The Perfect 10-Day Italy Itinerary: Rome, Florence, Lake Como & Milan

Planning a trip to Italy? This 10-day itinerary is built around two weekends and one workweek — a sweet spot for seeing the best of Italy without burning out. You'll visit Rome, Florence, and Milan, with a lakeside pause in the middle to recharge.

It’s designed the way we’d plan a trip for a friend: curated, balanced, and full of the good stuff — not just famous sights, but scenic walks, memorable meals, and time to breathe.

✈️ Day 1 (Saturday): Arrive in Rome

• Stroll past the Pantheon, Piazza Navona, and Trevi Fountain
• Dinner near your hotel — Roman classics, nothing fussy
• JAM Tip: Walk off the jet lag with a first gelato and a slow wander — this isn’t the night to do too much

🏛️ Day 2 (Sunday): Ancient Rome, Quiet Streets & an Evening Passeggiata

Morning:

• Book an early slot at the Colosseum and Roman Forum
• Walk up to Capitoline Hill for a great Forum view

Lunch + Afternoon:

• Lunch in the historic Jewish Quarter — try carciofi alla giudia if in season
• Break: siesta, slow walk, or museum visit

Evening:

• Follow the golden light into Trastevere
• Use our Rome guide for a curated evening walk
• Dinner in Trastevere

🎨 Day 3 (Monday): Vatican Morning, Florence by Night

• Morning: Vatican Museums, Sistine Chapel, St. Peter’s
• Afternoon: Train to Florence (~1.5 hrs)
• Evening: Light stroll past Piazza della Signoria, Duomo, and Ponte Vecchio
• Dinner at a central trattoria

🖼️ Day 4 (Tuesday): Art, David, and Duomo Views

• Uffizi Gallery (8:15 AM)
• Accademia Gallery to see David
• Lunch near Mercato Centrale
• Duomo climb, Baptistery, or Museum
• Dinner at a central trattoria

🍷 Day 5 (Wednesday): A Day in the Tuscan Countryside

• Wine tour via Viator
• Hill town visit (San Gimignano, Siena, or Volterra)
• Bike tour option

Planning Florence? Get our Florence & Tuscany guide

🚆 Day 6 (Thursday): Florence → Lake Como

• Train to Varenna via Milan
• Lunch by the lake, visit Villa Monastero, optional ferry to Bellagio
• Dinner in Varenna

🌊 Day 7 (Friday): Explore Lake Como

• Visit Villa Carlotta or explore by ferry
• Hike, bike, paddleboard — or relax
• Dinner in Varenna with wine and gelato

🏙️ Day 8 (Saturday): Milan — Last Supper, Duomo, and Navigli

• Train to Milan
• Visit The Last Supper (pre-book), Santa Maria delle Grazie
• Lunch near Via Dante, shop in the Galleria Vittorio Emanuele II
• Sunset on the Duomo rooftop, aperitivo and dinner in Navigli

📍Exploring Milan and the Lakes?
Our Milan & Lake Como guide includes step-by-step instructions for booking The Last Supper, tips for avoiding tourist traps in Navigli, and our favorite lakeside dinner spots. Grab the guide here

✈️ Day 9 (Sunday): Departure

If you’re flying back to the U.S., Canada, or Australia, you’re likely departing from Milan Malpensa (MXP). For shorter European hops, Linate (LIN) is often more convenient.

This itinerary works whether you’re planning a honeymoon, a first big family trip, a celebration getaway, or just your first time in Italy. We’ve taken versions of this route ourselves, and we’ve shared it with friends in all stages of life — couples, retirees, families with teens.

🎟️ Want the Full Experience?

This blog post gives you the outline. But our JAM Italy guides give you the details — the exact restaurants we send our friends to, the best wine tours we’ve personally taken, and the walking routes we’ve mapped out ourselves. Each guide includes:

• Full itinerary with daily suggestions
• Sight commentary and planning tips
• Restaurant and gelato picks
• Google Map with clickable pins
• Viator experiences we’ve actually booked and recommend

Buy all three and get 20% off with code ITALY → Shop the Italy Collection