San Gimignano Vacation Packages 2026 from $935

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.

The Latest San Gimignano vacation packages

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

The Moon Boutique Hotel & Spa

Historic Centre of Florence

$935

per person

Dec 14 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.6/10 Exceptional! (605 reviews)

Extremely clean, breakfast service was awesome. Absolutely beautiful room . Shower with steam and jacuzzi settings was wonderful.

Reviewed on Oct 2, 2026

Aurum Uffizi

Historic Centre of Florence

$1,581

per person

Dec 26 - Jan 1

found 16 hours ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

7.6/10 Good! (1,003 reviews)

Aurum Firenze

Historic Centre of Florence

$1,497

per person

Dec 26 - Jan 1

found 16 hours ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

7.4/10 Good! (1,015 reviews)

Rooms are way smaller than described and the shower was so small that you feel trapped. Street traffic and music from businesses awful. Mosquitoes would get in from under door. The buffet was terrible we didn’t finish our food and elected to pay for outside food each morning. The only positive was short walk to train station.

Reviewed on Oct 6, 2026

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

$1,220

per person

Nov 20 - Nov 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Florence (FLR)

9/10 Wonderful! (1,002 reviews)

Hotel La Scaletta exceeded our expectations! Everything about the property - location, amenities, breakfast, room, and helpful staff - was excellent. I had stayed in the hotel (and loved it) decades before but it has ascended from a pensione to a true hotel. I hope to return one day!

Reviewed on Oct 2, 2026

Bernini Palace

Historic Centre of Florence

$1,702

per person

Nov 20 - Nov 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Florence (FLR)

9.8/10 Exceptional! (1,006 reviews)

Alexandro and Lorenzo were fantastic! Extremely helpful and gracious!

Reviewed on Oct 6, 2026

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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. 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

Florence Day Trip: Medieval Villages & Cooking Class

$183

per adult

86% of travellers recommend

Tuscan Wine Tasting and Local Cheeses

$60

per adult

San Gimignano: Evening Flavors Dinner & Wine tasting

$65

per adult

See all activities in San Gimignano

San Gimignano Hotel Deals

Poderi Arcangelo

Localita Capezzano San Gimignano SI

Fully refundableReserve now, pay when you stay

$113 nightly

$129 total

Nov 4 - Nov 5

Total with taxes and fees

9/10 Wonderful! (377 reviews)

"Beautiful property, nice and helping staff. We enjoy our stay ."

Reviewed on Oct 1, 2026

La Cisterna

Piazza Della Cisterna 23 San Gimignano SI

Fully refundableReserve now, pay when you stay

$90 nightly

$105 total

Nov 5 - Nov 6

Total with taxes and fees

9.2/10 Wonderful! (660 reviews)

"It was an okay stay for one night. Clean and a comfortable bed."

Reviewed on Oct 3, 2026

Hotel Casolare Le Terre Rosse

Loc. San Donato San Gimignano SI

Fully refundableReserve now, pay when you stay

$146 nightly

$168 total

Oct 24 - Oct 25

Total with taxes and fees

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.

Find the Best San Gimignano Vacation Packages

Things to do near San Gimignano

San Gimignano offers a romantic and entertaining getaway with a variety of outdoor activities. You can indulge in spa treatments, enjoy local theater, or embark on wine tours to taste the region's renowned wines. Explore unique San Gimignano experiences through organized trips and tours, making it the perfect destination for a memorable day trip. Whether you're strolling through charming streets or savoring local delicacies, there's something for everyone in this picturesque Tuscan town.

Shopping

In San Gimignano, check out Rossi Alabastri Volterra for unique alabaster gifts, located 10 miles away. If you're up for a drive, visit The Mall Luxury Outlet for luxury brands and family-friendly entertainment, 27 miles away, or the Central Market for a vibrant local experience, 24 miles away.

Recreation

Experience tranquility at Alta Val d'Elsa River Park, just 7 miles from San Gimignano, where you can enjoy nature walks and peaceful picnics. For a blend of culture and entertainment, visit Teatro del Silenzio, located 15 miles away. Golf enthusiasts will love the scenic Castelfalfi Golf Course, 11 miles from town.

Adventure

Explore the breathtaking Sentierelsa Trail, a hiking trail 5 miles from San Gimignano, surrounded by stunning scenery. For outdoor thrills, try Tuscany MTB Guide, located 19 miles away, offering exciting biking adventures. For speed enthusiasts, the Siena Circuit karting experience, 24 miles away, promises adrenaline-pumping fun.

Nightlife

Experience the vibrant nightlife in San Gimignano with a visit to Il Fiaschetto, a lively drinking pub located 12 miles away. Enjoy the romantic vibes and entertainment that make for a perfect evening out in this charming Tuscan town.

*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 perfect blend of romance and entertainment for outdoor enthusiasts. Explore its rich culture by visiting the stunning San Gimignano Cathedral, the historic castle, and nearby Castel San Gimignano. Don't miss the opportunity to discover the beautiful Tuscany region and take a short trip to Siena for an unforgettable experience. This charming town caters to all travelers seeking a unique city experience filled with history and romance.

San Gimignano Communal Palace: This historic Civic Government Building offers a glimpse into the rich cultural heritage of San Gimignano. Visitors can admire its stunning architecture and explore its art-filled interiors, which reflect the town's medieval past.
Piazza Duomo: A vibrant square at the heart of San Gimignano, Piazza Duomo is surrounded by beautiful buildings and offers a lively atmosphere. It's the perfect spot to soak in the local culture, enjoy a coffee, or simply people-watch.
Medieval Criminal and Torture Museum: Dive into the darker side of history at this intriguing museum. With exhibits showcasing medieval justice and punishment, it provides a unique and thought-provoking experience about the era’s legal practices.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	41.2°F (5.1°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	43.3°F (6.3°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	48.4°F (9.1°C)	Light Rain	Mostly Sunny	Average	Average
April	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Average
May	61.5°F (16.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	70.7°F (21.5°C)	Light Rain	Sunny	Slightly High	Slightly High
July	76.3°F (24.6°C)	No Rain	Sunny	Slightly High	Average
August	75.9°F (24.4°C)	No Rain	Sunny	Average	Average
September	67.6°F (19.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	59.0°F (15.0°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	50.4°F (10.2°C)	Light Rain	Mostly Sunny	Slightly High	Slightly Low
December	43.3°F (6.3°C)	Light Rain	Mostly Sunny	Average	Average

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	50ºF
Max Temp Summer	85ºF
Top Sights	Tenuta Torciano Winery, Monteriggioni Castle and Sovestro in Poggio Winery

More vacations you might like

Frequently asked questions

What's included in a San Gimignano vacation package?

A San Gimignano vacation package lets you combine round-trip flights, hotel stays, and rental cars. Nearly all hotels in the area offer airport shuttle services, making transfers to and from Florence (FLR-Peretola) convenient. Most hotels also include free breakfast, which can be a practical saving during your trip.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How can I save money on a San Gimignano vacation package?

When you bundle, you can save up to 30%*. To save money on a San Gimignano package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What's the best vacation package for San Gimignano?

For a truly luxurious San Gimignano vacation package, consider a stay at Tenuta Bartoli, a 5-star property rated 9.9 out of 10, offering a spa, outdoor pool, and complimentary breakfast for around $680 per night. This option is ideal for travelers seeking premium amenities and a serene setting.Couples looking for a romantic escape might prefer Mormoraia, a 4.5-star hotel rated 9.3 out of 10, with a spa, outdoor pool, and bar/lounge for around $740 per night. Travelers often praise the charming staff and great food, noting the pool is also great for relaxing.Another excellent choice for a high-quality San Gimignano vacation package is Torraccia di Chiusi, a 5-star hotel rated 9.6 out of 10, available for around $260 per night. It features an outdoor pool, restaurant, and bar/lounge, with travelers frequently highlighting the wonderful food and relaxing pool time, along with fabulous breakfast and amazing staff.*Package availability and prices may change depending on dates and demand.

Is San Gimignano better suited for a beach vacation or a cultural trip?

San Gimignano is primarily a cultural destination, known for its rich medieval history and well-preserved architecture. A San Gimignano vacation offers a deep dive into Tuscan heritage, with attractions like the Vernaccia di San Gimignano Wine Museum and the historic Piazza della Cisterna, both within a 5-minute walk of the city center.Travelers seeking a San Gimignano vacation package will find themselves immersed in a landscape of ancient towers, Romanesque and Gothic buildings, and a history that dates back to Etruscan times, making it an ideal choice for those interested in art, history, and local traditions.

Is San Gimignano a good choice for a family vacation package?

San Gimignano is a good choice for family vacation packages, offering a blend of cultural exploration and amenities that cater to all ages. Most hotels offer kids clubs, playgrounds, and babysitting services, with nearly a third also providing family rooms.For a comfortable stay, consider a package with Agriturismo Macinatico 1, a 4-star property rated 9.3 out of 10 by travelers, which features family rooms, an outdoor pool, and a playground.Families can explore the Archaeological Museum - Spezieria Santa Fina - Raffaele De Grada Modern and Contemporary Art Gallery, about a 5-minute walk from central San Gimignano, or visit the Sant'Agostino Church, about a 10-minute walk away, known for its frescoes. The SanGimignano1300 museum also offers an engaging reconstruction of the medieval city.

Are luxury vacation packages in San Gimignano suitable for couples?

Luxury San Gimignano vacation packages are well-suited for couples seeking a romantic and refined escape in the Tuscan countryside.Mormoraia, a 4.5-star property rated 9.3 out of 10 by travelers, offers a spa, restaurant, and bar/lounge, with travelers praising the charming staff and great food. For a 5-star experience, Torraccia di Chiusi, rated 9.6 out of 10, provides an outdoor pool, restaurant, and bar/lounge, with guests highlighting the amazing staff and wonderful food.Another excellent option is Agriturismo Il Segreto di Pietrafitta, a 4.5-star adults-only property rated 9.9 out of 10, featuring an outdoor pool, restaurant, and bar/lounge, ideal for a tranquil couples' retreat.Explore luxury vacation packages in San Gimignano and romantic vacation packages in San Gimignano on Expedia to find the perfect couples' stay.

What luxury vacation packages are available in San Gimignano?

San Gimignano, known for romantic getaways, offers a selection of luxury San Gimignano vacation packages that include stays at highly-rated properties. There are nearly a third of luxury hotels available for your San Gimignano vacation package, many featuring spas and fine dining:Browse luxury vacation packages in San Gimignano on Expedia to compare options.

Are there adult-only vacation packages in San Gimignano?

Yes, your San Gimignano vacation package can include an adults-only hotel, providing a tranquil setting for your trip to this romantic destination:Browse adults-only resorts in San Gimignano on Expedia to compare options.

Which San Gimignano vacation packages include a pool?

Nearly all San Gimignano vacation package hotels offer both outdoor and indoor pools, making it easy to find a stay with refreshing water access.Fattoria Abbazia Monte Oliveto, rated 9.2 out of 10, provides an outdoor pool and kitchenettes, ideal for a comfortable stay.Hotel Pescille by Double Hospitality, rated 9.1 out of 10, also features an outdoor pool, along with kitchenettes and complimentary breakfast.For a hotel with a highly-rated pool, consider Hotel Casolare Le Terre Rosse, rated 8.9 out of 10, which also offers an outdoor pool, free breakfast, and airport shuttle service. Travelers loved the pool and found the food good, with amazing staff.Filter by pool type when comparing San Gimignano vacation packages to find the setup that works for your stay.

Which San Gimignano vacation packages include a mountain view?

A select few of San Gimignano vacation packages include hotels with mountain views, offering scenic outlooks over the surrounding Tuscan landscape. For example, the 5-star Residenza d'Epoca Palazzo Buonaccorsi is rated 8.6 out of 10 by travelers, and Palazzo al Torrione is rated 8.8 out of 10 by travelers. When booking your San Gimignano vacation package, you can often filter for rooms with these picturesque views.

Do luxury vacation packages in San Gimignano include spa or wellness facilities?

Yes, luxury San Gimignano vacation packages often feature hotels with spa and wellness facilities, though specific treatments might cost extra. Most luxury hotels here offer a spa, and nearly all include hot tubs. Top picks include the 5-star Tenuta Bartoli, rated 9.9 out of 10 by travelers, the 4.5-star Agriturismo Il Segreto di Pietrafitta, also rated 9.9 out of 10, and the 4.5-star Mormoraia, rated 9.3 out of 10 by travelers. All these properties offer spa access.Browse luxury vacation packages in San Gimignano on Expedia to compare.

Are airport transfers included in San Gimignano vacation packages?

Nearly all San Gimignano hotels offer airport shuttle services, which can be a convenient way to arrange transfers from airports like Florence (FLR-Peretola). While these services are a hotel-level amenity, their availability and whether they are complimentary or incur an additional fee can vary by property and package. It's always a good idea to confirm the specifics with your chosen hotel or package provider when booking your San Gimignano vacation package.

What are the top things to do in San Gimignano?

A San Gimignano vacation offers a rich array of historical and cultural experiences:Browse and book things to do in San Gimignano on Expedia.

Do you need to rent a car in San Gimignano, or is public transport enough?

While San Gimignano's historic center is highly walkable, a rental car offers the most flexibility for exploring the wider Tuscan region. The town itself is very compact, and you can walk from one end to the other in about 20 minutes. An electric shuttle bus also operates within the town, connecting key points like Porta San Giovanni and Piazza della Cisterna.For travelers arriving via San Gimignano vacation packages with flights, nearly all hotels offer airport shuttle services to and from Florence (FLR-Peretola). However, if you plan to visit vineyards, other hill towns, or the countryside beyond San Gimignano, a rental car is recommended for convenience and independence.

Are San Gimignano vacation package hotels conveniently located?

San Gimignano vacation package hotels are generally well-located, with many properties offering easy access to the historic center and surrounding countryside.For instance, B & B La Cornice - Gina Room With Bathroom and Private Terrace, rated 9.7 out of 10, is about a 10-minute walk from central San Gimignano. Tenuta Sovestro - Agriturismo e Winery, a 4-star property rated 9.5 out of 10, is about 1 mile from the center, while Agriturismo Il Segreto di Pietrafitta, rated 9.9 out of 10, is about 2 miles away.This means you can choose between staying directly within walking distance of the town's attractions or enjoying a slightly more secluded setting with a short drive.

Are there vacation package hotels in San Gimignano within walking distance of restaurants and shops?

San Gimignano vacation package hotels put restaurants and shops within walking distance, especially those located in or near the historic center.For example, Palazzo Mari, rated 9 out of 10, and Hotel L' Antico Pozzo San Gimignano, rated 8.8 out of 10, are both about a 5-minute walk from the Vernaccia di San Gimignano Wine Museum, placing you close to central dining and shopping. B & B La Cornice - Gina Room With Bathroom and Private Terrace, a 4.5-star property rated 9.7 out of 10, is also conveniently located about a 10-minute walk from central San Gimignano.Always check the specific hotel's location on a map to confirm its proximity to your preferred restaurants and shops.

Can I change or cancel my San Gimignano vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking San Gimignano vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later San Gimignano vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your San Gimignano vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to San Gimignano?

To find last-minute vacation packages to San Gimignano, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on San Gimignano vacation packages?

Free cancellation on a San Gimignano vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a San Gimignano vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your San Gimignano getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my San Gimignano vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.

San Gimignano Vacations from $935

Book a Hotel + Flight or Car together to unlock savings

Room 1

Your San Gimignano Vacation

The Latest San Gimignano vacation packages

The Moon Boutique Hotel & Spa

Aurum Uffizi

Aurum Firenze

Hotel La Scaletta Al Ponte Vecchio

Bernini Palace

Stay near popular San Gimignano attractions

Piazza della Cisterna

San Gimignano Communal Palace

Piazza Duomo

Piazza delle Erbe

Tenuta Torciano Winery

Medieval Criminal and Torture Museum

Vernaccia di San Gimignano Wine Museum

Sovestro in Poggio Winery

What to do in San Gimignano

Florence Day Trip: Medieval Villages & Cooking Class

Tuscan Wine Tasting and Local Cheeses

San Gimignano: Evening Flavors Dinner & Wine tasting

San Gimignano Hotel Deals

Poderi Arcangelo

La Cisterna

Hotel Casolare Le Terre Rosse

Find the Best San Gimignano Vacation Packages

Things to do near San Gimignano

Find the best attractions in San Gimignano

Best time to go to San Gimignano

Tips to save on your trip to San Gimignano

San Gimignano Essential Information

More vacations you might like

Frequently asked questions

Explore a world of travel with Expedia