My first memory of Rome as a lucky teenage traveler is standing on a sidewalk with the Colosseum looming ahead. But to get there meant crossing a broad, fast-flowing avenue. No crosswalks or traffic signals (or at least none that the traffic paid attention to). And then up strolls a no-nonsense woman of Rome who scoped out our plight in a nano-second. She moved to the front of our little knot of pedestrians, gave us a don’t-worry-my-friends smile, and crooked her finger in an unmistakable command to follow the leader. Into the traffic she stepped and, miraculously, it all stopped or zagged to miss us. She never deigned to look at a driver or even to pause. She just knew what to do. Oh yes, it’s good to hang out with the locals.

Colosseum in Rome

Italy – and the wonderful Italians I’ve been lucky enough to know – taught me so much as an impressionable young traveler. There were the obvious lessons in history and Renaissance art and, well, pizza without tomato sauce. They taught me to laugh at the world rushing around me, how to linger at the dinner table, and that if you want to grab a shield and pretend you’re a gladiator, you absolutely must.
You’ll be delighted how our handcrafted and carefully curated family trip to Venice, Florence and Rome recaptures all of that and more. It’s a kick to watch your kids encounter three of the world’s most famous cities. Our local guides give you that peaceful, easy feeling that you only get when you trust yourself to a friend who lives in the neighborhood.
The adventure begins in Venice. As huge as La Serenissima is in everyone’s imagination, the floating city is quite small and easy to cover. Your time here will be a just-right blend of iconic sights like Piazza San Marco and the Bridge of Sighs and a gondola ride into some of the narrowest canals. Then, before “palazzo fatigue” sets in, you take a water taxi to the station for a high-speed train ride to Florence.
Man on Gondola in Venice

Many tourists think they need days in Florence, but that’s because they do things like wait four hours to see Michelangelo’s David. You, on the other hand, will come into near-magical possession of tickets that let you skip the line. From 20+ years of traveling with kids, we know that this is the right moment to break out of city mode and retreat to a Tuscan village where your hosts are a count and countess and the infinity edge pool overlooks vineyards and olive groves. Your country interlude is a great way to let off steam walking in vineyards, making pizzas, biking in Siena, and ogling at the towers of San Gimignano.
By the time you de-train in Rome, you’ll all feel like Italian pros. You know the walks to the Colosseum and the Forum will last just long enough. The Sistine Chapel? Of course we score rare tickets in advance. While the turisti shuffle off to another monument, your family goes for a cool gladiator training session. Rome unfolds for you all without overwhelming anyone.

Gladiator Training in Italy
If you love to treat and inspire the young travelers in your family, you can’t find a better way to do it than with a week in Venice, Florence and Rome. In a world that moves too fast, it’s good to be the one who knows how to crook your finger and say, “Come with me, and let’s have some unforgettable fun.”