San Gimignano Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Residenza Florentia
Historic Centre of Florence
Price was CA $2,031, price is now CA $1,468 per person
CA $1,468
per person
Jun 16 - Jun 19
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.4/10 Very Good! (50 reviews)
The hotel staff were extremely friendly and highly professional – honestly, I’ve rarely experienced this level of service.
The hotel is in a perfect location, right in the city center, which is a huge advantage.
Everything was clean, well-maintained, and very comfortable. I would highly recommend this place to anyone looking for quality accommodation.
Reviewed on Apr 6, 2026
Eurostars Florence Boutique
Historic Centre of Florence
Price was CA $3,141, price is now CA $2,309 per person
CA $2,309
per person
Jun 15 - Jun 21
found 8 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Florence (FLR)
8.6/10 Excellent! (486 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
Il Malaspina
Historic Centre of Florence
Price was CA $4,052, price is now CA $3,149 per person
CA $3,149
per person
Jun 15 - Jun 21
found 8 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Florence (FLR)
9.8/10 Exceptional! (90 reviews)
everyone was very nice and helpful. they were very fast to address any questions I had. the room had good space. the breakfast was excellent. the location is excellent. I will defintiely be staying there again next time I am in Florence.
Reviewed on May 8, 2026
Columbus Urban Resort
Campo di Marte
Price was CA $3,127, price is now CA $2,431 per person
CA $2,431
per person
Jun 15 - Jun 21
found 8 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Florence (FLR)
8.8/10 Excellent! (25 reviews)
Spent 2 nights here for a short break. Lovely hotel.... Spa was used both days and was lovely after long days sightseeing! Staff were very helpful and nothing was too much trouble.... Room was also excellent...spacious, comfy and had all amenities needed. It was rather warm in our room but we had a balcony so just opened the door. Didn't bother us enough to mention it to staff though! Breakfast was also good, plenty of choice and freshly cooked. All in all would definitely recommend!!
Reviewed on Apr 2, 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 $215 per night from Jun 7 to Jun 8
CA $215
CA $246 total
Jun 7 - Jun 8
includes taxes & fees
9.2/10 Wonderful! (458 reviews)
We had the loveliest stay in Hotel Casolare! From the minute we arrived the staff were warm and welcoming and couldn't be more helpful! We stayed in the Cipresso apartment and it was perfect for the 4 of us staying with a well equipped kitchenette and a lovely patio area to sit out on! All very clean ...
Reviewed on May 6, 2026
Poderi Arcangelo
Localita Capezzano San Gimignano SI
The price is CA $258 per night from Jun 11 to Jun 12
CA $258
CA $292 total
Jun 11 - Jun 12
includes taxes & fees
9/10 Wonderful! (337 reviews)
Very nice stay. Perfect location to visit San Gimignano, Certaldo and other locations in the area.
Reviewed on May 9, 2026
Mormoraia
Agriturismo San Gimignano San Gimignano SI
The price is CA $890 per night from May 20 to May 21
CA $890
CA $987 total
May 20 - May 21
includes taxes & fees
9.6/10 Exceptional! (216 reviews)
Great sty ! All was fantastic.
Reviewed on Apr 28, 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 relaxing 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
Florence Day Trip: Medieval Villages & Cooking Class
CA $226
per adult
86% of travellers recommend
Explore a world of travel with Expedia
- Barberino Val d'Elsa Hotels
- Bibbiano Hotels
- Campiglia Hotels
- Lgbt Friendly Hotels in Castel San Gimignano
- Castel San Gimignano Hotels
- Hotels near Castello di Monsanto
- Hotels near Castelvecchio
- Certaldo Alto Hotels
- Luxury Hotels in Certaldo
- Certaldo Hotels
- Colle di Val d'Elsa Hotels
- Lgbt Friendly Hotels in Gambassi Terme
- Gambassi Terme Hotels
- Lano Hotels
- Lucciana Hotels
- Luia Hotels
- Hotels near Magione Castle
- Hotels near Medieval Criminal and Torture Museum
- Mensanello Hotels
- Condo Rentals in Monsanto
- Monsanto Hotels
- Resorts in Monsanto
- Pancole Hotels
- Pastine Hotels
- Pignano Hotels
- Castles in Poggibonsi
- Poggibonsi Hotels
- San Donnino Hotels
- San Filippo Hotels
- San Gimignano City Centre Hotels
- Sensano Hotels
- Staggia Hotels
- Ulignano Hotels
- Aparthotels in Val d'Elsa
- B&B in Val d'Elsa
- Chalets in Val d'Elsa
- Guest Houses in Val d'Elsa
- Hostels in Val d'Elsa
- Hotels & Resorts for Couples in Val d'Elsa
- Hotels with Waterslides in Val d'Elsa
- Luxury Hotels in Val d'Elsa
- Pet-Friendly Hotels in Val d'Elsa
- Val d'Elsa Hotels
- Inns in Val d'Elsa
- Resorts in Val d'Elsa
- Varna Hotels
- Villa del Monte Hotels
- 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
- Orgia Vacations
- Visit Pancole
- Piazza della Cisterna
- Piazza Luigi Pecori
- Visit Poggibonsi
- Province of Siena Vacations
- Roman Theatre
- Rosia Vacations
- 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.
