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

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Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
The price is S$279 per night from 9 Mar to 10 Mar
S$279
9 Mar - 10 Mar
includes taxes & fees
Stay at this luxury country house in Montepulciano. Enjoy free Wi-Fi, free parking and an on-site winery. Our guests praise the helpful staff in their reviews. ...
9.8/10 Exceptional! (279 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 5 Dec, 2025

Relais Villa Grazianella - UNA Esperienze
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6 Cortona AR
The price is S$974 per night from 6 Apr to 7 Apr
S$974
6 Apr - 7 Apr
includes taxes & fees
Stay at this luxury hotel in Cortona. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff in their reviews. Popular ...
9.8/10 Exceptional! (228 reviews)
Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly

Reviewed on 6 Nov, 2025

Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
The price is S$405 per night from 15 Mar to 16 Mar
S$405
15 Mar - 16 Mar
includes taxes & fees
Stay at this luxury hotel in Cortona. Enjoy free breakfast, free Wi-Fi and a full-service spa. Our guests praise the helpful staff in their reviews. Popular ...
Monastero di Cortona Hotel & Spa
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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
Stay at this business-friendly residence in Trequanda. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Monastery of Sant'Anna in Camprena ...
8.8/10 Excellent! (168 reviews)
Room was beyond expectations. Helpful staff and overall great experience.

Reviewed on 7 Dec, 2025

Abbadia Sicille Relais
Residenza Fabroni

Residenza Fabroni

Via di Gracciano nel Corso, 12 Montepulciano SI
Stay at this historic residence in Montepulciano. Enjoy free Wi-Fi, an on-site winery and a rooftop terrace. Popular attractions Torre di Pulcinella and Palazzo ...
8.8/10 Excellent! (96 reviews)
The parking states “on site”, as if there was a parking lot easy and close to get to and from, especially with luggage. The parking lot is a maze to get to and quite difficult to navigate to through the tiny streets. Other then that, place was clean, staff was great Very old school italy Also the ...

Reviewed on 19 Jan, 2026

Residenza Fabroni
Il Tosco

Il Tosco

Via del Poliziano 13 Montepulciano SI
Stay at this luxury residence in Montepulciano. Enjoy free Wi-Fi, free parking and room service. Popular attractions Medici Fortress and Torre del Pulcinella ...
10/10 Exceptional! (116 reviews)
Best stay of my life!

Reviewed on 31 Dec, 2025

Il Tosco
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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

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

Archaeological Museum

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

Archaeological Museum

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

Cassero Tower

Find out about the history of Castiglion Fiorentino when you take a trip to Cassero Tower. You can enjoy the wineries while in the area.

Cassero Tower

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

Things to do

Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

S$30
per adult
Oil museum and oil mill in Tuscany: tour and tasting
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

S$37
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Tasting with Private Walk in a Cellar in Tuscany

Tasting with Private Walk in a Cellar in Tuscany

S$37
per adult
Tasting with Private Walk in a Cellar in Tuscany
2-Hour Private Wine Tasting in the Cellar in Mugliano

Private Tasting of Organic Wines in the Cellar in Mugliano

S$45
per adult
Private Tasting of Organic Wines in the Cellar in Mugliano
Montepulciano Wine Tasting with typical Tuscan Cold Cuts

Montepulciano Wine Tasting with typical Tuscan Cold Cuts

S$67
per adult
Montepulciano Wine Tasting with typical Tuscan Cold Cuts
Montepulciano: Wine Tour with Tasting & Appetizers in the Cellar

Montepulciano: Wine Tour with Tasting & Appetizers in the Cellar

S$119
per adult
Montepulciano: Wine Tour with Tasting & Appetizers in the Cellar
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