Culture Trip's Guide to Tuscany

Set among rolling hills and surrounded by vines, this 15th-century villa is the perfect blend of luxurious and low key. Breakfast is served daily on the terrace, so you can make the most of the rural landscapes over a cappuccino, before taking part in cooking lessons with in-house chef Paolo. (His secret ingredient is the house olive oil, grown and pressed on site.)

Belmond Castello di Casole sits on 4,200 acres (1,700ha) of sun-dappled land, dotted with olive groves and vineyards, and featuring a fitness centre, croquet lawn and cinema. Despite its size, the hotel somehow maintains the family-run vibe that Tuscan hotels are known for. Aspiring nonnas can take a pizza-making class on site, learning how to knead, roll and bake like true Italians. If you’d rather sample local delights without any effort, pull up a chair at Tosca for an adventurous yet delightfully classic Italian feast – the menu includes dishes like linguine vongole and beef fillet tartare.

Explore Italy’s most famous wine regions on this full-day tour that will have you exploring vineyards, tasting wines and eating sublime Italian food. Setting off from Florence, you’ll travel through the countryside in a four-by-four, visiting historical villas, wine estates and a cellar that specialises in the distinctive Chianti Classico bottles. While locally sourced cheese and charcuterie will accompany your wine tastings, be sure to leave room for the three-course meal of local dishes and freshly made pasta.

For those who have wanted to try their hand at Italian cooking, this tour is for you. Collecting you from Florence, your guide will take you to a traditional food market in the city and guide you through the sourcing and purchasing of the ingredients you’ll need. You’ll then be taken to a farmhouse in the countryside where a local chef will teach you to cook four different dishes. Picture yourself sipping on regional wine as you roll fresh pasta, dice plump tomatoes and grill tender meat. Finally, you’ll get to dine on your creations, with wine to accompany your four-course meal.

Make like the Italians do and take to the Tuscan roads on a classic Vespa. Whether you’re a beginner or a biking aficionado, your guide will make sure you’re all ready to ride, talking you through the basics and providing you with ample road tips to make sure you have a safe trip. Once you’re feeling comfortable, you’ll set off through Florence into the Tuscan hills. Stopping off at historic churches and traditional villas, you will have time to explore these incredible structures before making your way to the final stop – lunch. Fuel up on creamy burrata and zingy bruschetta for the ride back into the city.

A 30-minute walk from Il Segreto di Pietrafitta is the medieval hilltop town of San Gimignano. The dining scene here lives up to the spectacular setting, and our pick of the bunch is Osteria Delle Catene, a secret little spot where you’ll be dining amongst locals. Their meat comes from one of Italy’s best butchers – Dario Cecchini – and the fare is traditionally Tuscan. Expect delicious dishes like pappardelle with truffle mushroom sauce.

Just a 20-minute drive from Belmond Castello lies this restaurant with two Michelin stars. Hidden within the unassuming town of Colle di Val d’Elsa, it is helmed by the Trovato brothers, and the restaurant’s low-key setting will make you feel as though you’re dining in someone’s home, albeit with spectacular views of the hillsides through arched windows. The food, however, quickly reveals that this is no ordinary place. The ever-changing tasting menu will parade plates of locally sourced, seasonal dishes in front of you, and the Trovato brothers are experts at pushing traditional Italian cooking to its limits, showing what it can become with a little imagination.