Best Stops Between Rome And Florence

Why bother leaving the fast train

Rome and Florence are both, understandably, magnets. Most visitors treat the space between them as dead time, something to be minimized rather than used. But this stretch of Umbria and Tuscany is where a lot of what people love about central Italy actually happened: hill towns built for defense, wine country that never needed to advertise itself, cathedrals funded by wool money rather than papal money.

The trade-off is real. You give up speed and a single ticket for a looser itinerary with connections, occasional waits, and the small friction of moving luggage more than once. For a lot of travelers that is exactly the point.

Orvieto: the first stop, and worth more than a layover

Orvieto sits on a plateau of volcanic tuff, which means the town has a naturally defensible position and a habit of surprising people who thought they'd seen enough Italian hill towns. The cathedral facade is the reason most people come: a wall of gold mosaic that catches the light differently depending on the hour, backed by a Luca Signorelli fresco cycle of the apocalypse that is, by most accounts, underrated relative to its quality.

Below ground there's a different Orvieto, a network of tunnels and wells carved into the tuff over centuries, some of it Etruscan in origin. An hour in the underground city plus an hour in the cathedral is a reasonable half-day, though the town rewards a full one if you have it.

Getting off the main line for Arezzo

Arezzo requires slightly more effort to reach from Orvieto since it sits on a different rail line, usually meaning a change in Terontola or a short detour through Chiusi. It's worth it. The town is less polished than Siena and less visited than either Rome or Florence, which is part of the appeal.

The Basilica di San Francesco holds Piero della Francesca's fresco cycle The Legend of the True Cross, one of the major achievements of early Renaissance painting, and viewable without the crowds you'd fight in Florence for something of similar rank. The Piazza Grande, sloped and irregular, hosts an antiques fair on the first weekend of each month that's worth timing a visit around if your dates allow.

Siena, the anchor stop

If you can only add one stop to a Rome-Florence trip, most people would tell you to make it Siena. The Piazza del Campo, a shell-shaped square that slopes down toward the Palazzo Pubblico, is one of the great public spaces in Europe and the site of the Palio, a bareback horse race run twice each summer that turns the whole city inward for a few days.

Siena's cathedral, striped in dark green and white marble, is dense enough with detail (an inlaid marble floor, a Piccolomini Library with vivid fresco cycles) that it can absorb a couple of hours on its own. The city is compact enough to walk in a day but atmospheric enough to want a night in it, ideally with dinner somewhere off the main tourist streets near San Domenico.

• Piazza del Campo, best visited early morning before the crowds and again after dinner
• Siena Cathedral and its inlaid marble floor
• Palazzo Pubblico's Museo Civico, for the Lorenzetti frescoes on good and bad government
• A contrada dinner if you happen to be there around Palio time

The last leg to Florence

From Siena, Florence is close, under an hour and a half by regional bus and not much longer by train with a change. Some travelers use this final stretch as an excuse to add a short detour through Chianti, renting a car for a day to drive the SR222 through vineyard country before dropping it in Florence, though this adds cost and complicates the otherwise train-based logic of the route.

Arriving in Florence after several days on slower roads changes how the city lands. It reads less like the obvious final item on a checklist and more like the payoff of a route you built yourself.