So you want to stay in Tuscany?  Tuscany is full of beautiful towns, vineyards, and unforgettable landscapes—but choosing the right base for your first visit can make a big difference in how much you enjoy and experience the region.

Whether you're planning a week of wine tasting, art and history, or relaxed countryside drives, here’s a guide to four of Tuscany’s most popular (and picturesque) areas: Chianti, Val d’Orcia, the Lucca area, and Cortona.

 

 🟢 Chianti – A Classic First-Time Base

Why stay here: 

Chianti is centrally located between Florence and Siena, which makes it the most convenient base for first-time travelers. It’s dotted with wine towns like Greve, Castellina, Panzano, and Radda, and connected by the scenic Chiantigiana Road.

Pros: 

- Easy day trips to Florence, Siena, San Gimignano, and Pisa 

- Shorter drive times and well-maintained roads 

- Ideal for wine lovers—Chianti Classico tastings everywhere 

- Plenty of charming hilltop villages and weekly markets 

Cons: 

- Can be more popular (and pricier) in high season 

- Less dramatic landscape than Val d’Orcia or Cortona 

 

 🟡 Val d'Orcia – Cinematic Beauty & Quiet Roads

Why stay here: 

A UNESCO World Heritage site, Val d'Orcia is known for its rolling hills, golden light, and iconic cypress-lined roads. Towns like Pienza, Montalcino, and Montepulciano are postcard-perfect and quieter than the Chianti region.

 

Pros: 

- Stunning, wide-open scenery 

- Fewer crowds, slower pace 

- Ideal for food, wine, and photography 

- Home to Tuscany’s best hot springs (like Bagno Vignoni) 

 

Cons: 

- Longer drives to Florence or other cities 

- More remote; better for travelers comfortable with countryside driving 

 

 

 🔵 Lucca Area – Charming, Coastal Access & Under-the-Radar

Why stay here: 

Located in northwest Tuscany, Lucca is a walled Renaissance city with a relaxed vibe and excellent access to the coast. It’s perfect for those who want to mix culture and seaside escapes.

 

Pros: 

- Flat, walkable city with lovely piazzas and bike-friendly walls 

- Close to the beaches of Versilia and the Cinque Terre 

- Easy day trips to Pisa, Florence, and even Liguria 

- Less touristy feel than other areas 

 

Cons: 

- Slightly less “classic countryside” than Chianti or Val d’Orcia 

- Not as centrally located for touring all of Tuscany 

 

---

 

 ❤️ Cortona – Elegant, Elevated, and Full of Soul

Why stay here: 

Perched on a hillside near the border of Umbria, Cortona was made famous by Frances Mayes book “Under the Tuscan Sun” #francesmayes it has a unique charm that’s hard to match. With breathtaking views, art and history, and a lively cultural scene, it’s long been a favorite for travelers looking for an authentic yet stylish base.

 

Pros: 

- Gorgeous town with artisan shops, galleries, and great restaurants 

- Easy access to both Tuscany and Umbria (Perugia, Assisi, Lake Trasimeno) 

- Dramatic countryside and sunflower fields 

- Ideal for those seeking a balance of quiet and character 

 

Cons: 

- Some hilly terrain (parking and walking may require a bit of effort) 

- Slightly farther from Florence (1.5–2 hrs), but great for slow travel 

 

 🏡 We Can Help You Decide

 

We offer a carefully curated selection of villas and agriturismo stays in all four regions—whether you're dreaming of sunset dinners in Chianti, quiet mornings in the Val d’Orcia hills, beach day escapes from Lucca, or evenings on a terrace in Cortona.

 

📩 Contact us to talk through your ideas and travel style. We’ll help you find the perfect base—or even plan a two-location stay to experience the best of both worlds.

follow us on instagram

@classicvacationrental