Chianti Region Vacations from $723

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Your Chianti Region Vacation

Lock in a vacation 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 travelers 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 traveling, Expedia will help turn your Chianti Region vacation into reality.

The Latest Chianti Region vacation packages

Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa
The Sense Experience Resort
Aurum Uffizi
Grand Hotel Cavour
Palazzo Firenze by Baglioni Hotels & Resorts
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Discover the most popular places to visit in Chianti Region

What to do in Chianti Region

Chianti Region Hotel Deals

Hotel Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A, Poggibonsi, SI
Fully refundableReserve now, pay when you stay
$51 nightly
The price is $63 total per night from Aug 31 to Sep 1
$63 total
Aug 31 - Sep 1
Total includes taxes and fees
8/10 Very Good! (450 reviews)
Good Value for the cost !
"The hotel was good value for the price. The room was clean. The hotel is in a good, safe area. The A/C was able to keep up with the 98F temps outside. Check in was easy. The breakfast was very good. Parking is a little tricky but not to bad. The only issues we had with our room was the safe wouldnt ..."

Reviewed on Jul 7, 2025

Hotel Ristorante Alcide
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Via Spaltenna 13, Gaiole in Chianti, SI
Fully refundableReserve now, pay when you stay
$431 nightly
The price is $486 total per night from Aug 25 to Aug 26
$486 total
Aug 25 - Aug 26
Total includes taxes and fees
9.4/10 Exceptional! (244 reviews)
"Beautiful hotal located in such a paradise location amazing view very good food. The staff was very nice. The service was amazing. I definitely recommend the place. It’s a beautiful relaxing, gorgeous."

Reviewed on Aug 13, 2025

Castello di Spaltenna- Small Luxury Hotels of the World
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

4 out of 5
Via Roma 191, Barberino Tavarnelle, FI
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $180 total per night from Aug 28 to Aug 29
$180 total
Aug 28 - Aug 29
Total includes taxes and fees
9.2/10 Wonderful! (446 reviews)
"The Borgo was exactly what we were looking for. A great pool, lounge chairs, view of the rolling hills, and wonderful outdoor pool side bar service. Easy access to Siena, Florence, and anywhere else in the area to explore. The decor is dated, but was we loved the unpretentious charm."

Reviewed on Aug 16, 2025

Hotel Borgo di Cortefreda Relais
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.

Things to do near Chianti Region

The Chianti Region in Tuscany is perfect for a romantic getaway or outdoor adventure. Visitors can indulge in relaxing spa treatments and explore charming local shops. Key activities include guided Chianti wine tours, tastings of exquisite wines, and luxury tours that showcase the region's stunning landscapes and rich culture. Don't miss the opportunity to immerse yourself in the enchanting world of Italian wines while enjoying the picturesque scenery.

Shopping

In the Chianti Region, visit The Mall Luxury Outlet, just 13 miles away, for luxury brands in a vibrant setting. Also, check out Fashion Groove, located 12 miles away, offering a fun shopping atmosphere. Ra-Ma snc, another store 12 miles away, is perfect for unique gifts and souvenirs.

Recreation

Experience luxury at Villa a Sesta Polo Club, where you can indulge in wellness treatments amidst serene countryside vibes. For a blend of culture and entertainment, visit Teatro dei Rinnovati, offering captivating performances perfect for families and couples alike.

Adventure

Explore the Sentierelsa Trail for a scenic hiking experience, located 14 miles from Chianti Region, where you can immerse yourself in stunning landscapes. For a thrilling ride, head to the Siena Circuit, situated 16 miles away, and enjoy an exhilarating karting adventure.

Nightlife

The Chianti Region offers a charming nightlife atmosphere, perfect for unwinding after a day of exploration. A great spot is Il Fiaschetto, a cozy drinking pub located 17 miles away. Enjoy its romantic vibes and lively entertainment, making it an ideal place to sip local wines and mingle.

*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 romantic and entertaining outdoor vacation experience. Travelers can explore charming churches, castles, and picturesque piazzas while immersing themselves in the rich culture and romance of the area. Don't miss the chance to visit renowned Chianti vineyards, taste the region's finest wines, and discover its historic castles for an unforgettable experience in this beautiful wine region.

  • Castello di Albola: Nestled 2 miles from Chianti, this enchanting castle offers a romantic atmosphere steeped in history and culture. Explore its beautiful grounds and vineyards while enjoying stunning views of the Tuscan landscape, making it a perfect spot for couples and history enthusiasts alike.
  • Piazza Matteotti: Located 5 miles from Chianti, this vibrant square is a cultural hub surrounded by charming cafes and shops. Experience the lively city vibes as you mingle with locals, admire the architecture, and savor authentic Tuscan cuisine in the heart of the community.
  • Pieve di San Leolino: Situated 3 miles away, this historic church showcases remarkable architectural beauty and offers a serene atmosphere. Immerse yourself in its rich cultural heritage while appreciating the stunning artworks and peaceful surroundings that make it a spiritual oasis.

Best time to go to Chianti Region

The best time to visit Chianti Region is dependant 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

  • 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.

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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.