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In the southern part of Tuscany lies the region of Siena, holding some of the most beautiful villages in all of Italy. It makes sense that this region is one of the most visited in Tuscany, making Siena a perfect point of entry to the region. Each town has different look to it, offering plenty to see, eat, and do while in southern Tuscany.

When we spent time in Tuscany, we spent two days in San Gimignano, spending one of it exploring Chianti. Afterwards, we made our way a bit further south to explore other towns I had high on my bucket list, like Montepulciano and Pienza. Every minute was magical, and it felt like a dream driving through the rolling hills. Popping in and out of towns by car was the best way to explore, and I couldn’t recommend it more!

Here’s a quick guide to a mini road trip through Siena Province, Tuscany.


Where to Stay in Siena Province, Tuscany

  • Castello Di Casole: This luxurious hotel sits atop a beautiful property, with views of Tuscany. The infinity pool, expansive spa, and castle like hotel is truly one of a kind. It’s location is central to Siena and other surrounding areas.
  • Poggio Piglia: Based out of Chiusi, this small boutique hotel has 9 rooms in an old villa, with a views over the valley. Located further south in Tuscany, and driving distance to most areas.


Places to Visit in Siena Province via Car:

Siena: One of the largest towns in Tuscany, this iconic walled city is also one of the busiest. It is definitely worth stopping by to see it, and the Piazza del Campo is stunning.

Montalpuciano: We drove through it, and wish we would of jumped out to see more of it. A smaller town, it has many shops and cafes to spend the afternoon in. It is a medieval and Renaissance commune rich with with history.

Pienza: Set in the Val d’Orcia (where all the iconic Tuscany photos are from) is now a World Heritage Site for its cultural landscapes and Renaissance history. One of my favorite stops in Tuscany, where you can find an endless supply of fresh pecorino and cured meats.

San Quirico d’Orcia: A very small town to stop in for an hour or so for a stroll.

Montalcino: The most beautiful of them all, the views are breathtaking. Save plenty of time to explore this town as it has plenty to offer.  This area has plenty of wineries you can stop in to try the Brunello di Montalcino wine!


Restaurants in Siena Province to Check Out

  • Walter Redaelli: Reccomended by Michelin Guide, this old farmhouse has a Tuscan feel both inside and out. Local ingredients with a high emphasis on meats create a fantastic menu.
  • Santa Chiara: Set in an old convent, this pre-fixed menu has fresh pasta and regional dishes.
  • Tuscany Divine: A local has setup one of the best and fair-priced meals in the region, where you get to try a bit of everything for a pre-fixed price.
  • Restaurant at Poggio Piglia: An elegant, white-linen style dinner with a small seasonal menu.
  • Osteria Enoteca Osticcio: The restaurant with a view that surely books far in advance. Tried to eat here, but couldn’t get a seat!

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PS — Are You Booking a Trip Soon? Use My Booking Checklist!

These are the sites I use most to book my own trips. Using the links below is a great way to support Bon Traveler’s travel journalism at no extra cost to you. If you need help organizing your itinerary, get my free travel itinerary template here.

1. Book Your Flights

Use Skyscanner to find the best flights. It searches 100s of airlines and websites across the globe to ensure you’re not missing out on any route options or deals.

2. Book Your Accommodations

Use Booking.com for hotels and guest houses. They have the biggest inventory and consistently offer the best rates.

3. Book Your Tours & Experiences

Use Viator or Get Your Guide to find the best tours and experiences. They are my favorite tour search engines. I always check both as their inventory varies depending on the destination.

4. Book Your Car

Use Discover Cars or Rentalcars.com to find the best car rental deals. I recommend comparing rental agency reviews on Google to ensure you are booking with the best company in that destination, as the reviews are often more accurate than the car rental search engines.

5. Don’t Forget Airport Lounge Access

Get a Priority Pass membership to gain access to 1,400+ VIP lounges and airport experiences worldwide. The Priority Pass app is the first thing I check when I have a layover. I’ve been a member for over a decade, and having a comfortable place to relax before and between flights makes air travel so much more enjoyable.

6. Don’t Forget Travel Insurance

I never leave the country without travel insurance. It provides comprehensive protection in case anything goes wrong (ie. illness, injury, theft, and cancelations, etc.). I use it frequently for my travels to stay protected.

My favorite companies that offer the best coverage and rates are:


Xx,
Jessica

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