Chianti Region Vacations 2025 from CA $1,518

Chianti Region flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Aurum Uffizi

Historic Centre of Florence

per person

Jun. 29 - Jul. 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

Stay at this 4-star hotel in Florence. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Uffizi Gallery and Historic Centre of Florence are located nearby.

Hotel Bencista

per person

Jul. 8 - Jul. 13

found 24 hours ago

Roundtrip flight included

Toronto (YYZ) to Florence (FLR)

Stay at this 3-star beach hotel in Pietrasanta. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Forte dei Marmi Beach and Viareggio Beach are located nearby.

The Moon Boutique Hotel & Spa

Santa Maria Novella

per person

Jun. 22 - Jun. 28

found 15 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Florence (FLR)

Stay at this 4-star spa hotel in Florence. Enjoy free WiFi, a full-service spa, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Historic Centre of Florence and Cathedral of Santa Maria del Fiore are located nearby.

Eurostars Florence Boutique

Historic Centre of Florence

per person

Jun. 22 - Jun. 28

found 15 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Florence (FLR)

Stay at this 4-star boutique hotel in Florence. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Popular attractions Uffizi Gallery and Cathedral of Santa Maria del Fiore are located nearby.

Palazzo Firenze by Baglioni Hotels & Resorts

Historic Centre of Florence

per person

Jul. 8 - Jul. 14

found 15 hours ago

Roundtrip flight included

Toronto (YYZ) to Florence (FLR)

Stay at this 5-star luxury hotel in Florence. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Popular attractions Uffizi Gallery and Cathedral of Santa Maria del Fiore are located nearby.

Top Chianti Region hotels deals

Hotel Borgo di Cortefreda Relais

Via Roma 191, Barberino Tavarnelle, FI

Free cancellation

Reserve now, pay when you stay

CA $164

CA $190 total

includes taxes & fees

May 12 - May 13

Stay at this 4-star spa hotel in Barberino Tavarnelle. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Santa Lucia al Borghetto Church and Abbey of Passignano are located nearby.

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13, Gaiole in Chianti, SI

Free cancellation

Reserve now, pay when you stay

CA $610

CA $687 total

includes taxes & fees

May 12 - May 13

Stay at this 5-star spa hotel in Gaiole in Chianti. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Church of San Sigismondo and Gaiole in Chianti Stadium are located nearby.

Hotel Ristorante Alcide

Viale Marconi, 67/A, Poggibonsi, SI

Free cancellation

Reserve now, pay when you stay

CA $92

CA $111 total

includes taxes & fees

May 11 - May 12

Stay at this 4-star business-friendly hotel in Poggibonsi. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Church of San Lorenzo and Archeodromo di Poggibonsi are located nearby.

Hu Norcenni Girasole Village

Via Norcenni 7, Figline e Incisa Valdarno, FI

Get rates

Stay at this 4-star spa campground in Figline e Incisa Valdarno. Enjoy free parking, 7 outdoor pools, and 3 restaurants. Popular attractions Franciscan Monastery of St. Francis and Museum of Terranuova Tuscany are located nearby.

Castello di Fonterutoli Wine Resort

Via Puccini 4, Castellina in Chianti, SI

Free cancellation

Reserve now, pay when you stay

CA $337

CA $377 total

includes taxes & fees

May 25 - May 26

Stay at this B&B in Castellina in Chianti. Enjoy free WiFi, an attached winery, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Mazzei Winery and Walls of Monteriggioni are located nearby.

Il Borro - Relais & Châteaux

Località Borro, 1, San Giustino Valdarno, Loro Ciuffenna, AR

Free cancellation

Reserve now, pay when you stay

CA $738

CA $812 total

includes taxes & fees

May 25 - May 26

Book a stay at this golf farm stay in Loro Ciuffenna. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Il Borro Wines and La Salceta Winery are located nearby.

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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.

Popular places to visit

Meleto Castle

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.

Buondonno Winery

You can enjoy a tasting or tour at Buondonno Winery during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this quaint area.

Antinori nel Chianti Classico

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.

Frequently asked questions

How much are vacation packages to Chianti Region?

Prepare to be surprised — you can unwind in Chianti Region for only CA $1,518. Let Travelocity save you money and hassle with our awesome vacation package deals. With hotels, flights and tours all ready to go at our one-stop shop, why wait?

Where can I get the best vacation package deals for Chianti Region?

For an amazing Chianti Region package deal, turn to Travelocity. Take your pick of 400 partner airlines and 1,000,000 properties worldwide to create your ultimate trip — simple as that.

Why should I book my Chianti Region vacation package via Travelocity?

From our 24/7 customer support to our range of amazing destinations, we are committed to giving you the most unforgettable escape. All you need to do is click and book — our Price Match Guarantee will ensure you score the best price.

Will I save money on my Chianti Region car rental if I book it with hotels and flights?

Bundling your bookings into a Chianti Region vacation package will save you a tidy sum. You can bundle a car and flight; a hotel, car and flight; or a hotel and car. You won’t find a better way to discover the greater Chianti Region area than from the comfort of your own rental car. You can also add experiences and tours to your Travelocity package.

Which airport is best for Chianti Region?

Arranging where you land in Chianti Region is a breeze — most airlines fly in and out of Peretola Airport (FLR).

What is there to do in Chianti Region?

Chianti Region boasts hidden surprises around every turn, but be sure you get to Collegiate Church of Santa Maria Assunta and Antinori nel Chianti Classico while you’re here. These attractions can’t be missed.