San Gimignano Vacation Packages
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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, Tenuta Torciano Winery and Piazza Duomo 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
Historic Centre of Florence
Price was CA $2,365, price is now CA $1,649 per person
CA $1,649
per person
Apr 2 - Apr 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
8.6/10 Excellent! (476 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
Residenza Florentia
Historic Centre of Florence
Price was CA $3,039, price is now CA $2,067 per person
CA $2,067
per person
Apr 26 - May 2
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Florence (FLR)
8.4/10 Very Good! (46 reviews)
Location, accommodations, and communication. Simple but comfortable. A basic facilities, and nice AC, elevator, and luggage storage.
Reviewed on Jun 12, 2025
Art Atelier
Historic Centre of Florence
Price was CA $2,559, price is now CA $1,824 per person
CA $1,824
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
Our room was beautiful, the staff was incredible helpful, and the location was perfect - walking distance to everything.
Reviewed on Feb 4, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
Price was CA $3,247, price is now CA $2,322 per person
CA $2,322
per person
Apr 26 - May 2
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Florence (FLR)
9.6/10 Exceptional! (495 reviews)
The spa was wonderful though the jacuzzi could be hotter I think! The only complaint was that the bed wasn’t very comfortable (it was pretty hard) and the pillows were rather flat.
Reviewed on Jan 2, 2026
Hotel Alessandra
Historic Centre of Florence
Price was CA $3,274, price is now CA $2,374 per person
CA $2,374
per person
Apr 26 - May 2
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Florence (FLR)
9.2/10 Wonderful! (828 reviews)
Clean room, amazing staff, location is great
Reviewed on Feb 2, 2026
San Gimignano Hotel Deals
Hotel Casolare Le Terre Rosse
Loc. San Donato San Gimignano SI
9/10 Wonderful! (446 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
Mormoraia
Agriturismo San Gimignano San Gimignano SI
The price is CA $373 per night from Mar 12 to Mar 13
CA $373
CA $419 total
Mar 12 - Mar 13
includes taxes & fees
9.4/10 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
Poderi Arcangelo
Localita Capezzano San Gimignano SI
The price is CA $140 per night from Mar 8 to Mar 9
CA $140
CA $162 total
Mar 8 - Mar 9
includes taxes & fees
8.8/10 Excellent! (325 reviews)
Beautiful but the dinner wasn’t very good
Reviewed on Oct 13, 2025
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.
Discover the most popular places to visit in San Gimignano
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.
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.
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.
What to do in San Gimignano
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
CA $79
per adult
78% of travellers recommend
Organic Wine Tour&Tasting overlooking Chianti Classico Vineyards
CA $39
per adult
Chianti Half Day Wine Tour from Florence
CA $79
per adult
88% of travellers recommend
Explore a world of travel with Expedia
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- Arno River
- Boboli Gardens
- Buondonno Winery
- Casa Vinicola Luigi Cecchi
- Visit Castel San Gimignano
- Cathedral of Volterra
- Chianti Region Vacations
- Church of San Sigismondo
- Visit Colle di Val d'Elsa
- Collegiate Church of Santa Maria Assunta
- Fortezza Medicea
- Galileo Museum - Institute and Museum of the History of Science
- Visit Gambassi Terme
- Le Miccine
- Medici Fortress
- Medieval Criminal and Torture Museum
- Monsanto Vacations
- Montegufoni Castle
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- Visit Pancole
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- Visit Poggibonsi
- Province of Siena Vacations
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- Ruffino - Tenuta di Poggio Casciano
- Visit San Donnino
- Sezzate Castle
- Siena Vacations
- Tenuta Torciano Winery
- Tuscany Vacations
- Uffizi Gallery
- Val d'Elsa Vacations
- Visit Vico d'Elsa
- Volterra Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
