Montecchio

Travel Guide

The Castle of Montecchio Vesponi is a walled, castle with turrets and battlements, which occupies the top of a hill (Montecchio), overlooking the Val di Chiana, named and drawn on a well-documented survey map by Leonardo da Vinci in 1503. Many cultural events have taken place within its walls, including art exhibitions (the last being one of works of Manzù), concerts, folklore festivals, re- enactments and events in the local dialect. Famous visitors to the Castle have included the late Queen Elizabeth, The Queen Mother (of England) who came to learn Documentary Moviesmore about the castle and the area and owned in 1384 by another Englishman, Sir John Hawkwood (known in Italian as Giovanni Acuto). Hawkwood appears in the world famous fresco by Paolo Uccello in the Cathedral of Santa Maria del Fiore, The Duomo of Florence. #Tuscany #Castle #Montecchio #Vesponi #Valdichiana #Castiglion Fiorentino
The Castle of Montecchio Vesponi is a walled, castle with turrets and battlements, which occupies the top of a hill (Montecchio), overlooking the Val di Chiana, named and drawn on a well-documented survey map by Leonardo da Vinci in 1503. Many cultural events have taken place within its walls, including art exhibitions (the last being one of works of Manzù), concerts, folklore festivals, re- enactments and events in the local dialect. Famous visitors to the Castle have included the late Queen Elizabeth, The Queen Mother (of England) who came to learn Documentary Moviesmore about the castle and the area and owned in 1384 by another Englishman, Sir John Hawkwood (known in Italian as Giovanni Acuto). Hawkwood appears in the world famous fresco by Paolo Uccello in the Cathedral of Santa Maria del Fiore, The Duomo of Florence. #Tuscany #Castle #Montecchio #Vesponi #Valdichiana #Castiglion Fiorentino
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
Book a stay at this business-friendly country house in Montepulciano. Enjoy free WiFi, free parking, and an attached winery. Our guests praise the helpful staff ...
9.6/10 Exceptional! (278 reviews)
Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!

Reviewed on Dec 5, 2025

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Relais Villa Grazianella - UNA Esperienze
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
Book a stay at this luxury hotel in Cortona. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
9.8/10 Exceptional! (259 reviews)
Everything was great! Lovely hotel

Reviewed on Jan 4, 2026

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Monastero di Cortona Hotel & Spa
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10 Montepulciano SI
Book a stay at this luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (123 reviews)
Perfect escape
Fantastic hotel in an incredible setting. Staff were extremely helpful, attentive and understanding. The perfect location for a relaxing break and a centre for exploring Tuscany

Reviewed on Oct 27, 2025

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Precise Tale Poggio Alla Sala
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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.
Abbadia Sicille Relais

Abbadia Sicille Relais

4 out of 5
SP 14 Loc. Abbadia Sicille Trequanda SI
Book a stay at this business-friendly residence in Trequanda. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Monastery of Sant'Anna ...
8.8/10 Excellent! (162 reviews)
Room was beyond expectations. Helpful staff and overall great experience.

Reviewed on Dec 7, 2025

Abbadia Sicille Relais
Rhythms and atmospheres of the past, the comforts of the present a stone's throw from the city

Rhythms and atmospheres of the past, the comforts of the present a stone's throw from the city

Arezzo Toscana
Book a stay at this family-friendly vacation home in Arezzo. Enjoy free WiFi, private pools, and a garden. Popular attractions UCI Cinemas Arezzo and Casa Vasari ...
10/10 Exceptional! (32 reviews)
Beautiful property!!! Accurate photos on listing. All amenities here in this very comfortable Valletta. 6 minute drive to Arezzo and wonderful walking paths everywhere. Hosts were helpful and keep property so well maintained!! We did not use pool because it was too cool but it looks like it would ...

Reviewed on Oct 2, 2025

Rhythms and atmospheres of the past, the comforts of the present a stone's throw from the city
Il Poggio dell'Eremita

Il Poggio dell'Eremita

Sinalunga Tuscany
Stay at this villa in Sinalunga. Enjoy free WiFi, a garden, and patios. Popular attractions Torre Il Cassero and Piazza del Tribunal are located nearby.
10/10 Exceptional! (59 reviews)
The place was great! Everything as available and the host was extremely helpful and kind. Would definitely stay here again. The views of the small nearby towns are amazing. We loved it.

Reviewed on Nov 17, 2025

Il Poggio dell'Eremita
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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.

Popular places to visit

Tennis Club Castiglionese

Catch an event at Tennis Club Castiglionese during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.

Tennis Club Castiglionese

Archaeological Museum

You can browse the exhibits at Archaeological Museum, a museum with a storied past, during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.

Archaeological Museum

Agricola Buccelletti Winery

You can enjoy a tasting or tour at Agricola Buccelletti Winery during your travels to La Strada-Santa Cristina. Discover the area's countryside and wineries.

Agricola Buccelletti Winery

Vasari Loggia

You can find out about the history of Castiglion Fiorentino with a trip to Vasari Loggia. You can enjoy the wineries while in the area.

Vasari Loggia

Municipal Art Gallery

You can study the exhibits at Municipal Art Gallery, a museum with a storied past, during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.

Municipal Art Gallery

Cassero Tower

Find out about the history of Castiglion Fiorentino when you spend time at Cassero Tower. You can enjoy the wineries while in the area.

Cassero Tower

Things to do

Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

$23
per adult
Oil museum and oil mill in Tuscany: tour and tasting
Pizza Party and Open Bar in Private Garden

Pizza Party and Open Bar in Private Garden

$175
per adult
Pizza Party and Open Bar in Private Garden
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Cities near Montecchio

Cortona featuring a city and farmland

Cortona

Looking out the window on a fast train ride to Florence from Rome...

Castiglion Fiorentino