Title: San Gimignano Vacation Packages & Trips 2026 from CA $1,938 | Expedia.ca

[San Gimignano Travel Guide](https://expedia.ca/San-Gimignano.dx11091)[Hotels in San Gimignano](https://expedia.ca/San-Gimignano-Hotels.d11091.Travel-Guide-Hotels)[Vacation Rentals in San Gimignano](https://expedia.ca/San-Gimignano-Vacation-Rentals.d11091.Travel-Guide-VacationRentals)[Flights to San Gimignano](https://expedia.ca/Cheap-Flights-To-San-Gimignano.d11091.Travel-Guide-Flights)[Things to do in San Gimignano](https://expedia.ca/Things-To-Do-In-San-Gimignano.d11091.Travel-Guide-Activities)[San Gimignano Car Rentals](https://expedia.ca/Car-Rentals-In-San-Gimignano.d11091.Car-Rental-Guide)

![](https://images.trvl-media.com/place/11091/d03de615-2cbf-4c14-9fbd-54622308a833.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# San Gimignano Vacation Packages

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

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Plan, book, travel with confidence
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Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
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#### Your San Gimignano Vacation

With every last detail planned before you go, our San Gimignano vacation packages mean you can focus more on having fun. Whether you're based in the neighborhood of Montegabbro, which is good for history, or somewhere else in town, this lively city offers a wealth of discoveries. [Collegiate Church of Santa Maria Assunta](https://www.expedia.ca/Collegiate-Church-Of-Santa-Maria-Assunta-San-Gimignano-City-Centre.d6105346.Vacation-Attraction), [Tenuta Torciano Winery](https://www.expedia.ca/Tenuta-Torciano-Winery-San-Gimignano.d6252546.Vacation-Attraction) and [Piazza Duomo](https://www.expedia.ca/Piazza-Duomo-San-Gimignano-City-Centre.d6105352.Vacation-Attraction) are just a few of the attractions you'll want to explore during your trip to San Gimignano. Whatever your travel plans or the size of your budget, organizing your ultimate tailored San Gimignano vacation is simple with Expedia.

## Top San Gimignano Vacation Deals

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

![Eurostars Florence Boutique](https://images.trvl-media.com/lodging/2000000/1170000/1167000/1166901/88283612_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eurostars Florence Boutique

Historic Centre of Florence

CA $1,938

per person

May 23 - May 28

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

8.6/10 Excellent! (483 reviews)

The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

![Hotel La Scaletta Al Ponte Vecchio](https://images.trvl-media.com/lodging/2000000/1610000/1604300/1604285/d1c916cb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

CA $2,334

per person

May 17 - May 23

found 7 hours ago

Roundtrip flight included

Montreal (YMQ) to Florence (FLR)

8.8/10 Excellent! (967 reviews)

Fantastic location for everything whilst not being in the middle of it all. The staff were all lovely and everything super clean. Only issue was the aircon didn't work and we couldn’t open the windows due to mosquitoes (discovered this after the first night with it open - didn’t make that mistake again!). It’s quite an unusual interior with a tiny lift and lots of stairs so just be aware of that - it didn’t bother us though, we loved the charm.

Reviewed on Mar 12, 2026

![Relais Uffizi, Tailor made Hotel](https://images.trvl-media.com/lodging/3000000/2550000/2542800/2542717/3e59e5ae_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Relais Uffizi, Tailor made Hotel

Historic Centre of Florence

CA $3,006

per person

May 19 - May 24

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Florence (FLR)

9.4/10 Exceptional! (127 reviews)

The room was stunning, it was large, the bed was comfy and the design was unique. Staff were very friendly and helpful.

Reviewed on Feb 26, 2026

![Il Rivalta - Place of Charme](https://images.trvl-media.com/lodging/46000000/45800000/45790300/45790281/9555d572_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Il Rivalta - Place of Charme

Historic Centre of Florence

CA $2,875

per person

May 17 - May 23

found 7 hours ago

Roundtrip flight included

Montreal (YMQ) to Florence (FLR)

9.2/10 Wonderful! (472 reviews)

This was probably the best hotel I have ever stayed in. It felt so luxurious, clean, and beautiful. You can tell they really take pride in the property. The breakfast was delicious and the staff was top notch!

Reviewed on Mar 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_11091)

## Ready to book your vacation to San Gimignano?

Choose your dates

## San Gimignano Hotel Deals

![Hotel Casolare Le Terre Rosse](https://images.trvl-media.com/lodging/2000000/1840000/1834100/1834037/2faaea98_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Casolare Le Terre Rosse

Loc. San Donato San Gimignano SI

CA $167

CA $194 total

Apr 7 - Apr 8

includes taxes & fees

9.2/10 Wonderful! (450 reviews)

We enjoyed our stay. The biggest complaint is they did not supply assistance with bringing our luggage to the room. Especially, with the distance of the parking lot.

Reviewed on Oct 4, 2025

[](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=1834037&PinnedHotelID=1834037&HadPinnedHotel=true&regionId=11091)

![Mormoraia](https://images.trvl-media.com/lodging/6000000/5130000/5126300/5126300/0f16f384_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Mormoraia

Agriturismo San Gimignano San Gimignano SI

Fully refundableReserve now, pay when you stay

CA $347

CA $390 total

Mar 18 - Mar 19

includes taxes & fees

9.6/10 Exceptional! (209 reviews)

This resort is gorgeous and every single staff member was so gracious and friendly! It was a short drive away from San Gimignano which was nice to explore. The restaurant was delicious and their spa was very nice!

Reviewed on Nov 20, 2025

[](https://expedia.ca/Hotel-Search?startDate=18%2F03%2F2026&endDate=19%2F03%2F2026&selected=5126300&PinnedHotelID=5126300&HadPinnedHotel=true&regionId=11091)

![Hotel Leon Bianco](https://images.trvl-media.com/lodging/2000000/1320000/1315000/1314959/6c69e565_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Leon Bianco

Piazza Della Cisterna 13 San Gimignano SI

Fully refundableReserve now, pay when you stay

CA $137

CA $161 total

Mar 27 - Mar 28

includes taxes & fees

9.4/10 Exceptional! (575 reviews)

It is right in the center of the town square.

Reviewed on Mar 8, 2026

[](https://expedia.ca/Hotel-Search?startDate=27%2F03%2F2026&endDate=28%2F03%2F2026&selected=1314959&PinnedHotelID=1314959&HadPinnedHotel=true&regionId=11091)

[See all 510 properties in San Gimignano](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=16%2F03%2F2026&endDate=17%2F03%2F2026&regionId=11091)

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 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 relaxing 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 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)

![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)

![The Winery view](https://mediaim.expedia.com/localexpert/1142212/3b6918a9-7b30-4ae7-97da-0e415b38ca8e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Discover Chianti Through its Wines

CA $68

per adult

[](https://expedia.ca/things-to-do/discover-chianti-through-its-wines.a1142212.activity-details)

[See all activities in San Gimignano](https://expedia.ca/things-to-do/search?rid=11091)

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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.

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