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.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,741, price is now CA $1,598 per person
CA $1,598
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
Right near the attractions. Easy to get around

Reviewed on Sep 4, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $3,127, price is now CA $1,983 per person
CA $1,983
per person
Oct 20 - Oct 26
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Good value for price and location.

Reviewed on Sep 8, 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
Price was CA $3,141, price is now CA $2,113 per person
CA $2,113
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
10/10 Exceptional! (2 reviews)
Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was CA $2,624, price is now CA $1,773 per person
CA $1,773
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
8.6/10 Excellent! (472 reviews)
Great little hotel. Everything is within walking distance. The view from the terrace was amazing.

Reviewed on Aug 6, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
Price was CA $14,503, price is now CA $9,887 per person
CA $9,887
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Florence (FLR)
9.4/10 Exceptional! (232 reviews)
Gorgeous boutique hotel, like museum Beautiful rooms!!! Thank you Giovanni for all ur help and knowledge organizing everything for us, and breakfast waiters were great!!!

Reviewed on Aug 21, 2025

Ready to book your vacation to Chianti Region?

 

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Chianti Region Hotel Deals

Hotel Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A, Poggibonsi, SI
Fully refundableReserve now, pay when you stay
The price is CA $82 per night from Sep 14 to Sep 15
CA $82
CA $100 total
Sep 14 - Sep 15
includes taxes & fees
Hotel Ristorante Alcide
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Via Spaltenna 13, Gaiole in Chianti, SI
The price is CA $517 per night from Oct 6 to Oct 7
CA $517
CA $585 total
Oct 6 - Oct 7
includes taxes & fees
Castello di Spaltenna- Small Luxury Hotels of the World
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

4 out of 5
Via Roma 191, Barberino Tavarnelle, FI
Fully refundableReserve now, pay when you stay
The price is CA $236 per night from Oct 9 to Oct 10
CA $236
CA $269 total
Oct 9 - Oct 10
includes taxes & fees
Hotel Borgo di Cortefreda Relais
See all 5,165 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.
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Discover the most popular places to visit in Chianti Region

Tenuta Torciano Winery

5/5(1 review)

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.

Tenuta Torciano Winery

Montegufoni Castle

Find out about the history of Montegufoni with a stop at Montegufoni Castle. Visit the stunning cathedral and notable monuments in this walkable area.

Montegufoni Castle

Croce del Pratomagno

You can learn about the history of Loro Ciuffenna when you stop by Croce del Pratomagno. Discover the countryside in this relaxing area, or seek out the campsites.

Croce del Pratomagno

What to do in Chianti Region

Chianti Wineries Tour with 7 Wine Tastings from Florence

Chianti Wineries Tour with 7 Wine Tastings from Florence

CA $137
per adult
Chianti Wineries Tour with 7 Wine Tastings from Florence
Chinati vineyard

Essence of Chianti Small Group Tour with Lunch and Tastings from Florence

CA $239
per adult
100% of travellers recommend
Essence of Chianti Small Group Tour with Lunch and Tastings from Florence
Experience the Magic of Tuscany from a Hot Air Balloon

Experience the Magic of Tuscany from a Hot Air Balloon

CA $432
per adult
100% of travellers recommend
Experience the Magic of Tuscany from a Hot Air Balloon
See all activities in Chianti Region
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.