Chianti Region Holidays

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Things to do near Chianti Region

The Chianti Region in Tuscany is perfect for a romantic and adventurous getaway, offering a variety of outdoor activities. Visitors can indulge in spa treatments or embark on delightful Chianti wine and tasting tours. There's also the opportunity to explore the picturesque landscapes on foot with local walking tours, while culinary excursions provide a taste of the region's rich gastronomy. Immerse yourself in the charm and beauty of Chianti for an unforgettable experience.

Shopping

The Mall Luxury Outlet, located 20.9km from Chianti, offers luxury brands in a vibrant setting. Fashion Groove, 19.3km away, is another excellent shopping destination. Don’t miss Ra-Ma snc, a charming store also 19.3km from Chianti, perfect for unique gifts and souvenirs.

Recreation

The Stadio Artemio Franchi offers a vibrant atmosphere for sports enthusiasts, located 22.5km from Chianti. For a celestial experience, visit the Chianti Observatory, just 9.7km away, where families can explore the wonders of the universe. Indulge in luxury at Villa a Sesta Polo Club, also 22.5km away.

Adventure

Embark on the Sentierelsa Trail, a stunning hiking route 22.5km from Chianti, soaking in breathtaking scenery. Experience adrenaline at the Siena Circuit karting venue, located 25.7km away. For mountain biking enthusiasts, Tuscany MTB Guide offers thrilling outdoor adventures, also 22.5km from Chianti.

Nightlife

For an enjoyable night out in the Chianti Region, visit Il Fiaschetto, a charming drinking pub located 27.4km away. This venue offers a romantic atmosphere with lively entertainment, perfect for unwinding after a day of exploring the picturesque Tuscan countryside.

*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, Italy, offers a delightful blend of romance, entertainment, and outdoor activities. Visitors can explore charming churches, majestic castles, and lively piazzas while immersing themselves in the region's rich culture. With its renowned Chianti wine, beautiful landscapes, and proximity to Florence, this enchanting area promises a memorable experience for all who seek romance and adventure in a picturesque setting.

  • Verrazzano Castle: Located 11.3km from the Chianti Region, Verrazzano Castle offers a romantic atmosphere steeped in history. Explore its impressive architecture and enjoy breathtaking views of the surrounding vineyards, immersing yourself in the rich culture of Tuscany.
  • Church of San Sigismondo: Situated 8.0km away, this charming church is a hidden gem showcasing exquisite artwork and serene ambiance. The Church of San Sigismondo encapsulates the spiritual and cultural heritage of the area, making it a tranquil spot for reflection.
  • Palazzo Pubblico: This historic palace, 22.5km from Chianti, boasts stunning architecture and fascinating art. As a symbol of local governance, the Palazzo Pubblico invites visitors to delve into Tuscany's political history while appreciating its cultural significance.

Best time to go to Chianti Region

The best time to visit Chianti Region is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is sunny with no rain. January is its coolest month on average. At this time, 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

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to February and November) for more affordable package holidays to Chianti Region.
  • 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.

Top hotels in Chianti Region

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 S$98 per night from 28 Jul to 29 Jul
S$98
28 Jul - 29 Jul
includes taxes & fees
8.2/10 Very good! (350 reviews)
"Room was clean, staff was helpful and easy to park."

Reviewed on 27 Jun, 2026

Hotel Toscana Ambassador
Castello Vicchiomaggio

Castello Vicchiomaggio

Via Vicchiomaggio, 4 Greve in Chianti FI
Fully refundableReserve now, pay when you stay
The price is S$298 per night from 16 Jul to 17 Jul
S$298
16 Jul - 17 Jul
includes taxes & fees
9.4/10 Exceptional! (397 reviews)
"Great trip! Staff was very helpful and few places with free breakfast"

Reviewed on 8 Jul, 2026

Castello Vicchiomaggio
Relais Villa Olmo

Relais Villa Olmo

Via Imprunetana Per Tavarnuzze 19 Impruneta FI
Fully refundableReserve now, pay when you stay
The price is S$314 per night from 2 Aug to 3 Aug
S$314
2 Aug - 3 Aug
includes taxes & fees
9.4/10 Exceptional! (248 reviews)
"Beautiful property."

Reviewed on 28 Jun, 2026

Relais Villa Olmo
See all 4,927 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. Visit the churches and wineries in this walkable area.
See properties

What to do in Chianti Region

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

S$43
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Small-Group Wine Tasting Experience in the Tuscan Countryside

Small-Group Wine Tasting Experience in the Tuscan Countryside

S$132
per adult
98% of travellers recommend
Small-Group Wine Tasting Experience in the Tuscan Countryside
People riding scooters in Tuscany

Florence Vespa Tour: Tuscan Hills, Food and Chianti Wine

S$164
per adult
100% of travellers recommend
Florence Vespa Tour: Tuscan Hills, Food and Chianti 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.