Bossi Vacations from $965

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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.

The Latest Bossi vacation packages

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 $1,338, price is now $965 per person
$965
per person
Jan 20 - Jan 25
found 23 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
7.4/10 Good! (1,016 reviews)
Encantada de ubicación,limpieza , comida y servicio

Reviewed on Nov 5, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,471, price is now $1,012 per person
$1,012
per person
Jan 20 - Jan 25
found 23 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Perfect location

Reviewed on Nov 2, 2026

Portrait Firenze - Lungarno Collection

Portrait Firenze - Lungarno Collection

5 out of 5
Historic Centre of Florence
Price was $3,208, price is now $2,378 per person
$2,378
per person
Jan 20 - Jan 25
found 23 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (320 reviews)

Hotel L'Orologio Firenze

Hotel L'Orologio Firenze

4 out of 5
Historic Centre of Florence
Price was $1,804, price is now $1,378 per person
$1,378
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (1,000 reviews)
Staff was great room needs a bigger bed side table to accommodate a cpap

Reviewed on Oct 29, 2026

Hotel Berchielli

Hotel Berchielli

4 out of 5
Historic Centre of Florence
Price was $1,503, price is now $1,148 per person
$1,148
per person
Jan 20 - Jan 25
found 23 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (1,001 reviews)

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What to do in Bossi

Siena: Cathedral Complex Pass with Audio Guide

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

$22
per adult
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

$28
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Pasta-making class at a Cesarina's home with tasting - Siena

Pasta-making class at a Cesarina's home with tasting - Siena

$201
per adult
Pasta-making class at a Cesarina's home with tasting - Siena
See all activities in Bossi

Bossi Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $104 total per night from Nov 29 to Nov 30
$104 total
Nov 29 - Nov 30
Total with taxes and fees
9.2/10 Wonderful! (1,006 reviews)
"This is a lovely hotel. The front desk staff were very friendly and helpful. Breakfast and dinner were great as was the hospitality shown by the dining room staff. The room was comfortable and clean. The rooftop terrace is an amazing place to enjoy beautiful views and the sunset. I would highly recommend ..."

Reviewed on Nov 4, 2026

Hotel Athena
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

5 out of 5
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
$273 nightly
The price is $307 total per night from Dec 6 to Dec 7
$307 total
Dec 6 - Dec 7
Total with taxes and fees
Grand Hotel Continental Siena – Starhotels Collezione
Hotel Chiusarelli

Hotel Chiusarelli

3 out of 5
Viale Curtatone 15 Siena SI
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $92 total per night from Dec 1 to Dec 2
$92 total
Dec 1 - Dec 2
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Perfect in location, cleanliness,staff, amenities.... Wonderful 👍"

Reviewed on Oct 24, 2026

Hotel Chiusarelli
See all 5,537 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.

Find the Best Bossi Vacation Packages

Bossi Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Top Sights
Terra di Seta, San Felice Winery and Vittorio Alfieri Theater

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Frequently asked questions

How much does a Bossi vacation package cost?
You can pick up a vacation package to this popular destination from $965 on Expedia. But how much your vacation to Bossi costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Bossi?
If you're hoping to score a cheap Bossi vacation package, consider planning a trip in August, November and December. You'll generally find lower prices on hotels and flights during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Bossi?
The ideal duration for your Bossi vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to hit all the major attractions and discover some hidden treasures along the way.
How to find the best Bossi package deals?
Finding a cheap Bossi package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Bossi package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Bossi vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging accommodations and flights separately. Better still, you can personalize your Bossi getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Bossi?
If you've got your Bossi travel dates locked in, book as soon as you can to snap up some outstanding deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for quick escapes.
How to plan a trip to Bossi?

  1. Choose when to travel: Check your diary and get packing. Your preferred season and the activities on offer will also help you decide when to escape to Bossi.
  2. Budget wisely: As well as the price of your stay, you should consider other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Bossi.
  3. Discover Bossi using our trip planning tool: Gain insights into the top attractions and best properties for your trip to Bossi. You can also save your favorite locations, collaborate with your group and organize all your plans in one place.
  4. Set the duration of your trip: Start by making a list of all the activities and attractions you want to experience in Bossi. Then, estimate how long you'll need at each, as well as any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Bossi vacation package.
  6. Book activities and experiences ahead of time: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on Bossi's best offerings. Find all the exciting things to do in Bossi with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Bossi vacation packages?
If you're anything like us, you love going away but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Bossi vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.

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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.