Chianti Region Vacation Packages

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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 travellers 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 travelling, Expedia will help turn your Chianti Region vacation into reality.

Top Chianti Region Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Eden Rock Resort

Eden Rock Resort

CA $1,562
per person
Oct 2 - Oct 5
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9.8/10 Exceptional! (109 reviews)
This was a beautiful property about 10 mins away from Florence. You get the beauty of Tuscany without having to go too far. The hotel only has 12 rooms and everyone knows you by name. We traveled with 2 kids and the rooms were very spacious. Staff are wonderful, Onsite restaurant was great. Views were breathtaking. We didn't have a car, and the hotel was able to help us with cabs easily. Service was excellent and we would highly recommend this hotel!

Reviewed on Jul 18, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

CA $3,650
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (155 reviews)
The place it’s an Amazing. Very clean. Is more beautiful than the pictures.

Reviewed on Aug 2, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence
CA $2,360
per person
Oct 2 - Oct 5
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
Hotel Caravaggio

Hotel Caravaggio

Historic Centre of Florence
CA $1,777
per person
Oct 20 - Oct 26
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9/10 Wonderful! (1,009 reviews)
Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

Oltrarno
CA $1,817
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.8/10 Excellent! (422 reviews)
Wonderful property, amazing hosts. 20 minutes outside of Florence center-easy to get a taxi. My family loved everything about our stay here!

Reviewed on Jul 7, 2026

Things to do near Chianti Region

The Chianti Region in Tuscany, Italy, offers a perfect blend of romance and outdoor adventure. Visitors can indulge in rejuvenating spa treatments and enjoy the beautiful landscapes. A must-do is exploring Chianti through wine tours, which showcase the area’s renowned vineyards. Additionally, consider package tours for a comprehensive experience of Italy's charm and the stunning Chianti countryside.

Shopping

Experience shopping in the Chianti Region at The Mall Luxury Outlet, just 20.9km away, featuring exclusive brands. Ra-Ma snc is a charming store located 19.3km away, perfect for unique finds. Fashion Groove, also 19.3km away, offers a vibrant atmosphere for family-friendly shopping.

Recreation

Experience the wonders of the Chianti Observatory, where family entertainment meets the cosmos, just 9.7km away. Indulge in luxury at the Villa a Sesta Polo Club, 22.5km from the heart of Chianti. For relaxation, explore the serene Alta Val d'Elsa River Park, located 24.1km away.

Adventure

Embark on the Sentierelsa Trail, a scenic hiking experience 22.5km from Chianti Region, where adventure awaits amid breathtaking landscapes. For a thrilling ride, check out the Siena Circuit, a karting venue 25.7km away, perfect for adrenaline enthusiasts. Explore the outdoors with Tuscany MTB Guide, also 22.5km away.

Nightlife

The Chianti Region offers a charming nightlife experience. Visit Il Fiaschetto, a cozy drinking pub located 27.4km away, where you can enjoy a romantic atmosphere filled with entertainment. Sip on local wines and mingle with fellow travellers for a memorable evening in Tuscany.

*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 an enchanting destination perfect for romantic and outdoor vacations. Visitors can explore beautiful churches, castles, and charming piazzas while indulging in the renowned Chianti wines. This area is a cultural haven, offering a mix of city experiences and breathtaking landscapes. Don't miss the chance to tour the famous Chianti vineyards and discover its celebrated wine region, making your trip truly memorable.

  • Monteriggioni Castle: This historic palace, located 19.3km from the Chianti Region, offers a captivating glimpse into the past with its well-preserved walls and towers. Explore the charming village within, where medieval architecture meets stunning views of the surrounding countryside, providing a truly unique cultural experience.
  • Medieval Tower of Barbischio: Just 9.7km from Chianti, this historic site features an impressive tower that dates back to the medieval era. Its striking architecture and panoramic vistas of the landscape create a sense of stepping back in time, perfect for history enthusiasts.
  • Church of San Sigismondo: Located only 8.0km away, this beautiful church is renowned for its serene atmosphere and artistic elements. Visitors can appreciate the intricate details and local heritage while enjoying the peaceful surroundings of this spiritual landmark.

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.

Ready to book your vacation to Chianti Region?

Choose your dates

Chianti Region Hotel Deals

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI
Fully refundableReserve now, pay when you stay
CA $189
CA $217 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (449 reviews)
"This was a fabulous stay. The property is beautiful, the grounds were fun to walk and the swimming pool was lovely. Breakfast every morning was delicious. Hotel was very quiet during the week but was noticeably busier starting Friday (I think local people come just for the weekend). Our room was ..."

Reviewed on Aug 1, 2026

Villa I Barronci Resort & Spa
Hotel Toscana Ambassador

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI
Fully refundableReserve now, pay when you stay
CA $106
CA $126 total
Aug 22 - Aug 23
includes taxes & fees
8.2/10 Very good! (357 reviews)
"Room was clean, staff was helpful and easy to park."

Reviewed on Jun 27, 2026

Hotel Toscana Ambassador
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
Fully refundableReserve now, pay when you stay
CA $554
CA $625 total
Aug 16 - Aug 17
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 4,923 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 relaxing area.
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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 charming coffeehouses in this walkable 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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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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Piazza Matteotti

9.4/10 (21 reviews)
Find out about the history of Greve in Chianti when you take a trip to Piazza Matteotti. Discover the beautiful countryside in this walkable 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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What to do in Chianti Region

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

CA $40
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour

Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour

CA $29
per adult
80% of travellers recommend
Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour
Siena: Cathedral Complex Pass with Audio Guide

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

CA $29
per adult
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
See all activities 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 CA $1,562. 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.