Name: Maramaldo Sangiovese Shared Pool, Chianti
Address: Castelfiorentino

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

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

Aurum Uffizi

Historic Centre of Florence

$696

per person

Jan 18 - Jan 23

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Florence (FLR)

7.8/10 Good! (1,015 reviews)

Clean but small Breakfast is ok location is perfect

Reviewed on Nov 15, 2025

The Moon Boutique Hotel & Spa

Historic Centre of Florence

$1,884

per person

Dec 31 - Jan 6

found 14 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

19.2/10 Exceptional! (494 reviews)

My husband Felix and I had the pleasure of celebrating both our wedding anniversary and my birthday at The Moon Boutique Hotel in Florence, and we couldn’t have asked for a more perfect experience. From the moment we arrived, the warmth and professionalism of the staff made us feel truly welcomed. A special mention goes to the tall gentleman with glasses from Calabria—his courteous demeanor and exceptional customer service stood out throughout our stay. He went above and beyond to ensure we were comfortable and well-informed, adding a personal touch that made our visit even more special. The housekeeping team deserves equal praise. Their attention to detail was remarkable, and our room was consistently immaculate, creating a serene and luxurious atmosphere that enhanced our celebration. The Moon Boutique Hotel is more than just a place to stay—it’s a haven of elegance, comfort, and genuine hospitality. We left with beautiful memories and deep appreciation for the team that made our milestone moments unforgettable.

Reviewed on Nov 12, 2025

Aurum Firenze

Historic Centre of Florence

$812

per person

Jan 26 - Jan 31

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

15.2/10 Exceptional! (1,003 reviews)

Convenient location to fast food and train station

Reviewed on Nov 7, 2025

Browse tours and tickets to explore Castle of Oliveto

Tours & day trips

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

Free cancellation available

Classes & workshops

See all 32 activities

Private Ceramics Course in Tuscany

Free cancellation available

Adventure & outdoor

See all 3 activities

Private Tuscan meal with Wine and EVO oil tasting

Free cancellation available

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 quaint 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 quaint area.

Church of Saint Jacob and Saint Philip

Church of Saint Jacob and Saint Philip is just one of the places to see in Certaldo, so why not enjoy the other things to explore during your travels? Discover the beautiful countryside and wineries in this culturally rich 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.