San Casciano in Val di Pesa Vacations from $1,002

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Your San Casciano in Val di Pesa Vacation

Lock in a San Casciano in Val di Pesa vacation package and get ready for a fantastic adventure. Renowned for its rich history and spectacular views, there's plenty to love about this interesting city. Eager to explore? Antinori nel Chianti Classico, Montegufoni Castle and Florence Charterhouse are just a few of the best places to visit during a trip to San Casciano in Val di Pesa. A few quick clicks is all it takes to create your perfect San Casciano in Val di Pesa vacation on Expedia.

The Latest San Casciano in Val di Pesa 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 $1,572, price is now $1,002 per person
$1,002
per person
Sep 1 - Sep 6
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,025 reviews)
The location is excellent. Close to the train station, shops and restaurants. Room was very clean. Breakfast was included. all good.

Reviewed on Jun 19, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,995, price is now $1,280 per person
$1,280
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,011 reviews)
The hotel was conveniently located, and the service was good. Overall, it was a pleasant stay. However, I hope the hotel improves its Wi-Fi coverage, as the connection can become unstable when multiple guests are accessing the network.

Reviewed on Jun 5, 2026

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $3,256, price is now $2,232 per person
$2,232
per person
Aug 24 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (20 reviews)
Lovely stay. Highly recommend it!

Reviewed on Jun 11, 2026

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Save 100% on your flight
Price was $2,321, price is now $1,599 per person
$1,599
per person
Aug 21 - Aug 26
found 5 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (201 reviews)
This place was the best part of my trip! The property is absolutely stunning. The pool is beautiful. The view is breathtaking. The staff is amazing. The food at the restaurant is high quality. It is about 25-30mins from Siena and it’s higher in a hill/mountain. We loved everything about Borgo Scopeto and would definitely be back again. It is so peaceful and relaxing.

Reviewed on Jun 17, 2026

Bernini Palace

Bernini Palace

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,922, price is now $1,328 per person
$1,328
per person
Aug 13 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (1,000 reviews)
The staff. The breakfast. The bar. All perfect. We really really loved our stay here. Planning on staying every year!

Reviewed on Jun 18, 2026

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Discover the most popular places to visit in San Casciano in Val di Pesa

A woman on a spiral stairway, part of the modern architecture at Antinori Winery Nel Chianti Classico, San Casciano in Val di Pesa, Tuscany, Italy.

Antinori nel Chianti Classico

You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Check out the stunning cathedral and wineries in this walkable area.

Antinori nel Chianti Classico

Monastery of Sorelle Clarisse

Find out about the history of San Casciano in Val di Pesa when you spend time at Monastery of Sorelle Clarisse. Discover the area's acclaimed art scene and notable monuments.

Monastery of Sorelle Clarisse

Torre Del Chianti

You can find out about the history of San Casciano in Val di Pesa with a stop at Torre Del Chianti. Stroll along the riverfront or visit the stunning cathedral in the area.

Torre Del Chianti

What to do in San Casciano in Val di Pesa

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

$34
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Skip-the-Line Duomo: Priority-Access 30-Minute Guided Tour

Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour

$23
per adult
82% of travellers recommend
Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour
People riding scooters in Tuscany

Florence Vespa Tour: Tuscan Hills, Food and Chianti Wine

$129
per adult
100% of travellers recommend
Florence Vespa Tour: Tuscan Hills, Food and Chianti Wine
See all activities in San Casciano in Val di Pesa

San Casciano in Val di Pesa Hotel Deals

Villa "Torre in Chianti", 8 ensuite bedrooms,A/C, Private Pool, WiFi, Florence

Villa "Torre in Chianti", 8 ensuite bedrooms,A/C, Private Pool, WiFi, Florence

San Casciano in Val di Pesa Tuscany
10/10 Exceptional! (131 reviews)
"Great house. Hosts Bea and Jacopa were terrific. Great breakfasts and dinners. Arranged tours, car rentals, transportation, restaurant reservations. 12 of us, 3 generations, had a wonderful stay. Highly recommended."

Reviewed on Jun 13, 2026

Get rates
Villa "Torre in Chianti", 8 ensuite bedrooms,A/C, Private Pool, WiFi, Florence
The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
Viale Spartaco Lavagnini 70 72 Florence FI
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $144 total per night from Jul 5 to Jul 6
$144 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (1,410 reviews)
"Room is clean. Tram stop is just outside of the hotel. Very good breakfast"

Reviewed on Jun 19, 2026

The Social Hub Florence Lavagnini
The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

4 out of 5
Viale Belfiore, 55 Florence FI
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $120 total per night from Jun 21 to Jun 22
$120 total
Jun 21 - Jun 22
Total with taxes and fees
9.4/10 Exceptional! (585 reviews)
"Ideal for a single traveler there for work."

Reviewed on Jun 15, 2026

The Social Hub Florence Belfiore
See all 14,970 properties in San Casciano in Val di Pesa
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 Casciano in Val di Pesa Vacation Packages

San Casciano in Val di Pesa Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Peretola Airport (FLR)
Population
6,200
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Cathedral of Santa Maria del Fiore, Uffizi Gallery and Pitti Palace

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Frequently asked questions

How much does a San Casciano in Val di Pesa vacation package cost?
You'll find cheap prices from $1,002 on Expedia for your San Casciano in Val di Pesa escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to San Casciano in Val di Pesa costs.
What are the cheapest months to go to San Casciano in Val di Pesa?
You can generally find reduced prices and better availability in September, November and December. Browse our cheap San Casciano in Val di Pesa vacation packages and you could land some excellent off-season deals.
How many days is enough for San Casciano in Val di Pesa?
With about 3 days, you'll have enough time to visit popular neighborhoods such as Tavarnuzze and Montegufoni during your San Casciano in Val di Pesa vacation. Make sure to also add Monastary of Sorelle Clarisse and Church of San Martino ad Argiano to your must-see list. Searching for more adventures? Consider venturing outside of San Casciano in Val di Pesa on day trips and tours.
Is it worth booking a vacation package to San Casciano in Val di Pesa?
San Casciano in Val di Pesa has all the ingredients you need for a memorable getaway — views, bars and pubs and dining are just the start. Whether you'd like to check out attractions such as Monastary of Sorelle Clarisse and Torre Del Chianti, or venture off the beaten track, you'll find plenty to do on your San Casciano in Val di Pesa vacation.
How to find the best San Casciano in Val di Pesa package deals?
Finding a cheap San Casciano in Val di Pesa package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, add some filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most affordable San Casciano in Val di Pesa package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a San Casciano in Val di Pesa vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still get the freedom to create a customized San Casciano in Val di Pesa vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to San Casciano in Val di Pesa?
If you've got your San Casciano in Val di Pesa travel dates finalized, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to San Casciano in Val di Pesa?

  1. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to travel to San Casciano in Val di Pesa.
  2. Set a budget: Factor in expenses such as food, flights and transportation when calculating how much to put aside for your trip to San Casciano in Val di Pesa. Then, pick a property that matches your budget, whether that's a wallet-friendly stay or a more luxurious retreat.
  3. Use Expedia's trip planning tool to discover San Casciano in Val di Pesa: Research every aspect of your trip to San Casciano in Val di Pesa with this comprehensive planner. Invite your friends and family to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how long to go for: Now that you're more familiar with San Casciano in Val di Pesa, you can work out the perfect length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
  5. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a San Casciano in Val di Pesa vacation package that brings all your bookings together.
  6. Book experiences or activities in advance: Whether it's entrance to a big attraction or a day trip in nature, you won't have to worry about missing out on San Casciano in Val di Pesa's highlights. Find all the incredible things to do in San Casciano in Val di Pesa with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later San Casciano in Val di Pesa vacation packages?
If you're anything like us, you love traveling the world but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your San Casciano in Val di Pesa trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you see them.

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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.