Top Day Trips from Siena (Updated October 2026)

Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay...

Embrace the medieval charms of Tuscany's towns on a full-day trip to San Gimignano and Volterra from Siena. With an attentive local guide, walk round...

Combine Chianti's fine wines with its impressive castles on a full-day trip from Siena! Giving the rugged Tuscan landscape a remarkable grandeur, these stunning Italian...

To fully experience la "Bella vita", you need to get out of the city. Taste the local wines & tour the cellars of select family-run,...

Private guided wine tour and tasting in Montalcino, Tuscany to discover Brunello and the most amazing wine estates and cellars that give birth to this...

On this afternoon and evening tour from Siena to Chianti and San Gimignano, explore the beautiful Chianti region – an area rich with dense oak...

Follow your experienced guide on a ride through the Chianti hills on comfortable and easy to use Electric Bikes: you must have cycling experience to...

Taste Tuscany's delicious cheeses and the great Brunello di Montalcino red wines on a full-day private guided tour. See the beautiful Val d'Orcia and receive...

* Only small, authentic, family-run activities * Off-the-beaten path itineraries * Private, exclusive, customizable, flexible, door-to-door tour of Pienza, Val d'Orcia, Montalcino * Local, small...

This is a semi-private which means a maximum of 6 people in tour, so you will have a private vehicle and all the attention you...

This is a semi- private with maximum 6 people in tour so you will have all the attention you need. This tours will give you...

One day bike tour to discover the Chianti region, one of the most important wine area in the world, for the quality of its wines...

Intact, unspoiled nature in the Maremma Park with a carriage ride of about an hour or, depending on the availability of the Park Guides or...

* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan...

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in...

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a...

Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and...

While we take care of every detail, leave the chaos behind and enjoy the best of Tuscany’s landscapes from your stylish Vespa — perfect not...

* Customizable, door-to-door tour of San Gimignano and Chianti Classico, wine and food Tour from Siena * Private and exclusive service * 8 hours in...

Explore Tuscany's picturesque rolling hills on a private, full-day hiking and sight-seeing tour with transport from Siena. Enjoy a scenic, full-day adventure with your expert...

Explore the medieval charm of Lucignano and the artistic treasures of the city of Arezzo. Enjoy a farm-fresh Tuscan lunch with wine before visiting Cortona,...