Val d'Orcia
A province of Siena, and UNESCO World Heritage Site, this is one of the most breathtaking places on earth. There are several places in the Val d'Orcia that you can stop and see, beautiful views for lunch, some of the oldest abbeys in the world, and small towns with castles and forts.
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Price: free to arrive and explore the area
Hours: open always, it's a province so there is no restriction on driving through stopping in.
What to wear: If you're planning on climbing one of the forts, it would be wise to wear closed shoes and nothing too short ladies, just because you will be climbing ladders. If not, you can wear whatever you feel most comfortable in depending on the season.
What to know about Val d'Orcia: My best friend and I had a car and we were trying to hit all of the towns found on several blogs and in the Lonely Planet book in one day, we found it was too much so we split it into two and really got to enjoy our time in each place. I would recommend doing that.
Helpful link: https://www.discovertuscany.com/valdorcia/
Abbey of Sant'Antimo
Close to the town of Montalcino is this beautiful Abbey built in the 12th century. Located in the middle of the Tuscan countryside, it's natural Travertine color fits it's surroundings making the whole thing a spectacular experience. Go and learn the legend behind the famous Abbazia di Sant'Antimo and Charles the Great.
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Price: free, can give a donation or offering inside if you'd like to
Hours: Weekdays 10:30 am - 12: 30 pm and 3:30 pm - 5:30 pm. Sundays and Holidays 9 am - 10 am and 3:30 pm - 6:00 pm.
What to wear: This church is quiet and people went in and out wearing sleeveless shirts. I wore a t-shirt just in case, skirts and shorts are perfectly fine.
What to know about this church: it's out of the way, the best way to get there is by car.
Address: 53024 Castelnuovo dell'Abate (SI)
Helpful link: http://www.antimo.it/en/
Helpful link: http://www.discovertuscany.com/montalcino/abbey-of-sant-antimo.html
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Antinori
The Marchesi Antinori vineyard is one of the most breathtaking places in the world. Home to delicious wine, you can go up to the restaurant Rinuccio 1180 which is wonderful, it's best to make a reservation. You can also take a wine tour with a group, that ends in a wine tasting. There are also private wine tours available for groups 10 people or more. Both of these tours you need to book in advance. The guided tour lasts about an hour and a half. Taking you through the wine cellars and explaining the process of making the wine. The tours are available in English and Italian.
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Price: 32 euros per adult, 8 euros per junior ticket (6-17 years old), free for anyone 6 years or younger
What to wear: Wear something comfortable to do the tour, you will be walking around, the tour doesn't take you through the vineyards so don't worry about ruining your shoes. The restaurant isn't very fancy but it's nice, I recommend a summer dress or something that you won't be too hot in the summer months.
Helpful Website: https://www.antinori.it/en/
Pienza
This beautiful little town is less than 20 km away from Montepulciano and Montalcino (both of which are amazing). This small town has spectacular views, a charming little piazza, and some seriously delicious ice cream. Pope Pius II was born here, giving the town it's name. This little renaissance town is another UNESCO World Heritage Site, with views of the Val d'Orcia.
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Price: free to visit
What to wear: wear whatever you would wear to see any little Italian city in whichever season you're visiting in. It's a small town, you won't be doing lots of walking here.
Helpful Website: https://www.visittuscany.com/en/ideas/5-reasons-to-visit-pienza/
Tentennano Fortress
A photo taken from the top of one tower of the fortress, you can see the other tower in the left of photo. This fortress was very important for the Republic of Siena to exert their power of rivaling families, the history dating back to 1100s.
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Price: 3 euros
What to wear: wear shoes to climb, I did it sandals that stay on my feet (aka not flip flops). Ladies, like most towers you have to climb there is a ladder, be careful wearing short skirts or dresses. The top of the tower was really windy so hold on to your hats and sunglasses.
Helpful Website: https://www.visittuscany.com/en/attractions/tentennano-fortress/
San Gimignano
San Gimignano is a gorgeous medieval town between Florence and Siena. This town is another UNESCO World Heritage Site. It's definitely worth climbing the tower, the view is wonderful at the top, and unlike the tower in Siena, or several other towers, this one is just stairs in a wide open space making it one of the easier towers to climb. I recommend grabbing a glass of wine at Divinorum. San Gimignano also claims to have the best ice cream in the world, I had better in Florence and Pienza, but you should see for yourself.
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Price: free, price to climb the tower is 9 euros
What to wear: wear shoes to climb, I did it sandals that stay on my feet (aka not flip flops).
Helpful Website: https://www.discovertuscany.com/san-gimignano/
