Chianti Region Vacation Packages 2026 from $931

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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.

Aurum Firenze

Historic Centre of Florence

$931

per person

Nov 23 - Nov 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

7.6/10 Good! (1,003 reviews)

Good location- close to all the attractions. We were there for 3 days. One day, had a downpour of rain- came back to the hotel soaking wet asked for dry towels, they declined- you only have the same towels ( which were wet from our morning shower)for your stay. Shower was a lot smaller than previous hotels that we stayed at when in Italy. Breakfast and coffee were horrible

Reviewed on Sep 22, 2026

Relais Uffizi, Tailor made Hotel

Historic Centre of Florence

$2,047

per person

Oct 24 - Oct 31

found 2 hours ago

Roundtrip flight included

New York (LGA) to Florence (FLR)

9.2/10 Wonderful! (161 reviews)

LOVE this hotel! Perfect location, amazing breakfast, fantastic staff, beautiful rooms, excellent bathrooms. Made our Florence trip amazing highlight of our time in Italy!

Reviewed on Sep 15, 2026

Hotel Duomo Firenze

Historic Centre of Florence

$980

per person

Dec 1 - Dec 6

found 20 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.2/10 Wonderful! (1,001 reviews)

I can’t understand how the property even considers selling a room the size I was in under a staircase with a shower which barely trickles.

Reviewed on Sep 19, 2026

Hotel Santa Maria Novella

Historic Centre of Florence

$1,507

per person

Dec 1 - Dec 6

found 20 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.6/10 Exceptional! (1,007 reviews)

Great location. Hotel was nice and maintained. Rooms were spacious for a family of 3. Bathrooms were nice as well with a big window that I was able to see the plaza. Bed was comfortable. Bar was nice and outdoor seating was great as well. Will stay here again.

Reviewed on Sep 22, 2026

The Moon Boutique Hotel & Spa

Historic Centre of Florence

$976

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.6/10 Exceptional! (592 reviews)

Great location. We suggest taking the river down to the city center every day. The free breakfast and coffee is great way to start your day. Schedule a spa day at least once so you can relax before the walk to dinner! Reception was super nice and even helped us call a taxi.

Reviewed on Sep 21, 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.

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.

Stay near popular Chianti Region attractions

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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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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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 Bus Tour

$29

per adult

76% of travellers recommend

Florence: Pasta Cooking Class with Unlimited Wine

$19

per adult

94% of travellers recommend

Accademia timed-entry Ticket with Instant Delivery & Priority Access

$45

per adult

94% of travellers recommend

See all activities in Chianti Region

Chianti Region Hotel Deals

Fattoria di Vegi

Località Vegi, 16 Castellina in Chianti SI

$295 nightly

$331 total

Oct 22 - Oct 23

Total with taxes and fees

10/10 Exceptional! (25 reviews)

"What an amazing hotel. The attention to detail on the refurb of the property is phenomenal. Once the tennis court, spa etc are completed this will easily be high hundreds per night. We visited all the other properties in the surrounding area and nothing came close to this hotel. The food and drinks ..."

Reviewed on Sep 16, 2026

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI

$133 nightly

$153 total

Oct 23 - Oct 24

Total with taxes and fees

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI

$394 nightly

$445 total

Oct 21 - Oct 22

Total with taxes and 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

See all 4,918 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.