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8 Days in Italy: The Real Guide Nobody Gave Me (So I’m Giving It to You)

Rome → Florence → Tuscany → Milan → Lake Como

I spent 8 days traveling through Italy – and let me be completely honest, it was one of the most beautiful trips of my life. But it was also the trip where I got scammed out of €250 at the airport, almost missed a train, and actually did miss another one.

So here’s the real guide. Not the Instagram version. The version I wish someone had handed me before I landed.

The €250 Mistake I Made So You Don’t Have To

I landed in Rome feeling excited and carefree. I didn’t pre-book an airport transfer because I figured I’d just grab a taxi – how hard could it be?

Very hard, apparently.

The taxi guys at Rome’s airport saw me coming. I ended up paying €250 for what should have been a €48 ride. Two hundred and fifty euros. Before I even checked into my hotel.

Please hear me on this: pre-book your airport transfer before you land. Book your Rome airport transfer here → or arrange it through your hotel. Only use the white licensed cabs if you must grab one on the spot. This is not optional. This is the single most important piece of advice in this entire post.

Day 1–2: Rome — Eternal City, Early Alarms

Rome hits different. The history is just there, woven into every street corner and piazza like it’s no big deal. My first evening, I visited the Basilica of Saint Paul Outside the Walls — free, uncrowded, and the mosaics are absolutely stunning. Then I hit the Vatican Museums. Pro tip: book the Friday evening entry. Way fewer crowds than daytime slots.

The next morning, I set my alarm for something unreasonable to get to the Trevi Fountain early. I’m talking 6 AM early. And you know what? It was already getting crowded. If you’re visiting during peak season, you might need to be there by 5:30 to get that clean shot without a hundred selfie sticks in frame. It’s worth every lost minute of sleep, though — seeing Trevi in the soft morning light before the chaos hits is genuinely magical.

The Colosseum, Roman Forum, and Palatine Hill are a combined ticket (around €16–18), and skip-the-line is non-negotiable unless you enjoy standing in the sun for two hours. Book Colosseum, Forum & Palatine Hill skip-the-line →The Pantheon is free with a €5 reservation — reserve your Pantheon entry here → — and it’s one of those places where you just stand there with your mouth open.

What to book for Rome:

Where I ate in Rome: Trastevere is the neighborhood. Da Enzo al 29 for cacio e pepe, Trapizzino for stuffed pizza pockets, and Fatamorgana for gelato that ruined all other gelato for me. Roscioli’s carbonara is also unreal.

Day 3: The Smoothest Part of the Trip — Rome to Florence

After climbing St. Peter’s Basilica dome (551 steps, €8–10, best view in Rome — book dome climb tickets →), I caught the high-speed train to Florence. And honestly? This was the smoothest part of the entire trip. You scan your ticket, find your seat, and 90 minutes later you’re in Florence. Tickets run €20–50 depending on when you book — earlier is cheaper. Book Rome → Florence train →

I stepped off the train and walked straight to Ponte Vecchio at sunset. If you time it right, the light on the Arno River is incredible. Dinner was in Oltrarno at Trattoria 4 Leoni — the pear and pecorino ravioli is a must.

Day 4: Florence — David, Domes, and Golden Hour

Florence is a Renaissance fever dream. The Duomo, Brunelleschi’s Dome (463 steps, €30 combo), the Uffizi Gallery, Michelangelo’s David at the Accademia — it’s all within walking distance and it’s all overwhelming in the best way.

What to book for Florence:

After a full day of art and architecture, I headed to Piazzale Michelangelo for sunset. This is THE panoramic viewpoint of Florence. Get there 30–45 minutes before golden hour to claim your spot. Bring wine from the market. Trust me.

For the best sandwich of the trip — possibly the best sandwich of my life — hit All’Antico Vinaio. Under €10, the line moves fast, and it’s worth every second of waiting.

Day 5: Tuscany — Wine, Towers, and Rolling Hills

A day trip through Tuscany was the highlight of the entire trip. Morning in Siena walking through the medieval Piazza del Campo with espresso and ricciarelli (almond cookies). Then the Chianti wine region for a vineyard tour, wine tasting, and a long Tuscan lunch with olive oil, fresh bruschetta, and pecorino. That lunch alone was worth the flight to Italy.

The afternoon was the Leaning Tower of Pisa (about €20 to climb). Is it touristy? Absolutely. Did I still take the obligatory holding-up-the-tower photo? Also absolutely.

Book a small group tour (8–15 people) instead of a big bus. Completely different experience. Around €65–120 per person and so worth it.

What to book for Tuscany:

Day 6: Milan — And the Train I Missed

Here’s where things went sideways.

I needed to get from Florence to Milan. Simple enough — it’s a 2-hour train ride. Except we couldn’t get an Uber. Uber barely works in Italy. We tried taxis. Nothing. We ended up scrambling onto a bus to the train station, but by the time we got there, our train was gone.

We bought new tickets, waited for the next one, and eventually made it to Milan. But I lost money and time because I didn’t plan the simplest part of the trip — getting to the station.

Download the itTaxi or Free Now app. Call 30–40 minutes ahead. And if you have an early departure, stay near the train station the night before. Don’t be me.

Milan itself is gorgeous. The Duomo rooftop (€10–14) lets you literally walk among the spires. Book Duomo Rooftop Terraces → Galleria Vittorio Emanuele II is stunning. And the move in Milan is aperitivo in Brera — you get a cocktail and a free buffet spread for €8–12. Bar Basso for a Negroni Sbagliato, or Ceresio 7 if you want a rooftop vibe.

If you can swing it, book Da Vinci’s Last Supper. But do it weeks ahead — they only allow 15-minute viewing slots and they sell out fast. Book Da Vinci’s Last Supper Skip-the-Line →

What to book for Milan:

Day 7: Lake Como — Pure Magic

The bus and train combo from Milan to Lake Como takes about an hour. And then you take the ferry from Como to Bellagio, and honestly, this is where Italy becomes a movie. Mountains on every side, pastel-colored villas, crystal clear water.

Bellagio is cobblestone streets, Villa Melzi Gardens (€8), and a lakeside lunch at Ristorante Bilacus. It’s the kind of place where you sit by the water and wonder why you ever leave.

Check the last ferry times back — they stop earlier than you’d expect. Don’t get stranded (I’ve made enough transit mistakes for both of us).

What to book for Lake Como:

Day 8: Departure (or Keep Going)

Fly out of Milan Malpensa (MXP). The Malpensa Express train is €13 and runs every 30 minutes — easy. Book Malpensa Express →

Or, if you’re not ready to go home (and you won’t be), Italy is perfectly positioned to extend into Switzerland (Lugano is 1 hour by train), the French Riviera (Nice is 5 hours), or Barcelona, Munich, or Croatia by short flight.

The Practical Stuff

Flights: Book open-jaw — fly INTO Rome (FCO) and OUT OF Milan (MXP). Don’t backtrack.

Trains: Book 2–3 weeks ahead on Trenitalia or Italo for the best fares. First class upgrade on the Rome→Florence route is worth it.

Connectivity: Get an eSIM before you land. Airalo → and Holafly → both work well.

Budget: Plan for roughly €100–180 per day per person covering food, transport, and activities.

Pre-book these or regret it: Vatican Museums, Uffizi Gallery, Accademia (David), Colosseum, and Da Vinci’s Last Supper.

Where to Stay

These are my picks across every budget — all centrally located in the neighborhoods I actually recommend.

Rome (Stay in Trastevere or near the historic center)

Luxury:

Mid-Range:

Budget:

Florence (Stay near the Duomo or in Oltrarno)

Luxury:

Mid-Range:

Budget:

Milan (Stay in Brera or near the Duomo)

Luxury:

Mid-Range:

Budget:

Browse all hotels on Booking.com →

All Booking Links in One Place

Everything from this post, organized so you can open tabs and knock it all out in one sitting.

Rome: Airport Transfer → · Vatican Museums Skip-the-Line → · Colosseum + Forum + Palatine Hill → · Pantheon Reservation → · Roma Pass (48hr/72hr) →

Florence: Uffizi Gallery Skip-the-Line → · Accademia / Michelangelo’s David → · Duomo Dome Climb →

Tuscany: Siena, Chianti & Pisa Day Trip → · Chianti Wine Tasting + Lunch → · Leaning Tower of Pisa Climb →

Milan: Duomo Rooftop Terraces → · Da Vinci’s Last Supper →

Lake Como: Lake Como + Bellagio Day Trip →

Trains: Rome → Florence → · Florence → Milan → · Malpensa Express →

Essentials: Hotels on Booking.com → · Airalo eSIM → · Holafly eSIM →

Final Thoughts

Italy will steal your heart. It stole mine — even with the scams, the missed trains, and the 5:30 AM alarms. Every plate of cacio e pepe, every sunset over the Arno, every cobblestone street in Bellagio made it worth it ten times over.

Go with an open mind, a charged phone, and — I cannot stress this enough — a pre-booked airport transfer.

For the full day-by-day breakdown with hotel picks, restaurant recs, and all booking links, grab my 8-Day Italy Travel Guide.

@ColorsOfAyo — Helping you curate authentic travel experiences.

This post contains affiliate links. If you book through them, I earn a small commission at no extra cost to you. It helps me keep creating free travel content — thank you!

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