Chianti Region Vacation Packages 2026 from $1,024

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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.

Dimora Palanca Boutique & SPA

Historic Centre of Florence

$1,024

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.2/10 Wonderful! (75 reviews)

Hotel Duomo Firenze

Historic Centre of Florence

$1,033

per person

Dec 10 - Dec 16

found 17 hours ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

9.2/10 Wonderful! (1,004 reviews)

Absolutely everything was perfect - from checkin to deprture- Gelato and cookies available all day, wonderful breakfast, room was SO Awesome facing the Duomo, assist to schedule a taxi - lift so less stairs - would absolutely recommend !!!

Reviewed on Oct 2, 2026

Donati Luxury Tower Suites

Historic Centre of Florence

$1,536

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.8/10 Exceptional! (77 reviews)

Excellent lodging option very close to the Duomo and central to Florence. It is a terrific location in that it is close to everything but secluded off a very small road that only gets traffic for people checking in or leaving the property. The lodging is in a very old tower that has been converted to about 10 rooms. The front desk is excellent and surprised us when we checked in by telling us they would deliver an assortment of pastries to our room every day for breakfast. We had the Gemma suite which was not large but well laid out with a very comfortable bed and furniture and a very nice bathroom.

Reviewed on Oct 4, 2026

Portrait Firenze - Lungarno Collection

Historic Centre of Florence

Save 100% on your flight

$2,206

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.8/10 Exceptional! (318 reviews)

We couldn’t have had a more enjoyable day at this fabulous hotel. The staff responded to our every whim and even anticipated some! And its location right in the center of historic Florence cannot be beat. We will be back again!

Reviewed on Oct 4, 2026

Monastero di Cortona Hotel & Spa

Cortona Old Town

$1,292

per person

Dec 12 - Dec 18

found 13 hours ago

Roundtrip flight included

New York (JFK) to Florence (FLR)

10/10 Exceptional! (337 reviews)

From the moment we arrived at Monastero di Cortona, everything was wonderful. We were welcomed with a cold, delicious drink and invited to sit and relax while the staff took care of everything else for us. Anna then gave us a lovely tour of the hotel, which was such a nice way to begin our stay. When we walked into our room, there was a beautiful welcome table waiting for us with waters, chocolates, and even a lovely necklace charm, which was such a thoughtful touch. The room smelled absolutely amazing, and the view was stunning. Even the shower felt like a spa experience, with chromotherapy lighting and water that left our skin feeling incredibly soft. The complimentary breakfast was amazing, beautifully presented, and the staff was so attentive and made sure we had everything we needed. We also spent time at the spa and absolutely loved it. The Turkish bath, sauna, and massaging pool were all incredibly relaxing, and we also had massages that were absolutely amazing. Even as we were leaving, the thoughtfulness continued—the housekeeping staff left us a departing gift, which was such a sweet and unexpected touch and made us feel special right up until the end. From the beautiful surroundings to all the thoughtful little details and wonderful service, our stay felt luxurious, peaceful, and very special. We truly felt taken care of from the moment we arrived until the moment we left.

Reviewed on Oct 5, 2026

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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 di Monsanto.

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.

Morrocco

While there might not be top attractions in Morrocco, you can explore the larger area and discover places like Abbey of Passignano and Chianti Observatory.

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 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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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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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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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

Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine

$21

per adult

94% of travellers recommend

Florence: Pasta Cooking Class with Unlimited Wine

$21

per adult

94% of travellers recommend

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

$21

per adult

See all activities in Chianti Region

Chianti Region Hotel Deals

Fattoria di Vegi

Località Vegi, 16 Castellina in Chianti SI

Fully refundableReserve now, pay when you stay

$239 nightly

$270 total

Oct 26 - Oct 27

Total with taxes and fees

10/10 Exceptional! (35 reviews)

"The entire estate was perfectly curated, every aspect was completely flawless. Food and wine…. 10/10. Best place we’ve ever stayed."

Reviewed on Oct 4, 2026

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI

$331 nightly

$375 total

Oct 30 - Oct 31

Total with taxes and fees

9.6/10 Exceptional! (291 reviews)

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Reviewed on Oct 2, 2026

hu Firenze Certosa camping in town

Via San Cristofano 2 Impruneta FI

Fully refundableReserve now, pay when you stay

$42 nightly

$49 total

Oct 12 - Oct 13

Total with taxes and fees

8.4/10 Very Good! (108 reviews)

"Don't needs to worry about check in. It is 24 hours, but in not in the check in details"

Reviewed on Sep 14, 2026

See all 4,882 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.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	40.6°F (4.800000000000001°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
February	42.8°F (6.0°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
March	47.5°F (8.6°C)	Light Rain	Mostly Sunny	Average	Average
April	54.0°F (12.2°C)	Light Rain	Mostly Sunny	Average	Average
May	60.4°F (15.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	69.8°F (21.0°C)	Light Rain	Sunny	Average	Slightly High
July	75.9°F (24.4°C)	No Rain	Sunny	Moderately High	Average
August	75.6°F (24.200000000000003°C)	No Rain	Sunny	Moderately High	Average
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
October	58.5°F (14.7°C)	Light Rain	Mostly Sunny	Average	Average
November	50.0°F (10.0°C)	Light Rain	Mostly Sunny	Average	Slightly Low
December	43.2°F (6.2°C)	Light Rain	Mostly Sunny	Moderately Low	Average

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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Frequently asked questions

What's included in a Chianti Region vacation package?

A Chianti Region vacation package in Greve in Chianti lets you combine flights, hotel stays, and rental cars. Your flight will typically arrive at Florence (FLR-Peretola) Airport. Nearly a third of hotels in Greve in Chianti offer free breakfast, and nearly a third also provide airport shuttle service.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How can I save money on a Chianti Region vacation package?

When you bundle, you can save up to 30%*. To save money on a Chianti Region package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

Which destinations should I consider for a Chianti Region vacation?

For a Chianti Region vacation, several towns offer distinct experiences as a base:

Greve in Chianti: This town is a popular choice for those seeking a central base with a wide range of lodging options and a lively atmosphere, known for cultural attractions and outdoor activities.
Barberino Tavarnelle: Consider this destination for a romantic getaway with a focus on cultural exploration and outdoor pursuits, offering many places to stay.
San Casciano in Val di Pesa: This area is well-suited for travelers looking for romantic getaways, with a good selection of lodging and opportunities for cultural and outdoor experiences.
Castellina in Chianti: A charming option for romantic getaways, this town provides a mix of cultural attractions and outdoor activities, with plenty of hotels.
Bucine: This destination is ideal for those prioritizing outdoor activities and romantic getaways, offering a selection of hotels for a tranquil stay.

Is Chianti Region better suited for a beach vacation or a cultural trip?

The Chianti Region is primarily an outdoor and nature destination, renowned for its rolling hills, vineyards, and charming villages, making it ideal for a Chianti Region vacation focused on scenic beauty and relaxation.The region also offers a rich cultural experience, with numerous historic castles and abbeys. Travelers can explore sites like Meleto Castle and Castle of Brolio, or visit the Archaeological Museum of Chianti in Castellina in Chianti.This blend of natural landscapes and historical depth makes the Chianti Region a strong choice for those seeking both outdoor activities and cultural immersion.

Which airport should I use for a Chianti Region vacation?

For a Chianti Region vacation, travelers typically use Florence (FLR-Peretola) or Bologna (BLQ-Guglielmo Marconi) airports. Florence is often the most convenient gateway, serving the wider Tuscany region, including the Chianti area. Bologna also provides good access, especially for those arriving from further afield, with onward travel to the various towns and villages of the Chianti Region.

What are the top things to do in Chianti Region?

The Chianti Region vacation is best explored from a base like Greve in Chianti, with many sights throughout the area:Browse and book things to do in Chianti Region on Expedia.

Can I change or cancel my Chianti Region vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Chianti Region vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Chianti Region vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Chianti Region vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Chianti Region?

To find last-minute vacation packages to Chianti Region, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Chianti Region vacation packages?

Free cancellation on a Chianti Region vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Chianti Region vacation as a package or separately?

An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Chianti Region getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Chianti Region vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.

Chianti Region Vacations from $1,024

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Chianti Region Vacation

The Latest Chianti Region vacation packages

Dimora Palanca Boutique & SPA

Hotel Duomo Firenze

Donati Luxury Tower Suites

Portrait Firenze - Lungarno Collection

Monastero di Cortona Hotel & Spa

Where to stay in Chianti Region

Tavarnelle Val di Pesa

Barberino Val d'Elsa

San Donato in Poggio

Certaldo Alto

Morrocco

Stay near popular Chianti Region attractions

Antinori nel Chianti Classico

The Mall Luxury Outlet

Tenuta Torciano Winery

Verrazzano Castle

Castello di Albola

Castle of Brolio

Meleto Castle

Piazza Matteotti

What to do in Chianti Region

Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine

Florence: Pasta Cooking Class with Unlimited Wine

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

Chianti Region Hotel Deals

Fattoria di Vegi

Castello di Spaltenna- Small Luxury Hotels of the World

hu Firenze Certosa camping in town

Find the Best Chianti Region Vacation Packages

Things to do near Chianti Region

Find the best attractions near Chianti Region

Best time to go to Chianti Region

Tips to save on your trip to Chianti Region

Chianti Region Essential Information

More vacations you might like

Frequently asked questions

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