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.
Aurum Firenze
Historic Centre of Florence
CA $1,367
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
Room very small, no chairs inside, ants everywhere, including the breakfast area.
Quadruple room has a double bed and a single bed, apparently this was the biggest room in the hotel. We book for 4 people ( 2 adults and 2 children 12 and 16 and they had to squeeze in a single bed.
Reviewed on Aug 12, 2026
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
CA $2,174
per person
Oct 14 - Oct 19
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9/10 Wonderful! (1,006 reviews)
We had a wonderful stay at La Scaletta in Florence! The hotel was extremely clean, and the staff was always friendly, welcoming, and very helpful throughout our stay.
The location is fantastic, just steps from the Ponte Vecchio, with so many great shops, restaurants, and beautiful sights within easy walking distance.
One of the things we loved most was the combination of history and modern comfort. Staying in such a beautiful historic building, surrounded by gorgeous frescoes and architectural details, made the experience feel very special, while the rooms still had a fresh, modern vibe.
The terrace bar was another highlight and a wonderful place to relax and enjoy Florence. Beautiful hotel, excellent location, and great service. We would definitely recommend La Scaletta and would happily stay here again!
Reviewed on Aug 12, 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 $191
CA $218 total
Sep 3 - Sep 4
includes taxes & fees
Hotel Pescille by Double Hospitality
Strada Statale 47 San Gimignano SI
CA $248
CA $283 total
Sep 6 - Sep 7
includes taxes & fees
9.4/10 Exceptional! (365 reviews)
"Superb stay, lovely pool, views are amazing, really nice breakfast and evening meal. Highly recommended."
Reviewed on Jun 18, 2026
Hotel Casolare Le Terre Rosse
Loc. San Donato San Gimignano SI
Fully refundableReserve now, pay when you stay
CA $250
CA $284 total
Sep 10 - Sep 11
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 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.
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 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.
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.
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.
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.
Casa e Torre Campatelli
9.4/10 (33 reviews)
Learn about the local history of San Gimignano when you take a trip to Casa e Torre Campatelli. Discover the area's beautiful countryside and wineries.
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
Chianti Half Day Wine Tour from Florence
CA $39
per adult
88% of travellers recommend
Organic Wine Tour&Tasting overlooking Chianti Classico Vineyards
CA $45
per adult
Frequently asked questions
How much does a San Gimignano vacation package cost?
You'll find cheap prices from CA $1,367 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
