📍 Italy

GROSSETO JEWELS: MEDIEVAL VILLAGES AND ETRUSCAN HERITAGE

Medieval towers piercing sky, volcanic tuff cliffs glowing, fortresses guarding the coast. Southern Grosseto, hidden treasure.

≈ 5
Days
203
Km
5
Stops
📖 3 min read 🔄 Last updated: 2026-01-17

Explore Massa Marittima and its mining past, then discover Santa Fiora and its volcanic springs. Approach Pitigliano suspended from tuff cliffs, then follow the coast to Porto Ercole and its Spanish fortifications. Southern Tuscany reveals a mineral Mediterranean beauty.

Your day-by-day itinerary

1
Day

Massa Marittima

mining town gothic cathedral heart

Massa Marittima - Photo 1Massa Marittima - Photo 2Massa Marittima - Photo 3Massa Marittima - Photo 4Massa Marittima - Photo 5Massa Marittima - Photo 6
6 photos
Day 1
🔍

Discover

1
San Cerbone Cathedral (Romanesque-Gothic)
2
Piazza Garibaldi
3
Palazzo del Podestà and Archaeological Museum
4
Museum of Sacred Art
🎯

Activities

→
Fonti dell'Abbondanza
→
Cassero Senese and Torre del Candeliere
→
Medieval village of the Metalliferous Hills
🚗
Next stop
Distance: 80 km
Travel time: 1h36
2
Day

Santa Fiora

volcanic village renaissance gardens

Santa Fiora - Photo 1Santa Fiora - Photo 2Santa Fiora - Photo 3Santa Fiora - Photo 4Santa Fiora - Photo 5Santa Fiora - Photo 6Santa Fiora - Photo 7Santa Fiora - Photo 8Santa Fiora - Photo 9Santa Fiora - Photo 10
10 photos
Day 2
🔍

Discover

1
Parish Church of Saints Flora and Lucilla (Della Robbia terracottas)
2
Aldobrandeschi castle towers
3
Mining Museum
🎯

Activities

→
La Peschiera (picturesque basin)
→
Medieval village of Monte Amiata
🚗
Next stop
Distance: 30 km
Travel time: 36min
3
Day

Pitigliano

etruscan tufa cliffs fortress

Pitigliano - Photo 1Pitigliano - Photo 2Pitigliano - Photo 3Pitigliano - Photo 4Pitigliano - Photo 5Pitigliano - Photo 6Pitigliano - Photo 7Pitigliano - Photo 8Pitigliano - Photo 9Pitigliano - Photo 10
10 photos
Day 3
🔍

Discover

1
Village on tufa spur (Little Jerusalem)
2
Medici Aqueduct
3
Palazzo Orsini (two museums)
4
Cathedral
+1 Places visited
🎯

Activities

→
Walk in the tuff area
→
Remains of Etruscan civilization
🚗
Next stop
Distance: 60 km
Travel time: 1h12
4
Day

Porto Ercole

coastal town spanish fortress guard

Porto Ercole - Photo 1Porto Ercole - Photo 2Porto Ercole - Photo 3Porto Ercole - Photo 4Porto Ercole - Photo 5Porto Ercole - Photo 6
6 photos
Day 4
🔍

Discover

1
Piazza Santa Barbara (panorama over the sea)
2
Rocca Spagnola
3
Forte Stella
🎯

Activities

→
Feniglia Beach
→
Cala Galera
→
Spiaggia Lunga
+2 Optional activities
🚗
Next stop
Distance: 33 km
Travel time: 40min
5
Day

Giglio Castello

island village where tradition thrives

Giglio Castello - Photo 1Giglio Castello - Photo 2Giglio Castello - Photo 3Giglio Castello - Photo 4Giglio Castello - Photo 5Giglio Castello - Photo 6
6 photos
Day 5
🔍

Discover

1
Rocca Pisana
2
Medieval village at 400m altitude
3
Medieval village at 400m altitude
🎯

Activities

→
Ferry crossing to Isola del Giglio
→
Panorama over the Tyrrhenian Sea, Giannutri, Montecristo, Elba and Corsica
→
Panorama over the Tyrrhenian Sea, Giannutri, Montecristo, Elba and Corsica

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🛡️ Travel advice - Italy

Check official recommendations

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❓ Frequently asked questions

What weather should you expect?

Spring (April-June): Perfect weather, blooming landscapes, comfortable temperatures, fewer crowds, excellent value, Easter celebrations, ideal touring conditions.

Summer (July-August): Warmest weather, peak tourist season, highest prices, crowded attractions, vibrant atmosphere, beach season, festival time.

Fall (September-October): Excellent weather, harvest season, wine tourism, comfortable temperatures, fewer crowds, beautiful colors, culinary focus.

Winter (November-March): Mild southern weather, Christmas markets, lowest prices, minimal crowds, cultural focus, cozy atmosphere, indoor attractions.

How many days should I plan?

We believe you will enjoy this itinerary best by dedicating between 4 and 6 days. The next step will allow you to adjust the duration of your stay.

What to discover in Italy?

Cultural masterpiece with incredible art, cuisine, and historical heritage from Rome to Venice. Experience Renaissance treasures, regional diversity, and authentic Italian lifestyle. The country offers cultural immersion with culinary excellence and artistic heritage. Italy provides complete cultural experiences with historical significance and natural beauty.