Destination guide · Tuscany, Italy

Tuscany, worth knowing.

A few things about Tuscany that make the trip better once you know them, each checked against at least two sources (linked below it). Then a handful of questions to bring with you, because the conversations you have somewhere new tend to stay attached to the place.

Fun facts about Tuscany

  1. 1Twice every summer, on July 2 and August 16, Siena turns its shell-shaped Piazza del Campo into a racetrack for the Palio, a horse race between the city's neighbourhoods.Source: Visit Tuscany; Wikipedia
  2. 2Medieval San Gimignano once bristled with dozens of stone tower-houses, families building ever higher. More than a dozen still stand, giving this tiny hill town a skyline like no other.Source: Visit Tuscany; Wikipedia
  3. 3In Lucca, there are oak trees growing on top of a medieval tower. Climb the Torre Guinigi and you come out in a little rooftop garden high above the red roofs.Source: Visit Tuscany; Wikipedia
  4. 4The Leaning Tower of Pisa started tilting while it was still being built, before the builders even reached halfway. They carried on anyway, and it has been leaning ever since.Source: Opera della Primaziale Pisana; Wikipedia
  5. 5Every August, Montepulciano holds the Bravio delle Botti: teams from the town's eight districts race by pushing huge wooden wine barrels uphill through the old streets to the main square.Source: Visit Tuscany; Wikipedia
  6. 6Each September, Pienza celebrates its pecorino with a game of rolling whole cheese wheels across the main square, aiming at a wooden spindle. It's called the Palio del Cacio al Fuso.Source: Visit Tuscany; Wikipedia

Things to do in Tuscany

  • ◦Lucca's Piazza dell'Anfiteatro is a perfect oval because it was built inside a Roman amphitheatre. The houses follow the old arena's curve, and cafes now fill the ring.Source: Visit Tuscany; Wikipedia
  • ◦In the Val d'Orcia village of Bagno Vignoni, the main square is a big stone pool of steaming hot-spring water. It's for looking, not bathing, so wander down to the old mills below.Source: Visit Tuscany; Wikipedia
  • ◦Pienza was redesigned in just a few years in the 1400s as an ideal Renaissance town. Stand in Piazza Pio II, then find Palazzo Piccolomini's hanging garden overlooking the whole Val d'Orcia.Source: Visit Tuscany; Wikipedia
  • ◦Walk or bike the top of Lucca's Renaissance walls: a tree-lined loop of more than 4 km that circles the whole old town, with views over the rooftops.Source: Visit Tuscany; Wikipedia
  • ◦Soak in the Cascate del Mulino at Saturnia, tiers of milky-blue natural pools where warm spring water, around 37°C, spills over a little waterfall. Open to everyone, all year round.Source: Visit Tuscany; Wikipedia
  • ◦Walk the ramparts of Monteriggioni, a hilltop ring of walls and 14 towers so striking that Dante wrote it into the Divine Comedy.Source: Visit Tuscany; Wikipedia

Questions to bring to Tuscany

From Sojourn's journeys. Ask one over a long dinner or on a slow walk, and let the place do some of the work.

Going together

  • When do you feel most like yourself?
  • What does rest actually look like for you?
  • What is one thing you wish we did more of?

Going solo

  • What is the first thing this place is showing you that you didn't expect?
  • What does this version of you know that the home version tends to forget?

Free printable

25 questions for your Tuscany trip.

A printable PDF to fold into your bag and open somewhere new. Written by a licensed marriage and family therapist.

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From Sojourn, a guided journey for before you go, while you're there and after you're home, for couples and solo travelers. It's a reflection companion, not therapy. Facts last checked 2026-11-03. Spotted something out of date? Email support@sojourntravel.app.

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