Chianti Region Vacations from $793

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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

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Aurum Firenze
Eurostars Florence Boutique
Aurum Uffizi
The Moon Boutique Hotel & Spa
Hotel Leonardo Da Vinci
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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
$53 nightly
The price is $58 total per night from Feb 15 to Feb 16
$58 total
Feb 15 - Feb 16
Total with taxes and fees
8/10 Very Good! (462 reviews)
I highly recommended

Reviewed on Oct 14, 2025

Hotel Ristorante Alcide
Villa La Borghetta Resort

Villa La Borghetta Resort

4 out of 5
Via del Cesto Figline e Incisa Valdarno FI
$114 nightly
The price is $128 total per night from Jan 26 to Jan 27
$128 total
Jan 26 - Jan 27
Total with taxes and fees
7.8/10 Good! (85 reviews)
Beautiful experience!

Reviewed on Jul 1, 2025

Villa La Borghetta Resort
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
$96 nightly
The price is $112 total per night from Feb 18 to Feb 19
$112 total
Feb 18 - Feb 19
Total with taxes and fees
9.4/10 Exceptional! (475 reviews)
The hotel and services exceeded my expectations.

Reviewed on Nov 30, 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.

Find the Best Chianti Region Vacation Packages

Things to do near Chianti Region

The Chianti Region in Tuscany, Italy, offers a romantic and outdoor vacation experience filled with entertainment. Visitors can indulge in luxurious spa treatments, enjoy scenic Chianti and wine tours, and participate in delightful wine tastings that showcase the area's renowned vineyards. Whether you're seeking relaxation or adventure, Chianti is the perfect destination for a memorable getaway.

Shopping

In the Chianti Region, indulge in a shopping spree at The Mall Luxury Outlet, just 13 miles away, featuring high-end brands. Fashion Groove, located 12 miles away, offers a vibrant atmosphere with diverse shops. Don't miss Ra-Ma snc, a charming store also 12 miles from the region.

Recreation

At the Chianti Observatory, enjoy an enchanting experience under the stars in this family-friendly planetarium. For luxury, visit Villa a Sesta Polo Club, where you can indulge in exclusive amenities. Finally, relax at Alta Val d'Elsa River Park, a beautiful spot for wellness and rejuvenation amidst nature.

Adventure

Embark on the Sentierelsa Trail, a stunning hiking experience located 14 miles from Chianti, where you'll enjoy breathtaking outdoor scenery. For thrill-seekers, the Siena Circuit offers exhilarating karting 16 miles away, while Tuscany MTB Guide promises unforgettable mountain biking adventures, also 14 miles from the region.

Nightlife

In the Chianti Region, enjoy a vibrant nightlife at Il Fiaschetto, a cozy pub just 17 miles away. With its romantic atmosphere and lively entertainment, it's the perfect spot to unwind, sip on local wines, and immerse yourself in the region's charming evening energy.

*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, is perfect for a romantic and outdoor getaway, featuring enchanting churches, historic castles, and lively piazzas. Visitors can immerse themselves in the rich culture while exploring renowned Chianti wine areas, sampling the best wines, and discovering fascinating destinations. This picturesque region seamlessly blends romance and adventure, making it an ideal choice for travelers seeking unforgettable experiences.

  • Castello di Albola: Located 2 miles from the Chianti Region, this enchanting castle offers a romantic atmosphere steeped in culture. Visitors can explore the stunning architecture and picturesque vineyards, making it a perfect spot for wine lovers and history enthusiasts alike.
  • Piazza Matteotti: Situated 5 miles away, this vibrant piazza is the heartbeat of local life, showcasing the rich culture of the area. Enjoy the lively atmosphere, cafes, and shops while soaking in the beautiful surroundings and engaging with the community.
  • Church of Santa Maria Assunta: Just 3 miles from Chianti, this charming church features impressive architecture and a serene ambiance, making it a wonderful place to appreciate local artistry and spirituality.

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 Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Galileo Galilei Airport (PSA)

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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.