Castel San Gimignano Vacation Packages
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Your Castel San Gimignano Vacation
With everything organized before you head off, our Castel San Gimignano vacation packages mean you can simply focus on enjoying your getaway. Whether you're staying in the neighborhood of Montegabbro, which is great for history, or someplace else, this lively city offers a wealth of discoveries. Make your trip to Castel San Gimignano even more fulfilling by including some sightseeing. Collegiate Church of Santa Maria Assunta, Piazza Duomo and Medieval Criminal and Torture Museum are some of the top attractions worth exploring. A few quick clicks is all it takes to put together your perfect Castel San Gimignano vacation on Expedia.
Top Castel San Gimignano Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Eurostars Florence Boutique
Historic Centre of Florence
CA $1,676
per person
Jan 9 - 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
Aurum Uffizi
Historic Centre of Florence
CA $2,418
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
A great budget hotel in a fantastic central location. Despite being so central it was in a side street so quiet at night. Rooms were cleaned daily and breakfast was buffet-style with cereal, fruit, croissants etc. I stayed there for 2 weeks and have no complaints at all. Excellent value for money.
Reviewed on Oct 24, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
CA $2,077
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.6/10 Exceptional! (605 reviews)
Everything was wonderful about our stay at The Moon Hotel and Spa. The room was beautiful and clean, the staff were friendly and helpful and it was a great location for sightseeing in Florence. We especially appreciated the very generous breakfast that was always served efficiently and with a smile. We would definitely stay again.
Reviewed on Oct 23, 2026
Bernini Palace
Historic Centre of Florence
CA $2,132
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.8/10 Exceptional! (1,006 reviews)
Had a fantastic stay at Bernini Palace. Our room was extremely comfortable and beautifully appointed. The public spaces are beautiful. Service was excellent. Breakfast in the beautiful breakfast room was divine. The location of the hotel was central and a stone's throw from Piazza della Signoria. I would absolutely stay here again!
Reviewed on Oct 23, 2026
Monastero di Cortona Hotel & Spa
Cortona Old Town
CA $1,876
per person
Dec 12 - Dec 18
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
10/10 Exceptional! (337 reviews)
Amazing service and care. Especially Sara, Mathilda, Fredrico and Allesandro. The manager was so helpful as well. A must stay!
Reviewed on Oct 20, 2026
Ready to book your vacation to Castel San Gimignano?
Castel San Gimignano Hotel Deals
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
CA $145
CA $165 total
Nov 24 - Nov 25
includes taxes & fees
Castelfalfi
Località Castelfalfi Montaione FI
CA $1,155
CA $1,286 total
Oct 25 - Oct 26
includes taxes & fees
Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
CA $471
CA $527 total
Nov 10 - Nov 11
includes taxes & fees
9.2/10 Wonderful! (643 reviews)
"Excellent location. Very nice service."
Reviewed on Oct 23, 2026
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.
What to do in Castel San Gimignano
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
CA $78
per adult
78% of travellers recommend
Chianti Half Day Wine Tour from Florence
CA $39
per adult
88% of travellers recommend
San Gimignano: Evening Flavors Dinner & Wine tasting
CA $89
per adult
Frequently asked questions
How much does a Castel San Gimignano vacation package cost?
Offering great value package deals from CA $1,676 on Expedia, you'll be pleasantly surprised at how much a vacation to Castel San Gimignano costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Castel San Gimignano?
Plan your trip for the low or shoulder season and you're likely to score cheap Castel San Gimignano vacation packages. Bear in mind that public holidays and local festivals and events can have an impact on prices, so do a little research before you go.
How many days is enough for Castel San Gimignano?
Typically, a handful of days is ideal for a Castel San Gimignano vacation. With a well-organized schedule, you can check out all the popular sights including Sovestro in Poggio Winery, as well as explore some hidden treasures along the way.
How to find the best Castel San Gimignano package deals?
Use Expedia's filters to find some tempting Castel San Gimignano package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Castel San Gimignano package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Castel San Gimignano vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights separately. Better still, you can personalize your Castel San Gimignano trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Castel San Gimignano?
If you have your Castel San Gimignano travel dates finalized, book as soon as you can to grab some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Castel San Gimignano?
- Choose when to get away: Check your calendar and get your bags packed. Your preferred time of year and the type of activities on offer will also help you decide when to visit Castel San Gimignano.
- Figure out your budget: Make sure you have enough money to pay for everything from transportation and dining out to activities and flights. Your hotel will likely be the biggest expense during your trip to Castel San Gimignano.
- Decide your trip length: Consider how much time you want to spend discovering Castel San Gimignano. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Castel San Gimignano vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
