You might be encouraged to visit today, but Fortress of Montestaffoli hasn't always been so welcoming! Learn the story behind this mighty stronghold and exactly what it was built to defend.

This history-filled fortress in San Gimignano City Centre comes recommended by travelers, so be sure to put it on your must-see list. However, don't end your sightseeing there. There are a lot more spots ready for you to enjoy after Fortress of Montestaffoli. Collegiate Church of Santa Maria Assunta, Tenuta Torciano Winery, and Piazza Duomo are nearby.

Plan a trip to see Fortress of Montestaffoli

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

Aurum Firenze

Historic Centre of Florence

Save 100% on your flight

$931

per person

Oct 11 - Oct 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

7.6/10 Good! (1,008 reviews)

Right near the attractions. Easy to get around

Reviewed on Sep 4, 2025

Aurum Uffizi

Historic Centre of Florence

Save 100% on your flight

$958

per person

Oct 11 - Oct 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

7.8/10 Good! (1,000 reviews)

This hotel is in a great location close to all the sites in the old city. The rooms are nice but small. It was clean and bed was comfortable. A great option for a weekend stay.

Reviewed on Sep 4, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Historic Centre of Florence

Save 100% on your flight

$4,547

per person

Oct 11 - Oct 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.4/10 Exceptional! (232 reviews)

Gorgeous boutique hotel, like museum Beautiful rooms!!! Thank you Giovanni for all ur help and knowledge organizing everything for us, and breakfast waiters were great!!!

Reviewed on Aug 21, 2025

Browse tours and tickets to explore Fortress of Montestaffoli

Tours & day trips

See all 49 activities

Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch

Free cancellation available

History & culture

See all 17 activities

Horseback Riding with Wine Tour from Florence

Free cancellation available

Holiday & seasonal tours

See all 3 activities

San Gimignano: Dinner in the Winery with Wine Tasting

Free cancellation available

Popular places to visit

Piazza delle Erbe

Watch the world go by and admire San Gimignano’s medieval architecture from the comfort of a café terrace at this central square.

San Gimignano Communal Palace

You can browse the exhibits at San Gimignano Communal Palace, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.

Piazza Duomo

Browse the collections of ancient art, which grace the walls of the medieval landmarks that surround this resplendent public square.

Collegiate Church of Santa Maria Assunta

You can browse the exhibits at Collegiate Church of Santa Maria Assunta, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.

Piazza della Cisterna

Admire the palaces and towers that frame this beautiful square, which was once a medieval marketplace. Today, it’s a venue for cultural events.

Rocca of Montestaffoli

After visiting Rocca of Montestaffoli, make a plan to see the other sights and activities in San Gimignano. Discover the countryside in this walkable area.