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

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top San Gimignano vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Sept 14 - Sept 20

    Columbus Urban Resort + Flight

    Campo di Marte
    5 nights
    5.0 star property
    9.0/10 - Wonderful (29 reviews)
    "A beautiful hotel. Staff were very friendly and helpful"
    Reviewed July 25, 2026
    Roundtrip Toronto (YYZ) - Florence (FLR)
    YYZ - FCO1 stop FCO - YYZ1 stop
    CA $2,798
    CA $2,025
    per traveller
    found 1 day ago
    Columbus Urban Resort
  • Aug 31 - Sept 6

    Hotel La Scaletta Al Ponte Vecchio + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    "i don't like the hotel has a small bathroom . everything is close to restaurants and stuff"
    Reviewed July 26, 2026
    Roundtrip Montreal (YMQ) - Florence (FLR)
    YUL - FLR1 stop FLR - YUL1 stop
    CA $3,298
    CA $2,277
    per traveller
    found 1 day ago
    Hotel La Scaletta Al Ponte Vecchio
  • Sept 14 - Sept 20

    L'Andana + Flight

    Castiglione della Pescaia
    5 nights
    5.0 star property
    9.4/10 - Exceptional (91 reviews)
    "Breathtaking views of the Tuscan countryside, as well as incredibly attentive staff."
    Reviewed June 9, 2026
    Roundtrip Toronto (YYZ) - Florence (FLR)
    YYZ - FCO1 stop FCO - YYZ1 stop
    CA $3,699
    CA $2,569
    per traveller
    found 1 day ago
    L'Andana
  • Aug 30 - Sept 5

    Plaza Hotel Lucchesi + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    9.4/10 - Exceptional (1,010 reviews)
    Roundtrip Montreal (YMQ) - Florence (FLR)
    YUL - FLR1 stop FLR - YUL1 stop
    CA $2,852
    CA $2,036
    per traveller
    found 1 day ago
    Plaza Hotel Lucchesi
  • Sept 14 - Sept 20

    Dimora Palanca Boutique & SPA + Flight

    Historic Centre of Florence
    5 nights
    5.0 star property
    9.2/10 - Wonderful (68 reviews)
    "Lovely hotel, very friendly staff and great location just outside hustle and bustle of Florence."
    Reviewed April 21, 2026
    Roundtrip Toronto (YYZ) - Florence (FLR)
    YYZ - FCO1 stop FCO - YYZ1 stop
    CA $3,626
    CA $2,630
    per traveller
    found 1 day ago
    Dimora Palanca Boutique & SPA

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 Duomo and San Gimignano Communal Palace.

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 $2,025 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.