Cavallari Vacations from $1,086

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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 22 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,007 reviews)
Perfect stay for family

Reviewed on Aug 9, 2025

Hotiday Room Collection - Massa Alta

Hotiday Room Collection - Massa Alta

3 out of 5
Save 100% on your flight
per person
Sep 28 - Oct 4
found 13 hours ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
No reviews
Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (230 reviews)
I VERY MUCH ENJOYED THE STAY

Reviewed on Jul 18, 2025

Collegio alla Querce - Auberge Resorts

Collegio alla Querce - Auberge Resorts

5 out of 5
Le Cure
Save 100% on your flight
per person
Oct 22 - Oct 28
just found
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
10/10 Exceptional! (2 reviews)
LHP River Club

LHP River Club

5 out of 5
Santa Croce
Save 100% on your flight
per person
Oct 12 - Oct 18
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
10/10 Exceptional! (1 review)
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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

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 walkable 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 quaint area, or enjoy its local tours.

Archaeological Museum of Chianti

What to do in Cavallari

Dinner in Chianti Vineyards with Wine Tasting

From Florence: Dinner in Chianti Vineyards with Wine Tasting

$128
per adult
80% of travellers recommend
From Florence: Dinner in Chianti Vineyards with Wine Tasting
Cooking class in Tuscany

Cooking Class in Tuscany

$294
per adult
Cooking Class in Tuscany
Cooking Class in Tuscan Farmhouse from San Gimignano

Private Cooking Class in Chianti from San Gimignano

$431
per adult
Private Cooking Class in Chianti from San Gimignano
See all activities in Cavallari

Cavallari Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
$152 nightly
The price is $173 total per night from Aug 23 to Aug 24
$173 total
Aug 23 - Aug 24
Total includes taxes and fees
9.2/10 Wonderful! (999 reviews)
"Beautiful location overlooking the hills of Tuscany! Right from Martina checking us in, and the beautiful room with views, everything was amazing! Very clean rooms and comfortable bed. Very nice bathroom and all the amenities. We enjoyed the breakfast each morning, nice selection of food to choose ..."

Reviewed on Aug 3, 2025

Hotel Athena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $126 total per night from Aug 12 to Aug 13
$126 total
Aug 12 - Aug 13
Total includes taxes and fees
9.2/10 Wonderful! (684 reviews)
Just beautiful
"The building, the views, the staff, the food, everything was just incredible. It was so quiet we felt like we were the only people there until we went for breakfast and realised there were others in the hotel. The view from the our room at the back of the hotel over the Tuscan hills will live with ..."

Reviewed on Aug 9, 2025

Palazzo Ravizza
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
$94 nightly
The price is $120 total per night from Aug 24 to Aug 25
$120 total
Aug 24 - Aug 25
Total includes taxes and fees
8.2/10 Very Good! (205 reviews)
"Its in a rural and beautiful area but the only transport link are taxis ao bare that in mind when budgeting."

Reviewed on Aug 1, 2025

Fattoria il Milione Agriturismo
See all 7,456 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.

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Frequently asked questions

How much does a Cavallari vacation package cost?
Offering excellent value package deals from $1,086 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.