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 $2,018, price is now CA $1,632 per person
CA $1,632
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.6/10 Excellent! (484 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
Terme di Saturnia Natural Spa & Golf Resort - The Leading Hotels of the World
Price was CA $3,542, price is now CA $2,691 per person
CA $2,691
per person
Jun 2 - Jun 8
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (469 reviews)
The place and staff are amazing!! Hope to stay every year. Michael the front reception was superb and Giuseppe in the bar area was so wonderful!!
Love this place!!
Reviewed on Mar 25, 2026
Dimora Palanca Boutique & SPA
Historic Centre of Florence
Price was CA $3,432, price is now CA $2,612 per person
CA $2,612
per person
Jul 19 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (62 reviews)
I particularly love the authenticity of the building being hundreds of hundreds of years old and yet well cut, beautiful staff beautiful spa only lacking in the dining aspect but everything else was perfect. Highly recommend but recommend going out for dinner.
Reviewed on Nov 5, 2025
The Moon Boutique Hotel & Spa
Historic Centre of Florence
Price was CA $2,754, price is now CA $2,180 per person
CA $2,180
per person
Jul 19 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (524 reviews)
The room is very clean and comfortable, breakfast is good with a lot of options. The staff are so accommodating, friendly and respectful
Reviewed on Apr 24, 2026
LHP River Club
Santa Croce
Price was CA $3,281, price is now CA $2,605 per person
CA $2,605
per person
Jul 19 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (26 reviews)
Amazing hotel and amazing staff. We had the standard loft with a hot tub inside our bedroom! Loved it. Even though the reception is only open 9am-5pm, the hotel staff were very good at communicating with us through WhatsApp even when outside of these hours. The hotel feels very private. Love love love.
Reviewed on Apr 17, 2026
San Gimignano Hotel Deals
Hotel Casolare Le Terre Rosse
Loc. San Donato San Gimignano SI
The price is CA $235 per night from May 13 to May 14
CA $235
CA $268 total
May 13 - May 14
includes taxes & fees
9.2/10 Wonderful! (455 reviews)
Great staff who were amazing with my 1 year old. Beautiful grounds and the patio area outside the room was lovely and gave us some free time whilst baby slept. The bar food and breakfast was excellent and the restarting on the 2nd evening was equally has good. Thank you!!
Reviewed on Apr 21, 2026
Poderi Arcangelo
Localita Capezzano San Gimignano SI
The price is CA $216 per night from May 17 to May 18
CA $216
CA $246 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (335 reviews)
Nice place, staff very responsive, good food and great service.
Reviewed on Apr 28, 2026
Cappuccina Country Resort
Loc La Cappuccina 46/a San Gimignano SI
The price is CA $287 per night from May 11 to May 12
CA $287
CA $327 total
May 11 - May 12
includes taxes & fees
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
4.5/5(17 reviews)
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
5/5(1 review)
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
Chianti Half Day Wine Tour from Florence
CA $40
per adult
88% of travellers recommend
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 $57
per adult
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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
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- Visit Pancole
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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.
