Chianti Region Adventure Holidays
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Top Adventure holiday packages in Chianti Region
Price found within the past 48 hours. Click for updated prices.
- Villa San Lucchese
21 Sept - 27 SeptVilla San Lucchese + Flight
Poggibonsi6 nights4.0 star property9.4/10 - Exceptional (351 reviews)"Our one-week stay at this villa from the moment we arrived until the day we left, every aspect of our experience was exceptional. The highlight of our stay was the restaurants both breakfast and dinner. Without question, Every meal was outstanding, with incredible flavors, beautifully prepared dishes, and an atmosphere that made every dinner memorable. What truly set this property apart, however, was the people. The service was consistently warm, professional, and attentive. The front desk..."Reviewed July 20, 2026Return • Manchester (MAN) - Florence (FLR)MAN - FCO • 1 stop FCO - MAN • 1 stopHK$6,756HK$5,337found 1 day agoper traveller - Villa Casagrande Resort & SPA
21 Sept - 27 SeptVilla Casagrande Resort & SPA + Flight
Figline e Incisa Valdarno6 nights4.0 star property9.2/10 - Wonderful (402 reviews)"If you are thinking of staying anywhere else in toscana…DON’T! This was the most amazing stay. We extended our stay because it was so beautiful and full of history. The amenities are also wonderful!"Reviewed June 14, 2026Return • Manchester (MAN) - Florence (FLR)MAN - FCO • 1 stop FCO - MAN • 1 stopHK$8,560HK$7,422found 1 day agoper traveller
Discover the most popular places to visit in Chianti Region
What to do in Chianti Region
City Sightseeing Florence Hop-on Hop-off Bus Tour
HK$259
per adult
76% of travellers recommend
Florence Vespa Tour: Tuscan Hills, Food and Chianti Wine
HK$986
per adult
100% of travellers recommend
The Best of Tuscany Tour: Siena, San Gimignano, Pisa and Lunch at a Winery
HK$620
per adult
98% of travellers recommend
Top Adventure Chianti Region Hotels
Villa Casagrande Resort & SPA
Villa Casagrande Resort & SPA4.0 star property
12.5 km from Chianti Region
9.2 out of 10, Wonderful, (402 reviews)
9.2/10
Wonderful
(402 reviews)
"If you are thinking of staying anywhere else in toscana…DON’T! This was the most amazing stay. We extended our stay because it was so beautiful and full of history. The amenities are also wonderful!"
The price is HK$1,205
HK$1,205
HK$1,362 total
includes taxes & fees
23 Aug - 24 Aug
Hotel Palazzo San niccolò & Spa
Hotel Palazzo San niccolò & Spa4.0 star property
5.4 km from Chianti Region
9.2 out of 10, Wonderful, (194 reviews)
9.2/10
Wonderful
(194 reviews)
"We stayed at this property for three nights in mid July 2026. The property was very clean and the staff were very friendly. The property was close too many restaurants and shops. There is no parking on site. However, parking is available about 5 to 10 minute walk from the property. We were a little disappointed with the pool access. There could only be four people at a time at the indoor pool and had to make reservations well in advance to get a decent timeslot. The outdoor pool was a 5 km...
The price is HK$894
HK$894
HK$1,038 total
includes taxes & fees
31 Aug - 1 Sept
Palazzo Leopoldo Dimora Storica & Spa
Palazzo Leopoldo Dimora Storica & Spa4.0 star property
5.4 km from Chianti Region
9.2 out of 10, Wonderful, (294 reviews)
9.2/10
Wonderful
(294 reviews)
"very well maintained hotel with friendly staff"
The price is HK$1,208
HK$1,208
HK$1,383 total
includes taxes & fees
4 Aug - 5 Aug
9.4 out of 10, Exceptional, (351 reviews)
9.4/10
Exceptional
(351 reviews)
"Our one-week stay at this villa from the moment we arrived until the day we left, every aspect of our experience was exceptional.
The highlight of our stay was the restaurants both breakfast and dinner. Without question, Every meal was outstanding, with incredible flavors, beautifully prepared dishes, and an atmosphere that made every dinner memorable.
What truly set this property apart, however, was the people. The service was consistently warm, professional, and attentive. The front desk...
The price is HK$1,086
HK$1,086
HK$1,249 total
includes taxes & fees
21 Aug - 22 Aug
Villa I Barronci Resort & Spa
Villa I Barronci Resort & Spa4.0 star property
21.2 km from Chianti Region
9.2 out of 10, Wonderful, (446 reviews)
9.2/10
Wonderful
(446 reviews)
"This was a fabulous stay. The property is beautiful, the grounds were fun to walk and the swimming pool was lovely. Breakfast every morning was delicious. Hotel was very quiet during the week but was noticeably busier starting Friday (I think local people come just for the weekend). Our room was spacious and very clean. Bed was very comfortable. There is a bar near the pool that serves drinks in the afternoon and dinner nightly on the terrace. The nearby town was so cute and had a coop as well...
The price is HK$1,515
HK$1,515
HK$1,721 total
includes taxes & fees
25 Aug - 26 Aug
8.2 out of 10, Very good, (357 reviews)
8.2/10
Very good
(357 reviews)
"Room was clean, staff was helpful and easy to park."
The price is HK$533
HK$533
HK$640 total
includes taxes & fees
8 Aug - 9 Aug
Hotel Borgo di Cortefreda Relais
Hotel Borgo di Cortefreda Relais4.0 star property
15.6 km from Chianti Region
9.4 out of 10, Exceptional, (510 reviews)
9.4/10
Exceptional
(510 reviews)
The price is HK$1,524
HK$1,524
HK$1,731 total
includes taxes & fees
1 Sept - 2 Sept
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK4.6 km from Chianti Region
9.4 out of 10, Exceptional, (23 reviews)
9.4/10
Exceptional
(23 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
The price is HK$730
HK$730
HK$1,435 total
includes taxes & fees
4 Aug - 5 Aug
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find awesome Chianti Region adventure vacations
How can I book the best Chianti Region adventure trips?
Choose your own adventure in Chianti Region, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.
How can I plan the perfect Chianti Region family adventure vacation?
Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Chianti Region. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.
Can I book all-inclusive Chianti Region adventure vacation packages?
By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.
Why should I book a Chianti Region adventure vacation for couples?
Book a Chianti Region couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.
How can I find the best deals on adventure packages in Chianti Region?
It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.
Can I book an adventure vacation package in Chianti Region with free cancellation and/or flexible dates?
Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.
Why should I book a Chianti Region adventure trip with Expedia?
Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.
What types of mountain accommodations are available in Chianti Region?
5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to Chianti Region. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation.