Chianti Region Vacation Packages 2026 from $860

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

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

$860

per person

Nov 18 - Nov 23

found 12 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

7.4/10 Good! (1,009 reviews)

Very good breakfast, Clean room, air conditioning. The shower space was tight.

Reviewed on Sep 29, 2026

Hotel Duomo Firenze

Historic Centre of Florence

$1,025

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

9.2/10 Wonderful! (1,004 reviews)

The room was tiny and everyone could hear every conversation in other rooms. The AC didn’t work and it was so hot in the room that we had to open the windows and then woke up covered in bug bites. Staff knocked on our door one night at 11pm to tell us someone complained about us being loud. We weren’t watching tv or anything, just laughing. The staff were kind of passive aggressive as well with every interaction. Wouldn’t go back.

Reviewed on Sep 29, 2026

Hotel Ginori al DUOMO

Historic Centre of Florence

$957

per person

Nov 17 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

8.8/10 Excellent! (62 reviews)

Fantastic stay, thank you for the upgrade, spacious, cool rooms. Great location, walk to the station and across the road is a convenience store and great restaurants and gelato in the same street

Reviewed on Sep 4, 2026

The Moon Boutique Hotel & Spa

Historic Centre of Florence

$946

per person

Dec 14 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.6/10 Exceptional! (592 reviews)

We totally loved our stay at this hotel. It’s an easy walk to all the main attractions. The spa is a major plus that we took advantage of. Really clean hotel. Really friendly staff. I would definitely recommend this property.

Reviewed on Sep 28, 2026

Dimora Palanca Boutique & SPA

Historic Centre of Florence

$1,398

per person

Dec 13 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.2/10 Wonderful! (73 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Chianti Region

View all trips

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.

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

What to do in Chianti Region

City Sightseeing Florence Hop-on Hop-off Bus Tour

$33

per adult

76% of travellers recommend

Florence: Pasta Cooking Class with Unlimited Wine

$21

per adult

94% of travellers recommend

Accademia timed-entry Ticket with App Guide

$45

per adult

90% of travellers recommend

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

$234 nightly

$264 total

Oct 26 - Oct 27

Total with taxes and fees

10/10 Exceptional! (30 reviews)

"We had a lovely night stay at this villa in September. It is a 900 year-old hunting lodge that has been converted to spacious rooms many with balconies. The views are incredible, the rooms have been renovated with character fixtures, but includes excellent air-conditioning. The view from the pool ..."

Reviewed on Sep 29, 2026

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI

Fully refundableReserve now, pay when you stay

$336 nightly

$380 total

Oct 30 - Oct 31

Total with taxes and fees

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI

$89 nightly

$104 total

Oct 30 - Oct 31

Total with taxes and fees

9.2/10 Wonderful! (467 reviews)

"Excellent dinner, spacious rooms, pol and jacuzzi, and incredible views!"

Reviewed on Sep 28, 2026

See all 4,909 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.