Updated July 2024
In the southern part of Tuscany lies the region of Siena, which holds some of the most beautiful villages in Italy. It makes sense that this region is one of the most visited in Tuscany, making Siena a perfect point of entry. Each town has a different look and offers 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!
Read on for my quick guide to a mini road trip through Siena Province, Tuscany.
Short on Time? Here Are My Top Picks for the Best Hotels in Siena Province:
- Poggio Piglia, for the best boutique hotel
- Castello Di Casole, for the best luxury hotel
Travel Tip: The best way to explore Tuscany is by driving yourself. We use Discover Cars for our rental cars in Europe, choose full coverage insurance, and opt for trusted companies like Alamo, Hertz, or Sixt. Renting a car and driving in Tuscany is quite easy. Book your car with Discover Cars here.
Where to Stay in Siena Province, Tuscany
Poggio Piglia
Based out of Chiusi, Poggio Piglia is a small, 9-room boutique hotel set in an old villa, with a views over the valley. Located further south in Tuscany, and driving distance to most areas. Book the best rates here.
Castello Di Casole
Castello Di Casol is a luxurious hotel that sits atop a beautiful property, with views of Tuscany. The infinity pool, expansive spa, and castle-like hotel are truly one of a kind. Its location is central to Siena and other surrounding areas. Book the best rates here.
Places to Visit in Siena Province by 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 Montalpuciano, 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), Pienza 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
San Quirico d’Orcia is a very small town to stop in for an hour or so for a stroll.
Montalcino
The most beautiful of them all, the views from Montalcino 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!
Where to Eat in Siena Province
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.
Albergo Ristorante Santa Chiara
Set in an old convent, this pre-fixed menu has fresh pasta and regional dishes.
The Restaurant at Poggio Piglia
An elegant, white-linen style dinner with a small seasonal menu.
Osticcio Ristorante Enoteca
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 Accommodations
I use Booking.com for hotels and Airbnb for vacation rentals. They have the biggest inventory and consistently offer the best rates.
2. Book Your Rental Car
Self-driving is the best way to explore most destinations. I use Discover Cars for our rental cars, select full coverage insurance, and opt for a reputable company like Alamo, Hertz, or Sixt.
3. Book Your Tours & Experiences
I use Viator, Airbnb, and Get Your Guide to find the best tours and experiences. They are my favorite tour search engines. I always check all three as their inventory varies depending on the destination.
4. Book Your Private Transfers
For easy, reliable private transfers, I use Welcome Pickups. It’s my go-to for arranging a driver in advance — whether it’s an airport pickup, a hotel-to-hotel transfer, or a day trip. The experience is seamless, with English-speaking drivers and upfront pricing, so you can travel stress-free at every stage of your trip.
5. Get Cell Data for Your Trip
I use Holafly for international cell data. Their unlimited data eSIMs are easy to install, activate instantly on arrival, and let you skip local SIM cards and expensive roaming fees.
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, or cancellations).
My favorite companies that offer the best coverage and rates are:
- World Nomads (best for all-around)
- Safety Wing (best for frequent travelers)
Xx,
Jessica
