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Great Runs Spring 2022 Road Trip: Tuscany

Great Runs had the privilege of spending two weeks in Tuscany this past May. It was mainly a bike trip, which doubles as an efficient way to scout fantastic running routes. But we also did plenty of running, hiking, and walking. The plentiful eating was justified by 300 miles & 40,000 feet of climbing on a gravel bike over 10 days.

May is a fantastic time of year to go to Tuscany. The hillsides are deliciously green, the flowers are gorgeous, the weather warm but not yet hot, and it’s not peak tourist season. The map below shows the itinerary, and below that are some of our Tuscany running/traveling observations.

Here are a few tips for running & traveling in Tuscany:

  • It’s gonna be hilly. Most of the classic Tuscan towns such as Montelpuciano and San Gimignano are atop a hill, so the roads leading and from them involve a steep climb. And once you’re there, there aren’t typically a lot of flat options.
  • The bad news: very few of the countryside roads have a shoulder or sidewalk, so you need to do the research on which roads are safest for running. The good news: there are many quiet roads that are relatively traffic free…and we’ve done a lot of the research for you.
Strade Bianche
  • The running highlight in Tuscany are the Strade Bianche — the huge network of unpaved, quiet roads winding through the Tuscan countryside. We’ve recommended some particularly scenic sections. One thing to be aware of is that these roads can get dusty if it’s been dry…but we noticed eight out of ten drivers slowing down when they see a runner/walker/cyclist.
  • Florence Tip: The go-to run in Florence is to combine a section of the river with Cascine Park. Go early. Other Florence tip: fantastic running to, from, and in nearby Fiesole (and also Pistoia and Prato).
  • Stunning running discoveries: There are some gorgeous, smaller hilltop towns in the Val d’Orcia that have a wonderful network of valley trails just below them that are fantastic for a hike or moderate trail run. Here are a few: Pienza, Monticchiello, Montisi, Castelmuzio, and Trequanda. In the Chianti area, we loved the town of Rada.

  • While San Gimignano, Montelpuciano, and Montalcino get all the love, we were particularly enchanted by Pienza, Cortona, and Volterra.
  • Stay in an Agrituismo. These are working farms/vineyards that also have lodging. They’re generally off the beaten track, and the rooms might be a bit spartan, but the setting is usually spectacular.
Path to Castello Pasquini in Castiglioncello

We also spent three days working our way down the coast toward Rome. A few tips for the coastal section:

  • Skip Livorno, go to Castiglioncello. Our seaside promenade route in Livorno is nice enough, but the town is busy, a bit industrial, and a major departure point for ferries. Instead, drive 25 km south to Castiglioncello. There’s a fantastic run there along a seaside path and a tree-shaded park leading to Castello Pasquini.
Via Dei Cavalleggeri Path, Piombino-Populonia
  • Skip Grosseto, go to Populonia & Piombino. Unless you’re planning to spend time in Maremma’s Nature Reserve (which is worth it, for running/hiking/cycling), head 45 minutes north to these towns on the border between the Ligurian Sea and the Tyrrhenian Sea. Here’s a way to spend a perfect day in this area:
    • Take at least a couple of hours to explore the large Archaeological Park in Populonia, for its huge collection of Etruscan remains. It’s worth the the 25
    • Then take a siesta on pretty Baratti beach.
    • Do an early morning or early evening run on the promontory trails between Populonia and Piombino (start in either town), especially the ancient Via Dei Cavalleggeri road, now a walking trail.
    • Cap it off with a sunset drink by the beach in Populonia or at the restaurant/bar next to Calamoresca beach in Piombino (near the Piombino terminus of the Via Dei Cavalleggeri trail).
Beach run in Ostia

A final pro running tip: If you’re hoping to get a run in before catching a flight out of Rome, there are seafront promenades and runnable beaches in Fiumicino and Ostia, which are located ten minutes from the airport.

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