Poggibonsi Vacations from $548

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Your Poggibonsi Vacation

When you book a vacation package to Poggibonsi, you can relax and enjoy your break knowing your travel plans have been made in advance. Uncover the wonders of this city from your base in a neighborhood like Mensanello, which is great for history. If your trip to Poggibonsi includes some sightseeing, don't miss well-known attractions like Collegiate Church of Santa Maria Assunta, Tenuta Torciano Winery and Piazza Duomo. Don't delay your visit to this city any longer. Your dream Poggibonsi vacation is only a few clicks away with Expedia.

The Latest Poggibonsi vacation packages

Price found within the past 48 hours. Click for updated prices.
Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $694, price is now $548 per person
$548
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.6/10 Excellent! (474 reviews)
Great little hotel. Everything is within walking distance. The view from the terrace was amazing.

Reviewed on Aug 6, 2025

Maxim Axial

Maxim Axial

3 out of 5
Historic Centre of Florence
Price was $1,253, price is now $1,021 per person
$1,021
per person
Jan 6 - Jan 12
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
8.4/10 Very Good! (1,009 reviews)
Great location, great staff would highly recommend!

Reviewed on Nov 4, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,477, price is now $1,016 per person
$1,016
per person
Jan 1 - Jan 6
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.8/10 Good! (1,015 reviews)
Location was amazing for dinning options. Easy access to bus routes. And walkable to many sites. Have to mention the cleanliness of the rooms and shared areas

Reviewed on Nov 5, 2025

25hours Hotel Florence Piazza San Paolino

25hours Hotel Florence Piazza San Paolino

4 out of 5
Historic Centre of Florence
Price was $759, price is now $602 per person
$602
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (895 reviews)
Room spacoous, lights not very convinient

Reviewed on Nov 3, 2025

Bernini Palace

Bernini Palace

5 out of 5
Historic Centre of Florence
Price was $979, price is now $778 per person
$778
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (1,009 reviews)
Great staff. Friendly and helpful.

Reviewed on Nov 5, 2025

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Discover the most popular places to visit in Poggibonsi

Archeodromo di Poggibonsi

You can study the exhibits at Archeodromo di Poggibonsi, a museum with a story of its own, during your travels to Poggibonsi. Discover the beautiful countryside in this quaint area, or enjoy its local tours.

Archeodromo di Poggibonsi

San Lucchese Convent

You can learn about the history of Poggibonsi with a stop at San Lucchese Convent. Discover the beautiful countryside and wineries in this quaint area.

San Lucchese Convent

Poggio Imperiale Fortress

Learn about the local history of Poggibonsi when you take a trip to Poggio Imperiale Fortress. Discover the beautiful countryside and wineries in this relaxing area.

Poggio Imperiale Fortress

What to do in Poggibonsi

Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

$139
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group 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 Poggibonsi

Poggibonsi Hotel Deals

Hotel Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A, Poggibonsi, SI
Fully refundableReserve now, pay when you stay
$50 nightly
The price is $55 total per night from Nov 23 to Nov 24
$55 total
Nov 23 - Nov 24
Total with taxes and fees
8/10 Very Good! (459 reviews)
I highly recommended

Reviewed on Oct 14, 2025

Hotel Ristorante Alcide
Hotel Toscana Ambassador

Hotel Toscana Ambassador

4 out of 5
Via Salceto, 11, Poggibonsi, SI
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $69 total per night from Nov 8 to Nov 9
$69 total
Nov 8 - Nov 9
Total with taxes and fees
8/10 Very Good! (297 reviews)
Excellent emplacement pour explorer la région. Facile de se trouver un stationnement gratuit en face de l'hôtel. Chambre propre, mais relativement sans charme, plutôt impersonnelle côté déco, mais tout ce dont on a besoin y est toutefois, donc je recommande si vous cherchez qqchose d'efficace, abordable ...

Reviewed on Oct 21, 2025

Hotel Toscana Ambassador
Hotel Villa San Giorgio

Hotel Villa San Giorgio

3 out of 5
Località Cinciano, 5, Poggibonsi, SI
Fully refundableReserve now, pay when you stay
$56 nightly
The price is $62 total per night from Nov 23 to Nov 24
$62 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (104 reviews)
Loved the breakfast amazing !!! Such a beautiful place woujd love to go in summer and lay by the pool

Reviewed on Oct 21, 2025

Hotel Villa San Giorgio
See all 716 properties in Poggibonsi
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 Poggibonsi Vacation Packages

Poggibonsi Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Peretola Airport (FLR)
Population
21,700
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Tenuta Torciano Winery, Monteriggioni Castle and Castello di Radda Winery

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Frequently asked questions

How much does a Poggibonsi vacation package cost?
You can snap up a vacation package to this top destination from $548 on Expedia. However, how much your vacation to Poggibonsi costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Poggibonsi?
February, November and December are great times to search for cheap Poggibonsi vacation packages. Choosing to travel in quieter periods means you'll typically find lower prices on flights and hotels.
How many days is enough for Poggibonsi?
With around 3 days, you'll have plenty of time to experience popular neighborhoods such as San Gimignano City Centre and Casone during your Poggibonsi vacation. Make sure to also add Church of San Lorenzo and Poggio Imperiale Fortress to your must-see list. In the mood for more adventures? Consider exploring outside of Poggibonsi on day trips and tours.
Is it worth booking a vacation package to Poggibonsi?
Well known for its views, family-friendly attractions and history, a Poggibonsi vacation has something for everyone. Be sure to check out key sights like Church of San Lorenzo and Poggio Imperiale Fortress, and consider renting some wheels for day trips to experience even more.
How to find the best Poggibonsi package deals?
Start your search for a Poggibonsi package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Poggibonsi package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Poggibonsi adventure underway.
Is it cheaper to book a Poggibonsi vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still have the freedom to create a tailored Poggibonsi vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Poggibonsi?
If you've got your Poggibonsi travel dates locked in, book as soon as you can to score some awesome deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Poggibonsi?

  1. Choose your travel dates: The things you want to do in Poggibonsi and your preferred season will help you decide when to travel.
  2. Calculate your budget: Ensure you have enough money to pay for everything from dining out and transportation to flights and activities. Your hotel will likely be the biggest expense during your trip to Poggibonsi.
  3. Use Expedia's trip planning tool to discover Poggibonsi: Research every aspect of your trip to Poggibonsi with this handy planner. Invite family or friends to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how long to go away for: Now that you're up to speed on Poggibonsi, you can work out the ideal length of your vacation. Put together a draft plan and give yourself enough time to get through everything on your must-do list.
  5. Combine your accommodations and airfare: After you've settled on your travel dates and duration, book the perfect Poggibonsi vacation package for you.
  6. Book any excursions or activities: Now to the fun part — organizing everything you want to see and do. Browse some of the incredible things to do in Poggibonsi and book your tickets in advance to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Poggibonsi vacation packages?
Your Poggibonsi getaway should be an escape from your busy life, not a source of money-related stress. So to give you a bit more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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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.