Chianti Region Vacations from ¥350,548

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The Latest Chianti Region Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Eurostars Florence Boutique
The Moon Boutique Hotel & Spa
Hotel Santa Maria Novella
Hotel Garibaldi Blu
Villa Tolomei Hotel & Resort

Find the Best Chianti Region Vacation Packages

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

Hotel Toscana Ambassador

Hotel Toscana Ambassador

4 out of 5
Via Salceto, 11 Poggibonsi SI
Fully refundableReserve now, pay when you stay
The price is ¥10,455 per night from Jul 28 to Jul 29
¥10,455
¥12,609 total
Jul 28 - Jul 29
includes taxes & fees
8.2/10 Very Good! (352 reviews)
"Room was clean, staff was helpful and easy to park."

Reviewed on Jun 27, 2026

Hotel Toscana Ambassador
Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

4 out of 5
Via Sorripa 10 San Casciano in Val di Pesa FI
The price is ¥35,915 per night from Jul 19 to Jul 20
¥35,915
¥40,618 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (440 reviews)
"An amazing place to stay and relax in Florence. Highly recommend if you want a place to relax and away from the crowds . The staff was very respectful, polite and accommodating. Breakfast was amazing especially the chocolate croissants. Great value for the price. Thank you villa I Barronci!"

Reviewed on Jul 13, 2026

Villa I Barronci Resort & Spa
Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

4 out of 5
Via del Puglia, 61 Figline e Incisa Valdarno FI
Fully refundableReserve now, pay when you stay
The price is ¥25,753 per night from Aug 2 to Aug 3
¥25,753
¥29,070 total
Aug 2 - Aug 3
includes taxes & fees
9.2/10 Wonderful! (398 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 on Jun 14, 2026

Villa Casagrande Resort & SPA
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

What to do in Chianti Region

Frequently asked questions

How much does a Chianti Region vacation package cost?
Live it up in Chianti Region from as low as ¥350,548. 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.