Italy Travel Tuscany

Tuscany in the Fall : 5 Reasons to Visit

November 3, 2019
Looking out on the winding tuscan road

Tuscany in the Fall: has a nice ring to it right? While the most popular time to visit this region is in the summer, it can be hot, crowded and expensive. The fall, though? Bellisima! We just got back from 3 days in Tuscany in late October and wow was it spectacular. I’m going to tell you the 5 reasons why a trip to Tuscany in the fall will make your year. 

1. The Weather

Now I’ll be honest, I wasn’t quite sure how the weather situation would shake out for us. I’ve heard that it can go either way for late October. I was checking obsessively every day, seeing rain in the forecast but hoping it would change. Luckily for our 3 days in Tuscany we had ABSOLUTELY perfect weather*. An average of 75 degrees daily, almost no clouds. 

*Just as an FYI: the locals told us the weather in late October is usually chillier and more overcast. Of course, no one can 100% predict the weather but planning your trip for late September/Early October might be safer for expecting those perfect temps. 

(From top left: Views near our AirBnB, Sunny days in Siena, Approaching Golden Hour near Asciano.)

2. The Prices

I had to rub my eyes in disbelief when checking AirBnB pricing for Tuscany for our trip. Everything looked amazing and most options were under $150 a night (for 4 people!) I’m talking stone villas with pools and unreal views. We ended up booking this option which had an infinity pool, hot tub, fireplace and 2BR 2BATH, all for $108/night. 

Chianti for Four (AirBnB)

Scenes from our AirBnB

“There are almost no words to describe how perfect our stay was at this property. We had the place virtually to ourselves as it was off season and it felt like our own little Tuscan Paradise. The view and the accommodations are even better than the photos and we thoroughly enjoyed the use of the hot tub & fireplace. It was a bit chilly to use the infinity pool but it was still open, enhancing the view. With 2 couples staying there it was perfect -you have your own private area of the house with your own bathroom and can use the common areas together.

Fernando, the local host provides plenty of tips about the area, restaurant recommendations, and you can look forward to a gifted a bottle of olive oil that he harvested as well as a bottle of local wine. It’s a bit off the beaten path, so quiet, but within a 30 minute drive of Siena and the Val d’Orcia. I would 100% stay here again and recommend to anyone looking to have a tranquil and relaxing vacation in Tuscany.”

My review for our AirBnB

3. The Scenery

Driving around the countryside I had Sting’s “Fields of Gold” playing in my head constantly, as it is an accurate description of what was surrounding me. Tuscany in Autumn is literally rolling golden hills dotted with vines and cyprus trees (with the occasional villa). It’s breathtaking and dreamy and can’t be missed.

I would recommend doing a day of driving around the Val D’Orcia (a Unesco World Heritage Sight), which is known as the prettiest drive in Tuscany.

Great stops along the way:

  • Buonconvento: Charming walled village, great spot for lunch
  • Capella Madonna di Vitaleta: Tiny chapel in the middle of a field
  • Winding Road near Asciano: Gorgeous view (see top photo in post), go for golden hour
  • Pienza: Another walled city, very charming.

(From top left: Aperol Spritz in Buonconvento, Rolling Hills in Val D’Orcia, Twirling near the Tuscan Winding Road, Tiny Bouquet at the Capellla, the Streets of Pienza.)

Here is a Google Map of the spots we visited in the Val D’Orcia for easy reference, also with the approximate location of the AirBnB:

4. The Seasonal Food/Drink

The region of tuscany is filled with farms so there is no shortage of fresh and local eats. Truffles are in season in autumn and therefor easier to obtain and afford. Speaking of mushrooms, Porcini are also in season and perfect with pasta. The farmers are harvesting the olives for new oil, the grapes for wine. If you are a meat eater, wild boar is hunted in the fall so the charcuterie game is strong. 

If you want an amazing farm-to-table culinary experience with a killer view (and animal friends), head to Podere Il Casale for an incredible meal. I recommend sampling the cheese plate (Pienza is known for it’s cheese) and homemade pasta. Walk to grounds to say hi to the resident fluffy dog, a heard of friendly goats, a loud burro and colorful peacocks.

A Few Other Places we Ate/Drank along the way:

La Locanda Dei Grulli | Via Vittorio Veneto 6 | Ambra Pietraviva, 52021, Bucine, Italy

A nice local restaurant with a mini Italian grocery on site. Delicious food and good service!

Fabbrica Pienza

A very modern organic vineyard with a sleek tasting room. 10 Euroes for 3 (hefty) tastes. Enjoy the sculpture on the grounds by Ugo Rondinone, the same artist who did the 7 Magic Mountains in Vegas. Tasting room open April-Late October.

Scenes from Podere Il Casale near Pienza

5. The Crowds

Or should I say, the lack of crowds? Not only was it easy to find a place to book only a week in advance, we were also able to see a lot of the “popular” sights in the region without throngs of people. The famous winding road and the Capella Madonna di Vitaleta were both surprisingly uncrowded (the former we even visited during golden hour and still got amazing “people free” photos.)

In conclusion, the fall is a perfect time to visit Tuscany. Have I convinced you yet? Your eyes, stomach and wallet will certainly thank you.

For other Fall Travel ideas, visit my guide to visiting Provence in Autumn!

Make sure to pin this post for when you plan your trip!

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