San Gimignano Holidays from £214

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Your San Gimignano Holiday

With every last detail planned before you go, our San Gimignano holiday packages mean you can focus more on having fun. Whether you're based in the neighbourhood 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, organising your ultimate tailored San Gimignano holiday is simple with Expedia.

Top San Gimignano Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Rocca Palazzaccio

Rocca Palazzaccio

3 out of 5
Save 100% on your flight
per person
19 Sept - 23 Sept
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9/10 Wonderful! (13 reviews)
The apartment is great as is the pool, and marco who looks after it is very nice. There is absolutely nothing in the area, you need to get the 37 bus to Florence if you want to eat or drink anything. The co-op is closed from 8pm and all day Sunday, the only restaurant closed down recently so at 7:30pm on a Saturday we found ourselves with nowhere whatsoever to eat. We had bread that we bought earlier at the shop, and on Sunday we ate in Florence before getting the bus back - be careful, half of the buses don’t turn up Recommended for sure if you have a car, the complex is excellent, but the local village is desolate

Reviewed on 24 Aug 2023

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
per person
15 Sept - 20 Sept
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.4/10 Exceptional! (228 reviews)
I VERY MUCH ENJOYED THE STAY

Reviewed on 18 Jul 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
6 Oct - 10 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on 6 Jun 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
Save 100% on your flight
per person
9 Sept - 16 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
No reviews
Hotel Bencista

Hotel Bencista

3 out of 5
Save 100% on your flight
per person
7 Sept - 14 Sept
found 5 hours ago
Return direct flight included
London (LON) to Florence (FLR)
7.2/10 Good! (12 reviews)

San Gimignano Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Peretola Airport (FLR)
Population
3,300
Max Temp Winter
10ºC
Max Temp Summer
29ºC
Top Sights
Tenuta Torciano Winery, Monteriggioni Castle and Isole e Olena Winery

Top hotels in San Gimignano

Villasanpaolo

Villasanpaolo

4 out of 5
Strada Provinciale Per Certaldo, San Gimignano, SI
Fully refundableReserve now, pay when you stay
The price is £183 per night from 24 Aug to 25 Aug
£183
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (215 reviews)
"Very nice hotel. Hope to stay there again."

Reviewed on 13 Jun 2025

Villasanpaolo
Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano, San Gimignano, SI
Fully refundableReserve now, pay when you stay
The price is £179 per night from 31 Aug to 1 Sept
£179
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (302 reviews)
"Exceptional views from this property. The room was for 4. It had a rustic farm house vibe. Unfortunately there was mold in the bathroom and a nest of spiders in the beams above the bed (which my husband was happy to sleep under - so we ignored). There is no noise insulation between floors and you ..."

Reviewed on 20 Jul 2025

Poderi Arcangelo
Cappuccina Country Resort

Cappuccina Country Resort

4 out of 5
Loc La Cappuccina 46/a, San Gimignano, SI
Fully refundableReserve now, pay when you stay
The price is £182 per night from 8 Aug to 9 Aug
£182
8 Aug - 9 Aug
includes taxes & fees
8.4/10 Very Good! (77 reviews)
"Really nice, quiet place to stay with an incredible view and convenient to San Gimignano. The staff and service was top notch with very friendly poolside service and at the restaurant. The room accommodations and beds are very comfortable, but the AC had trouble keeping up with the 90 degree days…especially ..."

Reviewed on 25 Jun 2025

Cappuccina Country Resort
See all 580 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Piazza della Cisterna which includes a city, street scenes 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
Piazza delle Erbe featuring heritage architecture

Piazza delle Erbe

Watch the world go by and admire San Gimignano’s medieval architecture from the comfort of a café terrace at this central square.

Piazza delle Erbe

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 quaint area.

Tenuta Torciano Winery

What to do in San Gimignano

Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

£104
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

£43
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Monteriggioni fortress

Tuscany Hiking Tour from Siena Including Wine Tasting

£48
per adult
Tuscany Hiking Tour from Siena Including Wine Tasting
See all activities in San Gimignano

Frequently asked questions

Why should I book my San Gimignano holiday with Expedia?
Choose Expedia to arrange your next escape easily and all in one convenient place. Our top tip for scoring a fabulous deal on a San Gimignano retreat? Bundle your accommodation, flights and/or car hire into a package holiday. Then add a few awesome tours and activities. Many bookings also come with flexible cancellation policies, so there's no need to panic if you have to change your travel plans. Round-the-clock assistance with changing and cancelling your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in San Gimignano?
Peak season falls in March, April and July and is a thrilling time to visit — if you don't mind the crowds. November, December and January are generally quieter times of the year. With daytime average temperatures of 4ºC, January is the coolest month in San Gimignano. The warmest month is July, when you can experience average temperatures of 24ºC throughout the day. Whatever the weather conditions, you'll find plenty of things to keep you busy here.
What are the top hotels for my holiday in San Gimignano?
One of the most sought-after places to stay in San Gimignano is Hotel Casolare Le Terre Rosse, in the neighbourhood of San Gimignano City Centre. Explore the city by day and then relax in your comfortable room after the sun goes down.
How do I get a cheap holiday to San Gimignano?
Find flights that fit your schedule, add a hotel to your booking and watch the savings grow with a San Gimignano holiday. It's that simple! From flights and hotels to activities and hire cars, Expedia is your gateway to cheap travel. And with over 400 partner airlines and 321,000 hotel options throughout the world to choose from, you won't be short of choice. Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my San Gimignano holiday?
There are so many things to do and see while on your holiday in San Gimignano. Collegiate Church of Santa Maria Assunta, Tenuta Torciano Winery, Piazza Duomo and Medieval Criminal and Torture Museum are a few of this city's major attractions.
What is the best neighbourhood to stay in when on holiday in San Gimignano?
If Collegiate Church of Santa Maria Assunta is high on your San Gimignano sightseeing list, base yourself in the neighbourhood of San Gimignano City Centre.
Do I need a visa for my San Gimignano holiday?
Check the latest rules on official government websites. Your nationality and whether you're visiting for leisure, business or study will determine if you'll require a visa for San Gimignano. Get familiar with the application process, including the required documentation, fees and turnaround times. Submit your application well in advance to allow enough time for processing. Some visas may take weeks or even months to go through, depending on the country.
What should I wear on my San Gimignano holiday?
Do some research into the sorts of things people in San Gimignano wear, and maybe even browse style blogs for some fashion inspiration. Aim to create a versatile wardrobe with pieces that suit your destination and showcase your unique style. Pack appropriately by checking the local weather conditions in San Gimignano. July brings the warmest temperatures, with daily averages of 24ºC, while January days average 4ºC, making it the coolest month.
What does an Expedia San Gimignano holiday include?
With Expedia, you can select any combination of flights, hotels and car hires to create your perfect San Gimignano travel package. Once you've made your booking, simply add on the fun things like activities and tours. Don't forget — the more you bundle, the bigger the savings! Discover a large selection of property types and choose one that matches your travel needs. The most sought-after holiday rentals here are apartments and villas. With Expedia, it's a breeze to customise your San Gimignano retreat just the way you like.
Does Expedia offer Book Now, Pay Later San Gimignano holidays?
Your bank balance shouldn't prevent you from going on holiday, so Expedia has devised a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a terrific getaway without making a dent in your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If paying in multiple instalments works for you, choose this option during the checkout process.
  • No-deposit holidays: If not paying ahead of time for your trip makes hitting that "book now" button easier, opt for a no-deposit holiday plan with Klarna so that you can Book Now, Pay Later!

Can I choose my airline with a San Gimignano Expedia holiday?
Definitely. Expedia has over 400 partner airlines to pick from around the world. With so much choice, finding the perfect carrier to bring you to San Gimignano will be a snap.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.