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 $3,191, price is now CA $2,093 per person
CA $2,093
per person
May 19 - May 25
found 19 hours ago
Roundtrip 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
Precise Tale Poggio Alla Sala
Price was CA $6,138, price is now CA $3,902 per person
CA $3,902
per person
May 19 - May 25
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.4/10 Exceptional! (124 reviews)
Most gorgeous setting, lovely staff and delicious food. We will definitely be back!
Reviewed on Apr 5, 2026
Il Rivalta - Place of Charme
Historic Centre of Florence
Price was CA $4,100, price is now CA $2,936 per person
CA $2,936
per person
Jun 15 - Jun 20
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.4/10 Exceptional! (492 reviews)
Such a beautiful and cool property!! The location was fantastic and the staff was really nice. We stayed in a king room, and the high ceilings and large open room was such a luxury. The room and bathroom were very clean, and the lighting in the bathroom is good too. The hotel is right along the river, and there are many restaurants and shops an easy walk away. We are so happy with our choice to stay at this property for our stay in Florence. We would highly recommend this hotel, and in fact I already recommended it to a friend who will be in Florence this summer!
Reviewed on Apr 4, 2026
The Place Firenze
Historic Centre of Florence
Price was CA $6,760, price is now CA $4,878 per person
CA $4,878
per person
May 16 - May 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.8/10 Exceptional! (193 reviews)
Fantastic location, hotel, and staff. We very much loved our stay and would highly recommend this hotel.
Reviewed on Apr 3, 2026
San Gimignano Hotel Deals
Hotel Casolare Le Terre Rosse
Loc. San Donato San Gimignano SI
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Apr 24 to Apr 25
CA $200
CA $230 total
Apr 24 - Apr 25
includes taxes & fees
9.2/10 Wonderful! (452 reviews)
.
Reviewed on Apr 7, 2026
Mormoraia
Agriturismo San Gimignano San Gimignano SI
Fully refundableReserve now, pay when you stay
The price is CA $432 per night from Apr 23 to Apr 24
CA $432
CA $483 total
Apr 23 - Apr 24
includes taxes & fees
9.6/10 Exceptional! (213 reviews)
Enjoyable vibes. Nice staff
Reviewed on Apr 8, 2026
Poderi Arcangelo
Localita Capezzano San Gimignano SI
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Apr 28 to Apr 29
CA $180
CA $206 total
Apr 28 - Apr 29
includes taxes & fees
9/10 Wonderful! (331 reviews)
Absolutely stunning scenery with beautiful rolling hills and surrounding wineries. Friendly and helpful staff. Seems to be family owned. If I were to suggest some areas of improvement, maybe the shower stalls can be cleaned more thoroughly. Breakfast varieties could also do with some expansion. But ...
Reviewed on Apr 3, 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.
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
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
CA $77
per adult
78% of travellers recommend
Chianti Half Day Wine Tour from Florence
CA $39
per adult
88% of travellers recommend
Tuscany Hiking Tour from Siena Including Wine Tasting
CA $95
per adult
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
- Monteriggioni Castle
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- Visit Pancole
- Piazza della Cisterna
- Piazza Luigi Pecori
- Visit Poggibonsi
- Province of Siena Vacations
- Roman Theatre
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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.
