Chianti Region Vacations

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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.

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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.

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San Donato in Poggio

Travelers 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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Sambuca

If you're looking for some top things to see and do in Sambuca and surrounding area, you can visit Abbey of Passignano and Passignano Abbey.

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Things to do near Chianti Region

Shopping

The Mall Luxury Outlet, located 20.9km from Chianti, offers a blend of luxury brands in a vibrant atmosphere. Nearby, Fashion Groove and Ra-Ma snc, both 19.3km away, provide unique shopping experiences with a mix of local charm and contemporary styles.

Recreation

Chianti Observatory offers a captivating experience under the stars, perfect for families seeking entertainment and wonder. Villa a Sesta Polo Club provides a luxurious retreat with elegant amenities, ideal for relaxation. Palasport Mens Sana caters to sports enthusiasts, featuring facilities for various athletic activities in a vibrant atmosphere.

Adventure

Explore the Sentierelsa Trail for a scenic hike, immersing yourself in the beautiful outdoors, located 22.5km from Chianti. Experience the thrill of karting at the Siena Circuit, situated 25.7km away, and enjoy the adventure vibes. For mountain biking enthusiasts, Tuscany MTB Guide offers fantastic outdoor experiences 22.5km from Chianti.

Nightlife

Experience the vibrant nightlife of the Chianti Region by visiting Il Fiaschetto, a charming drinking pub located 27.4km away. This venue offers a romantic atmosphere filled with entertainment vibes, perfect for relaxing with friends or enjoying a cozy evening out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Chianti Region

The Chianti Region in Tuscany is perfect for a romantic outdoor getaway, featuring charming churches, historic castles, and lively piazzas. Explore the stunning Chianti vineyards and discover the famous wine region known for its exceptional wines. Whether you're seeking cultural experiences or a romantic atmosphere, the area's captivating attractions will surely enhance your visit. Don't miss the opportunity to taste the best wines Chianti has to offer while enjoying the beautiful scenery.

  • Passignano Abbey: Nestled 11.3km from the Chianti Region, Passignano Abbey is a serene church steeped in history. The tranquil atmosphere and beautiful architecture invite visitors to explore its rich cultural heritage, making it a perfect spot for reflection and appreciation of medieval art.
  • Palazzo Pubblico: Located 22.5km away, Palazzo Pubblico is a stunning historic palace that showcases exquisite architecture and art. Its vibrant cultural vibes and historical significance make it a captivating destination for those interested in Tuscany's political past and artistic contributions.
  • Fortezza Medicea: Also 22.5km from Chianti, Fortezza Medicea is an impressive historic fort that offers panoramic views of the surrounding landscape. Its architectural grandeur and historical importance provide a fascinating glimpse into the region's defensive strategies and military history.

Best time to go to Chianti Region

The best time to visit Chianti Region can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Chianti Region falls in July, when visitor numbers are moderately high and weather is sunny with no rain. The coolest average temperature around Chianti Region falls in January, visitor numbers are moderately low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.6°F (4.800000000000001°C)Light RainMostly SunnyModerately LowSlightly Low
February42.8°F (6.0°C)Light RainMostly SunnyModerately LowSlightly Low
March47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
April54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
May60.4°F (15.8°C)Light RainMostly SunnyAverageSlightly High
June69.8°F (21.0°C)Light RainSunnyAverageSlightly High
July75.9°F (24.4°C)No RainSunnyModerately HighAverage
August75.6°F (24.200000000000003°C)No RainSunnyModerately HighAverage
September67.1°F (19.5°C)Light RainMostly SunnyModerately HighSlightly High
October58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
November50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly Low
December43.2°F (6.2°C)Light RainMostly SunnyModerately LowAverage

Tips to save on your trip to Chianti Region

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chianti Region.
  • Consider traveling to Chianti Region during the low season (January to February and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Chianti Region Hotel Deals

Fattoria di Vegi

Fattoria di Vegi

Località Vegi, 16 Castellina in Chianti SI
￥54,713
￥61,256 total
Sep 29 - Sep 30
includes taxes & fees
10/10 Exceptional! (19 reviews)
"Amazing! I wish I could have stayed forever!"

Reviewed on Sep 4, 2026

Fattoria di Vegi
Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI
￥27,359
￥31,167 total
Oct 8 - Oct 9
includes taxes & fees
Villa I Barronci Resort & Spa
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
￥61,416
￥69,345 total
Oct 5 - Oct 6
includes taxes & fees
9.6/10 Exceptional! (281 reviews)
"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"

Reviewed on Aug 4, 2026

Castello di Spaltenna- Small Luxury Hotels of the World
See all 4,924 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.

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. Check out 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 search for that perfect souvenir at The Mall Luxury Outlet. Discover the acclaimed art scene 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 with a trip to Verrazzano Castle. Discover the area's countryside and wineries.
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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 stop at Castle of Brolio. Discover the beautiful countryside and wineries in this walkable area.
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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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Meleto Castle

8.6/10 (10 reviews)
Find out about the history of Gaiole in Chianti when you spend time at Meleto Castle. Discover the beautiful countryside in this walkable area, or enjoy its local tours.
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Castello di Radda Winery

9.2/10 (12 reviews)
You can enjoy a tasting or tour at Castello di Radda Winery during your travels to Radda in Chianti. Discover the beautiful countryside in this quaint area, or enjoy its local tours.
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What to do in Chianti Region

Skip the Line: Florence's Accademia Gallery Priority Entrance Ticket

Skip the Line: Florence's Accademia Gallery Priority Entrance Ticket

￥5,802
per adult
86% of travellers recommend
Skip the Line: Florence's Accademia Gallery Priority Entrance Ticket
Florence: Pasta Cooking Class with Unlimited Wine

Florence: Pasta Cooking Class with Unlimited Wine

￥2,967
per adult
94% of travellers recommend
Florence: Pasta Cooking Class with Unlimited Wine
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Frequently asked questions

How much does a Chianti Region vacation 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 vacation 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 favorites. 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 vacation?
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 vacation 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 organizing 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 vacation 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 vacation package?
Your situation can change in a flash, so yes. You may be able to cancel or amend your Chianti Region vacation 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.