Cavallari Vacations from $635

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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 $993, price is now $635 per person
$635
per person
Mar 25 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
9 day stay. The property hit my must-haves! Central location, clean, affordable, and safe. 5/5 in all these areas! There is nothing they can do about dirty streets but the filth did not cross the threshold. T2 tram from the airport is 2 blocks away. The central market is 2 blocks in the other direction. Key card swipe after dark. 24 hour desk service. Breakfast on the 5th floor with views. Very courteous staff. The only complaint is breakfast tables are cleared very quickly while I went for a americano refill. Will definitely return here.

Reviewed on Jan 3, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,853, price is now $1,095 per person
$1,095
per person
Apr 4 - Apr 10
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.6/10 Excellent! (476 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

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,093, price is now $674 per person
$674
per person
Mar 25 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Great Locations walkable to all the placese.

Reviewed on Dec 15, 2025

Residenza Florentia

Residenza Florentia

1 out of 5
Historic Centre of Florence
Price was $1,027, price is now $695 per person
$695
per person
Feb 20 - Feb 25
just found
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.4/10 Very Good! (46 reviews)
Location, accommodations, and communication. Simple but comfortable. A basic facilities, and nice AC, elevator, and luggage storage.

Reviewed on Jun 12, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $2,744, price is now $1,862 per person
$1,862
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (467 reviews)
Nice property and staff.

Reviewed on Nov 13, 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

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

Archaeological Museum of Chianti

You can browse the exhibits at Archaeological Museum of Chianti, a museum with a story of its own, during your trip to Castellina in Chianti. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Archaeological Museum of Chianti

What to do in Cavallari

Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

$51
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

$61
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Florence Day Trip: Medieval Villages & Cooking Class

Florence Day Trip: Medieval Villages & Cooking Class

$163
per adult
86% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
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
$91 nightly
The price is $103 total per night from Feb 12 to Feb 13
$103 total
Feb 12 - Feb 13
Total with taxes and fees
9.2/10 Wonderful! (1,013 reviews)
It’s very beautiful

Reviewed on Jan 9, 2026

Hotel Athena
Borgo Grondaie

Borgo Grondaie

3 out of 5
Strada delle Grondaie, 15 Siena SI
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $93 total per night from Feb 13 to Feb 14
$93 total
Feb 13 - Feb 14
Total with taxes and fees
9.6/10 Exceptional! (441 reviews)
Amazing place, super clean, great staff, beautiful and cozy.

Reviewed on Jan 3, 2026

Borgo Grondaie
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
$82 nightly
The price is $93 total per night from Jan 15 to Jan 16
$93 total
Jan 15 - Jan 16
Total with taxes and fees
7.8/10 Good! (85 reviews)
Beautiful experience!

Reviewed on Jul 1, 2025

Villa La Borghetta Resort
See all 6,959 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 $635 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.