Four Day Trips to Take in Tuscany-1
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Four Day Trips to Take in Tuscany

Our guide through Italy's cultural wonderland

When you imagine Tuscany, you picture soft rolling hills illuminated by a hazy warm sun, architecture embedded with history from time periods you didn’t even know existed, charming villas straight from the sketches of a fairytale, and rustic boats skittering along the Mediterranean Sea. We hate to burst your bubble – but your fantasy visions are reality.

So where does one begin in this Italian heaven that’s a true paradise for anyone with an appreciation for the finer things in life – from gastronomes to art lovers. As overwhelming as the endless possibilities of Tuscany might seem, all you need is a little willingness to hop in the car and take a day to explore a different corner. We’ve organized a shortlist of four must-see destinations to get your imagination going.


The region’s capital city, “Firenze” fuses the vibes of rural Tuscan life with urban energy. It is home to some of the world’s most famous historical landmarks: an epicenter of European action in medieval times, the home of the renaissance, and the location of many trials and tribulations of famous Italian citizens. A walk through Florence is a walk through Europe’s visual history: The Palazzo Vecchio overlooking Piazza della Signoria that holds the iconic figure of Michelangelo’s David; the multiple corridors of The Uffizi; and countless landmark religious buildings from the Basilica of Santa Maria Novella to The San Giovanni Baptistery – home to Lorenzo Ghiberti’s Gates of Paradise. In a city of only 340,000 there is a world of culture. A day trip to Florence is a feast for the eyes: gain new insights into history through the original paint strokes and buildings of years’ past.


A quaint city sequestered in the Tuscan hills, Siena also boasts a wealth of artistic treasures. Particularly, the city is home to striking Gothic architecture – such as the Siena Cathedral and the Palazzo Chigi, home to the city’s conservatory of music. But one of the main reasons for a summer visit to Siena is the Palio di Siena – a long-standing traditional horse race that runs annually on July 2nd and August 16th. Ten of the seventeen Siena city wards are represented in the race, with each racer donning a traditional costume and riding bareback around the perimeter of Pizza del Campo. Thousands of spectators flock to the race site to see diligent jockeys attempt to negotiate the sharp turns, and often, witness the horse blast through the finish line without them. Andiamo!


The cream of the crop in central Tuscany, Chianti is the pride of this rural region. A wine tour through the region will treat your palate and senses to multiple treasured vintages – from Cabernet Sauvignon to Merlot. There might not be as many straw covered bottles as there used to be – most of the vineyards have moved to straight up glass bottles – but the taste is as authentic as ever. Negotiate the vine-lined region easily with a guided tour organized by our concierge team, and taste history first hand.


There’s a 99% chance you’ve seen the classic optical illusion of an excited tourist pretending to push the leaning tower of Pisa upright. But despite its reputation as a tourist trap, the tower is a world-famous landmark for good reason and its well worth a trip to see the 183ft. marble and stone mass looking set to tumble over in Piazza del Duomo. In addition, Pisa has many other historical sites to explore. For example, Giorgio Vassari’s Piazza dei Cavalieri, or one of the several astounding churches, such as the Church of Saint Nicola that houses works by Giovani Pisano and Francesco Traini.

See all Luxury Retreats in Tuscany

Photographs: Samot; M. Rohana; Irina Kovancova; /Shutterstock
Colleen McNamara