San Leonino Vacations from $792

Book a Hotel + Flight or Car together to unlock savings

Your San Leonino Vacation

When a fun city break is calling, answer it with a San Leonino vacation package. The neighborhood of Badia Coltibuono, which is great for families, nature and walking, makes a fantastic base for your adventures. Make your trip to San Leonino even more fun and exciting by going sightseeing. Casa Vinicola Luigi Cecchi, City Hall Castellina In Chianti and Walls of Monteriggioni are some of the leading attractions worth exploring. A couple of clicks is all it takes to create the ultimate San Leonino vacation on Expedia.

The Latest San Leonino 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 $1,118, price is now $792 per person
$792
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
Close to train station and everything you need.

Reviewed on Nov 21, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,413, price is now $931 per person
$931
per person
Feb 15 - Feb 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Breakfast was good. Staff super friendly. Overall the expected quality for the paid price.

Reviewed on Nov 20, 2025

Hotel Lungarno - Lungarno Collection

Hotel Lungarno - Lungarno Collection

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,667, price is now $1,159 per person
$1,159
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (593 reviews)
Excellent location! Truly a 5 star hotel ! Great service, breakfast, and service . Bedrooms were clean! Bathrooms were excellent!

Reviewed on Nov 19, 2025

Hotel degli Orafi

Hotel degli Orafi

4 out of 5
Historic Centre of Florence
Price was $1,456, price is now $1,025 per person
$1,025
per person
Feb 15 - Feb 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (1,001 reviews)
Spacious room much bigger than an average single.

Reviewed on Nov 27, 2025

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

4 out of 5
Historic Centre of Florence
Price was $1,529, price is now $1,092 per person
$1,092
per person
Feb 15 - Feb 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (120 reviews)
Phenomenal location!

Reviewed on Oct 18, 2025

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Discover the most popular places to visit in San Leonino

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 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 San Leonino

Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

$137
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

$50
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Monteriggioni fortress

Tuscany Hiking Tour from Siena Including Wine Tasting

$64
per adult
Tuscany Hiking Tour from Siena Including Wine Tasting
See all activities in San Leonino

San Leonino 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 $104 total per night from Dec 15 to Dec 16
$104 total
Dec 15 - Dec 16
Total with taxes and fees
9.2/10 Wonderful! (1,007 reviews)
Beautiful walk to the city center

Reviewed on Nov 28, 2025

Hotel Athena
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
$113 nightly
The price is $127 total per night from Dec 8 to Dec 9
$127 total
Dec 8 - Dec 9
Total with taxes and fees
7.8/10 Good! (85 reviews)
Beautiful experience!

Reviewed on Jul 1, 2025

Villa La Borghetta Resort
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34 Siena SI
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $108 total per night from Dec 5 to Dec 6
$108 total
Dec 5 - Dec 6
Total with taxes and fees
9.2/10 Wonderful! (742 reviews)
Very welcoming and attentive staff. Breakfast was amazing. I didn’t expect the gorgeous views!

Reviewed on Nov 4, 2025

Palazzo Ravizza
See all 6,123 properties in San Leonino
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 San Leonino Vacation Packages

San Leonino 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 San Leonino vacation package cost?
You can grab a vacation package to this destination from $792 on Expedia. But how much your vacation to San Leonino costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to San Leonino?
November, December and January are great times to search for cheap San Leonino vacation packages. Traveling in quieter periods means you can generally find reduced prices on flights and accommodations.
How many days is enough for San Leonino?
The ideal length for your San Leonino vacation depends on what you'd like to do. Typically, a few days to a week will give you plenty of time to go to all the major sights and explore some hidden treasures along the way.
How to find the best San Leonino package deals?
Bagging a cheap San Leonino package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly San Leonino package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a San Leonino vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component separately. And you'll still have the flexibility to create a customized San Leonino vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to San Leonino?
If you've got your San Leonino vacation dates confirmed, book as soon as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later San Leonino vacation packages?
If you're like us, you love exploring new places but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your San Leonino trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.