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

4 out of 5
Historic Centre of Florence
Price was CA $1,766, price is now CA $1,314 per person
CA $1,314
per person
Dec 10 - Dec 15
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (612 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

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was CA $2,890, price is now CA $1,829 per person
CA $1,829
per person
Dec 1 - Dec 8
found 7 hours ago
Roundtrip flight included
Ottawa (YOW) to Florence (FLR)
8.6/10 Excellent! (508 reviews)

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $2,170, price is now CA $1,403 per person
CA $1,403
per person
Dec 1 - Dec 8
found 7 hours ago
Roundtrip flight included
Ottawa (YOW) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
El hotel es lindo y limpio… un poco pequeño pero muy céntrico nos gustó mucho … volveremos 👏🌹

Reviewed on Oct 28, 2026

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was CA $3,533, price is now CA $2,479 per person
CA $2,479
per person
Dec 1 - Dec 8
found 7 hours ago
Roundtrip flight included
Ottawa (YOW) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Great location, very clean and beautiful views. Staff was very kind and helpful

Reviewed on Oct 28, 2026

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Price was CA $2,029, price is now CA $1,499 per person
CA $1,499
per person
Dec 1 - Dec 8
found 7 hours ago
Roundtrip flight included
Ottawa (YOW) to Florence (FLR)
8.8/10 Excellent! (445 reviews)
Beautiful hotel! We didn't realize the pool would be closed when we were there, but otherwise excellent stay.

Reviewed on Oct 13, 2026

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
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Nov 15 to Nov 16
CA $150
CA $173 total
Nov 15 - Nov 16
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 14 to Nov 15
CA $123
CA $144 total
Nov 14 - Nov 15
includes taxes & fees
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 $200 per night from Oct 30 to Oct 31
CA $200
CA $230 total
Oct 30 - Oct 31
includes taxes & fees
Hotel Casolare Le Terre Rosse
See all 486 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $1,314 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.