Tuscany Holidays

Even by Italian standards, Tuscany is a region of outstanding natural beauty and cultural riches - historic towns packed with architectural and artistic treasures, and surrounded by picture-postcard landscapes of rolling hills and cypress trees.

Harriet and Flora are here to help give you the inside track.

Why we think you’ll love it

  • The dominating themes behind any luxury holiday to Tuscany are architecture, food, wine and landscape landscape - what's not to love? The area has something for everyone and can be enjoyed at all times of the year.

Luxury Holidays to Tuscany: The Detail

Tuscany's highlights include Siena, which hosts the famous annual Palio horse race; the wonderfully preserved medieval city of San Gimignano, with its soaring towers; Pisa with its soaring and leaning tower; and of course Florence, the 'cradle of the Renaissance', with its magnificent duomo, Uffizi gallery and Ponte Vecchio. Added to this, Tuscany has miles of Mediterranean coastline. All rather perfect, we think you'll agree.

Original Travel has selected some of the best properties from across the region. Many of them are in rural settings, but within easy range of the main cultural attractions, giving you the best of both worlds, but we have some properties in the beautiful city of Florence itself.


Original Highlight

Staying at the rustic, luxury castle hotel Castello Di Vicarello and doing a one on one tailor made cooking class with the owner Aurora. They have a large organic garden, so we collected all the fresh vegetables first, and cooked up a Tuscan feast in the gorgeous stone clad kitchen.

Flora, Original Traveller

Weather in January January February March April May June July August September October November December
  • Average Temp. — 8°C / 46°F
  • Rainfall — 7cm / 3.1 inches
Flight from London

2:15 hrs

Time Difference

GMT +1 hr

Top picks for Tuscany

Castello di Vicarello

Castello di Vicarello


In one of the most unspoilt areas of Tuscan Maremma, well away from the main tourist routes, lies the exclusive luxury hotel Castello di Vicarello.

Where to stay

Castiglion del Bosco

Castiglion del Bosco


For a taste of life on a grand Tuscan estate, a stay at Castiglion del Bosco is highly recommended. There are a mere 4,500 acres for guests to explore but the first decision is whether to stay in one of the 23 immaculate suites in Il Borgo, formerly the estate’s central hub, or in one of nine farmhouse villas dotted around the estate and available for private hire.

Where to stay

Pool area at Borgo Santo Pietro, luxury hotel in Italy

Borgo Santo Pietro


A luxurious villa set amid 13 acres of private grounds in the Tuscan countryside.

Where to stay

Villa Mangiacane, luxury hotel in Italy

Villa Mangiacane


The property and its original Renaissance frescoes fell into disrepair but have now been painstakingly restored to their former splendour.

Where to stay




Located in a magnificent part of Tuscany between Chianti and Siena, L’Andana is surrounded by centuries old olive groves in quintessential Tuscan foothill country.

Where to stay

Palazzo Terranova

Palazzo Terranova


The hotel was completely restored from a ruin by a British couple, and is surrounded by unspoilt countryside.

Where to stay

We were particularly impressed by the level of contact from you. We have fairly intense jobs and the fact that you were so communicative and helpful made organisation so easy.


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