Discover the best places to stay in Tuscany — from Chianti’s vineyards to Cortona’s rolling hills and Lucca’s elegant countryside. Expert advice from ClassicVacationRental.com to help you choose the perfect villa or apartment for your group.

Planning a Trip to Tuscany?

Tuscany is a dream, golden light, vineyards, and medieval hill towns. But with so many postcard-perfect areas, choosing where to stay can be overwhelming.

As someone who’s explored and inspected villas across every corner of Tuscany for over twenty years, I know that the right base can make all the difference. Here’s how to find the perfect match for your travel style, group size, and dream experience.

1. The Chianti Region – For Wine Lovers and Countryside Dreamers

Imagine winding roads lined with cypress trees, vineyards stretching to the horizon, and the scent of rosemary in the air. The Chianti region, between Florence and Siena, is pure Tuscan countryside.

Best for: couples, friends, and small groups who love wine, scenic drives, and relaxed villa days.

Highlights:

• Vineyards and medieval villages like Castellina, Panzano, and Radda in Chianti

• Easy access to both Florence and Siena for day trips

• Excellent cooking classes and local trattorie

Keep in mind:
Roads are narrow and curvy — perfect for exploring slowly, not for rushing.

2. Near Cortona & the Val d’Orcia – For Family Gatherings and Timeless Tuscany

This is the Tuscany you’ve seen in Under the Tuscan Sun — soft hills, olive groves, and golden light.
Towns like Cortona, Montepulciano, Pienza, and Montalcino offer both rustic charm and cultural richness.

Best for: families, reunions, and longer villa stays.

Highlights:

• Larger properties with private pools and gardens

• Central for exploring Umbria, Siena, and southern Tuscany

• Peaceful countryside perfect for relaxing meals outdoors

Keep in mind:
You’ll need a car here, and Florence is a 1.5–2 hour drive away — ideal if you prefer serenity over city pace. 

3. Near Lucca – For Ease, Elegance, and Exploration

If you like the idea of a historic walled city surrounded by villas, olive groves, and easy train access, Lucca is your place.
It’s elegant, less hilly than southern Tuscany, and offers proximity to both Florence and the Ligurian coast.

Best for: families with young children or seniors, and travelers who prefer smoother logistics.

Highlights:

• Cycle the famous Lucca city walls

• Visit Pisa, CinqueTerre, and Florence easily by train

• Stylish countryside villas, often less isolated

Keep in mind:
It’s not as “vineyard postcard” as Chianti, but makes up for it with accessibility and charm.

4. Beyond Tuscany – The South of France Connection

For families spread across continents, pairing Tuscany and the South of France creates an unforgettable multi-generational holiday.
Imagine a week in a Tuscan villa followed by another near Lourmarin, Cotignac, or Antibes — perfect for reunions or milestone celebrations.

Why it works:

• Excellent air connections via Florence, Pisa, or Nice

• The ideal blend of Italian countryside and French Riviera relaxation

• Easy drives or train links between regions

Best for: large families, celebrations, and “bucket list” summer trips.

Tips for Choosing the Right Location

✅ Match your base to your pace: Want market days and lazy villa lunches? Chianti or Cortona. Prefer day trips and train access? Lucca.
✅ Think logistics: Consider which airport is most convenient for your route (Florence, Pisa, or Rome).
✅ Plan ahead: The best family and event villas book 9–12 months in advance.
✅ Ask an expert: With over two decades of site inspections, I know which villas and apartments will truly fit your group’s needs.

Final Thoughts

Choosing the right base in Tuscany sets the tone for your entire trip. Whether you dream of sipping Brunello overlooking the Val d’Orcia or gathering the family for dinner by a Lucca olive grove, the right villa makes it all possible.

✨ Let’s find your perfect match.
Visit ClassicVacationRental.com to explore hand-picked villas, boutique apartments, and the most charming places to stay in Italy and beyond.