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
- 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
- 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
- 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
- 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
- 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
- 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.