San Gimignano Vacations from $596

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
LHP River Club

LHP River Club

5 out of 5
Santa Croce
Price was $831, price is now $596 per person
$596
per person
Dec 7 - Dec 12
found 4 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9/10 Wonderful! (8 reviews)
Beautiful room and comfortable bed. Clean. Nice pool area. There are no elevators but the stairs are not long. AC is not very strong but suffices. Area is full of hidden gems from bakeries to late night pizza. Parking can be a challenge but not more than other parts of the city. About a 20 min walk to the center and plenty of shops and restaurants along the way.

Reviewed on Sep 23, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $1,988, price is now $1,358 per person
$1,358
per person
Dec 7 - Dec 12
found 4 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.8/10 Exceptional! (461 reviews)
The hotel is very beautiful, and the surrounding environment is also excellent.

Reviewed on Sep 26, 2025

Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,664, price is now $1,151 per person
$1,151
per person
Nov 16 - Nov 22
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (51 reviews)
Overall the property was great for our needs. It was very convenient for us because it had parking on the premises. The staff was amazing and the king room was beautiful. The only drawback is that it was a bit of a walk from the city center.

Reviewed on Oct 5, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,639, price is now $1,138 per person
$1,138
per person
Dec 28 - Jan 1
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,007 reviews)
Breakfast was excellent

Reviewed on Sep 29, 2025

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $918, price is now $641 per person
$641
per person
Dec 8 - Dec 14
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.6/10 Excellent! (472 reviews)
Great little hotel. Everything is within walking distance. The view from the terrace was amazing.

Reviewed on Aug 6, 2025

Don't see what you're looking for?
See all available trips from Columbus to San Gimignano
View all trips

Discover the most popular places to visit in San Gimignano

San Gimignano Communal Palace

San Gimignano Communal Palace

You can browse the exhibits at San Gimignano Communal Palace, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.

San Gimignano Communal Palace
Piazza Duomo showing a church or cathedral and heritage architecture

Piazza Duomo

Browse the collections of ancient art, which grace the walls of the medieval landmarks that surround this resplendent public square.

Piazza Duomo
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

What to do in San Gimignano

Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

$141
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
Monteriggioni fortress

Tuscany Hiking Tour from Siena Including Wine Tasting

$65
per adult
Tuscany Hiking Tour from Siena Including Wine Tasting
Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

$58
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
See all activities in San Gimignano

San Gimignano Hotel Deals

RELAIS SANTA CHIARA - TUSCANY CHARME

RELAIS SANTA CHIARA - TUSCANY CHARME

4 out of 5
Via Giacomo Matteotti, 15, San Gimignano, SI
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $92 total per night from Nov 2 to Nov 3
$92 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (388 reviews)
"Perfect stay in San Gimiano - thank you! The reception staff are fantastic - polite and very helpful. We loved our balcony Will be back hopefully for longer"

Reviewed on Sep 24, 2025

RELAIS SANTA CHIARA - TUSCANY CHARME
Hotel Pescille - Tuscany Charme

Hotel Pescille - Tuscany Charme

3 out of 5
Strada Statale 47, Localita Pescille, San Gimignano, SI
$91 nightly
The price is $108 total per night from Oct 20 to Oct 21
$108 total
Oct 20 - Oct 21
Total with taxes and fees
9.2/10 Wonderful! (321 reviews)
"Beautiful views!!!"

Reviewed on Sep 24, 2025

Hotel Pescille - Tuscany Charme
Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano, San Gimignano, SI
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $156 total per night from Oct 9 to Oct 10
$156 total
Oct 9 - Oct 10
Total with taxes and fees
8.8/10 Excellent! (318 reviews)
"Staff was wonderful, very helpful. Beautiful place, view was brethtaking. Food was delicious."

Reviewed on Sep 22, 2025

Poderi Arcangelo
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.

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

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a San Gimignano vacation package cost?
You can snap up a vacation package to this destination from $596 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'd like to score a cheap San Gimignano vacation package, consider visiting in November, December and January. You'll generally find lower prices on airfares and hotels during these quieter months — ideal for budget-conscious travelers.
How many days is enough for San Gimignano?
San Gimignano vacations can be short or long, but to get a true feel for this destination, we'd say 3 days is about right. With this timeframe, you can visit top sights like Museo Civico and Museum San Gimignano 1300 and track down some hidden gems. Don't skip neighborhoods such as San Gimignano City Centre and Bibbiano either. If you plan wisely, you may even be able to take a day trip outside of San Gimignano too.
Is it worth booking a vacation package to San Gimignano?
San Gimignano has everything you need for an amazing trip — walking trails, nature and history are just the start. Whether you'd like to visit sights such as Collegiate Church of Santa Maria Assunta and Piazza Duomo, or take the path less traveled, you'll have plenty to do on your San Gimignano vacation.
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: The things you plan to do in San Gimignano and your preferred season can help you decide when to get away.
  2. Set a budget: Factor in expenses like food, flights and transportation when calculating how much to save for your trip to San Gimignano. Then, choose a hotel that fits your budget, whether that's a low-cost stay or a more upscale retreat.
  3. Use Expedia's trip planning tool to discover San Gimignano: Research every part of your trip to San Gimignano with this comprehensive planner. Invite your friends and family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Determine how many days away: Start by compiling a list of the activities and attractions you want to get to in San Gimignano. Then, estimate how long you'll need for each, along with any travel time.
  5. Bundle your accommodations and airfare: Once you've nailed down your dates and duration, lock in the ideal San Gimignano vacation package for you.
  6. Add on excursions and experiences: Have a look at our travel guide to find some incredible things to do in San Gimignano. Book tickets or make reservations in advance to save time and skip the hassle of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later San Gimignano vacation packages?
If you're like us, you love discovering new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your San Gimignano vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

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.