Bossi Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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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.
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
CA $1,960
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9/10 Wonderful! (1,006 reviews)
Excellent location, quiet and nice view of the hillside. Comfortable bed. Plenty of towels for heatwave and many showers.
Reviewed on Aug 21, 2026
Grand Hotel Cavour
Historic Centre of Florence
CA $1,570
per person
Nov 2 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
Staff were very welcoming and helpful from check in to departure. We had the basic room which was very nice indeed, a decent size and nicely furnished. Rooftop bar reasonable value for a cocktail surrounded by the sights of Florence. Very central location. Aircon very good and controllable. Highly recommended.
Reviewed on Aug 19, 2026
Ready to book your vacation to Bossi?
Bossi Hotel Deals
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
CA $242
CA $274 total
Aug 27 - Aug 28
includes taxes & fees
9.2/10 Wonderful! (1,010 reviews)
"The hotel was close downtown Siena and parking was on site. The continental breakfast was delicious. The room was clean and bed was comfortable. The AC keep shutting off in the night, made it uncomfortable for sleep."
Reviewed on Aug 18, 2026
Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
CA $556
CA $628 total
Aug 23 - Aug 24
includes taxes & fees
9.2/10 Wonderful! (624 reviews)
"Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back"
Reviewed on Aug 18, 2026
Borgo Scopeto Wine & Country Relais
Strada Comunale 14 Siena - Vagliagli 18 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
CA $707
CA $793 total
Aug 26 - Aug 27
includes taxes & fees
9.4/10 Exceptional! (219 reviews)
"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming ..."
Reviewed on Aug 5, 2026
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.
What to do in Bossi
Chianti Half Day Wine Tour from Florence
CA $39
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
CA $84
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
CA $114
per adult
88% of travellers recommend
Frequently asked questions
How much does a Bossi vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,310 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?
- 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.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
