Siena is one of Tuscany’s dream destinations for anyone who loves all things Medieval. Immerse yourself in the world of the historic contrade, check out the the gorgeous piazza del Campo and feast your eyes on the ever-so-Gothic Duomo.
And after you’ve had your fill of Medieval beauty in Siena, you’re ready to explore its surroundings, that offer some of Tuscany’s top attractions: picturesque small towns just waiting to be explored, beautiful landscapes, ancient castles and wine tasting experiences that will leave you wanting more.
Here we’ve prepared a complete guide on what to do and see near Siena: places to visit (with or without a car), day trips, scenic drives and all the amazing experiences you can imagine!
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Best places to see and things to do near Siena
Visit the most Beautiful Small towns near Siena
You find, literally, countless picturesque small towns to visit near Siena. From the famed San Gimignano with its mighty towers, to off-the-beaten track Colle Val d’Elsa, or little gems like San Gusmè or Bagno Vignoni surrounded by gorgeous landscapes. Exploring the historic small towns and villages near Siena is one of Tuscany’s greatest experiences!
Here’s our complete guide to the 10 Most Beautiful Small Towns to Visit near Siena, some of which you can reach by public transport (bus from Siena).
Medieval Wonders near Siena
Are you a fan of the Medieval? If this is the case, you’ll have plenty to enjoy while exploring the surroundings of Siena. Gaze in awe at the wonderfully atmospheric ruins of San Galgano Abbey, see Tuscany’s legendary sword in the stone, and catch some Medieval castles and fortified villages like Monteriggioni => Find out more about the 5 Medieval Wonders to Visit near Siena that make perfect day trips from Siena, and how to travel there.
Wine Tasting near Siena
The Chianti region, Montalcino and Montepulciano, are the top wine areas in Tuscany, and all within easy reach of Siena, so ehrn it comes to the pleasures of the grape – you’re spoiled for choice! You can organise wine tasting by yourself if you’re planning to drive or rent a car, just remember to contact the cellar and book in advance. In Tuscany it’s not advisable to just turn up at a winery without pre-organising the visit.
For maximum comfort, you can join a wine tasting tour, like this Small Group Wine Tasting Experience near Siena or a wondrous Wine Tasting Experience in a family-run cellar in Montalcino to taste some of the glorious Brunello di Montalcino wine.
Scenic Drives around Chianti and Val d’Orcia
The areas around Siena offer some truly memorable views and idyllic landscapes. Try driving around the vineyards and olive groves in the Chianti, or losing yourself in the dreamy hills of Val d’Orcia. You can easily organise a one day driving from Siena, so check out which of these scenic drives in Tuscany suits you best.
Alternatively, you can join a Guided Tour to be shown around and appreciate the top attractions of the areas and the landscapes in complete relaxation.
Walking the Via Francigena
Some of the most spectacular stages of the pilgrim route via Francigena run near Siena. So if you’d like to add a bit of exercise to your holiday, immersed in beautiful idyllic nature, you can check out the stages of the via Francigena near Siena, and decide what length and landscape suit you. We can promise you that the serene atmosphere of this area will fill your eyes with beauty, and your heart with peace.
Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury to Rome. The rural route takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Once you get to the medieval village of Monteriggioni you’ll be rewarded with a wine tasting.
Tuscany castles to visit near Siena
The many castles that dot central Tuscany remind us that there was a time when battles and power struggles between cities were everyday events. Today these historic edifices watch over the countryside with their impressively fortified structures, some now serving as elegant residences and wine estates.
If you like the idea of wine tasting in grand style, check out Gabbiano or Meleto Castle. At Brolio Castle you can wander the beautiful garden and taste more Chianti wine in their nearby winery. At the beautiful Celsa Castle they offer guided tours of the garden (not the castle interior) by booking on their site.
For an historic tour better head to Sarteano Castle, an imposing fortress that dominates the small town of Sarteano, where you can see what’s left of an impregnable defensive structure that dates back to the 11th century – See their official FB page for info and updated timetable.
* See 8 Amazing Castles to Visit in Tuscany
Hot air balloon ride near Siena
Imagine seeing the gorgeous Tuscan landscape from the air! For a truly unforgettable experience, board a hot air balloon and fly over the hills that embrace Siena in a lovely patchwork of hundreds shades of green: vineyards, woods and olive groves.
Siena hot air balloon rides take off early in the morning so you can see the sunrise in all its glory. You’ll spend about an hour in the air, enjoying the magnificent views over the picturesque countryside, plenty of time to capture the best shots.
Following in the cycle tracks of the Eroica
Follow the heroes of L’Eroica, the annual cycling event in vintage gear was born in Gaiole in Chianti, near Siena, in 1997. Since then it has spread around the world with many Eroica-inspired events, but the original non-competitive cycling race originated in the beautiful and challenging hilly landscapes around Siena.
Church Spotting near Siena
If, like us, you love a good country church or monastery surrounded by ancient trees, near Siena you find two of Tuscany’s fascinating religious sites: the Abbey of Monte Oliveto Maggiore (40 minutes from Siena) in the area of the Crete Senesi, with an amazing Renaissance fresco cycle , and the lovely Romanesque beauty Sant’Antimo Abbey (1 hour from Siena) immersed in a peaceful landscapes of olive groves.
Arty Gardens
How about mixing art and nature? In the Chianti Sculpture Park , Pievasciata, contemporary art installations rub shoulders with trees and nature. It’s a great day trip from Siena to enjoy nature, perfect for kids to get away from sightseeing! How to get there? 25 minute drive from Siena – there’s the direct bus 102 from Siena that stops near the garden.
Swiss artist Daniel Spoerri has an intriguing sculpture garden in Southern Tuscany, called ‘Il Giardino di Daniel Spoerri’, that the artist himself calls the ‘sentimental garden’. You find 113 installations by 55 artists on an area of about 16 hectares, so take your time and wear comfy shoes!
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