San Gimignano Holidays

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Top Flight + Hotel Deals in San Gimignano

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

Historic Centre of Florence
€405
per person
28 Sept - 30 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
Grand Hotel Cavour

Grand Hotel Cavour

Historic Centre of Florence
€940
per person
25 Oct - 30 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
Fabulous

Reviewed on 9 Aug 2026

Il Pelagone Hotel & Golf Resort Toscana

Il Pelagone Hotel & Golf Resort Toscana

Save 100% on your flight
€793
per person
12 Sept - 18 Sept
found 1 hour ago
Return flight included
Dublin (DUB) to Pisa (PSA)
8.6/10 Excellent! (20 reviews)
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

Historic Centre of Florence
€507
per person
28 Sept - 30 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.6/10 Exceptional! (577 reviews)
Everything was great! Friendly staff, clean and comfortable rooms, and a relaxing atmosphere overall. We really enjoyed our stay!

Reviewed on 1 Aug 2026

Hotel San Luca

Hotel San Luca

Cortona Old Town
Save 100% on your flight
€760
per person
12 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
8.6/10 Excellent! (436 reviews)
Wonderful place to stay in Cortona Great breakfast

Reviewed on 23 Jul 2026

Things to do near San Gimignano

San Gimignano offers a delightful mix of romantic and outdoor activities, making it an ideal destination for a memorable vacation. Visitors can indulge in relaxing spa treatments, enjoy theatrical performances, or explore the beautiful surroundings through various sightseeing tours in Tuscany. Don't miss the chance to embark on a Chianti trip or take day trips to discover the enchanting landscapes and rich culture of the region.

Shopping

San Gimignano offers delightful shopping experiences with local artisans and quaint boutiques. If you're up for a drive, The Mall Luxury Outlet and I Gigli Shopping Center, both 43.5km away, provide a vibrant mix of luxury brands and family-friendly entertainment. Conte of Florence Factory Outlet, 41.8km away, is also worth a visit.

Recreation

Experience the serene Castelfalfi Golf Course, set amidst rolling hills, offering a refreshing outdoor atmosphere just 17.7km from San Gimignano. Alternatively, enjoy the vibrant energy at Palasport Mens Sana and Siena Stadium, both 25.7km away, perfect for sports enthusiasts seeking excitement and wellness.

Adventure

Explore the Sentierelsa Trail, a scenic hiking route located 8.0km from San Gimignano, offering stunning views and a true adventure experience. For a unique outdoor vibe, visit Biolago Geotermico Acqua Harda, situated 37.0km away, or enjoy family-friendly fun at Wonder Park, 48.3km from the town.

Nightlife

For a lively night in San Gimignano, visit Il Fiaschetto, a charming pub located 19.3km away. Here, you can enjoy a romantic atmosphere infused with entertainment vibes, making it a perfect spot to unwind and socialise after a day of exploring this beautiful town.

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

Find the best attractions in and around San Gimignano

San Gimignano, a picturesque medieval town in Tuscany, is ideal for romantic and outdoor getaways. Visitors can explore its enchanting churches, historic castles, and intriguing museums, immersing themselves in rich culture and captivating city experiences. Key attractions include the medieval city itself, the renowned Castel San Gimignano, and various tourist destinations that showcase the town's charm and history, making it a perfect spot for travellers seeking both adventure and romance.

  • Medieval Criminal and Torture Museum: Step into the haunting past at this intriguing museum, which showcases a chilling collection of medieval torture devices and criminal artifacts. The cultural experience immerses you in the darker aspects of history, offering a unique perspective on justice and punishment in the Middle Ages.
  • Piazza Luigi Pecori: This charming piazza is the heart of San Gimignano, where vibrant city life unfolds. Surrounded by stunning architecture, it’s the perfect spot to enjoy a leisurely coffee while soaking in the local culture and atmosphere, making it a delightful gathering place for visitors and locals alike.
  • Monteriggioni Castle: A short distance from San Gimignano, this historic castle is a remarkable example of medieval architecture. Surrounded by ancient walls, exploring the castle offers breathtaking views and a glimpse into the area's rich history, making it a must-visit for history enthusiasts.

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

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to San Gimignano.
  • Consider traveling to San Gimignano during the low season (January to February and November) for more affordable options.
  • 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.

Top hotels in San Gimignano

Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano San Gimignano SI
Fully refundableReserve now, pay when you stay
€136
3 Sept - 4 Sept
includes taxes & fees
Poderi Arcangelo
Hotel Pescille by Double Hospitality

Hotel Pescille by Double Hospitality

Strada Statale 47 San Gimignano SI
€162
12 Aug - 13 Aug
includes taxes & fees
9.4/10 Exceptional! (365 reviews)
"Superb stay, lovely pool, views are amazing, really nice breakfast and evening meal. Highly recommended."

Reviewed on 18 Jun 2026

Hotel Pescille by Double Hospitality
Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

Loc. San Donato San Gimignano SI
Fully refundableReserve now, pay when you stay
€192
23 Aug - 24 Aug
includes taxes & fees
Hotel Casolare Le Terre Rosse
See all 501 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.

Stay near popular San Gimignano attractions

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 square with stone buildings, a fountain, 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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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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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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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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Casa e Torre Campatelli

9.4/10 (33 reviews)
Learn about the local history of San Gimignano with a stop at Casa e Torre Campatelli. Discover the area's beautiful countryside and wineries.
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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

€49
per adult
78% of travellers recommend
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
Florence Day Trip: Medieval Villages & Cooking Class

Florence Day Trip: Medieval Villages & Cooking Class

€139
per adult
86% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
Chianti: Lunch with Wine Tasting at Poggio ai Laghi Winery

Chianti: Lunch with Wine Tasting at Poggio ai Laghi Winery

€35
per adult
Chianti: Lunch with Wine Tasting at Poggio ai Laghi Winery
See all activities in San Gimignano

Frequently asked questions

How much does a San Gimignano holiday package cost?
You can snap up a holiday package to this destination from €405 on Expedia. But how much your holiday to San Gimignano costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to San Gimignano?
If you're hoping to book a cheap San Gimignano holiday package, consider visiting in December, January and February. You'll generally find better rates on hotels and flights during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for San Gimignano?
To get the most out of your San Gimignano holiday, we recommend staying for 3 days. Divide your time between visiting Museo Civico, Museum San Gimignano 1300 and other must-see attractions, as well as experiencing neighbourhoods like San Gimignano City Centre and Bibbiano. If you've got some time to spare, include a day trip or tour in your San Gimignano holiday itinerary.
Is it worth booking a holiday package to San Gimignano?
Whether you're looking to check out major attractions such as Piazza Duomo and Collegiate Church of Santa Maria Assunta on your San Gimignano holiday, or coming for its great nature, views and walking trails, there's something for everyone here. With so many things to see and do, you'll soon learn why so many families think San Gimignano is a good holiday destination.
How to find the best San Gimignano package deals?
Bagging a cheap San Gimignano package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, add a few filters and see what's available. You can customise your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly San Gimignano package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a San Gimignano holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking stays and flights separately. Better still, you can personalise your San Gimignano trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to San Gimignano?
If you've got your San Gimignano holiday dates confirmed, book as early as you can to snap up some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to San Gimignano?
  1. Pick your dates: What you'd like to do in San Gimignano and your preferred season will help you decide when to get away.
  2. Budget wisely: On top of the price of your stay, you should factor in other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that may arise during your trip to San Gimignano.
  3. Decide your trip length: Consider how much time you want to spend exploring San Gimignano. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your airfare and accommodation: After you've nailed down your travel dates and duration, lock in the right San Gimignano holiday package for you.

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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.