Poggibonsi Vacations from $957
Book a Hotel + Flight or Car together to unlock savings
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.
The Moon Boutique Hotel & Spa
Historic Centre of Florence
$957
per person
Nov 30 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
Great location. We suggest taking the river down to the city center every day. The free breakfast and coffee is great way to start your day. Schedule a spa day at least once so you can relax before the walk to dinner! Reception was super nice and even helped us call a taxi.
Reviewed on Sep 21, 2026
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
$996
per person
Nov 30 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9/10 Wonderful! (1,005 reviews)
I would say this is a 3.5 star property. The room was clean but basic, same for the bathroom and amenities like soap etc. the location is very central but the room was still quiet. There is no concierge and the staff was not able to make any reservations for us.
Reviewed on Sep 19, 2026
Aurum Uffizi
Historic Centre of Florence
$1,189
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,001 reviews)
Clean, good location, free breakfast was good. Room was basic with no storage. Shower was small, dark and had no curtain or door, WiFi rarely worked.
Reviewed on Sep 21, 2026
Il Rivalta - Place of Charme
Historic Centre of Florence
$1,090
per person
Nov 30 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (605 reviews)
Il Rivata was above and beyond my expectations. It was an incredible value in a wonderful location
Reviewed on Sep 21, 2026
Stay near popular Poggibonsi attractions
Archeodromo di Poggibonsi
7.4/10 (3 reviews)
Step back in time at this full-scale reconstruction of a 9th-century Carolingian village. Watch costumed interpreters demonstrate medieval crafts and daily life in an authentic historical setting.
Church of San Lorenzo
9.0/10 (9 reviews)
This modest Romanesque church houses a remarkable 15th-century fresco by Pier Francesco Fiorentino. Combine your visit with a walk along the ancient Via Francigena pilgrimage route.
The Rock of Staggia
7.6/10 (5 reviews)
This medieval stronghold once guarded the strategic Via Francigena trade route between Florence and Siena. Explore its cylindrical towers and double walls on a guided tour through Tuscan history.
Magione Castle
8.0/10 (5 reviews)
This medieval complex once served as a hospital for pilgrims on the Via Francigena route. Explore its Romanesque church and discover the fascinating legacy of the Knights Templar through guided tours.
Poggio Imperiale Fortress
7.6/10 (4 reviews)
This Renaissance military fortress, designed by Giuliano da Sangallo, offers panoramic views across Chianti and Val d'Elsa. Explore the archaeological park with its reconstructed Frankish village.
Fountain of Fate
7.0/10 (8 reviews)
This 13th-century travertine fountain showcases medieval engineering with six double arches and pilasters. Explore its serene archaeological park setting, enhanced by Mimmo Paladino's contemporary art installations.
San Lucchese Convent
8.6/10 (4 reviews)
This 13th-century Franciscan Gothic convent honors Saint Lucchese with remarkable medieval frescoes and serene architecture. Explore the tranquil cloister while enjoying views of the Tuscan countryside.
What to do in Poggibonsi
Siena, San Gimignano, Monteriggioni & Chianti from Florence
$61
per adult
88% of travellers recommend
From Siena: Chianti and Castles Tour with Wine Tastings
$99
per adult
88% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
$185
per adult
86% of travellers recommend
Poggibonsi Hotel Deals
Hotel Toscana Ambassador
Via Salceto, 11 Poggibonsi SI
$66 nightly
$80 total
Oct 11 - Oct 12
Total with taxes and fees
8/10 Very Good! (365 reviews)
"The rooms are good and spacious. The staff too is helpful but there are a few things which is expected from a hotel. 1. A kettle is needed in the room at all times. 2. Iron board and iron is needed in the room 3. Drinking water should be provided everyday. It was only provided once during check in. ..."
Reviewed on Sep 19, 2026
Hotel Ristorante Alcide
Viale Marconi, 67/A Poggibonsi SI
8/10 Very Good! (487 reviews)
"Nice staff! Great breakfast buffet!"
Reviewed on Jul 23, 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.
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 |
More vacations you might like
Frequently asked questions
How much does a Poggibonsi vacation package cost?
You can snap up a vacation package to this top destination from $957 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?
- Choose your travel dates: The things you want to do in Poggibonsi and your preferred season will help you decide when to travel.
- 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.
- 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.
- 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.
- Combine your accommodations and airfare: After you've settled on your travel dates and duration, book the perfect Poggibonsi vacation package for you.
- 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.
Explore a world of travel with Expedia
- Privatevacationhomes in San Gimignano
- Hotels in Poggibonsi
- 5 Star Hotels in Monsanto
- Hotels in San Gimignano
- 4 Star Hotels in Poggibonsi
- Apartments in Colle di Val d'Elsa
- Four Seasons Hotels in Sciano
- Agritourism in Poggibonsi
- Spa in Poggibonsi
- Hotels in Colle di Val d'Elsa
- Bedandbreakfast in Poggibonsi
- Relais & Chateaux Hotels in Chianti Region
- Hotels in Castellina in Chianti
- Winery in Poggibonsi
- Certaldo Alto Hotels
- Hotels in Tavarnelle Val di Pesa
- Colle di Val d'Elsa Vacations
- Visit Castel San Gimignano
- Where to stay in Chianti Region
- Visit Val d'Elsa
- Empolese Val d'Elsa All Inclusive Vacation Packages
- Sentierelsa Trail
- Visit San Donato in Poggio
- Where to stay in Val d'Elsa
- Certaldo Vacations
- Chianti Region All Inclusive Vacation Packages
- San Gimignano Vacations
- Medieval Criminal
- Visit Panzano in Chianti
- Chianti Region All Inclusive Vacation Packages
- Visit Poggibonsi
- Val d'Elsa All Inclusive Vacation Packages
- Greve in Chianti Vacations
- Chianti Region All Inclusive Vacation Packages
- Visit Monteriggioni
- Chianti Region All Inclusive Vacation Packages
- Visit Vico d'Elsa
- Where to stay in Empolese Val d'Elsa
- Chianti Region All Inclusive Vacation Packages
- Visit Certaldo
- Where to stay in Siena
- Monteriggioni Vacations
- Visit Tavarnelle Val di Pesa
- Val d'Elsa All Inclusive Vacation Packages
- Val d'Elsa All Inclusive Vacation Packages
- Fountain of Fate
- Chianti Region All Inclusive Vacation Packages
- Chianti Region All Inclusive Vacation Packages
- Visit Castellina Scalo
- Tenuta Torciano Winery
- Visit Colle di Val d'Elsa
- Visit Castellina in Chianti
- Castello di Monsanto
- Castellina in Chianti Vacations
- Visit San Gimignano
- Chianti Region All Inclusive Vacation Packages
- Where to stay in Volterra
- Siena Vacations
- Monsanto Vacations
- Avis Rental Cars in Poggibonsi
- Mini Car Rentals in Colle di Val d'Elsa
- Car rentals in Poggibonsi
- Car rentals in San Gimignano
- Car rentals in Colle di Val d'Elsa
- Car rentals in Barberino Tavarnelle
- Pickup Car Rentals in Colle di Val d'Elsa
- Car rentals in San Filippo
- Car rentals in Monsanto
- Enterprise Rental Cars in Poggibonsi
- Things to do in Poggibonsi
- Things to do in Castelfiorentino
- Things to do in Barberino Val d'Elsa
- Things to do in Greve in Chianti
- Things to do in Tavarnelle Val di Pesa
- Things to do in Certaldo
- Things to do in Montefioralle
- Things to do in Colle di Val d'Elsa
- Things to do in Barberino Tavarnelle
- Things to do in Castellina in Chianti
- Things to do in Panzano in Chianti
- Things to do in San Gimignano
- Things to do in Ulignano
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.