Bossi Vacation Packages

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Your Bossi Vacation

Say farewell to planning worries and hello to a Bossi vacation package. With your travel details organized before you take off, you can focus on discovering this city, starting with Badia Coltibuono, which is good for families, nature and walking. You'll want to do some exploring during your trip to Bossi. Don't miss big-name attractions such as Siena Circuit, Chianti Sculpture Park and Piazza Marconi. Whoever you're going away with and whatever your budget, your ultimate Bossi vacation is only clicks away with Expedia.

Top Bossi Vacation Deals

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

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $2,629, price is now CA $1,589 per person
CA $1,589
per person
Aug 17 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Clean, conveniently located hotel with friendly, helpful staff.

Reviewed on Jul 5, 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,642, price is now CA $1,637 per person
CA $1,637
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
It was not entirely clean, the staff don't do much. Breakfast is from the day before. Air conditioning excellent.

Reviewed on Jul 3, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was CA $3,315, price is now CA $2,234 per person
CA $2,234
per person
Sep 19 - Sep 22
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) 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

Residenza Florentia

Residenza Florentia

1 out of 5
Historic Centre of Florence
Price was CA $2,733, price is now CA $1,875 per person
CA $1,875
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.4/10 Very good! (53 reviews)
Staff was helpful, the property was not very well maintained.

Reviewed on Jun 1, 2026

Grand Hotel Torre Fara

Grand Hotel Torre Fara

4 out of 5
Price was CA $3,190, price is now CA $2,241 per person
CA $2,241
per person
Sep 7 - Sep 12
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Pisa (PSA)
9.6/10 Exceptional! (174 reviews)
Wonderful hotel, great location and fantastic staff

Reviewed on Jun 15, 2026

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Bossi Hotel Deals

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Strada Comunale 14 Siena - Vagliagli 18 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
The price is CA $695 per night from Jul 12 to Jul 13
CA $695
CA $780 total
Jul 12 - Jul 13
includes taxes & fees
9.4/10 Exceptional! (209 reviews)
"This hotel is the definition of La Dolce Vita! Starting from the beginning, when first arrived to the hotel, they picked up our bags, showed us around the property and responded any questions that we had. Elisa was amazing! She showed us around the property, he gave us recommendations of where to ..."

Reviewed on Jul 1, 2026

Borgo Scopeto Wine & Country Relais
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Aug 2 to Aug 3
CA $233
CA $264 total
Aug 2 - Aug 3
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"El hotel está bien localizado. La propiedad está en buenas condiciones y el personal es muy atento. La comunicación del personal conmigo fue muy buena. Me hicieron buenas recomendaciones de restaurantes y se esmeraron en hacerme pasar unos hermosos dias. Lo recomiendo 100%."

Reviewed on Jul 5, 2026

Hotel Athena
Hotel Executive

Hotel Executive

4 out of 5
Via Nazareno Orlandi 32 Siena SI
Fully refundableReserve now, pay when you stay
The price is CA $107 per night from Jul 26 to Jul 27
CA $107
CA $126 total
Jul 26 - Jul 27
includes taxes & fees
8.4/10 Very good! (542 reviews)
"Nice clean hotel. Breakfast ok. Good parking"

Reviewed on Jul 6, 2026

Hotel Executive
See all 5,647 properties in Bossi
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.
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What to do in Bossi

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

CA $128
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

CA $36
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

CA $105
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
See all activities in Bossi

Frequently asked questions

How much does a Bossi vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,589 on Expedia. However, how much your vacation to Bossi costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Bossi?
To pick up cheap Bossi vacation packages, organize your trip outside of busy periods such as public holidays. You'll generally find better availability and lower prices when it's less busy.
How many days is enough for Bossi?
You can visit all the major sights in Bossi in a few days, including the must-see Villa a Sesta Polo Club. If you're looking for an extended Bossi vacation, check out what sort of activities and day tours are available close by.
How to find the best Bossi package deals?
Use Expedia's filter tool to find some unbeatable Bossi package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Bossi package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Bossi vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights separately. Better still, you can customize your Bossi getaway to fit your exact needs. Pick 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 Bossi?
If you have your Bossi vacation dates confirmed, book as soon as you can to score some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Bossi?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Bossi.
  2. Figure out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and airfares. Your accommodations will probably be the largest expense during your trip to Bossi.
  3. Set the duration of your trip: Start by compiling a list of the attractions and activities you'd like to get to in Bossi. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Bossi vacation package that brings all your bookings together.

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.