With searches for Tuscany climbing and anticipation building around Regé‑Jean Page’s upcoming film You, Me & Tuscany set for release on 10 April 2026, the region is enjoying a renewed burst of global attention.
For business travellers looking to elevate a work trip, or leisure visitors chasing the cinematic landscapes soon to hit the screen, Tuscany offers an almost unfair abundance of day‑trip possibilities.
From medieval hill towns to wine‑soaked valleys, here are the most rewarding escapes from Florence and Pisa, how to reach them, and what to expect when you arrive.
Lucca – Renaissance Calm Behind Ancient Walls
From Florence: 1 hr 20 mins by train
From Pisa: 25 mins by train
Lucca is one of Tuscany’s most quietly enchanting cities, wrapped in perfectly preserved Renaissance walls that you can cycle or stroll along in a full loop. Inside, the streets unfold into piazzas lined with pastel palazzi, Romanesque churches and cafés that feel blissfully unhurried. Climb the Torre Guinigi, crowned with oak trees, for views that stretch across terracotta rooftops to the Apuan Alps. It’s an easy, elegant day out and one of the most accessible from both Florence and Pisa.
Siena – Medieval Majesty and a Perfect Piazza
From Florence: 1 hr 30 mins by bus (faster than the train)
From Pisa: 2 hrs 15 mins by train
Siena is Tuscany at its most cinematic: a city of steep medieval lanes, striped Gothic architecture and the shell‑shaped Piazza del Campo, where the Palio horse race takes place each summer. The Duomo is a masterpiece of black‑and‑white marble, while the Museo dell’Opera offers rooftop views that rival anything in Florence. Siena’s compact size makes it ideal for a full day of wandering, espresso‑stopping and people‑watching.
San Gimignano – Tuscany’s Skyline of Stone Towers
From Florence: 1 hr 15 mins by bus (via Poggibonsi)
From Pisa: 2 hrs by train + bus
Often called the “Medieval Manhattan,” San Gimignano rises from the hills with a cluster of stone towers that once signalled the wealth of rival families. Today, the town is a UNESCO‑listed gem of narrow lanes, artisan shops and sweeping vineyard views. Try the local Vernaccia white wine, explore the frescoes in the Collegiata, and climb the Torre Grossa for a panorama that feels lifted straight from a film set and very fitting, given the renewed interest in Tuscany’s romantic landscapes.
Pienza – The Perfect Renaissance Town in the Val d’Orcia
From Florence: 2 hrs by car (public transport is possible but slow)
From Pisa: 2 hrs 30 mins by car
If You, Me & Tuscany inspires travellers to seek out the region’s dreamiest scenery, they’ll likely end up in the Val d’Orcia and Pienza is its crown jewel. Rebuilt in the 15th century as the ideal Renaissance town, it’s a place of honey‑coloured stone, quiet lanes and views that roll into infinity. Sample pecorino cheese from local producers, wander the Palazzo Piccolomini gardens, and take in the landscapes that have defined countless films and travel campaigns.
Volterra – Etruscan History and Windswept Drama
From Florence: 1 hr 45 mins by bus
From Pisa: 1 hr 30 mins by bus
Volterra is moodier and more atmospheric than many Tuscan towns – perched high on a ridge, shaped by Etruscan history and surrounded by dramatic, wind‑carved hills. Its archaeological museum is one of the best in Italy, and the Roman theatre is astonishingly well preserved. The town’s alabaster workshops offer a glimpse into a craft tradition that has survived for centuries. It’s a rewarding choice for travellers who prefer something a little less polished and more soulful.
Cortona – Hilltop Charm With Hollywood Credentials
From Florence: 1 hr 20 mins by train + bus
From Pisa: 2 hrs 30 mins by train + bus
Cortona has long been a favourite with international visitors thanks to Under the Tuscan Sun, and it’s easy to see why. The town climbs steeply from the valley floor, offering views across Lake Trasimeno and a maze of stone alleys lined with wine bars, boutiques and trattorias. It’s lively without being overwhelming, and its museums, particularly the MAEC offering a deep dive into Etruscan culture.
A Region Ready for Its Close‑Up
With Tuscany back in the cultural conversation, these day trips offer a chance to experience the landscapes, flavours and history that make the region so enduringly magnetic. Whether you’re travelling from Florence or Pisa, each town delivers its own blend of beauty and character and all feel like places where a film romance could unfold.