense that Milan is the fashion capital of Italy. It was the perfect time for a café stop and a quiet pause before our final evening.
A Jazz-Filled Night at Blue Note Milano
That evening, we walked to the legendary Blue Note Milano, one of Europe’s most iconic jazz clubs. It was International Jazz Day, and the concert was Celebrate New Orleans! — felt like the perfect way to end the trip. The atmosphere was intimate, the musicians were soulful, and every note reminded us why live music matters.
I had been worried about returning to the hotel at night, especially near the train station, but it was fine. The area was well-lit, and visible security was in the square right in front of the station, making the walk back feel safe and calm.
Day 6 – Farewell Italy: A Journey of Trains, Beauty & Jazz
Our flight back to Amsterdam was scheduled for the morning, departing from Milan Linate Airport, so we kept things simple and easy.
We took the M4 metro line, which now connects directly to the airport. It is clean, quiet, and incredibly efficient. Getting out of Milan was stress-free, even with luggage in tow. Milan’s public transport surprised us in the best way.
Once at the airport, we had breakfast right there, enjoying one last Italian coffee and pastry before boarding. It wasn’t fancy, but it was the right way to say goodbye.
Final Thoughts on Our Italy Itinerary 5 Days by Train
During this five-day Italy itinerary, we tried to see and do everything we had planned. We walked a lot, took in every detail, and overall felt incredibly welcomed by the kindness of the Italian people. There were moments when the crowds were overwhelming, especially in the big tourist spots, but it was worth it.
We learned that the key is to take things slowly and plan. Give yourself time, build in pauses, and make room for the unexpected—because that’s where the magic often happens.
To help you enjoy your trip as much as we did, here are a few important tips to keep your journey smooth and organized
Essential Travel Tips for Planning Your Italy Itinerary 5 Days by Train
1. Train tickets — Book like a local
Buy your train tickets in advance at Italo Treno. The site works very well and often offers discounts. We traveled in first class at nearly second-class prices! Create an account and start collecting points — you can use them toward future trips.
2. Milan Duomo tickets — Avoid third-party sites
Always book directly from the official Duomo site. Other platforms charge extra fees. We chose the ticket that included elevator access to the rooftop, a walk down the stairs, and entry to the cathedral — perfect for both the view and the whole experience.
3. Florence museums — Book early
Whether you’re visiting the Uffizi Gallery or the Pitti Palace, get your tickets from the official Uffizi website. Spots are limited, and it gets very crowded — booking ahead saves time and stress.
4. Venice entry — What to know
Venice now requires a city access permit for day visitors. You can get it online here.
If you’re staying at least one night, you’re exempt but still need to register.
If you’re only visiting for the day:
• €5 per person if paid at least 4 days in advance
• €10 per person if paid within 3 days of arrival
Avoid lines at kiosks by handling this online in advance here.
5. Blue Note Milano tickets — Buy ahead
We were lucky to catch a concert, but it was sold out! Book directly through Blue Note Milano’s official site to secure your seat, especially for popular shows.
6. Check museum schedules — Many are closed on Mondays
Plan accordingly: some of Italy’s most important museums — like the Uffizi Gallery, Pitti Palace, and even the Boboli Gardens — are closed on Mondays. If one of your 5 days in Italy falls on a Monday, use it for outdoor activities, neighborhood walks, or lesser-known sights.
7. Don’t forget the magic words — “Buon giorno, mi scusi…”
No one likes uninvited guests, especially in a busy café or small trattoria. In Italy, a simple “Buon giorno, mi scusi…” can open doors — literally. More than once, we arrived at restaurants that were clearly full, but just by greeting politely and asking with a smile, the staff made space for us.
Italians appreciate kindness and confidence. Don’t be shy — say hello, ask nicely, and you’ll be surprised how warmly they’ll welcome you.
This post shows you: Italy Itinerary 5 Days by Train: Milan, Florence & Venice Guide
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