A narrow street with stone buildings, Italian flags, and a shop with ceramic plates.

San Gimignano Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • 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.

Top San Gimignano vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Jan 18 - Jan 24

    Villa Olmi Firenze + Flight

    Bagno a Ripoli
    5 nights
    4.0 star property
    9.4/10 - Exceptional (822 reviews)
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FCO • 1 stop FCO - YUL • 1 stop
    CA $1,286
    CA $1,090
    per traveller
    found 14 hours ago
    Villa Olmi Firenze
  • Jan 18 - Jan 24

    The Hoxton, Florence + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    9.4/10 - Exceptional (386 reviews)
    "Very clean room! Smelled amazing! Loved the products that they had. Front desk was very friendly and very helpful they gave us really good recommendations and advice to stay away from tourist traps which was greatly appreciated! Would definitely stay here again and would recommend to others! They also have bikes on property that you can use if you would like to explore a little bit more of the city!"
    Reviewed November 8, 2026
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FCO • 1 stop FCO - YUL • 1 stop
    CA $1,616
    CA $1,230
    per traveller
    found 14 hours ago
    The Hoxton, Florence
  • Dec 27 - Jan 3

    The Place Firenze + Flight

    Historic Centre of Florence
    6 nights
    5.0 star property
    9.8/10 - Exceptional (203 reviews)
    Roundtrip • Montreal (YMQ) - Florence (FLR)
    YUL - FCO • 1 stop FCO - YUL • 1 stop
    CA $9,538
    CA $7,741
    per traveller
    found 1 hour ago
    The Place Firenze
  • Dec 17 - Dec 24

    Hotel L'Orologio Firenze + Flight

    Historic Centre of Florence
    6 nights
    4.0 star property
    9.6/10 - Exceptional (1,003 reviews)
    "Excellent hotel with many amenities, staff was helpful and friendly."
    Reviewed November 6, 2026
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FLR • 2 stops FLR - YUL • 2 stops
    CA $2,808
    CA $2,339
    per traveller
    found 3 hours ago
    Hotel L'Orologio Firenze
  • Dec 27 - Jan 3

    Grand Hotel Cavour + Flight

    Historic Centre of Florence
    6 nights
    4.0 star property
    9.4/10 - Exceptional (1,003 reviews)
    "Muy bueno"
    Reviewed November 7, 2026
    Roundtrip • Montreal (YMQ) - Florence (FLR)
    YUL - FCO • 1 stop FCO - YUL • 1 stop
    CA $6,380
    CA $5,402
    per traveller
    found 1 hour ago
    Grand Hotel Cavour

Where to stay in San Gimignano

Find the best San Gimignano areas and neighborhoods for the activities you enjoy most. Learn more about San Gimignano
Learn more about San Gimignano

San Gimignano City Centre

San Gimignano City Centre is noteworthy for its historic sites, and you can make a stop at top attractions like Piazza delle Erbe and Piazza Duomo.

Discover the most popular places to visit in San Gimignano

What to do in San Gimignano

San Gimignano Hotel Deals

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.

Frequently Asked Questions

How much does a San Gimignano vacation package cost?

You'll find cheap prices from CA $1,090 on Expedia for your San Gimignano getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to San Gimignano costs.

What are the cheapest months to go to San Gimignano?

If you're looking to book a cheap San Gimignano vacation package, consider travelling in December, January and February. You'll usually find better prices on flights and hotels during these quieter months — ideal for a budget-friendly break.

How many days is enough for San Gimignano?

Allow at least 3 days for your San Gimignano vacation to enjoy all that makes this destination unique. Explore popular neighbourhoods, including San Gimignano City Centre and Bibbiano. Then check out top sights like Sovestro in Poggio Winery and Sentierelsa Trail. With a good itinerary, you'll be kept busy with room for some downtime too. Want to venture beyond San Gimignano? Consider squeezing in a day trip or two.

Is it worth booking a vacation package to San Gimignano?

San Gimignano has everything you need for a fantastic break — nature, views and walking trails are just the start. Whether you want to visit attractions like Piazza Duomo and Collegiate Church of Santa Maria Assunta, or take the path less travelled, you'll find plenty to explore on your San Gimignano vacation.

How to find the best San Gimignano package deals?

Start your search for a San Gimignano package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal San Gimignano package deal right away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your San Gimignano adventure underway.

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

An Expedia vacation package could land you considerable savings when compared to booking stays and flights individually. Better still, you can customize your San Gimignano getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

When to book a vacation package to San Gimignano?

Secure incredible bargains by reserving your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment San Gimignano getaway.

How to plan a trip to San Gimignano?

  1. Pick your dates: What you'd like to do in San Gimignano and your favourite season can help you decide when to travel.
  2. Work out your budget: Make sure you have enough money to cover everything from meals and transportation to experiences and flights. Your accommodations will probably be the biggest expense during your trip to San Gimignano.
  3. Decide how long to go for: Now that you're more familiar with San Gimignano, you can work out the perfect length of your break. Put together a rough itinerary and allocate enough time for all the things you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a San Gimignano vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.