Roughly 123 miles (198 km) separates the center of Rome and Radda-in-Chianti, and the best way to tackle that distance is by driving through the scenic countryside. Whether you're renting or hiring a private transfer, the journey takes around 3 hours without traffic and is fairly direct, passing by the historic city of Orvieto and the city of Siena that's known for its medieval past.
Traveling by high-speed train is also another way of getting in between destinations. Depart from Rome to Florence on one of the main train companies in Italy that will get you to the Birthplace of the Renaissance in 1 hour and 30 minutes. From Florence, take a regional train to the town of Figline Valdarno, where you can take a taxi or rent a car the rest of the way to Radda-in-Chianti (or a private transfer, if you prefer).
You can sign up for this 6-day tour that takes you through Florence, through the Chianti region, and Rome. For those who like to bike, there's also a 5-day cycling tour that starts in Florence and ends in Siena, walking you through Radda-in-Chianti during the journey.
By Car or Private Transfer
Duration: 3 hours (without traffic)
Not only is renting a car and driving the most direct route to get from Rome to Radda-in-Chianti, but it's also best for seeing cities and towns along the way. Once you exit Rome, follow A1/E35 autostrada (a toll road) north for the next two hours until you hit the Casetta-Monteaperti exit. Then merge onto SP 111 that eventually leads you to Radda-in-Chianti. Along the way, stop in the historic city of Orvieto and the medieval city of Siena, if your schedule allows it.
Keep in mind that a private transfer is also available to drive you from Rome to Radda-in-Chianti. While it's on the more expensive side, you get what you pay for: a leisurely trip through the countryside with no obligations to navigate.
By Train and Car
Duration: 3-3.5 hours
If you're looking for a quick and comfortable way to get from Rome to Radda-in-Chianti, taking a high-speed train is the way to go. Head to Roma Termini station, where you can choose between the two main train companies in Italy: Trenitalia, the government-run rail, and Italo, a privately owned business. While no direct routes from Rome pull into Radda-in-Chianti, you can take the high-speed train to the Firenze S.Maria Novella in 1 hour and 30 minutes and connect to a regional train that arrives in Figline Valdarno in 48 minutes.
Once you arrive in Figline Valdarno, take a taxi or rent a car (especially if you're planning to explore the surrounding area) that takes around 28 minutes to get to the heart of Radda-in-Chianti.