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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Aurum Uffizi

Historic Centre of Florence

$761

per person

Jan 19 - Jan 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

7.8/10 Good! (1,015 reviews)

This hotel is all about location… close to everything about 10-15 mins by walking. The entrance of the hotel is a bit scary at night time on my personal view. The room is big and clean. Don’t expect much on breakfast … it’s enough for you to start the day.

Reviewed on Nov 11, 2025

The Moon Boutique Hotel & Spa

Historic Centre of Florence

$1,151

per person

Jan 1 - Jan 6

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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

Villa Tolomei Hotel & Resort

Oltrarno

$769

per person

Jan 20 - Jan 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

17.6/10 Exceptional! (399 reviews)

Great place to stay near Florence, it’s quite and relaxing. The pool is great.

Reviewed on Jul 31, 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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Siena: Pasta and Tiramisu Small Group Cooking Class with Wine

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 quaint 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 quaint 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.