A Family Journey from North to South · Jun 15–28, 2026
North to South, perfectly paced
| City | Nights | Highlights | Travel To Next |
|---|---|---|---|
| Milan | 3 | Duomo, Last Supper, Navigli, Lake Como | Frecciarossa 2h 15m |
| Venice | 2 | St. Mark's, Gondola, Murano | Frecciarossa 2h |
| Florence | 3 | Uffizi, Duomo, Siena & San Gimignano | Frecciarossa 1h 37m |
| Rome | 5 | Colosseum, Vatican, Tivoli, Trastevere | ✈️ Fly home |
| Total | 13 nights | 14 days of la dolce vita | |
📍 Via Gustavo Modena, 3, Milan, Lombardy 20129, Italy
Gothic masterpiece, rooftop terraces with panoramic views of the city
Must See Book Ahead
Leonardo da Vinci's masterpiece — 15 min viewing, books out months ahead
Must See Book ASAP
Renaissance castle with free courtyard + huge park — perfect for toddlers
Family Friendly Free Park
Canal-side bars & restaurants — Milan's aperitivo heartland
Food & Drink Free to Walk
Lakeside villages, ferries & alpine views — ~1h by train from Milan to Como or Varenna
Day Trip Great ViewsLake Como is locked in for Day 3 — about an hour by train, then ferries between Varenna and Bellagio. The Brera gallery & Quadrilatero della Moda are now optional extras to squeeze in on Day 2 if there's time.
✅ Confirmed · Day 3Frecciarossa · Milano Centrale (11:45) → Venezia Mestre (14:00)
🎫 Thu Jun 18 · Booking ref YTBMMN · arrives Venezia Mestre — right where the apartment is
Manage on Trenitalia →
📍 Via Podgora, 6, Venice, Veneto 30171, Italy
🚶 Directions from your host: From Venezia Mestre railway station, exit the main entrance and head toward Via Piave, in the direction of central Mestre. Continue straight until you reach Bar Pasticceria La Partenopea, then turn left onto Via Podgora. The apartment is at number 6.
Byzantine golden mosaics, stunning piazza — the heart of Venice
Must See Free Entry
Iconic stone bridge over Grand Canal — best at sunset
Must See Great Views
World-famous glass-blowing — watch artisans at work. 30 min by vaporetto
Family Friendly
Rainbow-colored houses — the most photogenic island in the lagoon
Family Friendly PhotogenicFrecciarossa · Venezia Mestre (10:38) → Firenze S. M. Novella (12:39)
🎫 Sat Jun 20 · Booking ref YTBTH5 · departs from Venezia Mestre (mainland station)
Manage on Trenitalia →
📍 Via Giuseppe Verdi, 16, Florence, Tuscany 50122, Italy
Botticelli, Leonardo, Michelangelo — world's greatest Renaissance art collection
Must See Book Ahead
Brunelleschi's iconic dome — climb 463 steps or admire from below
Must See Book Dome Climb
Medieval bridge lined with gold shops — Florence's most iconic landmark
Must See Free
THE panoramic viewpoint — all of Florence at your feet. Best at golden hour
Best Views Free
Medieval Manhattan — famous towers, world-champion gelato, Tuscan countryside
Day Trip Food
Shell-shaped Piazza del Campo — one of Italy's most beautiful squares
Day Trip Family FriendlyWe switched to the South route — the classic Tuscan hill-town tour. A private van + driver (with car seats) handles the winding country roads, the toddler can nap between stops, and a long countryside lunch gives the grandparents a proper rest. Siena's piazza and San Gimignano's lanes are full of open space for the little one to roam.
✅ Confirmed · Day 8Frecciarossa · Firenze S. M. Novella (11:33) → Roma Termini (13:10)
🎫 Tue Jun 23 · Booking ref YTB8PN
Manage on Trenitalia →
📍 Via Paola, 43, Rome, Lazio 00186, Italy
Ancient Rome's iconic amphitheater — stroller-accessible via elevator
Must See Book Ahead
Michelangelo's ceiling, Raphael Rooms — one of the world's greatest collections
Must See Book ASAP
2000-year-old temple with the world's largest unreinforced concrete dome
Must See Book (Free)
Toss a coin to guarantee your return to Rome — magical at night
Must See Free
Bernini sculptures + huge park with boat lake, playground & golf cart rental
Family Friendly Book Ahead
Rome's most charming neighborhood — cobblestone streets, ivy-covered trattorias
Food & Drink Family FriendlyTivoli stays our Day 11 plan — but if everyone's keen to head further south, we could swap one flexible Rome day (e.g. the Hidden Rome day) for one of these. Both go by high-speed train, no Pompeii required:
Making it work with a toddler & grandparents
Don't forget to book these in advance!