Title: Castel San Gimignano Vacation Packages & Trips 2026 from CA $1,338 | Expedia.ca

[Castel San Gimignano Travel Guide](https://expedia.ca/Castel-San-Gimignano.dx6285675)[Hotels in Castel San Gimignano](https://expedia.ca/Castel-San-Gimignano-Hotels.d6285675.Travel-Guide-Hotels)[Vacation Rentals in Castel San Gimignano](https://expedia.ca/Castel-San-Gimignano-Vacation-Rentals.d6285675.Travel-Guide-VacationRentals)[Flights to Castel San Gimignano](https://expedia.ca/Cheap-Flights-To-Castel-San-Gimignano.d6285675.Travel-Guide-Flights)[Castel San Gimignano Car Rentals](https://expedia.ca/Car-Rentals-In-Castel-San-Gimignano.d6285675.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Castel San Gimignano Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

#### 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](https://www.expedia.ca/Collegiate-Church-Of-Santa-Maria-Assunta-San-Gimignano-City-Centre.d6105346.Vacation-Attraction), [Piazza Duomo](https://www.expedia.ca/Piazza-Duomo-San-Gimignano-City-Centre.d6105352.Vacation-Attraction) and [Medieval Criminal and Torture Museum](https://www.expedia.ca/Medieval-Criminal-And-Torture-Museum-San-Gimignano-City-Centre.d6287299.Vacation-Attraction) 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.

![Aurum Firenze](https://images.trvl-media.com/lodging/29000000/28970000/28962000/28961941/26fd50f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Aurum Firenze

Historic Centre of Florence

CA $1,338

per person

Apr 4 - Apr 7

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Florence (FLR)

7.6/10 Good! (1,002 reviews)

Yes, to both questions. Wi-fi needs work.

Reviewed on Feb 7, 2026

![Cappuccina Country Resort](https://images.trvl-media.com/lodging/2000000/1350000/1343600/1343502/648002ed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cappuccina Country Resort

CA $1,974

per person

Apr 24 - Apr 30

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to Florence (FLR)

8.6/10 Excellent! (91 reviews)

Great stay. Very good experience.

Reviewed on Oct 20, 2025

![Hotel Villani](https://images.trvl-media.com/lodging/15000000/14940000/14932300/14932224/96d37b7c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Villani

Historic Centre of Florence

CA $2,102

per person

May 5 - May 11

found 19 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Florence (FLR)

8.6/10 Excellent! (422 reviews)

Nice room, great staff

Reviewed on Feb 4, 2026

![Hotel Miceli - Civico 50](https://images.trvl-media.com/lodging/32000000/31800000/31795300/31795212/36111d3b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Miceli - Civico 50

Historic Centre of Florence

CA $1,717

per person

Apr 24 - Apr 30

found 13 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9/10 Wonderful! (232 reviews)

I loved everything on and around this property. Sitting at the heart of that shopping district, every place I wanted to visit, was just max 15 mins walking distance.

Reviewed on Dec 29, 2025

![Hotel La Scaletta Al Ponte Vecchio](https://images.trvl-media.com/lodging/2000000/1610000/1604300/1604285/9b3b942d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

CA $2,020

per person

Apr 24 - Apr 30

found 13 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

8.8/10 Excellent! (939 reviews)

Very quiet, huge room. Very comfortable bed. In a perfect location, staff is very friendly.

Reviewed on Jan 13, 2026

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_6285675)

## Ready to book your vacation to Castel San Gimignano?

Choose your dates

## Castel San Gimignano Hotel Deals

![Hotel Athena](https://images.trvl-media.com/lodging/1000000/870000/866600/866580/ab5ee3fb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Athena

P Mascagni 55 Siena SI

Fully refundableReserve now, pay when you stay

CA $127

CA $147 total

Mar 3 - Mar 4

includes taxes & fees

9.2/10 Wonderful! (1,002 reviews)

Great hotel, beautiful view and excellent service from the personnel.

Reviewed on Jan 28, 2026

[](https://expedia.ca/Hotel-Search?startDate=03%2F03%2F2026&endDate=04%2F03%2F2026&selected=866580&PinnedHotelID=866580&HadPinnedHotel=true&regionId=6285675)

![Hotel Ristorante Alcide](https://images.trvl-media.com/lodging/2000000/1410000/1402100/1402058/d779a567_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Ristorante Alcide

Viale Marconi, 67/A Poggibonsi SI

Fully refundableReserve now, pay when you stay

CA $66

CA $73 total

Feb 22 - Feb 23

includes taxes & fees

8/10 Very Good! (462 reviews)

I highly recommended

Reviewed on Oct 14, 2025

[](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=1402058&PinnedHotelID=1402058&HadPinnedHotel=true&regionId=6285675)

![Grand Hotel Continental Siena – Starhotels Collezione](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/8b42326b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Grand Hotel Continental Siena – Starhotels Collezione

Banchi Di Sopra 85 Siena SI

Fully refundableReserve now, pay when you stay

CA $405

CA $461 total

Mar 2 - Mar 3

includes taxes & fees

9.2/10 Wonderful! (579 reviews)

Room, bathroom and breakfast were wonderful. WiFi was not great. Lovely location and pretty property.

Reviewed on Jan 27, 2026

[](https://expedia.ca/Hotel-Search?startDate=02%2F03%2F2026&endDate=03%2F03%2F2026&selected=796662&PinnedHotelID=796662&HadPinnedHotel=true&regionId=6285675)

[See all 6,154 properties in Castel San Gimignano](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=14%2F02%2F2026&endDate=15%2F02%2F2026&regionId=6285675)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Castel San Gimignano

![Piazza della Cisterna which includes street scenes, a city and a square or plaza](https://images.trvl-media.com/place/6105348/19428489-8453-4592-8815-109013b2cabe.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Piazza della Cisterna

Admire the palaces and towers that frame this beautiful square, which was once a medieval marketplace. Today, it’s a venue for cultural events.

[](https://expedia.ca/Piazza-Della-Cisterna-San-Gimignano-City-Centre.d6105348.Vacation-Attraction)

#### Tenuta Torciano Winery

You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this quaint area. 

[](https://expedia.ca/Tenuta-Torciano-Winery-San-Gimignano.d6252546.Vacation-Attraction)

#### Medieval Criminal and Torture Museum

This intriguing museum highlights the callousness of humans via displays of authentic and gruesome torture devices from around the world.

[](https://expedia.ca/Medieval-Criminal-And-Torture-Museum-San-Gimignano-City-Centre.d6287299.Vacation-Attraction)

### What to do in Castel San Gimignano

![Tuscany in 1 day: Pisa, San Gimignano and Siena with Lunch](https://mediaim.expedia.com/localexpert/236697/0f88e6e6-ef95-4a56-8618-2b7fc4f041a9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch

CA $79

per adult

**78%** of travellers recommend

[](https://expedia.ca/things-to-do/tuscany-in-1-day-from-florence-pisa.a236697.activity-details)

![Organic Wine Tour&Tasting overlooking Chianti Classico Vineyards](https://mediaim.expedia.com/localexpert/3575311/34d2cee2-49d7-407c-92ae-12e02671c095.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Organic Wine Tour&Tasting overlooking Chianti Classico Vineyards

CA $39

per adult

[](https://expedia.ca/things-to-do/organic-wine-tourtasting-overlooking-chianti-classico-vineyards.a3575311.activity-details)

![Chianti Half Day Wine Tour from Florence](https://mediaim.expedia.com/localexpert/510796/711ec9bb-4d40-40e5-a110-59519c36ce6d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chianti Half Day Wine Tour from Florence

CA $79

per adult

**88%** of travellers recommend

[](https://expedia.ca/things-to-do/chianti-half-day-wine-tour-from-florence.a510796.activity-details)

[See all activities in Castel San Gimignano](https://expedia.ca/things-to-do/search?rid=6285675)

## Explore a world of travel with Expedia

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app