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.
Floren Hotel
Historic Centre of Florence
CA $1,579
per person
Nov 19 - Nov 25
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.4/10 Exceptional! (267 reviews)
Fantastic location in the heart of Florence. They room was big, clean and the bed comfortable. Breakfast was great too.
Reviewed on Oct 8, 2026
Ready to book your vacation to San Gimignano?
San Gimignano Hotel Deals
Poderi Arcangelo
Localita Capezzano San Gimignano SI
Fully refundableReserve now, pay when you stay
CA $154
CA $177 total
Nov 8 - Nov 9
includes taxes & fees
9/10 Wonderful! (379 reviews)
"Beautiful property, nice and helping staff. We enjoy our stay ."
Reviewed on Oct 1, 2026
La Cisterna
Piazza Della Cisterna 23 San Gimignano SI
Fully refundableReserve now, pay when you stay
CA $127
CA $149 total
Nov 5 - Nov 6
includes taxes & fees
9.2/10 Wonderful! (662 reviews)
"The room was clean & staff at the desk was helpful with eating choices & travel options to other communities"
Reviewed on Oct 8, 2026
Hotel Casolare Le Terre Rosse
Loc. San Donato San Gimignano SI
Fully refundableReserve now, pay when you stay
CA $205
CA $235 total
Oct 21 - Oct 22
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.
Stay near popular San Gimignano attractions
Piazza della Cisterna
9.4/10 (327 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.
San Gimignano Communal Palace
9.4/10 (150 reviews)
You can browse the exhibits at San Gimignano Communal Palace, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.
Piazza Duomo
9.4/10 (295 reviews)
Browse the collections of ancient art, which grace the walls of the medieval landmarks that surround this resplendent public square.
Piazza delle Erbe
9.4/10 (21 reviews)
Watch the world go by and admire San Gimignano’s medieval architecture from the comfort of a café terrace at this central square.
Tenuta Torciano Winery
9.2/10 (40 reviews)
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
9.0/10 (66 reviews)
This intriguing museum highlights the callousness of humans via displays of authentic and gruesome torture devices from around the world.
Sovestro in Poggio Winery
9.2/10 (18 reviews)
You can enjoy a tasting or tour at Sovestro in Poggio Winery during your travels to San Gimignano. Discover the area's beautiful countryside and wineries.
Vernaccia di San Gimignano Wine Museum
9.2/10 (15 reviews)
You can browse the exhibits at Vernaccia di San Gimignano Wine Museum, a museum with a storied past, during your travels to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.
What to do in San Gimignano
Chianti Half Day Wine Tour from Florence
CA $39
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
Frequently asked questions
How much does a San Gimignano vacation package cost?
You'll find cheap prices from CA $1,337 on Expedia for your San Gimignano getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to San Gimignano costs.
What are the cheapest months to go to San Gimignano?
If you're looking to book a cheap San Gimignano vacation package, consider travelling in December, January and February. You'll usually find better prices on flights and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for San Gimignano?
Allow at least 3 days for your San Gimignano vacation to enjoy all that makes this destination unique. Explore popular neighbourhoods, including San Gimignano City Centre and Bibbiano. Then check out top sights like Sovestro in Poggio Winery and Sentierelsa Trail. With a good itinerary, you'll be kept busy with room for some downtime too. Want to venture beyond San Gimignano? Consider squeezing in a day trip or two.
Is it worth booking a vacation package to San Gimignano?
San Gimignano has everything you need for a fantastic break — nature, views and walking trails are just the start. Whether you want to visit attractions like Piazza Duomo and Collegiate Church of Santa Maria Assunta, or take the path less travelled, you'll find plenty to explore on your San Gimignano vacation.
How to find the best San Gimignano package deals?
Start your search for a San Gimignano package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal San Gimignano package deal right away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your San Gimignano adventure underway.
Is it cheaper to book a San Gimignano vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking stays and flights individually. Better still, you can customize your San Gimignano getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to San Gimignano?
Secure incredible bargains by reserving your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment San Gimignano getaway.
How to plan a trip to San Gimignano?
- Pick your dates: What you'd like to do in San Gimignano and your favourite season can help you decide when to travel.
- Work out your budget: Make sure you have enough money to cover everything from meals and transportation to experiences and flights. Your accommodations will probably be the biggest expense during your trip to San Gimignano.
- Decide how long to go for: Now that you're more familiar with San Gimignano, you can work out the perfect length of your break. Put together a rough itinerary and allocate enough time for all the things you want to do.
- Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a San Gimignano vacation package that brings all your bookings together.
Explore a world of travel with Expedia
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- Panoramic castle with large pool on the walls. Ideal for weddings and events
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- Mili house 3 bedrooms 2 bathrooms and garage
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- Isola SERENA Newly Expanded Private Luxury Villa
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- Visit Lilliano
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- Visit Colle di Val d'Elsa
- Medieval Criminal and Torture Museum
- Adventure Vacation Packages Empolese Val d'Elsa
- Visit Casole d'Elsa
- Piazza Luigi Pecori
- Visit Volterra
- Casa Vinicola Luigi Cecchi
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- Buondonno Winery
- Visit Castelfiorentino
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- Medici Fortress
- Visit Cortine
- Visit Gambassi Terme
- Piazza della Cisterna
- Visit Montaione
- Volterra Vacations
- Visit Vico d'Elsa
- Car rental Certaldo
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- Car rental Colle di Val d'Elsa
- Convertible Car Rentals in Casole d'Elsa
- Car rental Monteriggioni
- Car rental Poggibonsi
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
