San Gimignano Vacations from ¥352,933

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The Latest San Gimignano Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Glance Hotel In Florence

Glance Hotel In Florence

Historic Centre of Florence
¥352,933
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Florence (FLR)
9.4/10 Exceptional! (1,001 reviews)
Florence is a walkable city for most (uneven surfaces) making this a great location. It’s a 7 - 10 minute walk (depending on luggage) from the train station. Great rooftop pool with great views and service. The Club sandwich is among the best we have ever had. Sunset in the pool was amazing too. Breakfast was exceptional with great selection and great coffee !

Reviewed on Sep 28, 2026

Grand Hotel Cavour

Grand Hotel Cavour

Historic Centre of Florence
¥387,086
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Florence (FLR)
9.4/10 Exceptional! (1,000 reviews)
Staff was friendly and accommodating! Rooms were very clean and SPACIOUS! Would definitely return!

Reviewed on Oct 5, 2026

Il Rivalta - Place of Charme

Il Rivalta - Place of Charme

Historic Centre of Florence
¥406,652
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Florence (FLR)
9.4/10 Exceptional! (627 reviews)
Lovely hotel, great location.

Reviewed on Oct 7, 2026

Hotel degli Orafi

Hotel degli Orafi

Historic Centre of Florence
¥406,976
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Florence (FLR)
9.6/10 Exceptional! (1,005 reviews)
The perfect hotel for your Florence getaway. Charming hotel with a friendly and helpful staff. The location could not be more perfect. Full breakfast is served in the most elegant room. The rooftop bar is the best way to start or end your evening.

Reviewed on Oct 8, 2026

Plaza Hotel Lucchesi

Plaza Hotel Lucchesi

Historic Centre of Florence
¥367,089
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Tokyo (HND) 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 Oct 8, 2026

Find the Best San Gimignano Vacation Packages

Things to do near San Gimignano

Shopping

In San Gimignano, you can shop at Ra-Ma snc, a charming store just 6.4km away. If you're up for a drive, visit the Central Market 26.4km away for a vibrant public market experience, or head to The Mall Luxury Outlet, located 43.5km away, for luxury shopping and entertainment.

Recreation

Teatro del Silenzio offers a unique blend of romance and culture, showcasing enchanting performances in a stunning outdoor setting. For relaxation, the Alta Val d'Elsa River Park provides tranquil paths and natural beauty, perfect for unwinding. Meanwhile, Castelfalfi Golf Course invites sports enthusiasts to enjoy scenic outdoor golfing experiences.

Adventure

Explore the Sentierelsa Trail, a scenic hiking route located 8.0km from San Gimignano, perfect for outdoor enthusiasts. Dive into the refreshing Acquacalda Swimming Pool, located 25.7km away, or enjoy thrilling mountain biking with Tuscany MTB Guide, situated 30.6km from town, offering unforgettable adventures.

Nightlife

San Gimignano offers a charming nightlife with romantic vibes at Il Fiaschetto, a cozy drinking pub located 19.3km away. Enjoy the local atmosphere while sipping on craft cocktails and mingling with fellow travelers, making for an unforgettable evening in Tuscany.

*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 offers a charming blend of romance and culture, perfect for outdoor vacations. Explore its captivating churches, castles, and museums, including the San Gimignano Cathedral and the local museum. Nearby, don’t miss the chance to visit Siena and Castel San Gimignano for an enriching experience that captures the essence of this beautiful Tuscan region.

  • Piazza Duomo: This vibrant square is the heart of San Gimignano, surrounded by stunning medieval architecture. Experience the lively atmosphere, where locals and tourists mingle, and enjoy outdoor cafes offering local delicacies. The square is a perfect spot for people-watching and soaking in the rich culture of this historic town.
  • San Gimignano Communal Palace: A remarkable example of medieval civic architecture, the Communal Palace showcases beautiful frescoes and offers a glimpse into the town's governance history. Visitors can explore its impressive halls and enjoy panoramic views from its tower, immersing themselves in the region's artistic heritage.
  • Medieval Criminal and Torture Museum: This intriguing museum delves into the darker aspects of medieval justice. With fascinating exhibits on historical punishment methods, it provides a unique and thought-provoking insight into the past, making it a must-see 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

  • 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 Hotel Deals

Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano San Gimignano SI
Fully refundableReserve now, pay when you stay
¥17,029
¥19,617 total
Nov 8 - Nov 9
includes taxes & fees
9/10 Wonderful! (379 reviews)
"Beautiful property, nice and helping staff. We enjoy our stay ."

Reviewed on Oct 1, 2026

Poderi Arcangelo
La Cisterna

La Cisterna

Piazza Della Cisterna 23 San Gimignano SI
Fully refundableReserve now, pay when you stay
¥14,233
¥16,719 total
Nov 6 - Nov 7
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 Oct 8, 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
¥22,715
¥26,048 total
Oct 25 - Oct 26
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.

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. Savor Tuscan flavors 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

San Gimignano Campatelli Home and Tower Visit

San Gimignano Campatelli Home and Tower Visit

¥1,622
per adult
San Gimignano Campatelli Home and Tower Visit
Chianti: Lunch with Wine Tasting at Poggio ai Laghi Winery

Chianti: Lunch with Wine Tasting at Poggio ai Laghi Winery

¥6,306
per adult
Chianti: Lunch with Wine Tasting at Poggio ai Laghi Winery
Tootbus Tuscany Intercity Multi-day Pass

Tootbus Tuscany Multi-Day Tours from Florence: Explore at Your Own Pace

¥6,180
per adult
Tootbus Tuscany Multi-Day Tours from Florence: Explore at Your Own Pace
See all activities in San Gimignano

Frequently asked questions

How much does a San Gimignano vacation package cost?
You can snap up a vacation package to this destination from ¥352,933 on Expedia. But how much your vacation 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 vacation 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 vacation, 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 neighborhoods 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 vacation itinerary.
Is it worth booking a vacation 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 vacation, 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 vacation 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 customize your search by "Property class," "Number of bedrooms," "Traveler 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 traveling on a weekday, when prices are typically lower.
Is it cheaper to book a San Gimignano vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking stays and flights separately. Better still, you can personalize 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 vacation package to San Gimignano?
If you've got your San Gimignano vacation 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 accommodations: After you've nailed down your travel dates and duration, lock in the right San Gimignano vacation package for you.

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.