Sassofortino Vacation Packages

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Your Sassofortino Vacation

Experience the unique personality of Sassofortino with a customized Sassofortino vacation package. From its medieval heritage to its spectacular views, you'll never have a boring moment in this city. A trip to Sassofortino is a terrific opportunity to sightsee. Be sure to stop by renowned attractions like Podere Ristella Vineyards and Winery, I Canaloni del Torrente Farma and Church of San Nicola. Whatever your travel plans or budget, putting together the ultimate tailored Sassofortino vacation is simple with Expedia.

Top Sassofortino Vacation Deals

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

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,260, price is now CA $1,471 per person
CA $1,471
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
7.4/10 Good! (1,014 reviews)
Room was clean, breakfast was decent. In general, it was a good stay. Would likely consider staying again.

Reviewed on Jun 30, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was CA $7,058, price is now CA $4,536 per person
CA $4,536
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (147 reviews)
It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)

Reviewed on Jun 19, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $2,303, price is now CA $1,486 per person
CA $1,486
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
Highly recommended

Reviewed on Jun 30, 2026

Hotel San Luca

Hotel San Luca

4 out of 5
Cortona Old Town
Price was CA $2,056, price is now CA $1,501 per person
CA $1,501
per person
Sep 15 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (429 reviews)
Wonderful hotel with great view for Tuscany, good breakfast, perfect location to visit Cortona

Reviewed on Jun 30, 2026

Lilium Hotel

Lilium Hotel

3 out of 5
Historic Centre of Florence
Price was CA $3,096, price is now CA $2,291 per person
CA $2,291
per person
Sep 5 - Sep 11
found 1 hour ago
Roundtrip non-stop flight included
Calgary (YYC) to Florence (FLR)
9/10 Wonderful! (25 reviews)
Decent hotel, convenient and clean, some hot items on breakfast buffet. Not a 5 star hotel but very good

Reviewed on Jun 15, 2026

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Sassofortino Hotel Deals

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
The price is CA $3,263 per night from Jul 27 to Jul 28
CA $3,263
CA $3,605 total
Jul 27 - Jul 28
includes taxes & fees
Castiglion del Bosco, A Rosewood Hotel
SI Montalcino Hotel

SI Montalcino Hotel

3 out of 5
Via Osticcio 21 Montalcino SI
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Jul 14 to Jul 15
CA $148
CA $176 total
Jul 14 - Jul 15
includes taxes & fees
SI Montalcino Hotel
Hotel La Pineta

Hotel La Pineta

3 out of 5
Via Delle Collacchie, 67 Follonica GR
The price is CA $232 per night from Jul 16 to Jul 17
CA $232
CA $261 total
Jul 16 - Jul 17
includes taxes & fees
9/10 Wonderful! (311 reviews)
"Great hotel, excellent breakfast. Good location. The only problem was the Wi-Fi. didn't work and they don't have enough parking for the hotel."

Reviewed on Jun 29, 2026

Hotel La Pineta
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What to do in Sassofortino

La Maliosa Farm Experience & Wine Tasting

La Maliosa Summer Farm Experience & Wine Tasting

CA $72
per adult
100% of travellers recommend
La Maliosa Summer Farm Experience & Wine Tasting
Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal

Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal

CA $177
per adult
Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal
Welcome to Casale del Bosco

Welcome to Casale del Bosco

CA $56
per adult
Welcome to Casale del Bosco
See all activities in Sassofortino

Frequently asked questions

How much does a Sassofortino vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,471 on Expedia. But how much your vacation to Sassofortino costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Sassofortino?
To pick up cheap Sassofortino vacation packages, organize your getaway outside of peak times like public holidays and major events. You'll generally find lower prices and better availability in the off-season or when it's less busy.
How many days is enough for Sassofortino?
Typically, a handful of days is enough to go to the main attractions during your Sassofortino vacation. However, if you'd like to have some time to kick back or take day trips, consider extending your trip.
How to find the best Sassofortino package deals?
Bagging a cheap Sassofortino package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Sassofortino package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Sassofortino vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Sassofortino vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Sassofortino?
Enjoy amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Sassofortino getaway.
How to plan a trip to Sassofortino?

  1. Choose when to get away: Check your diary and pack your bags. Your favourite time of year and the type of activities available will also help you decide when to vacation in Sassofortino.
  2. Work out your budget: Ensure 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 Sassofortino.
  3. Decide how long to go away for: Now that you know more about Sassofortino, you can work out the right length of your break. Create a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose a Sassofortino vacation package that brings all your bookings together.

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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.