A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

Chianti Region Honeymoon Vacations

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    Save up to CA $4,200 when you book a flight and hotel together*
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Top Honeymoon vacation packages in Chianti Region

Price found within the past 48 hours. Click for updated prices.
  • Jan 18 - Jan 24

    Villa Olmi Firenze + Flight

    Bagno a Ripoli
    5 nights
    4.0 star property
    9.4/10 - Exceptional (822 reviews)
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FCO • 1 stop FCO - YUL • 1 stop
    CA $1,286
    CA $1,090
    per traveller
    found 14 hours ago
    Villa Olmi Firenze
  • Jan 18 - Jan 24

    The Hoxton, Florence + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    9.4/10 - Exceptional (386 reviews)
    "Very clean room! Smelled amazing! Loved the products that they had. Front desk was very friendly and very helpful they gave us really good recommendations and advice to stay away from tourist traps which was greatly appreciated! Would definitely stay here again and would recommend to others! They also have bikes on property that you can use if you would like to explore a little bit more of the city!"
    Reviewed November 8, 2026
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FCO • 1 stop FCO - YUL • 1 stop
    CA $1,616
    CA $1,230
    per traveller
    found 14 hours ago
    The Hoxton, Florence
  • Dec 26 - Jan 2

    Villa Tolomei Hotel & Resort + Flight

    Oltrarno
    6 nights
    5.0 star property
    8.8/10 - Excellent (449 reviews)
    "The property was lovely. A former 15th(?) century monastery located on a hilltop overlooking parts of Florence. Surrounded by olive and fruit trees, and gardens. It's past the Roman gate, about a 30 euro cab ride from the center of town. Though they didn't tell us until we asked, there's a shuttle that will take you down the hill to the Roman Gate where taxis and busses can be found. We arrived just after the hotel restaurant had closed for the afternoon by a minute. They were kind/professional..."
    Reviewed November 6, 2026
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FCO • 1 stop FCO - YUL • 1 stop
    CA $3,812
    CA $3,040
    per traveller
    found 22 hours ago
    Villa Tolomei Hotel & Resort
  • Dec 26 - Jan 2

    Hotel Calimala Florence + Flight

    Historic Centre of Florence
    6 nights
    4.0 star property
    9.6/10 - Exceptional (1,004 reviews)
    "The location is very well near or walking distance of many sites (restaurant, stores)"
    Reviewed November 8, 2026
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FCO • 1 stop FCO - YUL • 1 stop
    CA $4,224
    CA $3,532
    per traveller
    found 22 hours ago
    Hotel Calimala Florence
  • Jan 18 - Jan 24

    Palazzo Castri 1874 Spa & Garden + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    9.6/10 - Exceptional (1,003 reviews)
    "Stayed for 5 nights and found the hotel to be both an excellent position to view the wonderful sights of Florence, whilst also being in the slightly quieter part of the city, and fabulous inside with a large room and good facilities. We stayed in a junior suite which has a small living room area with a sofa. the room was immaculately clean throughout with a very large bathroom. The view from the room was over the adjacent square and it was good to be able to open the windows and enjoy the fresh..."
    Reviewed November 8, 2026
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FCO • 1 stop FCO - YUL • 1 stop
    CA $1,452
    CA $1,249
    per traveller
    found 14 hours ago
    Palazzo Castri 1874 Spa & Garden

Discover the most popular places to visit in Chianti Region

What to do in Chianti Region

Top Honeymoon Chianti Region Hotels

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.

Frequently Asked Questions

How much does a Chianti Region vacation package cost?

Live it up in Chianti Region from as low as CA $1,090. Choose from a wonderful selection of flights, hotels and rental cars to suit your travel style. You can pick up even more discounts when you add a couple of tours or experiences to your package.

How do I get a cheap travel package to Chianti Region?

Find flights that suit your busy schedule, add a hotel to your booking and watch how much you save with a Chianti Region vacation package. It's that easy! From flights and hotels to rental cars and activities, Expedia is your gateway to cheap travel. And with over 550 air carriers and 1,000,000 properties around the world to pick from, you won't be short of choice.

Where should I stay in Chianti Region?

Val dElsa is in the top spot on many Chianti Region must-see lists. Collegiate Church of Santa Maria Assunta is one reason why.

What are the top hotels in Chianti Region?

When it comes to hotels in Val dElsa, Grand Hotel Baglioni and Hotel Spadai are among the favorites. If you're spending time in Greve in Chianti, Hotel Pendini and The Market Urban Hotel will make you feel at home.

How far in advance should I book my Chianti Region vacation?

While prices change from time to time, we generally suggest booking your flight as soon as possible. Many international airfares can be compared on Expedia up to a year in advance. If circumstances have left you booking late, you may still get lucky. Low prices to Chianti Region sometimes emerge only weeks before departure.

What does an Expedia Chianti Region travel package include?

Much of that is up to you. You can pick from a variety of Chianti Region packages, such as a hotel, rental car and flight. You can also book a flight with a hotel, or a flight with a rental car. Once you've made your booking, you can add the fun stuff like experiences and tours. Whatever your perfect Chianti Region vacation looks like, get set to save!

What should I know before booking a Chianti Region travel package?

When you book your flights, hotels and car rentals together, you'll pick up fantastic discounts. Whether you're organizing a mountain getaway in a cabin or would rather stay in a fancy hotel in the city, Expedia will help make it happen.

Can I choose my airline with a Chianti Region Expedia vacation package?

Yes — that's one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have more than 550 partner airlines across the globe, so you have loads of choice when creating your Chianti Region adventure.

If I'm not able to travel, can I cancel my Chianti Region vacation package?

Your situation can change in a flash, so yes. You may be able to cancel or amend your Chianti Region vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still make the necessary changes, but your airline, hotel or car rental company may charge additional fees. Need more information? Look up our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.