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.
Hotel Villa Liana

Hotel Villa Liana

3 out of 5
Historic Centre of Florence
Price was CA $1,506, price is now CA $1,129 per person
CA $1,129
per person
Dec 1 - Dec 7
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
8.8/10 Excellent! (373 reviews)
My first day/night was not good. I was in a room that faced the traffic. Even with the shutters closed, it did nothing to alleviate the noise. The traffic didn't stop until midnight. The next morning I asked if I could be moved. Thankfully a room facing the quiet courtyard was found. Breakfast was very good, with many choices in a charming historic room.

Reviewed on Oct 14, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $1,948, price is now CA $1,254 per person
CA $1,254
per person
Dec 1 - Dec 7
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
A great budget hotel in a fantastic central location. Despite being so central it was in a side street so quiet at night. Rooms were cleaned daily and breakfast was buffet-style with cereal, fruit, croissants etc. I stayed there for 2 weeks and have no complaints at all. Excellent value for money.

Reviewed on Oct 24, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was CA $2,203, price is now CA $1,535 per person
CA $1,535
per person
Nov 30 - Dec 5
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (503 reviews)
The bed was comfortable but low to the floor. The shower was very slippery and could have used a shower mat. The breakfast was great. The staff were very nice and helpful.

Reviewed on Oct 10, 2026

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was CA $4,007, price is now CA $2,869 per person
CA $2,869
per person
Dec 28 - Jan 1
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (1,000 reviews)

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was CA $3,296, price is now CA $2,528 per person
CA $2,528
per person
Dec 28 - Jan 1
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (605 reviews)
Everything was wonderful about our stay at The Moon Hotel and Spa. The room was beautiful and clean, the staff were friendly and helpful and it was a great location for sightseeing in Florence. We especially appreciated the very generous breakfast that was always served efficiently and with a smile. We would definitely stay again.

Reviewed on Oct 23, 2026

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San Gimignano Hotel Deals

Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano San Gimignano SI
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Nov 27 to Nov 28
CA $145
CA $167 total
Nov 27 - Nov 28
includes taxes & fees
Poderi Arcangelo
La Cisterna

La Cisterna

3 out of 5
Piazza Della Cisterna 23 San Gimignano SI
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Nov 8 to Nov 9
CA $123
CA $145 total
Nov 8 - Nov 9
includes taxes & fees
9.2/10 Wonderful! (670 reviews)
"Room 63 was noisy all night from the kitchen and maybe people moving furniture next door? At midnight on a Saturday? Bizarre and noisy. Otherwise room was good"

Reviewed on Oct 25, 2026

La Cisterna
Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

3 out of 5
Loc. San Donato San Gimignano SI
The price is CA $201 per night from Oct 30 to Oct 31
CA $201
CA $231 total
Oct 30 - Oct 31
includes taxes & fees
9.2/10 Wonderful! (498 reviews)
"Absolutely lovely hotel. Best one we stayed at in Italy - in retrospect, we wish we booked to stay here a second night. The location is quiet and isolated so stars are visible at night, plenty of parking, and breakfast is worth the 20 EURS, best breakfast options we had during our stay. Highly recommend, ..."

Reviewed on Oct 22, 2026

Hotel Casolare Le Terre Rosse
See all 491 properties in San Gimignano
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 square with a prominent tower, stone buildings, outdoor seating, 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.
See properties

What to do in San Gimignano

Tuscany in 1 day: Pisa, San Gimignano and Siena with Lunch

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

CA $78
per adult
78% of travellers recommend
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

CA $39
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
San Gimignano: Evening Flavors Dinner & Wine tasting

San Gimignano: Evening Flavors Dinner & Wine tasting

CA $89
per adult
San Gimignano: Evening Flavors Dinner & Wine tasting
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 $1,129 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.