Take a late-summer break at one of To Tuscany’s gorgeous private villas.

Sean Caulfield founded To Tuscany in 1998 to connect holiday makers with villa owners in the region he’d made his home.

Twenty years on, his aim remains unchanged: “Our quest is clear – to provide you with an excellent service and a wide choice of high-quality villas and apartments in stunning settings.”

From forges to farmhouses and olive presses to palazzos, To Tuscany has over 715 handpicked properties on their books, and they are growing all the time.

Their website promises that they offer the best private rental villas in the region at the best possible prices; an efficient and friendly service and secure online booking system; and expert knowledge of the area and its attractions. They visit every one of the villas on offer, ensuring high standards and luxurious touches. They know how important their clients’ feedback is – and they value candid reviews.

The experts at To Tuscany say that September is a great time to visit the area. The days are long and warm, the cities are not so crowded and the grape harvest has begun (which means interesting wine festivals each weekend). So, we’ve selected four divine Chianti villas (each with a private pool) that still have availability in September. And relax…


A luxurious stone house set amid acres of vines, this place is perfect for a group of eight. Want the best news? The owner has added a 20 per cent discount to all free September weeks.

Il Poggetto a Vescinino

Brand new to the To Tuscany portfolio, this charming, three-bedroom villa is all about escape. It has breathtaking views, homely décor and great art on the walls.

Podere Terrena

Guests love the sense of tranquillity at this enchanting stone house. Cooking lessons, cook and dinner delivery service can be arranged via the owner – who lives on the ground floor – on arrival.

Tenuta lo Spugno

Elegance and class are the order of the day at this fabulous private retreat. The cherry on the cake is the fully equipped spa and wellness centre on site, which includes a Jacuzzi, sauna and Turkish bath.

July 2018