Siena and its surroundings: the charm of the Middle Ages, postcard hills, and the secrets of the Duomo

If you are staying at one of our properties across Lucca, Pisa, or Pistoia, there is a day trip you absolutely cannot miss. Located just a bit further south, Siena is about 120-140 km from the cities of our "perfect triangle."

How to get there: The best way to reach it from the coast or northern Tuscany is by car (about 1.5 to 2 hours), taking the Florence-Siena highway (FI-PI-LI up to Florence and then the southbound junction), which offers a pleasant, scenic drive through the rolling hills of Chianti. If you prefer the charm of rail travel, there are excellent train connections: Tuscan Regional lines are highly convenient and perfect for cycling enthusiasts, allowing you to easily bring your bike along for the ride.

Siena is a city that has remained magically untouched since the 14th century. A masterpiece of red brick and winding, uphill alleys, it treasures centuries-old traditions and a surrounding territory that looks as if it were painted by a Renaissance master.

What to do in the city…

• Step into the heart of Piazza del Campo: This world-famous, shell-shaped square is truly one of a kind. Lie down on its warm bricks—just like the locals do—and admire the majesty of the Palazzo Pubblico and the Torre del Mangia soaring into the sky. If you want to enjoy a bird's-eye view of the square, stop for a coffee, gelato, or an aperitif at La Costarella bar, a unique spot featuring a splendid private terrace overlooking the square.
• Experience the adrenaline and culture of the Palio: This is the event that defines the very soul of Siena. Beyond its tourist appeal and the passionate debates that such a visceral event can spark (especially regarding animal welfare), the Palio is not just a horse race, it is the core of social life for the Contrade (neighborhoods), keeping locals engaged all year round. The Palio takes place twice a year: on July 2nd and August 16th. If you visit during these periods, you will breathe in an atmosphere of vibrant and authentic medieval passion.
• The Duomo, the Gate of Heaven: A Gothic marvel in white, red, and green marble that leaves visitors speechless with its grandeur even before crossing the threshold. Inside, it houses extraordinary masterpieces, including the beautiful Piccolomini Library, magnificamente frescoed by Pinturicchio. If you want to see the Cathedral from a different perspective, you can do so by looking out from its very top. The  Porta del Cielo tour, opened only recently, allows you to visit a series of rooms that were inaccessible for  enturies to anyone except the master builders directed by history's greatest architects. Reaching above the starry vaults, you can walk "above" the sacred temple and admire breathtaking panoramic views both "inside" and "outside" the Cathedral.

Hidden gems… the spectacular uncovered floor

There is an extra reason to plan your visit to Siena during this season: the chance to walk on what Giorgio Vasari defined as "the most beautiful, largest, and most magnificent floor that was ever made."

• The marble carpet of the Duomo: Normally protected by covered sheets to prevent wear and tear, this incredible mosaic floor made of 56 marble panels is revealed to the public for just a few weeks a year. In 2026, the dates to mark in your calendar for this wonder are from June 27th to July 31st, from August 18th to October 30th, and from November 1st to November 15th. It is a unique opportunity to admire biblical stories and philosophical allegories carved into stone by great Renaissance masters.

Vineyards, clay hills, and mysticism: heading out of town

• Photograph the Crete Senesi and Val d'Orcia: If you are looking for those iconic Tuscan landscapes with cypress-lined avenues and golden hills, drive south. Pienza, San Quirico d'Orcia, and the moon-like landscapes of the Crete Senesi will yield the most beautiful photos of your trip.
• The mystery of the sword in the stone at San Galgano Abbey: About 40 minutes from Siena lies one of the most evocative places in Tuscany: a massive, roofless 13th-century Gothic abbey where the floor is made of grass and the sky serves as the ceiling. Just a few steps away, in the Hermitage of Montesiepi, you can see with your own eyes the real "sword in the stone" embedded by the knight Galgano in 1180.
• A toast among the vineyards of Chianti Classico: Before heading back north, treat yourself to a stop in Chianti. The homeland of Italy's most famous wine is dotted with fortified villages like Castellina and Radda, perfect for a cellar wine tasting.

Your Tuscan refuge awaits

Once back home, there is nothing better than sipping a glass of Sienese red wine by the pool or in the garden to wind down a Tuscan day you will surely never forget!

Discover our available properties and book your favorite:

• Chianti e Siena
• Il Troscione - 10 Sleeps
• Villa Santalberto - 12 Sleeps
• Lucca e dintorni
• Pisa e dintorni
• Pistoia e dintorni
• In Versilia