10/05/2026
Most Italy trips ask you to pick a city and build around it. This one doesn't make you choose.
You land in Venice and step straight onto a private water taxi, no line, no water bus crowd, gliding to a boutique hotel in Cannaregio, one of the city's quieter, more local corners. St. Mark's mosaics catch the afternoon light inside the basilica. A private, full-hour gondola ride carries you past palazzos that have been standing since before the city had bridges. In the evening, Cannaregio's bacari fill up: a glass of w**e, a plate of cicchetti, then the next bar, the way Venetians actually spend a Tuesday night.
Florence follows. You stand in front of Michelangelo's David at the Accademia with room to actually look at it. At dusk, you find a w**e window, one of the small holes cut into a palace wall five centuries ago to pass a bottle to the street, and order a glass the same way locals did back then. A day trip carries you past Siena's towers and San Gimignano's hilltop walls, ending at a Chianti w**ery for dinner as the sun drops over the vines.
Rome closes it out. You're inside the Vatican early, before the public gates open, walking rooms that are still empty. And at the Colosseum, you stand on the same arena floor where history happened, not behind a rope looking down at it. You taste delicacies off the beaten path on a golf cart food tour, and venture outside the city to marvel at Tivoli's ancient and majestic villas.
Venice, Florence, Rome: the three cities almost everyone tries to see in one 13-day trip, done right instead of rushed through.
Want to see the full itinerary, or talk about building your own version of this? Send me a message.
