Tuscany Road Trip (2 weeks): the ultimate route through hills, wine & hidden gems

Do you dream of rolling hills full of cypress trees, long tables under the Italian sun, and charming agriturismo in the heart of nature?
With this 2-week road trip through Tuscany, you discover the real Italy at your own pace. With tips for activities:From culture in Florence to wine tasting in Chianti and relaxing on the Tuscan coast: this is Tuscany at its best.

Week 1: Northern & Central Tuscany – Culture, wine & iconic landscapes

Stop 1: Florence & Chianti (3 nights)

Why start here?
Florence is the cultural gem of Tuscany. But you will stay just outside the city, in the tranquility of the Chianti region.

Activities:

• Visit the Duomo and Ponte Vecchio
• Uffizi Gallery (tip: book tickets in advance!)
• Wine tasting at a local Chianti vineyard
• Picnic among the vines
• Sunset at Piazzale Michelangelo

Accommodation tip: 4 – 6 person apartments in Reggelo

Stop 2: San Gimignano & Siena (3 nights)

Welcome to medieval Tuscany.

San Gimignano – known for its towers and delicious gelato.
Siena – romantic, atmospheric and authentic.

Activities:

• Climb the Torre Grossa for a panoramic view.
• Stroll through the Piazza del Campo in Siena
• Visit a local market
• Take a pasta or cooking workshop
• Taste Vernaccia wine in San Gimignano

Accommodation tip: apartments with swimming pool and restaurant

Week 2: Southern Tuscany & coast – Val d'Orcia, thermal baths & sea

Stop 3: Val d'Orcia (3 nights)

This is the Tuscany you know from postcards.

Activities:

• Visit Pienza (city of pecorino!)
• Wine tasting in Montalcino (Brunello!)
• Photo stop at the famous cypresses of San Quirico
• Relax in the natural thermal baths of Bagno Vignoni or Saturnia

Accommodation tip: Spacious apartments with modern interior

Stop 4: Tuscan Coast – Maremma (3 nights)

Time for sea, beach, and nature.

Why Maremma?
Less touristy, pure, and surprisingly versatile.

Activities:

• Beach day at Cala Violina
• Visit the Parco della Maremma nature park
• Rent bikes along the coast
• Day trip to the island of Elba
• Eating fresh fish in a small local harbor

Accommodation tip: Panoramic spot in the hills of the Maremma

Last night: Lucca or Pisa (1-2 nights)

End your tour in a relaxed way in the north.

Lucca: cycling over the city walls
Pisa: of course the famous tower, but also charming streets

Perfect if you are flying back from Pisa.

Accommodation tip: Cozy holiday villa with private pool

🚘 Practical tips for your Tuscany road trip

✔ Best time to visit: May–June & September (pleasant temperature, less crowded)
✔ A rental car is essential
✔ Don't plan too much – experience Tuscany the Italian way: at a leisurely pace
✔ Combine culture with relaxation
✔ Choose accommodations with a pool (especially lovely in the summer)