Monteriggioni Castle

The main square of the fortress of Monteriggioni

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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.

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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/

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Monteriggioni Travel Guide

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Hotel Mirage

￥206,811

per person

Apr 17 - Apr 20

found 6 hours ago

Roundtrip flight included

Tokyo (TYO) to Florence (FLR)

7/10 Good! (867 reviews)

Lobby is very nice, rooms are dated and poorly repaired, ours clearly had had water damage in the bathroom which was still evident. However, the beds are excellent. Had to open the window because the room was hot, and the outside noise woke us up.

Reviewed on Nov 21, 2025

Italiana Hotels Florence

￥214,989

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Apr 17 - Apr 20

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Tokyo (TYO) to Florence (FLR)

7.6/10 Good! (1,000 reviews)

Clean room with nice staffs on site and at the restaurant

Reviewed on Jan 4, 2026

Hotel Alex

Isolotto

￥212,525

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Apr 17 - Apr 20

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Tokyo (TYO) to Florence (FLR)

7.8/10 Good! (111 reviews)

Staff from front desk to gentleman who prepared the breakfast to the maids were all very friendly, nice and helpful.

Reviewed on Apr 23, 2025

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 relaxing area.

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 walkable area, or enjoy its local tours.

Lilliano Estate Winery

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

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 quaint area.

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.

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.

Best Lodging Options Near Monteriggioni Castle

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Hotel Il Piccolo Castello

Strada Provinciale Colligiana, 8 Monteriggioni SI

Farmhouse in old mill nestled in the beautiful Chianti hills

Monteriggioni Toscana

Fattoria Petraglia by Interhome

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Il Colombaio Winery and Rooms

Loc. Abbadia Isola Monteriggioni SI

Hotel Ristorante La Dama nella Vigna

Via Cassia Nord, 75 Monteriggioni SI

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

Monteriggioni SIENA Toscana

Chalet in Chianti with swimming pool and tennis court

Siena Siena

15th century barn fully renovated in a stylish style with gorgeous swimming pool

Toscana Provincia di Siena

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