Name: House with character in typical medieval borgo on the Chianti Classico hills
Address: Montespertoli

Piazza Machiavelli is one of the main stops on any tourist visit. Discover its historical background or just kick back and watch the world go by.

You'll have no end of sightseeing choices in Montespertoli. Piazza Machiavelli is a good place to kick off here, but there are many other worthwhile attractions to discover. Antinori nel Chianti Classico, Montegufoni Castle, and Monastary of Sorelle Clarisse are close to the public square and will top off your day nicely.

Plan a trip to see Piazza Machiavelli

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

Eurostars Florence Boutique

Historic Centre of Florence

$609

per person

Dec 9 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

8.6/10 Excellent! (472 reviews)

Great little hotel. Everything is within walking distance. The view from the terrace was amazing.

Reviewed on Aug 6, 2025

Aurum Firenze

Historic Centre of Florence

$1,138

per person

Dec 28 - Jan 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

7.8/10 Good! (1,007 reviews)

Breakfast was excellent

Reviewed on Sep 29, 2025

Monastero di Cortona Hotel & Spa

Cortona Old Town

$1,100

per person

Nov 11 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Florence (FLR)

10/10 Exceptional! (235 reviews)

Beautiful, unique property! Stunning views of the countryside. The staff were all very helpful and friendly. We will definitely recommend!

Reviewed on Sep 27, 2025

Browse tours and tickets to explore Piazza Machiavelli

Tours & day trips

See all 45 activities

Chianti Half Day Wine Tour from Florence

Free cancellation available

Classes & workshops

See all 22 activities

Cooking Class on a Family Farm in Chianti with Lunch

Free cancellation available

Private & custom tours

See all 7 activities

PRIVATE WINE TOUR TUSCANY Wines and Wineries of Chianti Classico

Free cancellation available

Adventure & outdoor

See all 5 activities

Chianti Wild Safari Adventure through Tuscan Vineyards

Free cancellation available

Popular places to visit

Museo Amedeo Bassi

You can spend time studying the exhibits at Museo Amedeo Bassi during your travels in Montespertoli. Discover the countryside in this relaxing area, or seek out the biking trails.

Castello Sonnino

You can enjoy a tasting or tour at Castello Sonnino during your travels to Montespertoli. Check out the churches and wineries in this walkable area.

Montespertoli City Hall

Montespertoli City Hall is just one of the places to see in Montespertoli, so why not enjoy the other things to explore during your travels? Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Il Fiaschetto

Enjoy an outing to Il Fiaschetto during your stay in Montespertoli. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Piazza del Popolo

You can find out about the history of Montespertoli with a stop at Piazza del Popolo. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Vine and Wine Museum

You can spend an afternoon browsing the exhibits at Vine and Wine Museum during your travels in Montespertoli. Check out the stunning cathedral and wineries in this walkable area.