Treasures of Tuscany: Siena & the Chianti Region

Leave behind the art-filled streets of Florence for a day and venture deep into the Chianti region to soak up the rural charm of Tuscany.

As you travel south, the rolling countryside unfolds before you – a patchwork of vineyards, olive groves, and ancient villages perched on hilltops, each with its own distinct atmosphere and story. This is the heart of Chianti Classico region, where nature and culture are deeply intertwined, leaving their unique mark on every wine’s character and palate.

You stop briefly in Castellina in Chianti, a honey-coloured hilltop town surrounded by vineyards – just as you might imagine Tuscany in your dreams. You’ll have time to grab a coffee and enjoy a little exploration before you continue your adventure. Wander its cobbled streets, then step into a covered medieval passageway. Once a defensive walkway, today it’s a hidden corridor offering perfect views of the rolling Tuscan hills at every turn.

Then it’s further south to Siena: a gorgeous red-brick city that celebrates Gothic architecture like no one else. Here your guide will show you its secrets on a 2-hour walking tour, bringing its history and traditions to life around every corner.

It’s time to rest, and there’s no better place than the shell-shaped Piazza del Campo. Enjoy a lunch of local flavours as you soak up the atmosphere of this remarkable square, home to the thrilling biannual Palio di Siena and, more recently, a dramatic James Bond chase in Quantum of Solace.

Next, you continue through the Tuscan countryside, and before long, the 14 towers of San Gimignano appear on the horizon. This UNESCO-listed town is one of the best-preserved medieval settlements in the world, and you’ll have ample free time to wander its streets and feel transported back to an age of rivalry, wealth and, power when noble families competed to build the tallest towers.

After a day exploring the narrow, cobbled streets of two medieval UNESCO-listed gems and discovering their secrets, it’s time to return to Florence. You travel back through the heart of Tuscany, across Chianti’s rolling landscapes dotted with charming villages and vineyards. Sit back, relax, take in the views, and reflect on the moments that made the day unforgettable.