Tuscany is one of Italy’s most sought-after regions, known for its exquisite wine, charming hilltop towns, breathtaking rolling hills, and meticulously curated vineyards. That said, the area is huge, so it can be overwhelming to know where to begin. After 15 years of visiting this beautiful region, I’m excited to share my insights on where to stay—and where to avoid—during your Tuscan adventure.
Pro Tip:
- Bookmark this post in your internet browser you can circle back to it later
- Check out our guidebook page on Tuscany for more advice/resources
- Sort through these tours and activities so get the most from your experience
What You Need to Know About Tuscany
Tuscany is a region of Italy famous for red wine and pretty incredible photos for social media. Jokes aside, in the correct areas, you’ll be surrounded by some of the most beautiful and curated countryside you’ve ever seen.
In the wrong areas, you’ll be trapped in the noise of highways and industrial parks. It’s rare, but it definitely exists.
There are some cities and regions you can get to in Tuscany by train and others that will require a car.For first-time visitors to Italy looking to explore Tuscany without a car, there are several charming destinations that are easily accessible by public transport. Here are some top picks that should definitely be on your list:
That said, I highly recommend driving in Tuscany as the roads are easy to navigate and it is very pleasurable. The only downside is cameras that give you speeding tickets which is avoidable if you don’t speed.
As a lover of stunning views, pleasant weather, and fine wine, my recommendations will focus on helping you achieve those goals. To make it easier for you, I’ve broken down my suggestions based on different traveler types, so you can find the perfect area for your needs. Plus, I’ll share my top accommodation picks to enhance your experience in Tuscany.
Our Partnership with Booking.com. We’ve partnered with Booking.com because they have the most options, great prices, and a solid loyalty program. While we receive a commission from your booking, which helps fuel our content, we do not choose hotels based on receiving a commission. Almost every hotel and rental property is on Booking.com, so we simply promote the best ones.
What we’ll cover:
Montalcino & Val d’Orcia
If you have a vision of Tuscany that you want to realize, Montalcino is the perfect picture. This stunning hilltop town and region is renowned for producing some of the finest wine in the world. Here, the land is prized, the inhabitants affluent, and the entire area is beautifully curated.
Montalcino is literally a scene ready to be framed. For wine enthusiasts, it serves as both the literal and figurative epicenter of Italy’s wine culture. The region is especially famous for its Brunello di Montalcino, made from the Sangiovese Grosso grape.
I recommend spending two to three nights in the area. While it’s undeniably beautiful, there’s not much to do beyond indulging in delicious food, sampling exquisite wines, and taking breathtaking photos. If you’re looking to unwind, there are some resorts where you can enjoy poolside relaxation and spa treatments, making it easier to extend your stay if you’re content with a cycle of relaxation: breakfast, pool, wine, food, spa, wine, pool, food, wine, sleep, and repeat.
Below are plenty of great accommodation options for Montalcino, both in city and in the countryside. If you are interested in this area and want to read more, check out our dedicated content on Montalcino.
Capanna Suites
€€€ | North of Montalcino | Great Views | Luxury | Pool
Capanna is a larger producer of wines in Montalcino who has done very well in the past decades. With open minds and ambitious goals, they built one of Montalcino’s most luxurious places to rest your head. It features an epic pool, restaurants, an outdoor deck overlooking wine country, and of course endless reserves of their wine.
Castello di Velona
€€€€ | Super Luxurious | Pools | Views | The Works!
If you are looking for an amazing experience, Castello di Velona is a great option. It’s a castle overlooking vineyards as far as the eye can see with tons of amenities. If you have the money it is a no-brainer!
Villa Le Prata Wine Resort
€€€€ | Luxury Residence | Pool | Epic Views
Looking for a zen-like vineyard with a hotel on site? Villa le Prata is a great choice for anyone looking to relax comfortably in a pristine setting. It is a special place for a lack of better words.
Borrgo Canaliccchio di Sopra Relais
€€€ | 5 Star | Pool
This is a beautiful property that is tranquil and luxuriouos in a low-key Tuscan way. The hotel is as curated and perfect as the vineyards themselves. A great choice.
Castello Banfi Il Borgo
€€€€ | Montalcino Countryside (SW) | 5 Star Accommodation | Michelin Dining | Epic Pool
Castello Banfi is by far the largest producer of Brunello wines on the planet as they own the most territory. Their grounds are absolutely immaculate and their structure is beautiful. A famous line of cypress trees lines their kilometer or so long driveway into their estate.
Siena
Hilltop Town | Accessible by Train | 2 hours from Florence
Siena is a medieval town that is larger than San Gimignano and smaller than Florence. Siena is known for a few things, including a famous horse race that happens in their center square known as the Palio.
Like most of Tuscany, Siena is famous for hearty meat dishes, including anything made from wild Boar meat.
Siena is deep in southern Tuscany and near the most famous wine producing region, Montalcino/Val D’Orcia. It is a great area to choose if you are looking for a larger Tuscan town accessible by train.
You could even stay in a countryside B&B/Agriturismo by taking the train to Venice and a taxi to your accommodation. Many B&Bs nearby would likely even pick you up at the train station.
Below are some hotel and B&B options, but if you want to read more about the area check out our dedicated content on Siena:
Relais degli Angeli Residenza d’Epoca
€€€ | B&B | Siena, Istrice & Lupa | Old-World Charm
This B&B feels more like a castle than anything else! Gorgeous victorian interior with luxury finishes and comfortable amenities.
Castello di Leonina
€€€ | 13th-Century Castle | Overlooking Tuscan Hills
Castello di Leonina, a historic noble residence from the 13th century, is nestled in Asciano and boasts breathtaking views of the rolling hills. This enchanting property features a wellness corner, a soothing Finnish sauna, and a swimming pool complete with a hydromassage area, making it the perfect retreat for relaxation and rejuvenation.
Castel Monastero
€€€ | 5-star hotel | Restored Medieval Monastery
Only a 26-minute drive from Siena, Castel Monastero is cradled in lush greens overlooking fields and century-old forests.
Bosco Della Spina
€€€ | Center of Tuscan CountrySide | Panoramic Views
Bosco Della Spina offers panoramic views of the Sienese hills, along with an outdoor infinity pool and a garden. The building was designed and built by the owner, and the restaurant serves traditional Tuscan dishes using local ingredients.
Gli Archi di Corsanello
€€€ | Agriturismo | Countryside | Swimming Pool
Only a 23-minute drive from Siena, Gli Archi di Corsanello offers garden views, an infinity pool, and an open-air bath so that you can enjoy that Tuscan air at all times.
Borgo San Lorenzo a Linari
€€ | 3 Star Hotel | Southwest Countryside | Pool & Tennis Courts
A really nice complex just southwest of Siena with a pool, tennis court, and a really cool stone courtyard equipped with a well. Love this style! Definitely click below for more photos.
Grand Hotel Continental Siena
€€€ | 5-Star Hotel | Near Piazza del Campo and the Duomo
This is the only 5-star hotel in the historic center of Siena, situated just steps away from Piazza del Campo and the Duomo. Set in a magnificent 16th-century building, it features an opulent ballroom and an impressive underground wine cellar that hosts daily wine tastings.
Palazzo Giorgi
€€ | Apartment | Siena, Piazza del Campo | Great Views!
Centrally located apartment in Siena with fantastic views and updated finishes.
Agriturismo La Roverella
€€ | Agriturismo | Southern Countryside | Vineyard
This quaint vineyard/agriturismo has a few rooms, great food, and great food. A great option for a night or two stop over on your way through Tuscany.
La Terrazza Sul Campo
€€ | Apartments | Siena, Piazza del Campo | Unbeatable Views
Extremely classy and finely finished apartments right in Siena’s main square which is Piazza del Campo. The photos say it all!
Il Chiostro del Carmine
€€ | B&B | Siena, Aquilla | Classic Medival touches
If you enjoy archways, stonework, and the feeling of a castle then this B&B is for you. Great prices and value here!
Palazzo del Papa
€€ | B&B | Siena, Piazza del Campo | Modern with Rustic Charms
A great little B&B right by Siena’s main square which has modern finishes and comfortable amenities. A great option with excellent reviews.
San Gimignano & Volterra
Hilltop Town | Picturesque Countryside | 1 hour from Florence | No Train Station
San Gimignano is a GORGEOUS hilltop town. It is large enough to explore it for a few days without getting bored but small enough that when you get to the edge of town, you are met with stunning views.
I highly recommend San Gimignano if you are A, okay renting a car or B, can afford to hire a car to drive you back and forth.
The only downside to San Gimignano is you are far from Tuscany’s best wine regions. Yes, you can find good wine in the area, but the best wines come from Val D’Orcia in the south of Tuscany. This is still our #1 recommendation due to its proximity to Florence and overall beauty. Besides, you can buy great wine from the south of Tuscany anywhere in Tuscany!
I highly recommend staying just outside San Gimignano, a 10 to 15-minute drive away, as opposed to staying in the center. Below are some more accommodation options and you can read our dedicated content on San Gimignano:
- Where to stay in San Gimignano
- Best restaurants in San Gimignano
- San Gimignano tours & things to do
- Top things to do in Tuscany
Borgo Pignano
€€€€+ | 5-Star | Infinity Pool | Views
If I have unlimited money, this is probably my choice. Boutique, luxurious, private, and overall incredible.
Castello di Casole, A Belmond Hotel
€€€€+ | 5-star | Pool | Views
A beautiful castle in the foothills of San Gimignano. Luxury meets luxury meets luxury. What else could you want?
COMO Castello Del Nero
€€€€+ | 5-star | Curated Luxury | Eclectic
This is actually a semi-reasonable priced 5 star hotel in Tuscany. Large great rooms that are decorated beautifully. Elegant interior, great service, and incredible amenities.
Agriturismo II Segreto di Pietrafitta
€€ | Ariturismo | Great Views | Pool
When I dream about Tuscany, Il Segreto di Pietrafitta is where that dream takes place. It has all the characteristics of a Tuscan paradise including the cypress trees, the views, and the old stone structure. It’s perfect.
B&B Countryhouse Villa Baciolo
€ | B&B | Great Views | Pool
This place is amazing value for what you get. The structure has a lot of gorgeous Tuscan characteristics such as stonework, climbing vines, and incredible views.
Il Borghetto Tuscan Holidays
€€ | Serviced Apartments | Pool | Great Views!
Il Borghetto is a great option since they offer really cool apartments inside a complex with a pool, restaurant, and other amenities. It is a great option for families or anyone who likes a little extra space!
Le Viole
€€ | Centro Storico | Apartment | Terrace!
Great 1000 square foot apartment with 1 bedroom, a couple of pull-out couches, and two bathrooms. The best part is the terrace which is a big factor for me when renting an apartment.
Hotel Leon Bianco
€ | 3 Star | Centro Storico | Lots of Amenities
While I appreciate rental properties, I prefer a hotel hands down. I like a quick check-in & out and I don’t want to mess around trying to coordinate when I will arrive. I also like the views here which makes it a great option!
Sangi Studio Apartment
€€ | Centro Storico | Apartment | Great Views!
Great central location which is right in the middle of the action. Incredible views of the main square of San Gimignano and Duomo.
Leave a Comment