San Gimignano Holidays from £253

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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.
Hotel Berchielli

Hotel Berchielli

Historic Centre of Florence
Save 100% on your flight
£253
per person
13 Dec - 16 Dec
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.4/10 Exceptional! (1,002 reviews)
Staff was amazing. Always attentive. Great breakfast. Would highly recommend

Reviewed on 2 Oct 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

Historic Centre of Florence
Save 100% on your flight
£699
per person
27 Dec - 1 Jan
found 1 day ago
Return direct flight included
Manchester (MAN) to Florence (FLR)
8.6/10 Excellent! (503 reviews)
Eurostar fell short of the brand. I stayed at the Eurostar Barcelona an outstanding hotel. This Eurostar hotel should be demolished!

Reviewed on 30 Sept 2026

Plaza Hotel Lucchesi

Plaza Hotel Lucchesi

Historic Centre of Florence
Save 100% on your flight
£278
per person
13 Dec - 16 Dec
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.4/10 Exceptional! (1,003 reviews)
The hotel’s location is excellent—away from the chaos but still close to the main Florence attractions. We were able to walk almost everywhere, which was very convenient. The staff was friendly and accommodating, and the rooftop bar, restaurant, and pool were wonderful. The property is very well located and offers some great amenities. The room was okay, The bathroom, in particular, is poorly designed. It is quite small, yet has a large sink, toilet, and bathtub, leaving very little space to move around. After a shower, there is barely enough room to dry yourself without the towel falling into either the toilet or the sink. Overall, the location, staff, and rooftop facilities are definite highlights.

Reviewed on 8 Oct 2026

The Hoxton, Florence

The Hoxton, Florence

Historic Centre of Florence
Save 100% on your flight
£389
per person
12 Nov - 15 Nov
found 1 day ago
Return flight included
Edinburgh (EDI) to Florence (FLR)
9.4/10 Exceptional! (358 reviews)
Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence
Save 100% on your flight
£481
per person
9 Nov - 14 Nov
found 1 day ago
Return direct flight included
London (LHR) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
This hotel was perfect for us. Right near Point Vecchio where hundreds of shops and restaurants are. The staff (especially Emanuel) were perfect. They took the time to speak with us and help when requested. Our room was a very spacious garden view on the first floor, the private garden was our front yard. The roof top bar was great too, get there early if you wish to watch the sunset with a drink. The next time we visit Florence we would certainly stay here again.

Reviewed on 8 Oct 2026

Things to do near San Gimignano

San Gimignano, nestled in the heart of Tuscany, is perfect for a romantic getaway or an outdoor adventure. Visitors can indulge in spa treatments, enjoy local theatre, and explore the stunning landscapes. Key activities include sightseeing in Tuscany, embarking on Chianti trips, and taking day excursions to nearby attractions, ensuring a memorable experience in this charming medieval town.

Shopping

In San Gimignano, you can explore local shops for unique souvenirs. For a wider selection, Pitti Vintage is a charming store nearby. If you're up for a drive, the Central Market and The Mall Luxury Outlet offer extensive shopping experiences with various vibes and entertainment options.

Recreation

At Alta Val d'Elsa River Park, immerse yourself in nature's tranquility while enjoying scenic walks and relaxation. Teatro del Silenzio offers a romantic cultural experience, perfect for families seeking entertainment. For sports enthusiasts, Castelfalfi Golf Course provides an invigorating outdoor atmosphere with stunning views.

Adventure

Experience the breathtaking Hedonistic Hiking trail, located 16.1km from San Gimignano, perfect for outdoor enthusiasts and nature lovers. For a unique outdoor experience, visit Biolago Geotermico Acqua Harda, situated 37.0km away. Families can enjoy the fun-filled Wonder Park, an adventure zone 48.3km from the town.

Nightlife

In San Gimignano, enjoy the vibrant nightlife at Il Fiaschetto, a charming drinking pub located 19.3km away. This venue offers a delightful atmosphere with entertainment and romantic vibes, perfect for unwinding after a day of exploring the stunning Tuscan landscape.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in San Gimignano

San Gimignano, a charming medieval town in Tuscany, is perfect for romantic and outdoor getaways. Visitors can explore its captivating churches, museums, and castles, immersing themselves in the rich culture and history. Key highlights include the historic centre, the iconic medieval architecture, and the enchanting Castel San Gimignano, making it an ideal destination for those seeking a blend of romance and city experience.

  • Piazza della Cisterna: This picturesque square is the heart of San Gimignano, surrounded by medieval towers and charming buildings. It's the perfect spot to soak in the local culture, enjoy a gelato, and watch the world go by while surrounded by stunning architecture.
  • Medieval Criminal and Torture Museum: Delve into the darker side of history at this intriguing museum, which showcases the grim realities of medieval justice. Exhibits feature authentic instruments of torture and offer a fascinating insight into the legal practices of the past.
  • Castelvecchio: Explore the ruins of this historic fortress, which offers breathtaking views of the surrounding countryside. A visit here provides a unique glimpse into the town's past, along with a serene atmosphere perfect for reflection.

Best time to go to San Gimignano

The best time to visit San Gimignano is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is sunny with no rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January41.2°F (5.1°C)Light RainMostly SunnySlightly LowSlightly Low
February43.3°F (6.3°C)Light RainMostly SunnySlightly LowSlightly Low
March48.4°F (9.1°C)Light RainMostly SunnyAverageAverage
April54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
May61.5°F (16.4°C)Light RainMostly SunnyAverageSlightly High
June70.7°F (21.5°C)Light RainSunnySlightly HighSlightly High
July76.3°F (24.6°C)No RainSunnySlightly HighAverage
August75.9°F (24.4°C)No RainSunnyAverageAverage
September67.6°F (19.8°C)Light RainMostly SunnyAverageSlightly High
October59.0°F (15.0°C)Light RainMostly SunnySlightly LowAverage
November50.4°F (10.2°C)Light RainMostly SunnySlightly HighSlightly Low
December43.3°F (6.3°C)Light RainMostly SunnyAverageAverage

Tips to save on your trip to San Gimignano

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to February and November) for more affordable package holidays to San Gimignano.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano San Gimignano SI
Fully refundableReserve now, pay when you stay
£94
8 Nov - 9 Nov
includes taxes & fees
9/10 Wonderful! (379 reviews)
"Beautiful property, nice and helping staff. We enjoy our stay ."

Reviewed on 1 Oct 2026

Poderi Arcangelo
La Cisterna

La Cisterna

Piazza Della Cisterna 23 San Gimignano SI
Fully refundableReserve now, pay when you stay
£79
6 Nov - 7 Nov
includes taxes & fees
9.2/10 Wonderful! (662 reviews)
"The room was clean & staff at the desk was helpful with eating choices & travel options to other communities"

Reviewed on 8 Oct 2026

La Cisterna
Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

Loc. San Donato San Gimignano SI
Fully refundableReserve now, pay when you stay
£125
25 Oct - 26 Oct
includes taxes & fees
Hotel Casolare Le Terre Rosse
See all 496 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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Where to go when
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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)
This medieval square showcases San Gimignano's noble past with its iconic 13th-century octagonal well. Savour Tuscan flavours at nearby cafés while admiring the ancient towers that frame this cobblestone gem.
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A historic town with medieval towers and terraced vineyards.

San Gimignano Communal Palace

9.4/10 (150 reviews)
This 13th-century palace houses medieval masterpieces, including Lippo Memmi's celebrated 'Maestà' fresco. Climb the Torre Grossa for breathtaking views of San Gimignano's medieval skyline and Tuscan countryside.
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A historic stone building with a tall tower and arched windows.

Piazza Duomo

9.4/10 (295 reviews)
Medieval Piazza del Duomo showcases San Gimignano's iconic towers and historic architecture. Enjoy a morning espresso at a café while admiring the Collegiata's intricate frescoes and the imposing Torre Grossa.
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A historic stone building with tall towers and a bell tower.

Piazza delle Erbe

9.4/10 (21 reviews)
This medieval square transforms into a vibrant marketplace on Saturdays, showcasing local produce amid historic towers. Sip espresso at a café terrace while admiring flower-filled balconies and elegant shuttered windows.
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Tenuta Torciano Winery

9.2/10 (40 reviews)
This family-run winery showcases 15 generations of Tuscan winemaking heritage through immersive tastings. Sample regional wines paired with local delicacies while overlooking San Gimignano's rolling hills.
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Medieval Criminal and Torture Museum

9.0/10 (66 reviews)
This haunting museum houses authentic medieval torture devices from the 12th to 16th centuries. Explore the Iron Maiden and Heretic's Fork while reading detailed historical context about judicial practices of the past.
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Vernaccia di San Gimignano Wine Museum

9.2/10 (15 reviews)
Housed in historic Rocca di Montestaffoli, this interactive museum celebrates Italy's first DOCG white wine. Sommeliers guide tastings while exhibits reveal Vernaccia's heritage against stunning Tuscan views.
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Sovestro in Poggio Winery

9.2/10 (18 reviews)
This family-run Tuscan winery offers intimate tastings paired with regional cuisine amid rolling vineyards. Sample their celebrated Vernaccia and Chianti wines while soaking in panoramic countryside views.
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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

£42
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

£21
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

£48
per adult
San Gimignano: Evening Flavors Dinner & 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.

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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. Flight-inclusive packages are ATOL protected.