Origins: The area has Etruscan and Roman roots, but the town as we know it began developing in the early Middle Ages.
Strategic Importance: During the 12th and 13th centuries, Castelfiorentino became a key defensive outpost between Florence and Siena, often caught in their power struggles.
Name: The name derives from "Castello di Firenze" — Castle of Florence — signifying its historical allegiance to Florence.
Peace of 1260: It was the site of the Peace of Castelfiorentino, which marked Florence's defeat by Siena after the Battle of Montaperti.
Renaissance Influence: The town flourished during the Renaissance and still preserves significant art and architecture from that period.
Description
Town Center: The historical center is compact and walkable, with narrow streets, medieval buildings, and local artisan shops.
Art & Architecture: Highlights include the Collegiata dei Santi Lorenzo e Leonardo, Church of San Francesco, and several frescoes by Benozzo Gozzoli, whose museum (Museo BeGo) is dedicated to his work.
Countryside: Surrounded by rolling hills, vineyards, and olive groves — classic Tuscan scenery.
Typical Foods
Like much of Tuscany, Castelfiorentino prides itself on simple, rustic cuisine:
Ribollita – A hearty vegetable and bread soup, perfect in colder months.
Pappardelle al cinghiale – Wide pasta with wild boar ragù, earthy and rich.
Crostini toscani – Toasted bread with chicken liver pâté.
Bistecca alla Fiorentina – Thick-cut grilled T-bone steak, often shared.
Cantucci e Vin Santo – Almond biscuits dipped in sweet dessert wine.
Local wines and olive oils are also a highlight, often produced in the surrounding hills.
Activities & Things to Do
Visit the Museo BeGo – A small but fascinating museum dedicated to Benozzo Gozzoli’s frescoes.
Explore the countryside – Ideal for hiking, cycling, or vineyard tours.
Attend local festivals:
Santa Verdiana Festival (Feb) – Dedicated to the town’s patron saint.
Mercantia (summer) – Nearby in Certaldo, a unique street-theater festival.
Local markets – Weekly markets feature fresh produce, cheese, meats, and handmade goods.
Day trips – Easy base to explore nearby towns like San Gimignano, Volterra, Florence, or Siena.