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/

Plan a trip to see Monteriggioni Castle

Price found within the past 48 hours. Click for updated prices.
The Hoxton Florence

The Hoxton Florence

4 out of 5
Historic Centre of Florence
Price was ฿60,429, price is now ฿48,931 per person
฿48,931
per person
11 Apr - 17 Apr
found 1 day ago
Return direct flight included
Bangkok (BKK) to Florence (FLR)
9.4/10 Exceptional! (147 reviews)
Great welcome, excellent quality, fabulous location

Reviewed on 19 Jan 2026

Art Hotel Villa Agape

Art Hotel Villa Agape

4 out of 5
Oltrarno
Price was ฿63,312, price is now ฿49,620 per person
฿49,620
per person
11 Apr - 17 Apr
found 1 day ago
Return direct flight included
Bangkok (BKK) to Florence (FLR)
9.8/10 Exceptional! (1,003 reviews)
Nice hotel, Heads up city tax is ridiculous Per day per person. Not in a central location

Reviewed on 17 Jan 2026

Castelfalfi

Castelfalfi

5 out of 5
Price was ฿135,846, price is now ฿111,351 per person
฿111,351
per person
11 Apr - 17 Apr
found 1 day ago
Return direct flight included
Bangkok (BKK) to Florence (FLR)
9.6/10 Exceptional! (161 reviews)
Incredible staff and incredible room. Large grounds and plenty of things to do. Spa and pool were always clean and well stocked

Reviewed on 10 Nov 2025

Tours & day trips

See all 165 activities
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

Activity duration is 10 hours and 30 minutes
8.8 out of 10 with 27 reviews
Free cancellation available
The previous price was ฿2,365 and current price is ฿1,892 per adult
Siena, San Gimignano, Monteriggioni & Chianti from FlorenceOpens in new tab

Private & custom tours

See all 98 activities
Tour of the historical cellars in Montepulciano

Tour of the historical cellars in Montepulciano

Activity duration is 2 hours and 30 minutes
Free cancellation available
Price is ฿2,146 per adult
Tour of the historical cellars in MontepulcianoOpens in new tab

Classes & workshops

See all 16 activities
Cooking Class: Italian Authentic Recipes with Lunch

Cooking Class: Italian Authentic Recipes with Lunch

Activity duration is 3 hours
Free cancellation available
Price is ฿4,001 per adult
Cooking Class: Italian Authentic Recipes with LunchOpens in new tab

Adventure & outdoor

See all 10 activities
Private Off Road Wine Tour in Chianti

Private Off Road Wine Tour in Chianti

Activity duration is 6 hours
Free cancellation available
Price is ฿12,113 per adult*
Private Off Road Wine Tour in ChiantiOpens in new tab

Air, helicopter & balloon tours

See all 5 activities
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
10.0 out of 10 with 1 review
Free cancellation available
Price is ฿9,785 per adult
Experience the Magic of Tuscany from a Hot Air BalloonOpens in new tab

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.

Alta Val d'Elsa River Park

The Rock of Staggia

Learn about the local history of Staggia when you take a trip to The Rock of Staggia. Discover the beautiful countryside in this walkable 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 quaint 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 relaxing area.

Le Caldane Thermal Baths

San Leonardo al Lago

Learn about the local history of Monteriggioni with a stop at San Leonardo al Lago. Discover the beautiful countryside in this walkable area or enjoy its local tours.

San Leonardo al Lago

Top Hotel Deals

Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna

Via Cassia Nord, 75 Monteriggioni SI
Hotel Ristorante La Dama nella Vigna
Hotel Borgo San Luigi

Hotel Borgo San Luigi

4 out of 5
STRADA DELLA CERRETA,7 Monteriggioni SI
Hotel Borgo San Luigi
Villa Lecchi Hotel Wellness

Villa Lecchi Hotel Wellness

4 out of 5
Località Lecchi snc, Staggia Senese Poggibonsi SI
Villa Lecchi Hotel Wellness
Hotel I Platani

Hotel I Platani

3 out of 5
Via Dell Abbadia 2 Monteriggioni SI
Hotel I Platani
See all 3,359 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.