Tuscany is one of the most beautiful regions in Italy. It’s peaceful, romantic, scenic, and filled with history, not to mention incredible wine and some of the best food in the country.

Deciding where to stay really depends on what you want this part of your trip to feel like. Are you craving a break from busy cities? Do you want to explore different wine regions? Would you rather stay inside a medieval town with cafés and restaurants outside your door?

There’s a lot to consider, especially depending on what the rest of your Italy itinerary looks like.

Staying in the Tuscany Countryside

This is what we chose, and we absolutely loved it.

Staying in the countryside is the perfect way to slow down between busier cities and fully immerse yourself in nature. All we wanted to do was take in the views, relax, and drink amazing wine, and that’s exactly what we did.

Even if you stay in the countryside, you can still explore medieval towns during the day and then return to your farmhouse or villa for peace and quiet in the evening.

It feels romantic. It feels slower. It feels like you’re in a movie.

We stayed in the Val d'Orcia region, close to Montefollonico. Our villa was beautiful, truly something out of a film. They made their own wine (which we were greeted with upon arrival), and they had a small restaurant on the property serving homemade meals for guests.

We spent afternoons enjoying their wine, ordering charcuterie boards, and relaxing by the pool overlooking the rolling hills and cypress trees. The rooms weren’t modern, but they were clean and comfortable, and honestly, the old-world charm added to the whole experience.

We loved staying here. It was peaceful, scenic, and perfectly located. This type of stay is ideal for couples or anyone wanting a slower pace and beautiful scenery.

Another popular countryside region is Chianti, which is closer to Florence and north of Siena. We chose Val d’Orcia because it’s exactly what I picture when I think of “Tuscany countryside.” It’s also close to some of the medieval towns we wanted to visit like Pienza, Montalcino, Montepulciano, and Monticchiello.

Staying in a Tuscan Town

You could also stay in one of the medieval towns like Pienza, Siena, or Montepulciano.

These towns are incredibly charming and walkable. Staying in town is a great option if:

You have a short stay
You don’t want to rent a car
You want restaurants, wine bars, cafés, and shops right outside your door

It’s more convenient and social. You can step outside at night for gelato or dinner without needing to drive dark country roads.

That said… I’m biased. I still think the countryside is magic. But it truly depends on your travel style.

Transportation: What You Need to Know

If you stay in the countryside, you will 100% need a car.

There is essentially no reliable public transportation between wineries, villas, and small villages. The roads are narrow and winding, and many properties are located on gravel roads.

For us, renting a car in Rome, driving to Tuscany, and returning it in Florence was the best decision. It gave us total flexibility. Yes, it cost a bit more, but the freedom to explore at our own pace was worth it.

We stopped on random scenic roads, visited tiny villages, explored thermal spas, and went to multiple wineries. Having a car is truly the best way to experience the countryside.

If you stay in a larger town like Siena, you can rely more on tours for winery visits, and some towns are connected by bus. However, transportation between smaller towns can be limited and time-consuming.

Parking worries a lot of people, but it’s honestly manageable. Most medieval towns are car-free in the center, so you’ll park outside the walls and walk in. Just follow the signs and watch what locals are doing.

One important warning: driving at night in Tuscany is pitch black. There are no street lights on country roads, and it can feel intense. Plan your evenings accordingly.

But truly, renting a car is the move.

Food and Dining Differences

Staying in town gives you more spontaneity. You can wander into a trattoria, grab gelato after dinner, and choose from several restaurants within walking distance.

In the countryside, dining requires a little more planning.

You might:

Drive into a nearby town for dinner
Cook at your villa
Eat at your property’s restaurant

We often chose to eat at our villa because it was easy and delicious. They also served breakfast each morning. One night we went to a small restaurant in a medieval village, and for lunches we either stopped at trattorias or paired wine tastings with light bites.

If you plan to dine at your accommodation or popular restaurants, reservations are usually required. I recommend asking your host to help call and make reservations, especially since English isn’t always widely spoken in rural areas.

Also, cell service in the countryside can be spotty, so don’t rely too heavily on Google Translate.

What’s Best for Different Travel Styles

Stay in the countryside if you:

Want romance and peace
Love scenic drives and wine
Are comfortable renting a car
Have at least 3–4 nights

Stay in a town if you:

Don’t want to rent a car
Are short on time
Want easy walkability
Prefer having restaurants and shops right outside

What I recommend

You can absolutely experience Tuscany through day trips if you stay in Florence or Siena.

But if you have the time, I recommend splitting your stay:

3 nights in the Tuscan countryside
3–4 nights in Florence

That way, you get the peaceful, cinematic countryside experience and the culture and energy of Florence.

Florence isn’t as chaotic as Rome, but it’s busy with tourists and packed with things to do. Tuscany countryside, on the other hand, felt like stepping into a romance movie, honestly like Under the Tuscan Sun.

You’ll start thinking, “Maybe I could retire here.”

We visited incredible wineries, learned about the winemaking process and history, wandered medieval towns, and drove some of the most scenic roads I’ve ever seen. And when we wanted to truly slow down, we just sat at our villa overlooking the rolling green hills.

I know I’ll visit Tuscany many more times in my life.

Where to Stay in Tuscany: Town vs. Countryside