Cavallari Vacations from $1,265

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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
Price was $1,865, price is now $1,265 per person
$1,265
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,008 reviews)
Front desk staff are helpful. Breakfast room attendants are good. Food is average.

Reviewed on May 6, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $6,423, price is now $3,827 per person
$3,827
per person
Jun 22 - Jun 28
found 23 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (61 reviews)
Fabulous old building but fully refurbished with modern suites. Only 12 suites, all unique with 2 on each floor. Loads of room. Staff fabulous. Only minus point is there’s no bar or restaurant, but it is located within an area that has literally hundreds on its doorstep. Would definitely stay there again.

Reviewed on Apr 23, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,865, price is now $1,265 per person
$1,265
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,001 reviews)
Excellent helpful staff let us store our bags in the lobby for a couple of hours after checkout- much appreciated- clean and quiet - central location was walkable to everywhere- and they were very nice to our 6 month old baby

Reviewed on May 2, 2026

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was $2,346, price is now $1,657 per person
$1,657
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
Excellent location, right outside of the Duomo with a beautiful terrace to sit outside in the evening. Good location for shopping. The ice cream selections at the snack bar are excellent, snacks and coffee provided in the morning. 24/7 staff available.

Reviewed on May 8, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $1,852, price is now $1,309 per person
$1,309
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.6/10 Excellent! (485 reviews)
The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

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Discover the most popular places to visit in Cavallari

Buondonno Winery

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.

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 Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

$29
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$54
per adult
86% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Tuscany Hiking Tour from Siena Including Wine Tasting

Tuscany Hiking Tour from Siena Including Wine Tasting

$71
per adult
100% of travellers recommend
Tuscany Hiking Tour from Siena Including Wine Tasting
See all activities in Cavallari

Cavallari Hotel Deals

Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

4 out of 5
Via Giovanni Agnelli 33 Florence FI
Fully refundableReserve now, pay when you stay
$217 nightly
The price is $256 total per night from May 16 to May 17
$256 total
May 16 - May 17
Total with taxes and fees
9/10 Wonderful! (42 reviews)
Very nice lobby, entrance, and main bar. The dining area and breakfast food were very good. The staff help accommodate any request we presented. Each member carried a sense of professionalism that was noteworthy and appreciated.

Reviewed on May 4, 2026

Radisson Blu Hotel, Florence
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$221 nightly
The price is $249 total per night from Jun 3 to Jun 4
$249 total
Jun 3 - Jun 4
Total with taxes and fees
9.2/10 Wonderful! (1,007 reviews)
Breakfast was great, the hotel staff were wonderful, and the parking was a nice treat.

Reviewed on May 5, 2026

Hotel Athena
Hotel Executive

Hotel Executive

4 out of 5
Via Nazareno Orlandi 32 Siena SI
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $102 total per night from Jun 7 to Jun 8
$102 total
Jun 7 - Jun 8
Total with taxes and fees
8.4/10 Very Good! (538 reviews)
excellent breakfast and very clean

Reviewed on Apr 27, 2026

Hotel Executive
See all 6,983 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 $1,265 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.