13 Days Across Italy — A Winter Family Trip
Milan → Florence → Pisa → Rome → Venice. A Christmas spa in Milan, NYE fireworks over Rome, and a gondola ride through Venice to kick off 2025. Here's everything we did, what it cost, and what I'd do differently next time.
Overview
Family trip — four of us, 13 days, five cities. Comfortable hotels, sit-down meals, and enough time in each city to actually enjoy it.
Italy gets 50+ million visitors a year. The history runs deep — Roman civilisation (753 BC), Etruscans in Tuscany (900 BC), the Renaissance in Florence (14th century). Nearly 3,000 years of history layered into one country. But that popularity means planning is tough. The Colosseum, the Vatican, The Last Supper — you can't just walk up. Tickets sell out months ahead. I wrote this post mainly so the ticket booking guide and planning timeline can save you the stress I went through.
Our trip coincided with the Catholic Jubilee Year 2025 — a once-every-25-years event. Pope Francis opened the Holy Door at St. Peter's on Christmas Eve 2024, and we got to walk through it. The Jubilee has since ended (January 2026), but Rome had a special energy — pilgrims everywhere, extra celebrations. The next one isn't until 2050.
We went in winter: 5–12°C, fewer crowds, Christmas markets, and you can stand in front of a painting at the Uffizi without someone's selfie stick in your face.
Is This Trip For You?
Route Map
Click on any marker to see what we did in each city.
40+ pins covering every hotel, restaurant, and attraction, organized by city. Click the Google Maps button to view instantly, or download the KML to import into your own Google My Maps.
Milan
Milan in December is cold and impossibly stylish. Christmas lights on every street, the Duomo lit up like a postcard. Fun fact: the Duomo took 600 years to complete (1386–1965) — started before Columbus, finished after the moon landing.
Florence
Florence is an entire city that decided to be a museum. Try the bistecca alla fiorentina (thick-cut T-bone, barely seasoned, rare over wood fire). Leather shops everywhere — they've been making leather here since the 1200s. You will eat your body weight in gelato. Our hotel (25hours) had a rooftop bar with Duomo views.
Rome
Rome is chaos, beauty, and carbs. Hotel was next to the Colosseum — could see it from the window. You'll stumble into 2,000-year-old temples on the way to get coffee.
Venice
Venice doesn't feel real. No cars. Streets are water. 118 islands, 400+ bridges. You will get lost — that's the point. Every wrong turn leads to a hidden piazza or a tiny bakery you'd never find otherwise.
What I'd Do Differently
Pair Vatican Museum + St. Peter's, give the Colosseum its own day
We did the Vatican Museum + Colosseum on the same day (Dec 31) because that's when I managed to get Attico tickets — I was checking daily for weeks. Then St. Peter's ended up on a separate day (Jan 2) because the Vatican Museum is closed on Jan 1, so we had to work around the holiday. It worked, but it wasn't ideal. If you're not constrained by holidays or timing, do the Vatican Museum and St. Peter's Basilica on the same day (they're right next to each other), then give the Colosseum its own day so you can take your time at Palatine Hill, the Roman Forum, and the surrounding area. Seriously — plan your Rome days early and camp the ticket sites. The Colosseum Attico slots drop in small batches and sell out in minutes. I was refreshing daily for weeks before I got lucky. Don't leave it to the last minute.
Book The Last Supper earlier
Tickets release 2–3 months ahead and sell out in days. 30 people per 15-min slot. I got lucky with a last-minute cancellation drop. Set a calendar reminder.
More time in Florence and Venice
Three nights in Florence was tight. With more time I'd have:
- Vasari Corridor — elevated passageway (built 1565) from the Uffizi across the Ponte Vecchio. Reopened 2024, was fully booked when I tried.
- Boboli Gardens — Renaissance garden behind Palazzo Pitti, 45,000 sqm of fountains and sculptures.
- Oltrarno — quieter side of the Arno, artisan workshops, fewer tourists.
Venice (2 nights) also felt short. Add a third night if you can — take the vaporetto to Burano (the colourful island).
Ticket Booking Guide
The most stressful part of planning. Every attraction has a different booking window. Here's what I learned — all links verified as official sites.
| Attraction | How Early to Book & Official Link |
|---|---|
| The Last Supper (Milan) | 2–3 months. Sells out in days. Only 30 people per 15-min slot. Check for last-minute cancellation drops 1–2 days before. cenacolovinciano.vivaticket.it (official ticketing partner) |
| Duomo di Milano (rooftop) | 1–2 weeks. Rooftop terrace tickets go faster than cathedral-only. duomomilano.it |
| QC Termemilano | 1 week. Walk-ins possible on weekdays. Book ahead for weekends and holidays. qcterme.com |
| Galleria dell'Accademia (Florence) | 2–4 weeks. Morning slots go first. 1.5–2 hours is enough for the museum. galleriaaccademiafirenze.it |
| Duomo di Firenze (dome climb) | 2–4 weeks. Timed entry — book the earliest slot for fewer crowds on the 463-step climb. tickets.duomo.firenze.it |
| Galleria degli Uffizi | 2–4 weeks. Manageable in winter, chaos in summer. Book a specific time slot. uffizi.it |
| Vasari Corridor (Florence) | 2–3 months. The elevated walkway from the Uffizi to Palazzo Pitti across the Ponte Vecchio. Reopened in 2024 after years of renovation. Extremely limited slots — I tried to book but it was fully booked. Start checking early. uffizi.it (same ticketing as Uffizi) |
| Vatican Museum + Sistine Chapel | 2–4 weeks. Book the first morning slot (7:30am). By 10am the queues are absurd. A guided tour is worth it. tickets.museivaticani.va (look for the .va domain — that's the Vatican) |
| Colosseum + Attico (Rome) | Check daily, 1–2 months out. Attico tickets released in small batches, sell out in minutes. Standard tickets are easier — 1–2 weeks is fine. ticketing.colosseo.it |
| Doge's Palace (Venice) | 1–2 weeks. Secret Itineraries Tour has limited spots but less competitive than Rome/Florence. palazzoducale.visitmuve.it |
| St. Mark's Basilica (Venice) | 1–2 weeks. Combo tickets available for Pala d'Oro + Museum + Loggia. tickets.basilicasanmarco.it |
| Gondola Ride (Venice) | No booking needed. Walk to any gondola station. Standard rate is EUR 80 per gondola (seats up to 6) — split with family/friends. |
- Always start from the links above or the attraction's official website — don't Google "buy tickets" and click the first ad.
- Official Italian sites use .it domains. The Vatican uses .va. Be skeptical of .com or .org sites with similar names.
- If the price is significantly higher than listed on the official site, you're on a reseller.
- Third-party platforms like GetYourGuide or Viator are legitimate but charge a premium. Useful if the official site is sold out, but try official first.
Planning Timeline
Counting backwards from your trip date:
| When | What to Do |
|---|---|
| 6 months before | Book flights. Prices from Singapore to Europe are best 5–6 months out. Look for open-jaw tickets (fly into one city, out of another) to avoid backtracking. |
| 3–4 months before | Book hotels. Good-location hotels in Rome and Venice go fast, especially around Christmas/NYE and summer. Check cancellation policies — flexible rates are worth the slight premium. |
| 2–3 months before | Book The Last Supper (tickets release ~2 months ahead and sell out in days). Set a calendar reminder for the exact release date. Also book Vatican guided tours — morning slots fill up fast. |
| 1–2 months before | Book trains on Trenitalia/Italo (cheapest fares at this window). Book Colosseum tickets — start checking daily for Attico access. Book Uffizi, Accademia, Duomo climbs. |
| 2–4 weeks before | Book Doge's Palace, St. Mark's Basilica, QC Termemilano. Download offline maps (Google Maps or Maps.me). Buy travel insurance. Check if you need a Schengen visa. |
| 1 week before | Confirm all bookings. Screenshot/print tickets (some attractions don't have reliable WiFi at the entrance). Pack layers — Italian winter weather is unpredictable. Bring a portable charger. |
| 1–2 days before each attraction | Check for last-minute cancellation drops. The Last Supper and Colosseum Attico sometimes have surprise availability when people cancel. Worth a quick check. |
When to Go — Seasons & Weather
Each season is a very different experience:
| Season | What to Expect |
|---|---|
| Spring Mar – May |
12–22°C. Pleasant walking weather, flowers blooming, moderate crowds. Arguably the best time to visit. Easter in Rome is a major event. Book early — spring is popular for good reason. |
| Summer Jun – Aug |
25–35°C. Peak tourist season. Long days and warm evenings, but the heat can be brutal — especially in Rome and Florence. Expect long queues everywhere. Venice can smell in the heat (the canals). Hotels are at peak prices. Best for: Amalfi Coast, Cinque Terre, beaches. |
| Autumn Sep – Nov |
10–22°C. Crowds thin out after September. Beautiful foliage in Tuscany. Wine harvest season (great for vineyard visits). Occasional rain in November. A strong alternative to spring. |
| Winter Dec – Feb |
5–12°C. What we did. Fewest crowds, lowest hotel prices, Christmas markets, festive atmosphere. Some attractions have reduced hours. Venice can get acqua alta (flooding) in Nov–Dec. Pack layers, a good jacket, and waterproof shoes. Best for: cities and indoor attractions. |
We chose winter for shorter queues and festive vibes. Trade-off: dark by 4:30pm in December. For a museum/church/food itinerary, winter is hard to beat.
Other Places to Consider
If you have extra days or are planning a return trip:
UNESCO World Heritage mountains. Jagged peaks, alpine lakes, hundreds of hiking trails. More affordable skiing than Swiss/French Alps. Easy add-on from Venice.
Pastel villages, mountain backdrop, completely different vibe from the cities. Bellagio sits where the lake splits into a Y-shape. Easy day trip or 1–2 night stay from Milan.
Positano, Amalfi, Ravello — colourful towns on cliffs above the Mediterranean. As stunning as the photos suggest. Avoid summer peak.
Five villages connected by hiking trails and a regional train. ~5 hours to hike all sections. Overnight in a village is better than a day trip.
Best pizza you'll ever eat (this is where pizza was invented). Pompeii is 30 min away — an entire Roman city preserved under volcanic ash from 79 AD.
Full Cost Breakdown
Sharing this in case it helps anyone planning a similar trip. All costs below are per person in SGD (we travelled as a family of 4). Food and daily local transport not included.
| Item | SGD |
|---|---|
| Transport | |
| Flight: Singapore → Milan | 555.00 |
| Flight: Venice → Singapore | 786.32 |
| Train: Milan → Florence | 113.38 |
| Train: Florence ↔ Pisa (return) | 28.38 |
| Train: Florence → Rome | 70.81 |
| Train: Rome → Venice | 138.49 |
| Hotels | |
| Hilton Milan (2 nights) | 339.78 |
| 25hours Hotel Florence (3 nights) | 560.43 |
| Mercure Rome Colosseum Centre (3 nights) | 707.47 |
| Hotel Saturnia & International, Venice (2 nights) | 292.51 |
| Attractions | |
| QC Termemilano (spa) | 70.95 |
| Cenacolo Vinciano — The Last Supper | 38.31 |
| Sforza Castle | 7.10 |
| Duomo di Milano (rooftop) | 44.70 |
| Galleria dell'Accademia | 28.38 |
| Duomo di Firenze | 42.57 |
| Galleria degli Uffizi | 41.15 |
| Vatican Museum + Sistine Chapel (guided) | 36.89 |
| Colosseum with Attico Access | 34.06 |
| Gondola Ride | 28.38 |
| Doge's Palace — Secret Itineraries | 36.89 |
| St. Mark's Basilica + Pala d'Oro + Museum | 28.38 |
| Total (per person) | 4,030.34 |
Photos
Click any photo to view full-size. (Photos coming soon — upload your favourites!)
Quick Tips
- Trains: Book Trenitalia/Italo 1–2 months ahead. Regional trains (e.g. Florence–Pisa) don't need advance booking.
- Venice vaporetto: Get a 24h/48h pass — individual rides are EUR 9.50 each.
- Money: Card accepted almost everywhere. Keep some cash for markets. Tipping not expected (coperto is included).
- EUR 1 ≈ SGD 1.42 at the time of our trip.
- Download offline maps before you go — WiFi can be spotty at some attractions.
- Public holidays: Christmas Day and Jan 1 = many places closed. St. Peter's Basilica stays open on Jan 1 (Vatican Museum doesn't). Hotels often extend breakfast hours. Pro tip: check Uber Eats — if a restaurant is delivering, it's open. Saved us a few times on holidays.
One of the best trips we've done as a family. Hope this helps with your planning — feel free to reach out if you have questions.