To explore this trekking route, make your way to Casole d'Elsa. You'll find lots of other things to see in the area, including Monteriggioni Castle, Museo del Cristallo di Colle di Val d'Elsa, and Sentierelsa Trail.

Plan a trip to see Hedonistic Hiking

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Hotel degli Orafi

Historic Centre of Florence

$799

per person

Jan 15 - Jan 20

found 1 day ago

Roundtrip flight included

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

9.6/10 Exceptional! (1,001 reviews)

Spacious room much bigger than an average single.

Reviewed on Nov 27, 2025

Portrait Firenze - Lungarno Collection

Historic Centre of Florence

Save 100% on your flight

$1,678

per person

Feb 11 - Feb 15

found 12 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.8/10 Exceptional! (299 reviews)

Great location and got fantastic service from the hotel. Room was very clean and comfortable. Definitely my first choice for staying in Firenze!

Reviewed on Nov 17, 2025

Hotel Duomo Firenze

Historic Centre of Florence

$847

per person

Feb 11 - Feb 16

found 14 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.2/10 Wonderful! (1,002 reviews)

The rooms were great, and the location is outstanding! Located right beside the Duomo. And the family-run establishment offered impeccable service. Highly recommend.

Reviewed on Dec 4, 2025

Browse tours and tickets to explore Hedonistic Hiking

Tours & day trips

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Chianti Half Day Wine Tour from Florence

Free cancellation available

Private & custom tours

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Tour of the historical cellars in Montepulciano

Free cancellation available

Classes & workshops

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Olive Mill Tour with Oil and Food Tasting in Chianciano

Free cancellation available

Adventure & outdoor

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Tuscany Hiking Tour from Siena Including Wine Tasting

Free cancellation available

Air, helicopter & balloon tours

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Experience the Magic of Tuscany from a Hot Air Balloon

Free cancellation available

Popular places to visit

Cascate del Diborrato - Parco fluviale dell'Elsa

Inside the residential area of Colle Val d'Elsa is a historic and natural landscape of enormous value thanks to the Elsa River which crosses the Val d'Elsa creating a unique territory. The river creates enchanting corners for hiking and observing: the engineering works for gathering water, the artifical canal system for carrying the water to the city, the caves. A particularly suggestive point is the Diborrato water falls, a 15m jump which is more than 10m deep, a sort of small lake where the locals used to go to cool off. Other places not to miss are the Grotta dell'Orso, the Conchina, the Masso Bianco, the Nicchia and the Spianata dei Falchi, each with its own particularities. This natural richness has been recognized with the institution of a protected area in the River Park of the Upper Val d'Elsa which includes the path of the river from the city of Colle Val d'Elsa which stretches from Ponte Santa Giulia to Ponte di Spugna and includes the Caldane, thermal springs which were known to the Etruscans and Romans.

Alta Val d'Elsa River Park

Explore the great outdoors at Alta Val d'Elsa River Park, a lovely green space in Colle di Val d'Elsa. Discover the countryside and spas in this relaxing area.

#TroveOn
View of the Castle from the via francigena, while the fog leaves the valley as the sun rises. Monteriggioni is a small medieval village 12 km far from Sienna and 43 from Florence. Absolutely beautiful, the best period to visit Tuscany is from May to July.

Monteriggioni Castle

4/5(6 reviews)

After visiting Monteriggioni Castle, make a plan to see the other sights and activities in Monteriggioni. Discover the area's beautiful countryside, or seek out its local tours.

Terre di Vini

Enjoy an outing to Terre di Vini during your stay in Pievescola. Discover the beautiful countryside and wineries in this walkable area.

Le Caldane Thermal Baths

Commune with nature and explore the great outdoors at Le Caldane Thermal Baths during your travels in Colle di Val d'Elsa. Find some time to visit the spas or temples in this relaxing area.

San Leonardo al Lago

Learn about the local history of Monteriggioni when you spend time at San Leonardo al Lago. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Archeological and Collegiate Church Museum

You can spend an afternoon exploring the galleries in Archeological and Collegiate Church Museum during your travels in Casole d'Elsa. Discover the beautiful countryside and wineries in this quaint area.