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.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

Historic Centre of Florence
CA $1,341
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
Excellent staff. Extremely helpful. Booked reservations for us and always happy to help. Hotel is nice and well maintained. Room was spacious for Italy. Shower was only tight squeeze

Reviewed on Sep 18, 2026

Grand Hotel Cavour

Grand Hotel Cavour

Historic Centre of Florence
Save 100% on your flight
CA $1,709
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (1,004 reviews)
Lovely hotel and great position in Florence. Staff were friendly and helpful. Breakfast was lovely plenty of choice. Wouldn’t hesitate to stay there again. Perfect for the usual sightseeing !

Reviewed on Sep 15, 2026

Aurum Firenze

Aurum Firenze

Historic Centre of Florence
Save 100% on your flight
CA $1,438
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Brilliant location, no more than 15-20 maximum minutes to walk to all the main sites. The staff worked hard and were very friendly and helpful.

Reviewed on Sep 17, 2026

Hotel Duomo Firenze

Hotel Duomo Firenze

Historic Centre of Florence
CA $1,775
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
I can’t understand how the property even considers selling a room the size I was in under a staircase with a shower which barely trickles.

Reviewed on Sep 19, 2026

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

Save 100% on your flight
CA $3,063
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9/10 Wonderful! (367 reviews)

Ready to book your vacation to San Gimignano?

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San Gimignano Hotel Deals

Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano San Gimignano SI
CA $180
CA $205 total
Sep 28 - Sep 29
includes taxes & fees
9/10 Wonderful! (369 reviews)
"The room had very little of the basic necessities. On arrival we had to carry all our luggage up a steep slope and climb stairs with no railings for leverage."

Reviewed on Sep 18, 2026

Poderi Arcangelo
Hotel Pescille by Double Hospitality

Hotel Pescille by Double Hospitality

Strada Statale 47 San Gimignano SI
CA $176
CA $203 total
Oct 9 - Oct 10
includes taxes & fees
9.2/10 Wonderful! (370 reviews)
"Superb stay, lovely pool, views are amazing, really nice breakfast and evening meal. Highly recommended."

Reviewed on Jun 18, 2026

Hotel Pescille by Double Hospitality
Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

Loc. San Donato San Gimignano SI
Fully refundableReserve now, pay when you stay
CA $206
CA $236 total
Oct 13 - Oct 14
includes taxes & fees
9.2/10 Wonderful! (488 reviews)
"If you are driving around in Tuscany and need a place to stay, look no further! The place is beautiful, clean, friendly staff and feels like a 5 star hotel without the price. location was central to all the wineries and Tuscany sites. Breakfast was fantastic. Awesome place!"

Reviewed on Sep 15, 2026

Hotel Casolare Le Terre Rosse
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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.
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Stay near popular San Gimignano attractions

A historic town with medieval towers and terraced vineyards.

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.
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A historic square with stone buildings, a fountain, and people walking.

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.
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A historic building with tall towers and arched windows.

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.
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A historic stone building with tall towers and a bell tower.

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.
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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.
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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.
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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.
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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.
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What to do in San Gimignano

Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

CA $36
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Tuscany in 1 day: Pisa, San Gimignano and Siena with Lunch

Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch

CA $79
per adult
78% of travellers recommend
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
Tootbus Tuscany Intercity Multi-day Pass

Tootbus Tuscany Multi-Day Tours from Florence: Explore at Your Own Pace

CA $55
per adult
Tootbus Tuscany Multi-Day Tours from Florence: Explore at Your Own Pace
See all activities in San Gimignano

Frequently asked questions

How much does a San Gimignano vacation package cost?
You'll find cheap prices from CA $1,341 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?
  1. Pick your dates: What you'd like to do in San Gimignano and your favourite season can help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.

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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.