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.
Hotel Duomo Firenze

Hotel Duomo Firenze

Historic Centre of Florence
CA $1,220
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
The location of this hotel is excellent in central Florence in a pedestrian only street steps across from the Duomo. Walkable to everything for choice of restaurants and shops. The staff was outstanding and the breakfast choices were very good and better than going to a cafe nearby. The room had great storage and the bathroom was renovated very nicely. The hotel is on the 4th floor of a historial building and has an elevator.

Reviewed on Sep 23, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

Historic Centre of Florence
CA $1,642
per person
Nov 8 - Nov 14
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
8.6/10 Excellent! (500 reviews)
mattresses were impossible to sleep on

Reviewed on Sep 14, 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

Historic Centre of Florence
CA $1,370
per person
Nov 30 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
Option on the breakfast could have been better, but overall, we had a good experience

Reviewed on Sep 24, 2026

Grand Hotel Cavour

Grand Hotel Cavour

Historic Centre of Florence
CA $1,401
per person
Nov 30 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (1,004 reviews)
Aurum Firenze

Aurum Firenze

Historic Centre of Florence
CA $1,403
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Good location, clean and helpful staff

Reviewed on Sep 24, 2026

Where to stay in Chianti Region

Find the best Chianti Region areas and neighborhoods for the activities you enjoy most. Learn more about Chianti Region
A rural landscape with vineyards, rolling hills, and scattered houses.

Tavarnelle Val di Pesa

Tavarnelle Val di Pesa is noteworthy for its wineries, and you can make a stop at top attractions like Passignano Abbey and Abbey of Passignano.

A historic stone church with a bell tower, surrounded by well-maintained hedges and a stone wall.

Barberino Val d'Elsa

Barberino Val d'Elsa is noteworthy for its wineries, and you can make a stop at top attractions like Casa Sola - Chianti Winery and Castello della Paneretta.

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San Donato in Poggio

Travelers like the restaurants in San Donato in Poggio, and Pieve di San Donato in Poggio is a top attraction you might want to visit.

A dilapidated brick structure with a chimney, surrounded by grass and trees.

Certaldo Alto

You'll enjoy the museums and monuments in Certaldo Alto. You might want to make time for a stop at Casa del Boccaccio or Palazzo Pretorio.

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Sambuca

If you're looking for some top things to see and do in Sambuca and surrounding area, you can visit Abbey of Passignano and Passignano Abbey.

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?

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Chianti Region Hotel Deals

Fattoria di Vegi

Fattoria di Vegi

Località Vegi, 16 Castellina in Chianti SI
CA $389
CA $438 total
Oct 24 - Oct 25
includes taxes & fees
10/10 Exceptional! (28 reviews)
"This is a newly renovated and opened property cared for by a wonderful family. Everything has been taken care of down to the last detail. The food is delicious, the rooms are well appointed and till we thoroughly enjoyed exploring the property and every interesting nook! There's lots to do including ..."

Reviewed on Sep 24, 2026

Fattoria di Vegi
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 $122
CA $144 total
Oct 25 - Oct 26
includes taxes & fees
Villa I Barronci Resort & Spa
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
CA $578
CA $652 total
Oct 5 - Oct 6
includes taxes & fees
9.6/10 Exceptional! (287 reviews)
"The experience was exceptional, the dinners in both restaurants on site were spectacular. The staff was amazing, friendly, and made our stay very memorable. We are planning to return soon."

Reviewed on Sep 15, 2026

Castello di Spaltenna- Small Luxury Hotels of the World
See all 4,913 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.
See properties
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.
See properties

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 quaint 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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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 wineries in this walkable area.
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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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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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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 quaint 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 $47
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Florence: Pasta Cooking Class with Unlimited Wine

Florence: Pasta Cooking Class with Unlimited Wine

CA $29
per adult
94% of travellers recommend
Florence: Pasta Cooking Class with Unlimited Wine
Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour

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

CA $37
per adult
80% of travellers recommend
Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour
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 $1,220. 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.