San Casciano in Val di Pesa Vacation Packages

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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.

Top San Casciano in Val di Pesa Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Eurostars Florence Boutique

Eurostars Florence Boutique

Historic Centre of Florence
CA $1,549
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
8.6/10 Excellent! (503 reviews)
The bed was comfortable but low to the floor. The shower was very slippery and could have used a shower mat. The breakfast was great. The staff were very nice and helpful.

Reviewed on Oct 10, 2026

Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

Save 100% on your flight
CA $1,856
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (144 reviews)
Hotel Duomo Firenze

Hotel Duomo Firenze

Historic Centre of Florence
CA $3,115
per person
Dec 28 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (1,000 reviews)
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

Historic Centre of Florence
CA $1,668
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (605 reviews)
Even having arrived very early our room was immediately available. All staff were very helpful. Our room was immaculately clean. The breakfast staff were outstanding very friendly and very hospitable. The highlight though was the spa facility - out of this world. Highly recommend The Moon Boutique.

Reviewed on Oct 16, 2026

Bernini Palace

Bernini Palace

Historic Centre of Florence
CA $2,014
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.8/10 Exceptional! (1,006 reviews)
Great location and staff. Very helpful with making restaurant reservations that are hard to get. Maid staff were excellent also. We will stay here again when we visit Florence.

Reviewed on Oct 17, 2026

Ready to book your vacation to San Casciano in Val di Pesa?

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San Casciano in Val di Pesa Hotel Deals

Plus Florence - Hostel

Plus Florence - Hostel

Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
CA $73
CA $93 total
Nov 17 - Nov 18
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"I had a private room was was fine for three nights. Location also not bad. The issue I had is with the noise. The hotel claims quiet hours are 10pm - 7am but there was so much noise in the hotel (loud music and people screaming) up to midnight. Bring earplugs…"

Reviewed on Oct 16, 2026

Plus Florence - Hostel
The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

Viale Belfiore, 55 Florence FI
Fully refundableReserve now, pay when you stay
CA $91
CA $123 total
Nov 15 - Nov 16
includes taxes & fees
9.4/10 Exceptional! (790 reviews)
"Staff is too young and untrained in hospitality to provide a solid experience, felt like student workers with little supervisors there to actually help them. Advertises with free laundry but you can only run one tiny machine at a time and one of them left my laundry smelling worse making me have ..."

Reviewed on Oct 17, 2026

The Social Hub Florence Belfiore
Hotel Paris

Hotel Paris

Via Banchi 2 Florence FI
Fully refundable
CA $175
CA $212 total
Nov 17 - Nov 18
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Old, unique hotel with a lot of stairs and a small, slow elevator. Our room was huge, but the laminate floor near the bathroom gave when we waled on it, felt like we might fall through. Location is great, between Santa Maria and the Duomo. Very easy to navigate from."

Reviewed on Oct 15, 2026

Hotel Paris
See all 14,890 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.

Stay near popular San Casciano in Val di Pesa attractions

Antinori nel Chianti Classico

9.4/10 (16 reviews)
You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Check out the churches and wineries in this walkable area.
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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.
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San Casciano Museum

9.0/10 (2 reviews)
You can browse the exhibits at San Casciano Museum, a museum with a storied past, during your trip to San Casciano in Val di Pesa. Discover the area's fascinating museums and notable monuments.
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Mangiacane Winery

You can enjoy a tasting or tour at Mangiacane Winery during your travels to Sant'Andrea in Percussina. You can enjoy the restaurants while in the area.
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Torre Del Chianti

10.0/10 (1 review)
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.
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Church of San Martino ad Argiano

9.0/10 (2 reviews)
Church of San Martino ad Argiano is just one of the places to see in San Casciano in Val di Pesa, so why not enjoy the other things to explore during your travels? Experience the area's fascinating museums and acclaimed art scene.
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Chiesa di Santa Maria del Gesù

After visiting Chiesa di Santa Maria del Gesù, make a plan to see the other sights and activities in San Casciano in Val di Pesa. Discover the countryside and wineries in this relaxing area.
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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

CA $47
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Florence: Pasta Cooking Class with Unlimited Wine

Florence: Pasta Cooking Class with Unlimited Wine

CA $29
per adult
94% of travellers recommend
Florence: Pasta Cooking Class with Unlimited Wine
Michaelangelo's David

Accademia timed-entry Ticket with App Guide

CA $63
per adult
90% of travellers recommend
Accademia timed-entry Ticket with App Guide
See all activities in San Casciano in Val di Pesa

Frequently asked questions

How much does a San Casciano in Val di Pesa vacation package cost?
You can snap up a vacation package to this destination from CA $1,549 on Expedia. But how much your vacation to San Casciano in Val di Pesa costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to San Casciano in Val di Pesa?
If you're hoping to score a cheap San Casciano in Val di Pesa vacation package, consider travelling in December, January and February. You're likely to find lower rates on hotels and airfares during these quieter months — ideal for budget-conscious travellers.
How many days is enough for San Casciano in Val di Pesa?
With about 3 days, you'll have plenty of time to visit popular neighbourhoods like Montegufoni and Tavarnuzze during your San Casciano in Val di Pesa vacation. Make sure to also add Monastary of Sorelle Clarisse and Circolo Golf Ugolino to your sightseeing itinerary. Looking 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?
Popular for its views, dining and bars and pubs, a San Casciano in Val di Pesa vacation is a hit with all kinds of visitors. Be sure to check out main sights like Monastary of Sorelle Clarisse and Torre Del Chianti, and consider renting some wheels for day trips to experience even more.
How to find the best San Casciano in Val di Pesa package deals?
Use Expedia's filter tool to help you find some terrific San Casciano in Val di Pesa package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for San Casciano in Val di Pesa package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a San Casciano in Val di Pesa vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels separately. Better still, you can tailor your San Casciano in Val di Pesa trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to San Casciano in Val di Pesa?
If you have your San Casciano in Val di Pesa vacation dates confirmed, book as early as you can to bag some terrific deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to San Casciano in Val di Pesa?
  1. Choose when to get away: Check your schedule and get your bags packed. Your favourite time of year and the type of activities available will also help you decide when to escape to San Casciano in Val di Pesa.
  2. Plan your budget wisely: As well as the price of your hotel, you'll need to factor in other expenses. These include flights, transportation and food. Also, put aside a little extra for unexpected costs that could crop up during your trip to San Casciano in Val di Pesa.
  3. Decide your trip length: Think about how much time you'd like to spend exploring San Casciano in Val di Pesa. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a tailored San Casciano in Val di Pesa vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.