Chianti Region Holidays

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Your Chianti Region Holiday

Lock in a holiday package to Chianti Region and enjoy what it means to travel on your own terms. You'll be charmed by its walking trails, cycling and views. Start your trip to Chianti Region with some time exploring San Gimignano visiting popular attractions like Medieval Criminal and Torture Museum and Piazza Duomo. Gaiole in Chianti is another city that draws travellers from near and far. Castello di Albola and Meleto Castle are two of the leading places to see in this destination. If you're ready to stop dreaming and start travelling, Expedia will help turn your Chianti Region holiday into reality.

Our guide on where to stay in Chianti Region

Find the best Chianti Region areas and neighborhoods for the activities you enjoy most. Learn more about Chianti Region
A rural landscape with vineyards, rolling hills, and scattered houses.

Tavarnelle Val di Pesa

Tavarnelle Val di Pesa is noteworthy for its wineries, and you can make a stop at top attractions like Passignano Abbey and Abbey of Passignano.

Find hotels in Tavarnelle Val di Pesa
A historic stone church with a bell tower, surrounded by well-maintained hedges and a stone wall.

Barberino Val d'Elsa

Barberino Val d'Elsa is noteworthy for its wineries, and you can make a stop at top attractions like Casa Sola - Chianti Winery and Castello di Monsanto.

Find hotels in Barberino Val d'Elsa
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San Donato in Poggio

Travellers like the restaurants in San Donato in Poggio, and Pieve di San Donato in Poggio is a top attraction you might want to visit.

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A dilapidated brick structure with a chimney, surrounded by grass and trees.

Certaldo Alto

You'll enjoy the museums and monuments in Certaldo Alto. You might want to make time for a stop at Casa del Boccaccio or Palazzo Pretorio.

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Morrocco

While Morrocco may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Abbey of Passignano and Chianti Observatory.

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Chianti Region Holiday

Chianti Region Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Galileo Galilei Airport (PSA)
Top Sights
Sentierelsa Trail, Castelvecchio Natural Reserve and Valle dellInferno e Bandella

Our pick of the best Chianti Region Hotel Deals

Fattoria di Vegi

Fattoria di Vegi

Località Vegi, 16 Castellina in Chianti SI
Fully refundableReserve now, pay when you stay
AU$399
25 Oct - 26 Oct
includes taxes & fees
10/10 Exceptional! (32 reviews)
"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding ..."

Reviewed on 30 Sept 2026

Fattoria di Vegi
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
AU$545
30 Oct - 31 Oct
includes taxes & fees
9.6/10 Exceptional! (290 reviews)
"From the moment we checked in, This place was a Gem. From the friendly and helpful staff to the beautiful grounds, we were so impressed. Its hard to put into words how wonderful this Hotel is. The food, and drinks were incredible. We also celebrated my wife's birthday at this resort and they did ..."

Reviewed on 1 Oct 2026

Castello di Spaltenna- Small Luxury Hotels of the World
Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI
AU$129
2 Nov - 3 Nov
includes taxes & fees
9.2/10 Wonderful! (468 reviews)
"Under renovation so it could have been better"

Reviewed on 30 Sept 2026

Villa I Barronci Resort & Spa
See all 4,909 properties in Chianti Region
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.
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Stay near popular Chianti Region attractions

A spiral staircase with a person standing on it.

Antinori nel Chianti Classico

9.4/10 (16 reviews)
You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Visit the churches and wineries in this walkable area.
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A grand, illuminated building with arched windows and a central fountain.

The Mall Luxury Outlet

8.8/10 (355 reviews)
During your visit to Leccio, you can enjoy retail therapy at The Mall Luxury Outlet. Discover the acclaimed art galleries and stunning cathedral in this walkable area.
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Tenuta Torciano Winery

9.2/10 (40 reviews)
You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this quaint area.
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Verrazzano Castle

9.8/10 (10 reviews)
You can find out about the history of Greve in Chianti when you stop by Verrazzano Castle. Discover the area's countryside and wineries.
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Castello di Albola

9.0/10 (9 reviews)
You can enjoy a tasting or tour at Castello di Albola during your travels to Radda in Chianti. Discover the beautiful countryside in this quaint area or enjoy its local tours.
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Castle of Brolio

9.2/10 (44 reviews)
You can find out about the history of Gaiole in Chianti with a visit to Castle of Brolio. Discover the beautiful countryside and wineries in this walkable area.
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Meleto Castle

8.6/10 (10 reviews)
Find out about the history of Gaiole in Chianti when you take a trip to Meleto Castle. Discover the beautiful countryside in this walkable area or enjoy its local tours.
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Piazza Matteotti

9.4/10 (21 reviews)
Find out about the history of Greve in Chianti with a stop at Piazza Matteotti. Discover the beautiful countryside in this quaint area or enjoy its local tours.
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What to do in Chianti Region

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

AU$47
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Florence: Pasta Cooking Class with Unlimited Wine

Florence: Pasta Cooking Class with Unlimited Wine

AU$29
per adult
94% of travellers recommend
Florence: Pasta Cooking Class with Unlimited Wine
Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine

Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine

AU$29
per adult
94% of travellers recommend
Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine
See all activities in Chianti Region

Frequently asked questions

How much does a Chianti Region holiday package cost?
Live it up in Chianti Region from as low as . Choose from a wonderful selection of flights, hotels and rental cars to suit your travel style. You can pick up even more discounts when you add a couple of tours or experiences to your package.
How do I get a cheap travel package to Chianti Region?
Find flights that suit your busy schedule, add a hotel to your booking and watch how much you save with a Chianti Region holiday package. It's that easy! From flights and hotels to rental cars and activities, Expedia is your gateway to cheap travel. And with over 550 air carriers and 1 000 000 properties around the world to pick from, you won't be short of choice.
Where should I stay in Chianti Region?
Val dElsa is in the top spot on many Chianti Region must-see lists. Collegiate Church of Santa Maria Assunta is one reason why.
What are the top hotels in Chianti Region?
When it comes to hotels in Val dElsa, Grand Hotel Baglioni and Hotel Spadai are among the favourites. If you're spending time in Greve in Chianti, Hotel Pendini and The Market Urban Hotel will make you feel at home.
How far in advance should I book my Chianti Region holiday?
While prices change from time to time, we generally suggest booking your flight as soon as possible. Many international airfares can be compared on Expedia up to a year in advance. If circumstances have left you booking late, you may still get lucky. Low prices to Chianti Region sometimes emerge only weeks before departure.
What does an Expedia Chianti Region travel package include?
Much of that is up to you. You can pick from a variety of Chianti Region packages, such as a hotel, rental car and flight. You can also book a flight with a hotel, or a flight with a rental car. Once you've made your booking, you can add the fun stuff like experiences and tours. Whatever your perfect Chianti Region holiday looks like, get set to save!
What should I know before booking a Chianti Region travel package?
When you book your flights, hotels and car rentals together, you'll pick up fantastic discounts. Whether you're organising a mountain getaway in a cabin or would rather stay in a fancy hotel in the city, Expedia will help make it happen.
Can I choose my airline with a Chianti Region Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have more than 550 partner airlines across the globe, so you have loads of choice when creating your Chianti Region adventure.
If I'm not able to travel, can I cancel my Chianti Region holiday package?
Your situation can change in a flash, so yes. You may be able to cancel or amend your Chianti Region holiday package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still make the necessary changes, but your airline, hotel or car rental company may charge additional fees. Need more information? Look up our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.