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 $3,150, price is now CA $1,884 per person
CA $1,884
per person
Oct 18 - Oct 24
found 14 hours ago
Roundtrip flight included
Ottawa (YOW) to Florence (FLR)
9.6/10 Exceptional! (469 reviews)
The hotel is located a 25 min walk away from the heart of Florence so very easy to access the main attractions within the city. The hotel itself is immaculate and the staff are extremely helpful with dealing with any questions you may have. Being able to access the spa everyday for 1 and 30 minutes is an excellent perk as the facilities are well worth a visit, you are also able to book massages for an extra fee. The breakfast also gives a variety of options to start each day and the room itself is spacious, with the shower particularly being very comfortable.

Reviewed on Aug. 13, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
Price was CA $5,934, price is now CA $3,957 per person
CA $3,957
per person
Oct 18 - Oct 24
found 14 hours ago
Roundtrip flight included
Ottawa (YOW) to Florence (FLR)
9.4/10 Exceptional! (230 reviews)
Gorgeous boutique hotel, like museum Beautiful rooms!!! Thank you Giovanni for all ur help and knowledge organizing everything for us, and breakfast waiters were great!!!

Reviewed on Aug. 21, 2025

Collegio alla Querce - Auberge Resorts

Collegio alla Querce - Auberge Resorts

5 out of 5
Le Cure
Price was CA $12,357, price is now CA $8,498 per person
CA $8,498
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
10/10 Exceptional! (2 reviews)
Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
Price was CA $3,295, price is now CA $2,344 per person
CA $2,344
per person
Oct 18 - Oct 24
found 14 hours ago
Roundtrip flight included
Ottawa (YOW) to Florence (FLR)
9.4/10 Exceptional! (46 reviews)
The staff went out of their way to be helpful with all queries

Reviewed on Jun. 21, 2025

NH Collection Firenze Porta Rossa

NH Collection Firenze Porta Rossa

5 out of 5
Historic Centre of Florence
Price was CA $7,888, price is now CA $5,635 per person
CA $5,635
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.4/10 Exceptional! (1,001 reviews)
Perfect location in Florence.

Reviewed on Nov. 24, 2024

Ready to book your vacation to San Gimignano?

 

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San Gimignano Hotel Deals

RELAIS SANTA CHIARA - TUSCANY CHARME

RELAIS SANTA CHIARA - TUSCANY CHARME

4 out of 5
Via Giacomo Matteotti, 15, San Gimignano, SI
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Aug 31 to Sep 1
CA $156
CA $183 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (383 reviews)
"We loved our stay. The hotel had really nice breakfasts included and the pool was fantastic after a hot day walking around the old city. We had a standard room and we were expecting it to be small. It was very small - it was difficult to find space for our cases and the shower was so small that it ..."

Reviewed on Jul. 20, 2025

RELAIS SANTA CHIARA - TUSCANY CHARME
Hotel Leon Bianco

Hotel Leon Bianco

3 out of 5
Piazza Della Cisterna 13, San Gimignano, SI
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from Aug 27 to Aug 28
CA $160
CA $186 total
Aug 27 - Aug 28
includes taxes & fees
9.4/10 Exceptional! (541 reviews)
"Excellent hotel but was a bit challenging to get to due to surrounding areas. Staff was excellent, check in was friendly. Super helpful"

Reviewed on Aug. 24, 2025

Hotel Leon Bianco
Villasanpaolo

Villasanpaolo

4 out of 5
Strada Provinciale Per Certaldo, San Gimignano, SI
Fully refundableReserve now, pay when you stay
The price is CA $294 per night from Aug 29 to Aug 30
CA $294
CA $335 total
Aug 29 - Aug 30
includes taxes & fees
8.8/10 Excellent! (216 reviews)
"Very nice hotel. Hope to stay there again."

Reviewed on Jun. 13, 2025

Villasanpaolo
See all 579 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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Discover the most popular places to visit in San Gimignano

Piazza della Cisterna which includes street scenes, a city and a square or plaza

Piazza della Cisterna

Admire the palaces and towers that frame this beautiful square, which was once a medieval marketplace. Today, it’s a venue for cultural events.

Piazza della Cisterna
Collegiate Church of Santa Maria Assunta

Collegiate Church of Santa Maria Assunta

You can browse the exhibits at Collegiate Church of Santa Maria Assunta, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.

Collegiate Church of Santa Maria Assunta

Tenuta Torciano Winery

You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this relaxing area.

Tenuta Torciano Winery

What to do in San Gimignano

A guided visit of San Gimignano

Horseback Ride in S.Gimignano with Tuscan Lunch Chianti Tasting

CA $305
per adult
100% of travellers recommend
Horseback Ride in S.Gimignano with Tuscan Lunch Chianti Tasting
Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

CA $191
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
Students and family friendly tours

Tuscany Vespa Tour from Florence with Wine Tasting

CA $322
per adult
100% of travellers recommend
Tuscany Vespa Tour from Florence with 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 $1,884 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.

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