Bossi Vacations from $1,107

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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 $1,621, price is now $1,107 per person
$1,107
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
We were able to check-in early. It is walkable from Santa Maria Novella train station and so are the points of interest. When we arrived, the electric metal blinds was not working. Letitia gave us a sheet to temporarily give us privacy. When we came back from our tour the next day, it was already fixed. Great place to stay. Worth the money we paid for. Santa Maria Novella Basilica is close by. Worth visiting. Well recommended.

Reviewed on Oct 19, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $2,144, price is now $1,438 per person
$1,438
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (485 reviews)
the hotel is located a little far from historic area of the town. but if you are a go walking person, it is 15 minutes walk. the hotel itself is very good. fresh and nice design, very nice buffet breakfast and kind stuff.

Reviewed on Oct 21, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,742, price is now $1,186 per person
$1,186
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,015 reviews)
Great location, friendly staff, clean. Basic but good basic.

Reviewed on Oct 27, 2025

Collegio alla Querce, Auberge Collection

Collegio alla Querce, Auberge Collection

5 out of 5
Le Cure
Price was $3,065, price is now $2,109 per person
$2,109
per person
Nov 27 - Nov 30
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
10/10 Exceptional! (3 reviews)
Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $2,416, price is now $1,708 per person
$1,708
per person
Jan 6 - Jan 11
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (465 reviews)
The hotel is very beautiful, and the surrounding environment is also excellent.

Reviewed on Sep 26, 2025

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Discover the most popular places to visit in Bossi

Siena Circuit

You can take time to visit Siena Circuit during your travels to Castelnuovo Berardenga. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Siena Circuit

Terra di Seta

You can enjoy a tasting or tour at Terra di Seta during your travels to Castelnuovo Berardenga. Discover the beautiful countryside and wineries in this walkable area.

Terra di Seta

Felsina

You can enjoy a tasting or tour at Felsina during your travels to Castelnuovo Berardenga. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Felsina

What to do in Bossi

Medieval Centre

Skip the Line: Siena Duomo and City Walking Tour

$47
per adult
100% of travellers recommend
Skip the Line: Siena Duomo and City Walking Tour
Monteriggioni fortress

Tuscany Hiking Tour from Siena Including Wine Tasting

$64
per adult
Tuscany Hiking Tour from Siena Including Wine Tasting
Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

$57
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
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
$84 nightly
The price is $96 total per night from Nov 26 to Nov 27
$96 total
Nov 26 - Nov 27
Total with taxes and fees
9.2/10 Wonderful! (1,008 reviews)
Excellent hotel with great service.

Reviewed on Oct 19, 2025

Hotel Athena
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Via Spaltenna 13, Gaiole in Chianti, SI
9.4/10 Exceptional! (259 reviews)
All good

Reviewed on Oct 20, 2025

Get rates
Castello di Spaltenna- Small Luxury Hotels of the World
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $106 total per night from Nov 10 to Nov 11
$106 total
Nov 10 - Nov 11
Total with taxes and fees
9.2/10 Wonderful! (733 reviews)
Beautiful quaint hotel. Beautiful view from the garden. Walkable to all of the sites and restaurants, at the top of the hill- but everything is on a hill. Nice breakfast. Very relaxing place to stay. Staff was very accommodating.

Reviewed on Oct 23, 2025

Palazzo Ravizza
See all 5,565 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 $1,107 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.