If you’re wondering about things to do in Tuscany in September, look no further. We have you covered. From witnessing the golden autumnal colours dazzling over the Ponte Vecchio in Florence, Italy this September to the dizzy heights of the famous towers of San Gimignano in September, this is truly a magical time to visit Tuscany.
Without the summer heat forcing its visitors to take shade, it’s the perfect time of year to try outdoor activities and explore the ancient cities and towns this region has to offer. A chance to see the changing colours of this almost movie-like backdrop that begs to be discovered. We’ll travel through the best known places to the best kept secrets of Tuscany and show you just why it’s the only place for your holiday this September.
In this article
September in Florence
September in Florence is one of the best times to visit this iconic city, the summer crowds start to disperse, and the weather softens into warm, golden days, while the city buzzes with festivals.
Wander through the historic center to see the Duomo and Ponte Vecchio in a more relaxed atmosphere, then head into the quieter Oltrarno, which literally means beyond the Arno, for artisan workshops and trattorias. This is where you will find a more local and traditional view of Florence away from the main tourist attractions. Our favourites include a visit to the lively Piazza Santo Spirito for an Apertivo, a museum visit in the fashionable Palazzo Pitti or stroll (passeggiata) through the breathtaking Boboli Gardens.
September also brings the Rificolona Festival (Festival of the Lanterns) on 7th September, when children parade through the streets with colorful paper lanterns in honor of the Virgin Mary.
Food lovers can enjoy seasonal Tuscan flavours at this time of year such as figs, grapes, and of course, the first taste of the grape harvest in nearby vineyards. A Tuscan delicacy at this time of year is schiacciata all’uva. A sweet bread made with this season’s grapes.
It’s the perfect month to combine Florence’s Renaissance treasures with the rhythms of local life, lingering in piazzas as the evenings stay pleasantly mild.
Sam Gimignano in September
As with visiting any Tuscan location at this time of year, San Gimignano’s weather in September strikes the ideal balance of that end of summer warm air during the day. Excellent for taking long strolls around the medieval town and having lunch al fresco in the local piazza. In the evening the temperature starts to drop a little, so it’s cool enough to have a comfortable sleep and still stay out soaking up the evening activities that San Gimignano has to offer.
Don’t miss the best panoramic views of San Gimignano and the Tuscan countryside from the tallest tower in town, the Torre Grossa. In fact there are numerous towers to explore that date back to the 14th century when the wealthy residents of the town fought to build the tallest tower leaving us with an incredible skyline to behold! There is also an excellent exhibit of a detailed hand crafted model of the town with historic information for any visiting history enthusiasts at the San Gimignano 1300 Museum.
In San Gimignano during September there is also the Festival Barocco which usually runs for the whole month although check ahead before your visit. This is a collection of incredible live events of baroque music hosted throughout the town held at church halls and piazza’s. There are also some lectures and workshops dedicated to learning more about baroque music. Another festival which is on during the first week in September is Medioevo in Rocca, medieval festival at the fortress, it is a living medieval pageant with a line up of costumed drummers, jugglers and musicians.
Prefer a quieter night? Take an evening stroll and sip some
Vernaccia vino, a local wine that has been produced for centuries, at one of the enotecas while you watch the world go by in the piazza!
Siena in September
September is one of the best times to visit Siena, when the summer crowds have thinned, but the city still buzzes with life after the famous Palio horse race in the Piazza del Campo. The warm Tuscan sun lingers, casting golden light over Siena’s medieval brick lanes, offering the best photo opportunities that capture the essence of the Tuscan light.
Meandering through the contrade, the city’s historic districts, you’ll still feel the festive spirit of the Palio as flags and colours hang proudly from windows and archways. Outdoor cafés spill out into the piazzas, perfect for lingering over a glass of Chianti or a plate of pici pasta, while the cooler evenings invite leisurely strolls along Siena’s sloping streets.
The two main attractions to see in Siena are the famous Piazza del Campo, an iconic shell shaped square in the heart of the town centre where they host the Palio horse race, surrounded by bustling cafes that are perfect for soaking up the Sienese vibes. Next discover Italian gothic architecture by exploring the Duomo di Siena, this stand out masterpiece is a landmark building with its famous black and white striped marble.
September also marks the grape harvest in the surrounding countryside, making it the ideal moment to combine city exploration with vineyard visits in the Chianti hills.
Tuscany’s best kept September secrets
If you think Tuscany is only rolling hills and Renaissance cities, September is the month to discover its wilder side. You can still swim in Tuscany in September, hike through volcanic landscapes, and stumble across hidden coves with hardly anyone around.
One of the most underrated areas is Maremma, in southern Tuscany. This region remains a well-kept secret compared to Chianti or Florence, yet it’s bursting with natural beauty and coastal gems. For hiking, head to Monterotondo Marittimo’s Le Biancane Nature Park, a surreal landscape of steaming vents and white rocks shaped by geothermal activity.
Swim in Tuscany in September
For seaside adventures, explore the coastal fishing towns, elegant harbors and local medieval streets that line the Maremma coast and are home to award winning beaches that you won’t find anywhere else. A few we love are:
- Talamone: A dramatic little seaside village perched on a rocky promontory, Talamone is perfect if you love wild beauty and adventure. Its crystal-clear waters and stony beaches are a haven for snorkelers and windsurfers, while the medieval fortress watching over the bay adds a touch of history to your beach day. There are cafes and restaurants hidden amongst the winding streets, grab some lunch and head to the little garden near the top for the perfect view and little breeze!
- Porto Ercole: Elegant and picturesque, Porto Ercole combines sandy coves with a chic seaside atmosphere. Surrounded by Spanish fortresses and lush Monte Argentario hills, it’s ideal for those who want sunbathing mixed with a bit of glamour, fine dining, and photo worthy views.
- Castiglione della Pescaia: Famous for its long stretches of golden sand and shallow waters, this is a family-friendly paradise. The clean, Blue Flag beaches pair beautifully with the old town’s castle and lively evening passeggiata, making it one of Tuscany’s most beloved coastal escapes.
- Cala Violina: A beach so pristine it feels like you’ve stepped into a postcard, definitely one of the best kept secrets in Tuscany. It’s said that the sand is so soft it plays music under your feet as you explore, absolutely magical and one of a kind.
Best hiking in Tuscany in September
September also makes for the best hiking in Tuscany: trails are cooler, vineyards and olive groves are at their most photogenic, and coastal routes reward you with refreshing swims at the end. Two excellent hikes in Maremma are:
- Uccellina Mountains Trail (Parco della Maremma): starting from Alberese, this hike takes you up through Mediterranean scrub and oak forests to panoramic ridges overlooking the Tyrrhenian Sea and even as far as the Argentario peninsula. Wild boar and deer often cross your path.
- Cala Violina Coastal Path: beginning near Puntone di Scarlino, this moderate seaside hike winds through pine woods and maquis scrub, with breathtaking sea views, before dropping down to Cala Violina itself—perfect for combining trekking with a swim.
Before you set off, make sure you know what to pack for Tuscany. Think light layers for cooler evenings, comfortable shoes for cobblestone streets and hikes, and swimwear for those last glorious swims in the Mediterranean.
So, what to do in Tuscany in September? Explore the hidden gems of Maremma, swim in secluded coves, wander Etruscan villages, hike along wild trails, and embrace the slower rhythm of late summer. It’s Tuscany with fewer crowds, golden light, and plenty of surprises waiting for you just off the beaten path.