This post shows you: Italy Itinerary 5 Days by Train: Milan, Florence & Venice Guide
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Planning an Italy itinerary 5 days by train can feel overwhelming. There’s so much to see and so many choices to make.
Italy is like a living museum — art, history, food, and landscapes create a unique journey. Every stop adds something unforgettable
This Italy trip planner will guide you step by step with tips from real experience.
*Disclosure: Some of the links above are affiliate links. We may earn a small commission at no extra cost to you.*
Italy Itinerary 5 Days by Train: Step by Step Guide to Milan, Florence & Venice
Day 1 – Milan Highlights
How to get from Linate to Milan center
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.
Visiting the Stunning Milan Duomo
After checking in and resting, we headed straight to Milan’s beating heart: Milan 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 — perfect for taking photos!
Galleria Vittorio Emanuele II & Coffee Break
We passed through the Galleria Vittorio Emanuele II, a beautiful but admittedly crowded space.
Afterward, we wandered into some quieter streets nearby to take a breather.
We visited the Starbucks Reserve out of curiosity. It’s housed in a beautifully restored post office and feels like a cathedral.
It was pretty crowded, and the traditional Italian coffee at the average small bar around the corner was much nicer.
Evening in Milan Navigli District
As the sun set, we walked for about half an hour around the Milan canal area, 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 quiet spot just outside the Naviglio Grande, where people were sipping wine, chatting under string lights, and watching the reflections dance on the water.
Day 2 – Discovering Florence
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From Milan, Visiting Florence Italy by Train
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, along the Tuscan countryside.
We arrived at 08:35 AM and walked to our guesthouse, Hotel Nella. It’s a small, friendly establishment located in a central yet tranquil area.
After leaving our luggage, we had plenty of things to do in Florence!
Italian Breakfast in Florence, Italy
Finding the best coffee in Florence can be tough, but at Antica Pasticceria Sieni, we offer a perfect coffee paired with a beautiful cornetto.
Florence coffee shops and bars are all around the city center and are definitely worth a visit!
Watching the barista work was a show — remembering everyone’s order by heart, juggling requests for espresso, macchiato, with or without milk… It was truly a performance.
Florence Itinerary: Galleria degli Uffizi
Our first stop was the Uffizi Gallery, 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. We stayed for over two hours, slowly weaving through the infinite halls— just come prepared with patience.
Where to Eat in Florence
After the museum, we walked just a few minutes to a hidden gem restaurant in Florence: Libreria Brac, A cozy vegetarian café.
If you ask yourself, where do locals eat? Well this is it! It’s part bookshop, restaurant, and art space with the best Prosecco of our trip!
I was impressed by the typical Italian dishes that have been adapted to be vegetarian. The service was extremely friendly, and we felt welcome.
Ponte Vecchio – The Iconic Bridge of Florence
One of the must places to go in Florence is the Ponte Vecchio. We crossed the Arno River under the 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
What is the best time to visit Piazzale Michelangelo? Some said at sunset, but we went in the afternoon, and the view from the top was breathtaking.
Taking the route along the river and through the small backstreets gave us a different perspective of Florence.
The entire city lay before us — the Florence Duomo, the rooftops, the Arno river, it was definitely worth the climb!
Evening Walk in Oltrarno
Before dinner, we strolled through the Oltrarno neighborhood, famous for its artisan workshops and the Basilica di Santo Spirito.
On the way back to the city center, we stopped at Giunti Odeon in Piazza degli Strozzi, a beautiful mix of cinema and bookstore.
Here we lingered, flipping through books, sipping espresso, and enjoying the elegant atmosphere.
Dinner at Mercato Centrale
For a casual dinner, we chose Mercato Centrale, a lively food hall in Florence.
It was the perfect answer to where to eat in Florence without breaking the budget.
Stalls offered everything from fresh pasta and pizza to Tuscan specialties.
We enjoyed the energy of the market and the variety of choices.
After the meal, we returned to our quiet Hotel Nella.
Florence: Non Touristy Things to Do
We had planned to see Boboli Gardens and Palazzo Pitti, but they were closed on Monday.
Since most Florence museums close that day, we turned to the outdoors.
Exploring gardens and open-air spaces was the perfect alternative.
The weather was beautiful, which made the change of plans even better.
Museums Closed on Mondays? Visit the Gardens Instead
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 Duomo.
We also explored the interior of the Bardini Villa, which added another layer to the experience—elegant rooms, and quiet exhibitions.
Lunch at Il Vegetariano
After the gardens, we walked across town to have lunch at Il Vegetariano, a spot slightly off the tourist path — another place where locals eat in Florence.
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 Florence 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.
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 dedicated his life to the art of mosaic.
He explained the ancient mosaic techniques, step by step, with passion and warmth.
This family-run business has passed down its craft for generations.
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 of the Medici opulence — all came together in a space that felt both historical and alive.
Day 4 – Venice: Highlights
Train from Florence to Venice
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We left Florence early and caught the 08:39 AM Italo Treno to Venice.
Thanks to an offer, we traveled in first class and enjoyed complimentary coffee.
The train was modern, quiet, and perfectly on time.
In just over two hours, we arrived at Venezia Santa Lucia Station.
As we stepped outside, the first view of the canals left us speechless.
Vaporetto (public water bus) and Venice Access Fee
From Santa Lucia Station, we boarded Vaporetto line 5.1 to Zattere, just a short walk from our hotel.
At the station exit, officials checked QR codes for the city’s access fee.
Overnight visitors are exempt from paying, but registration is still required.
Be sure to have your permit ready in case you’re asked to show it.
Staying in Dorsoduro Venice: Authentic and Calm
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 right away.
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 took us across Accademia Bridge, with sweeping views of the Grand Canal.
We lingered in Campo Santa Margherita, alive with students, cafés, and local buzz.
Through Castello’s alleys, noble houses and hidden palaces gave a cinematic feel.
At Basilica dei Santi Giovanni e Paolo, we admired its solemn grandeur in peace.
We ended at Santa Maria dei Miracoli, a luminous Renaissance jewel of perfect proportions.
Punta della Dogana – Free Things to do in Venice
In the late afternoon, after a gelato at Venchi, we walked back toward Dorsoduro.
From there, it was a short stroll to Punta della Dogana, close to our hotel.
This is where the Grand Canal meets the lagoon, one of Venice’s most stunning views.
After 5 PM, as day-trippers head back to the mainland, the city becomes calmer.
At the tip, facing San Marco in the golden light, Venice felt just perfect.
Day 5 – Last Day in Venice & Train to Milan
Early Morning in Piazza San Marco
We wanted to make the most of our last morning in Venice.
After breakfast at Casa Accademia — espresso with a cornetto and even soy milk — we set out early.
Piazza San Marco was almost empty, glowing softly in the morning light.
Inside the Basilica of St. Mark, golden mosaics and domes took our breath away.
Libreria (Bookstore) Acqua Alta
While exploring Venice, we visited Libreria Acqua Alta, one of the city’s quirkiest bookshops.
Hidden on a small side street by a canal, the store is chaotic yet charming.
A gondola sits right inside, piled high with books.
We browsed vintage titles and foreign editions surrounded by paper towers.
It’s a fun stop for book lovers or anyone wanting a quick escape from the crowds.
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 it was doable, and it was a final chance to experience the city at street level.
Train Back to Milan
At 13:57, we boarded the train from Venice to Milan. The journey took about 2.5 hours, arriving just after 16:25.
We checked back into Canova Hotel, right next to the station. Its location made it easy to drop our bags and head out again.
With only a few hours left, we set out to enjoy our last evening in Italy.
Via Montenapoleone & Via della Spiga
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 went to the legendary Blue Note Milano, one of Europe’s top jazz clubs.
It happened to be International Jazz Day.
The setting was intimate, the music soulful, and the vibe unforgettable.
I had worried about walking back near the station late at night, but it felt safe.
The area was well lit, with visible security in front of the station.
Day 6 – Farewell Italy: A Journey of Trains & Beauty
Our morning flight from Milan Linate meant keeping things simple.
We took the new M4 metro line, clean, quiet, and efficient.
The ride was stress-free, even with luggage, and quicker than expected.
At the airport, we grabbed breakfast — one last coffee and cornetto.
It was a simple farewell, but the perfect way to end the trip.
Final Thoughts on Our Italy Itinerary 5 Days by Train
In five days, we managed to see and do everything we had planned.
We walked endlessly, soaking in details and feeling welcomed by Italians.
At times the crowds were overwhelming, but every moment was worth it.
We learned the secret is to slow down and plan wisely.
Leave space for pauses and surprises — that’s where the magic happens.
Essential Travel Tips for an Italy Train Itinerary
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
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.
👉 Prefer a tour with skip-the-line access? Check this option on Viator.
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.
👉 Or secure your spot with a guided visit via Viator.
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…”
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.
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This post shows you: Italy Itinerary 5 Days by Train: Milan, Florence & Venice Guide