Discover Tuscany Chianti Region Short Break

Tuscany has long captured the imagination of travellers with its postcard landscapes and timeless charm. The Chianti region, nestled between Florence and Siena, is a land where vineyard-clad hills roll gently into the distance and every village seems lifted from a Renaissance painting.

Your stay begins at Fattoria La Torre, a peaceful farmhouse set among vineyards. This first night allows you to immerse yourself immediately in Tuscany’s rural life – where the smell of fresh earth, cypress trees, and rustic kitchens feels almost like stepping back in time. After this, you’ll spend three nights at Hotel Garden in Siena. Perched on the edge of the historic city, the hotel combines modern comfort with sweeping views of Siena’s terracotta rooftops. From here, you can wander into Siena’s medieval centre, famous for the Piazza del Campo, a shell-shaped square considered one of the most beautiful in Europe.

This short break gives you the freedom to experience Tuscany your way. Spend your days exploring vineyards and wine cellars, learning how the region’s famous Chianti Classico is made, or discover nearby hill towns such as San Gimignano with its medieval towers, or Monteriggioni with its intact castle walls. Art and history lovers can easily reach Florence by train or car, where masterpieces from Michelangelo and Botticelli still grace the galleries.

Evenings are best enjoyed the Tuscan way – a slow dinner of pasta, pecorino cheese, and local wines under the glow of soft lanterns. This package doesn’t just offer you a place to stay, but a chance to experience Tuscany’s rhythm: unhurried, authentic, and memorable.

• 1 night at Fattoria La Torre (rustic countryside farmhouse)
• 3 nights at Hotel Garden, Siena
• Daily bed and breakfast service
• Discover Tuscany’s Chianti wine region
• Explore Siena, one of Italy’s most enchanting medieval cities
• Opportunity to visit Florence, San Gimignano, and other nearby towns
• From £499.00 per person

The Chianti region of Tuscany is beautiful throughout the year, and each season brings its own unique character. This particular short break is set to depart on 12 November 2025, a wonderful time to experience Tuscany without the heavy crowds of summer. The cooler air of November adds a gentle freshness to the rolling hills, and the vineyards glow with the last autumn colours. It’s a season that feels slower, calmer, and more intimate – perfect for those who prefer to explore at a relaxed pace.

November is also harvest time for olives, so you may find local markets and villages alive with festivals celebrating the new olive oil. Wine cellars are welcoming, offering tastings of Chianti Classico alongside warm conversations with local producers. The weather tends to be mild, with cool evenings – ideal for cosy dinners of hearty Tuscan dishes paired with red wine.

For sightseeing, this time of year makes visiting Siena, Florence, and nearby hill towns much easier, as the streets are quieter and you can take in the beauty without rushing. Hotels and restaurants are more peaceful too, giving you space to enjoy the region in a more personal way.

Travelling in November also offers good value, as prices are generally lower compared to the busy summer months. If you’re seeking a trip that blends comfort, authenticity, and seasonal charm, this November departure is a wonderful opportunity to discover Tuscany’s timeless appeal.