Italy Ages 20s–40s Cultural Singles & Solo

Italy 360: Venice, Florence, Rome

Dec 4, 2026 – Dec 11, 2026 · 8 days · WeRoad

Overview

Some trips show you a country. This one takes you straight into the Italy everyone dreams of visiting at least once in their lifetime.

We start in Venice, among canals, narrow alleyways, St. Mark’s Square, and a welcome Spritz to toast the beginning of our adventure. From here, we travel by high-speed train to Florence and dive into the heart of the Renaissance, exploring the Duomo, Ponte Vecchio, one of the city’s most famous schiacciata sandwiches, and the art of making fresh pasta from scratch.

Then, for one day, we leave the city behind and head into the rolling hills of Chianti, surrounded by vineyards, picturesque villages, and a local winery where we’ll discover and taste one of Tuscany’s most iconic products.

The final chapter of our journey takes us to Rome: the Trevi Fountain, the Pantheon, Piazza Navona, Trastevere, and of course the Colosseum, Roman Forum, and Palatine Hill.

Three iconic cities, one full day in the Tuscan countryside, and only two major travel days: enough time to see Italy’s must-see highlights while still having time to slow down, grab an aperitivo, taste the local food, and simply enjoy being here.

Flights to and from Italy are not included in the package, giving everyone the freedom to choose the airline, airport, and schedule that works best for them.

We recommend flying into Venice Marco Polo Airport (VCE) and making your own way to our hotel.

We’ll meet as a group in the late afternoon. Once we’ve dropped off our bags and met our new travel crew, there’s only one proper way to kick off a trip to Italy: with a toast.

We head out through Venice’s narrow alleyways, bridges, and hidden squares for our first taste of the city before stopping for our Welcome Drink: a classic Venetian Spritz.

It’s the perfect chance to break the ice and officially kick off our Italian adventure.

The rest of the evening is ours to enjoy. We can decide together where to have dinner and start soaking up the atmosphere of Venice by night.