A trip to Castle of Oliveto makes history come alive. Stare up at its mighty walls and pull out your guidebook to find out about its once-great power.

You'll have sightseeing choices galore when in Castelfiorentino. Castle of Oliveto is a good place to start here, but there are many other fine places to consider. Montegufoni Castle, Castello Sonnino, and Casa del Boccaccio are not far from the fortified complex and will round out your day nicely.

Plan a trip to see Castle of Oliveto

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Aurum Uffizi

Historic Centre of Florence

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per person

Sep 16 - Sep 20

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Florence (FLR)

7.8/10 Good! (1,000 reviews)

The hotel was centrally located near the plaza, cathedral, and many local shops and restaurants. The entrance to the hotel is a small alleyway off the road. The rooms were decent, but there were a few details that could have made them better. There was a mildew smell from leaking pipes in the walls. The WiFi only worked for a few minutes the night we arrived. And the door to our room would not fully lock when closed (if given a push with a slight force, it would pop open). Other than that it was a good experience, with the front desk doing everything they could to accommodate us. They provided us with air fresheners for the smell, sent someone to check our door, and even provided us with to-go snacks when we couldnt make breakfast due to an early planned trip.

Reviewed on Jul 2, 2025

Collegio alla Querce - Auberge Resorts

Le Cure

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per person

Sep 3 - Sep 9

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

10/10 Exceptional! (1 review)

Grand Hotel Cavour

Historic Centre of Florence

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per person

Sep 16 - Sep 20

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Florence (FLR)

9.2/10 Wonderful! (1,003 reviews)

Fantastic people and best view in Florence at night. Breakfast the best in Florence. Would go back in a heart beat

Reviewed on Jun 25, 2025

Browse tours and tickets to explore Castle of Oliveto

Tours & day trips

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Tuscany Experience In Pisa, Siena, San Gimignano & Chianti

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Tuscan Cooking Class

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History & culture

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Truffle Hunting in Tuscany

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Adventure & outdoor

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Horseback Riding, Wine Tasting, and Cooking Class in Tuscany

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Dinner in Winery Garden and Wine Tasting in San Gimignano

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Popular places to visit

Teatro del Popolo

You can make plans for a show at Teatro del Popolo during your stay in Castelfiorentino. Discover the beautiful countryside and wineries in this relaxing area.

Benozzo Gozzoli Museum

You can spend an afternoon studying the exhibits at Benozzo Gozzoli Museum in Castelfiorentino. Discover the beautiful countryside and wineries in this quaint area.

Tenuta Maiano

You can enjoy a tasting or tour at Tenuta Maiano during your travels to Montespertoli. Discover the beautiful countryside and wineries in this quaint area.

Agricola Tamburini Emanuela

You can enjoy a tasting or tour at Agricola Tamburini Emanuela during your travels to Gambassi Terme. Discover the beautiful countryside and wineries in this relaxing area.

Church of Saint Jacob and Saint Philip

You can learn about the history of Certaldo with a trip to Church of Saint Jacob and Saint Philip. Discover the beautiful countryside and wineries in this relaxing area.

Museum of Sacred Art

You can study the exhibits at Museum of Sacred Art, a museum with a storied past, during your trip to Certaldo. Discover the beautiful countryside and wineries in this relaxing area.