Gaiole in Chianti Holidays
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Top Flight + Hotel Deals in Gaiole in Chianti
Price found within the past 48 hours. Click for updated prices.
Aurum Firenze
Historic Centre of Florence
€606
per person
23 Oct - 28 Oct
found 1 day ago
Return direct flight included
Athens (ATH) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
Room very small, no chairs inside, ants everywhere, including the breakfast area.
Quadruple room has a double bed and a single bed, apparently this was the biggest room in the hotel. We book for 4 people ( 2 adults and 2 children 12 and 16 and they had to squeeze in a single bed.
Reviewed on 12 Aug 2026
Top hotels in Gaiole in Chianti
Castello di Spaltenna- Small Luxury Hotels of the World
Via Spaltenna 13 Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
€361
6 Sept - 7 Sept
includes taxes & fees
9.6/10 Exceptional! (281 reviews)
"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"
Reviewed on 4 Aug 2026
Castello di Tornano Wine Resort
Loc. Tornano Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
€221
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (121 reviews)
"We really like this place. Pool was very nice and staff were mostly helpful. Its a pretty good location to visit multiple areas as well. Room air conditioner did an ok job upstairs in bedroom loft but struggled to keep it cool in the sitting area on main level. The view from the tower is awesome ..."
Reviewed on 13 Aug 2026
Ultimo Mulino Wellness Country Hotel
Localita La Ripresa di Vistareni Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
€157
9 Sept - 10 Sept
includes taxes & fees
8.8/10 Excellent! (162 reviews)
"Ac. Not working well Streets to get there not paved. Pitch black at night Staff at resto very rude!!"
Reviewed on 7 Aug 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.
Stay near popular Gaiole in Chianti attractions
Castle of Brolio
9.2/10 (44 reviews)
This ancestral seat of the Ricasoli family since 1141 stands as Italy's oldest winery, pivotal in Chianti Classico's development. Stroll through formal gardens before sampling estate wines in historic cellars.
Meleto Castle
8.6/10 (10 reviews)
This 11th-century Tuscan fortress houses an unexpected 18th-century theatre among its medieval walls. Tour the historic wine cellars and conclude with a tasting of the estate's renowned Chianti Classico wines.
Badia a Coltibuono
9.6/10 (12 reviews)
This 11th-century abbey turned winery showcases Tuscan history through frescoed rooms and gardens. Sample organic Chianti Classico wines and savour traditional cuisine made with estate-grown ingredients.
Cantalici Winery
10.0/10 (1 review)
This 16th-century Tuscan estate crafts organic Chianti Classico using traditional methods. Tour the historic cellars before savouring wine and olive oil tastings with the Cantalici brothers.
Gaiole in Chianti Stadium
This local sports venue serves as the athletic heart of Gaiole in Chianti. Visitors can catch regional football matches while experiencing authentic Italian community spirit.
Medieval Tower of Barbischio
8.0/10 (1 review)
This medieval watchtower once guarded Chianti's rolling hills as part of Florence's defensive network. Explore the ancient walls and savour panoramic countryside views from its strategic hilltop position.
Castello di Meleto Cantina
This 11th-century castle invites you to explore noble rooms, ancient cellars, and an 18th-century theatre. Conclude your visit with a guided tasting of their renowned Chianti Classico wines in the atmospheric enoteca.
PoggioBrandani
This Tuscan winery showcases Chianti's rich heritage through exceptional wines and olive oils. Enjoy a guided tasting paired with local delicacies after touring the winemaking museum.
What to do in Gaiole in Chianti
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
€79
per adult
88% of travellers recommend
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
€18
per adult
Siena, San Gimignano, Monteriggioni & Chianti from Florence
€52
per adult
88% of travellers recommend
Frequently asked questions
How much does a Gaiole in Chianti holiday package cost?
You'll find cheap prices from €436 on Expedia for your Gaiole in Chianti break. However, factors like the season, choice of hotel and length of stay will influence how much your holiday to Gaiole in Chianti costs.
What are the cheapest months to go to Gaiole in Chianti?
The off-season is the best time to head to Gaiole in Chianti if you're hoping to keep costs down. Another tip for getting cheap Gaiole in Chianti holiday packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Gaiole in Chianti?
With about 3 days, you'll have plenty of time to visit popular neighbourhoods such as Badia Coltibuono and Vertine during your Gaiole in Chianti holiday. Be sure to also add PoggioBrandani and Castle of Brolio to your must-do list. Up for some more adventures? Consider venturing outside of Gaiole in Chianti on day trips and tours.
Is it worth booking a holiday package to Gaiole in Chianti?
Gaiole in Chianti has everything you need for an amazing getaway — walking trails, cycling and bars and pubs are just the start. Whether you want to check out attractions such as Meleto Castle and Badia a Coltibuono, or take the path less traveled, you'll find plenty to experience on your Gaiole in Chianti holiday.
How to find the best Gaiole in Chianti package deals?
Start your search for a Gaiole in Chianti package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Gaiole in Chianti package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Gaiole in Chianti escape off to a flying start.
Is it cheaper to book a Gaiole in Chianti holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging accommodation and flights separately. Better still, you can customise your Gaiole in Chianti trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Gaiole in Chianti?
If you're considering an impromptu Gaiole in Chianti adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Gaiole in Chianti?
- Pick your travel dates: The things you want to do in Gaiole in Chianti and your favourite season can help you decide when to get away.
- Budget wisely: Besides the price of your stay, you'll need to consider other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected costs that may arise during your trip to Gaiole in Chianti.
- Decide how long to go away for: Now that you're up to speed on Gaiole in Chianti, you can figure out the right length of your holiday. Put together a draft plan and allocate enough time for all the things you want to do.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose a Gaiole in Chianti holiday package that brings all your bookings together.
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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.
