Cavallari Vacations from $615

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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 $842, price is now $615 per person
$615
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
Convenient location to fast food and train station

Reviewed on Nov 7, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $915, price is now $635 per person
$635
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,015 reviews)
This hotel is all about location… close to everything about 10-15 mins by walking. The entrance of the hotel is a bit scary at night time on my personal view. The room is big and clean. Don’t expect much on breakfast … it’s enough for you to start the day.

Reviewed on Nov 11, 2025

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Price was $1,012, price is now $769 per person
$769
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (397 reviews)
Great place to stay near Florence, it’s quite and relaxing. The pool is great.

Reviewed on Jul 31, 2025

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was $879, price is now $670 per person
$670
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (931 reviews)
Amazing property & the staff is incredible.Love this place.

Reviewed on Oct 18, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $2,234, price is now $1,754 per person
$1,754
per person
Dec 31 - Jan 5
found 17 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Florence (FLR)
9.6/10 Exceptional! (485 reviews)
My husband Felix and I had the pleasure of celebrating both our wedding anniversary and my birthday at The Moon Boutique Hotel in Florence, and we couldn’t have asked for a more perfect experience. From the moment we arrived, the warmth and professionalism of the staff made us feel truly welcomed. A special mention goes to the tall gentleman with glasses from Calabria—his courteous demeanor and exceptional customer service stood out throughout our stay. He went above and beyond to ensure we were comfortable and well-informed, adding a personal touch that made our visit even more special. The housekeeping team deserves equal praise. Their attention to detail was remarkable, and our room was consistently immaculate, creating a serene and luxurious atmosphere that enhanced our celebration. The Moon Boutique Hotel is more than just a place to stay—it’s a haven of elegance, comfort, and genuine hospitality. We left with beautiful memories and deep appreciation for the team that made our milestone moments unforgettable.

Reviewed on Nov 12, 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 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 wineries 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

Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

$139
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
Monteriggioni fortress

Tuscany Hiking Tour from Siena Including Wine Tasting

$64
per adult
Tuscany Hiking Tour from Siena Including Wine Tasting
Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

$57
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
See all activities in Cavallari

Cavallari Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $93 total per night from Dec 10 to Dec 11
$93 total
Dec 10 - Dec 11
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
La ubicación es genial, el personal es muy amable y la habitación está impecable.

Reviewed on Nov 8, 2025

Hotel Athena
Hotel Pescille - Tuscany Charme

Hotel Pescille - Tuscany Charme

3 out of 5
Strada Statale 47, Localita Pescille, San Gimignano, SI
9.2/10 Wonderful! (336 reviews)
The hotel is beautiful great view of San Gimignano on one side, and the tuscan countryside all around.

Reviewed on Oct 21, 2025

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Hotel Pescille - Tuscany Charme
Villa La Borghetta Resort

Villa La Borghetta Resort

4 out of 5
Via del Cesto, Figline e Incisa Valdarno, FI
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $101 total per night from Nov 19 to Nov 20
$101 total
Nov 19 - Nov 20
Total with taxes and fees
7.8/10 Good! (85 reviews)
Beautiful experience!

Reviewed on Jul 1, 2025

Villa La Borghetta Resort
See all 7,074 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 $615 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.