Chianti Region Vacation Packages 2026 from $1,010

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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 Uffizi

Historic Centre of Florence

$1,010

per person

Oct 14 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

7.6/10 Good! (1,003 reviews)

The room was exceptionally clean, including the floor (white napkin test). The staff was super friendly, and the check-in.check out quick. The breakfast is simple, yet with there was a good choice of all you can eat items: toast with a choice of cold ham, mozzarella cheese, tomato slices, salame, ect, mini-pancakes. They also offer freshly-baked croissant fillable with assorted jam, creams etc, cakes, etc. Plus, fresh squeezed orange juice, and other juices, and all type of coffees. The hotel was well located (close to the Uffizi Galley) and the Arno river (Ponte Vecchio).

Reviewed on Aug 10, 2026

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

Save 100% on your flight

$1,744

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9/10 Wonderful! (1,002 reviews)

Relais Uffizi, Tailor made Hotel

Historic Centre of Florence

Save 100% on your flight

$2,759

per person

Sep 21 - Sep 26

found 6 hours ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

9.2/10 Wonderful! (154 reviews)

While the bathrooms were clean I was very disappointed to see a stain on my bedsheets.

Reviewed on Aug 2, 2026

Eden Rock Resort

Save 100% on your flight

$1,638

per person

Oct 22 - Oct 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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

Grand Hotel Cavour

Historic Centre of Florence

Save 100% on your flight

$1,960

per person

Oct 22 - Oct 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.2/10 Wonderful! (1,001 reviews)

Fabulous

Reviewed on Aug 9, 2026

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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 Bus Tour

$28

per adult

76% of travellers recommend

The Best of Tuscany in One Day Sightseeing Tour

The Best of Tuscany Tour: Siena, San Gimignano, Pisa and Lunch at a Winery

$82

per adult

98% 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

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI

$179 nightly

$204 total

Aug 25 - Aug 26

Total with taxes and 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

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

Fully refundableReserve now, pay when you stay

$63 nightly

$77 total

Aug 19 - Aug 20

Total with taxes and fees

8.2/10 Very Good! (357 reviews)

"Room was clean, staff was helpful and easy to park."

Reviewed on Jun 27, 2026

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI

Fully refundableReserve now, pay when you stay

$397 nightly

$449 total

Aug 16 - Aug 17

Total with taxes and 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

See all 4,888 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.