Cavallari Vacations from $760

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Your Cavallari Vacation

From its highlights to its hidden gems, this city is best experienced with a Cavallari vacation package. Book a hotel in Badia Coltibuono, which is great for families, nature and walking. If your trip to Cavallari includes some sightseeing, take in famous attractions like Buondonno Winery, Casa Vinicola Luigi Cecchi and City Hall Castellina In Chianti. Don't put off your visit to this destination any longer. The perfect Cavallari vacation is only a few clicks away with Expedia.

The Latest Cavallari vacation packages

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

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
If one is not there for a fancy hotel room, but for sightseeing, this is a great, clean, bare bones room. It is close to the train station. We were on the 5th floor and had a great view! Breakfast was also on the 5th floor. Close proximity to all the museums and Duomo, 20 minute walk or less to everything. We walked everywhere!

Reviewed on Jun 21, 2025

Residenza Hotel Cimabue

Residenza Hotel Cimabue

3 out of 5
Historic Centre of Florence
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.6/10 Good! (362 reviews)
Great place and staff

Reviewed on Jun 6, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Great place to stay, so close to all attractions. Fantastic staff and service. A happy traveller.

Reviewed on Jun 25, 2025

Hotel Bencista

Hotel Bencista

3 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 7
found 14 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.2/10 Good! (11 reviews)
Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Fantastic people and best view in Florence at night. Breakfast the best in Florence. Would go back in a heart beat

Reviewed on Jun 25, 2025

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Discover the most popular places to visit in Cavallari

Castellina in Chianti which includes farmland

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 romantic area.

Buondonno Winery

City Hall Castellina In Chianti

5/5(1 review)

City Hall Castellina In Chianti is just one of the places to see in Castellina in Chianti, so why not enjoy the other things to explore during your travels? Discover the beautiful countryside and charming coffeehouses in this quaint area.

City Hall Castellina In Chianti

Casa Vinicola Luigi Cecchi

You can enjoy a tasting or tour at Casa Vinicola Luigi Cecchi during your travels to Castellina in Chianti. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Casa Vinicola Luigi Cecchi

What to do in Cavallari

Chianti Wine Tour with Tuscan Lunch Open Top Van

Chianti Wine Tour with Tuscan Lunch Open Top Van

$229
per adult
100% of travellers recommend
Chianti Wine Tour with Tuscan Lunch Open Top Van
Cooking class in Tuscany

Cooking Class in Tuscany

$288
per adult
Cooking Class in Tuscany
Truffle hunt

Private Truffle Hunting in Chianti

$391
per adult
Private Truffle Hunting in Chianti
See all activities in Cavallari

Cavallari Hotel Deals

Hotel Athena
Hotel Athena
4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
$145 nightly
The price is $165 total per night from Jul 26 to Jul 27
$165 total
Jul 26 - Jul 27
Total includes taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"From the moment we arrived for our two night stay Matteo and Tomasso were kind helpful and informative - We wanted a bigger room and were immediately accommodated - room was clean and comfortable and the hotel was in walking distance to all activities"

Reviewed on Jun 21, 2025

Hotel Athena
Fattoria il Milione Agriturismo
Fattoria il Milione Agriturismo
4 out of 5
Via Di Giogoli 12, Florence, FI
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $136 total per night from Jul 1 to Jul 2
$136 total
Jul 1 - Jul 2
Total includes taxes and fees
8/10 Very Good! (196 reviews)
"Amazing place. Only 10 min car drive from Porta Romana but far away from city noise. Huge property on a hill with beautiful views of the valleys and olive orchards. Ideal place to relax and enjoy Tuscan sun by a beautiful pool. Great breakfast buffet and restaurant."

Reviewed on Jun 24, 2025

Fattoria il Milione Agriturismo
Hotel Executive
Hotel Executive
4 out of 5
Via Nazareno Orlandi 32, Siena, SI
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $90 total per night from Jul 17 to Jul 18
$90 total
Jul 17 - Jul 18
Total includes taxes and fees
8.2/10 Very Good! (480 reviews)
"Really comfortable hotel , only stayed one night . A great nights sleep . All the staff without exception were friendly, helpful and could not do enough for us. Breakfast selection was in abundance but unfortunately the quality of the food was not great . Maybe less selection with better quality ..."

Reviewed on Oct 2, 2024

Hotel Executive
See all 7,403 properties in Cavallari
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 Cavallari Vacation Packages

Cavallari Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Peretola Airport (FLR)
Top Sights
Buondonno Winery, Casa Vinicola Luigi Cecchi and Archaeological Museum of Chianti

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Frequently asked questions

How much does a Cavallari vacation package cost?
Offering excellent value package deals from $760 on Expedia, you'll be surprised at how little a vacation to Cavallari costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Cavallari?
November, December and January are great times to search for cheap Cavallari vacation packages. Traveling in quieter periods means you'll typically find better prices on flights and accommodations.
How many days is enough for Cavallari?
With a well-planned schedule, you can easily visit the main Cavallari sights in a handful of days. But if you want to explore off the beaten track or go on day trips, consider booking your Cavallari vacation for longer.
How to find the best Cavallari package deals?
Bagging a cheap Cavallari package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply a few filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Cavallari package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Cavallari vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Cavallari vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Cavallari?
If you've got your Cavallari vacation dates finalized, book early to bag some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for impromptu escapes.
Does Expedia offer Book Now, Pay Later Cavallari vacation packages?
Your Cavallari break should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you that extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.