Monteriggioni Castle

The main square of the fortress of Monteriggioni
The main square of the fortress of Monteriggioni
#TroveOn Monteriggioni is a medieval walled town, located on a natural hillock, built by the Sienese in 1214-1219 as a front line in their wars against Florence,[3] by assuming command of the Via Cassia running through the Val d'Elsa and Val Staggia to the west. During the conflicts between Siena and Florence in the Middle Ages, the city was strategically placed as a defensive fortification. It also withstood many attacks from both the Florentines and the forces of the Bishop of Volterra. In 1554 the Sienese were able to place control of the town's garrison to Giovannino Zeti, who had been exiled from Florence. In 1554, in an act of reconciliation with the Medicis, Zeti simply handed the keys of the town over to the Medicean forces - considered a "great betrayal" by the town's people. ---------------------------------------------------------- The Via Francigena is the common name of an ancient road and pilgrim route running from France to Rome, though it is usually considered to have its starting point much further away, in the English cathedral city of Canterbury. As such, the route passes through England, France, Switzerland and Italy. The route was known in Italy as the "Via Francigena" ("the road that comes from France") or the "Via Romea Francigena" ("the road to Rome that comes from France"). In mediaeval times it was an important road and pilgrimage route for those wishing to visit the Holy See and the tombs of the apostles Peter and Paul.
The Medieval Festival of Monteriggioni. Here we are in the 24th year of what has become one of the most popular events on the Tuscan scene, which this year will allow you to savour the atmosphere of the “Delle Armi e degli Amori”. Info at: http://www.monteriggionimedievale.com/en/
The Medieval Festival of Monteriggioni. Here we are in the 24th year of what has become one of the most popular events on the Tuscan scene, which this year will allow you to savour the atmosphere of the “Delle Armi e degli Amori”. Info at: http://www.monteriggionimedievale.com/en/

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Hotel Caravaggio

Hotel Caravaggio

3 out of 5
Historic Centre of Florence
Price was ￥464,688, price is now ￥404,959 per person
￥404,959
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Florence (FLR)
9/10 Wonderful! (1,000 reviews)
Great hospitality, view from my windows and roof top bar!

Reviewed on Feb 21, 2026

Hotel Santa Maria Novella

Hotel Santa Maria Novella

4 out of 5
Historic Centre of Florence
Price was ￥613,172, price is now ￥492,938 per person
￥492,938
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Florence (FLR)
9.6/10 Exceptional! (1,003 reviews)
Super charming and stylish (traditional Florentine) hotel. Many rooms (eg mine) overlook beautiful Piazza Santa Maria Novella and its church. Lovely views. Nice bathroom, very professional and friendly service from all the personnel there. The street level bar (inside outside sections) seem to be favored by cool locals as well as guests. The food menu covered lots of bases and everything I sampled was delicious. Check out the Napoleon salon!

Reviewed on Mar 10, 2026

The Hoxton Florence

The Hoxton Florence

4 out of 5
Historic Centre of Florence
Price was ￥516,200, price is now ￥477,886 per person
￥477,886
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Florence (FLR)
9.6/10 Exceptional! (205 reviews)
Staff, the cafe and bar were great. Not much storage space in the bedroom and the central courtyard looks a little unloved. Comfortable bed and great pillows, so overall would recommend

Reviewed on Mar 8, 2026

Browse tours and tickets to explore Monteriggioni Castle

Tours & day trips

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Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Activity duration is 11 hours
8.8 out of 10 with 136 reviews
Free cancellation available
Price is ￥14,499 per adult
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Private & custom tours

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An Exclusive Horseback Experience in the Heart of Tuscany

An Exclusive Horseback Experience in the Heart of Tuscany

Activity duration is 1 hour
10.0 out of 10 with 56 reviews
Free cancellation available
Price is ￥12,848 per adult
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Classes & workshops

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Tuscan Cooking Class in Central Siena

Tuscan Cooking Class in Central Siena

Activity duration is 4 hours
9.6 out of 10 with 153 reviews
Free cancellation available
Price is ￥23,860 per adult
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Adventure & outdoor

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Tuscany Hiking Tour from Siena Including Wine Tasting

Tuscany Hiking Tour from Siena Including Wine Tasting

Activity duration is 4 hours
10.0 out of 10 with 71 reviews
Free cancellation available
Price is ￥11,012 per adult
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Air, helicopter & balloon tours

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Experience the Magic of Tuscany from a Hot Air Balloon

Experience the Magic of Tuscany from a Hot Air Balloon

Activity duration is 3 hours
9.8 out of 10 with 109 reviews
Free cancellation available
Price is ￥49,371 per adult
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Popular places to visit

Cascate del Diborrato - Parco fluviale dell'Elsa Inside the residential area of Colle Val d'Elsa is a historic and natural landscape of enormous value thanks to the Elsa River which crosses the Val d'Elsa creating a unique territory. The river creates enchanting corners for hiking and observing: the engineering works for gathering water, the artifical canal system for carrying the water to the city, the caves. A particularly suggestive point is the Diborrato water falls, a 15m jump which is more than 10m deep, a sort of small lake where the locals used to go to cool off. Other places not to miss are the Grotta dell'Orso, the Conchina, the Masso Bianco, the Nicchia and the Spianata dei Falchi, each with its own particularities. This natural richness has been recognized with the institution of a protected area in the River Park of the Upper Val d'Elsa which includes the path of the river from the city of Colle Val d'Elsa which stretches from Ponte Santa Giulia to Ponte di Spugna and includes the Caldane, thermal springs which were known to the Etruscans and Romans.

Alta Val d'Elsa River Park

Explore the great outdoors at Alta Val d'Elsa River Park, a lovely green space in Colle di Val d'Elsa. Discover the countryside and spas in this quaint area.

Alta Val d'Elsa River Park

The Rock of Staggia

Learn about the local history of Staggia with a stop at The Rock of Staggia. Discover the beautiful countryside in this culturally rich area, or enjoy its local tours.

The Rock of Staggia

Lilliano Estate Winery

You can enjoy a tasting or tour at Lilliano Estate Winery during your travels to Lilliano.

Lilliano Estate Winery

Casina di Cornia Winery

You can enjoy a tasting or tour at Casina di Cornia Winery during your travels to Castellina in Chianti. Discover the countryside and wineries in this relaxing area.

Casina di Cornia Winery

Le Caldane Thermal Baths

Commune with nature and explore the great outdoors at Le Caldane Thermal Baths during your travels in Colle di Val d'Elsa. Find some time to visit the spas or temples in this quaint area.

Le Caldane Thermal Baths

San Leonardo al Lago

Learn about the local history of Monteriggioni when you spend time at San Leonardo al Lago. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

San Leonardo al Lago

Best Lodging Options Near Monteriggioni Castle

Hotel Il Piccolo Castello

Hotel Il Piccolo Castello

4 out of 5
Strada Provinciale Colligiana, 8 Monteriggioni SI
Hotel Il Piccolo Castello
Farmhouse in old mill nestled in the beautiful Chianti hills

Farmhouse in old mill nestled in the beautiful Chianti hills

Monteriggioni Toscana
Farmhouse in old mill nestled in the beautiful Chianti hills
Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna

Via Cassia Nord, 75 Monteriggioni SI
Hotel Ristorante La Dama nella Vigna
Agriturismo Novelleto

Agriturismo Novelleto

Strada di Bracciano, 1 Monteriggioni SI
Agriturismo Novelleto
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

Monteriggioni SIENA Toscana
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Villa "Le Vallecchie" overlooking Siena and with private swimming pool

Villa "Le Vallecchie" overlooking Siena and with private swimming pool

Siena Tuscany
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Castel Pietraio

Castel Pietraio

Strada di Strove, 33 Monteriggioni SI
Castel Pietraio
Hotel Borgo San Luigi

Hotel Borgo San Luigi

4 out of 5
STRADA DELLA CERRETA,7 Monteriggioni SI
Hotel Borgo San Luigi
Relais Castel Bigozzi

Relais Castel Bigozzi

4 out of 5
Strada Di Bigozzi 13 Monteriggioni SI
Relais Castel Bigozzi
See all 3,434 properties in Monteriggioni Castle
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.