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.
Eurostars Florence Boutique

Eurostars Florence Boutique

Historic Centre of Florence
€476
per person
27 Nov - 1 Dec
found 4 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.6/10 Excellent! (503 reviews)
Eurostar fell short of the brand. I stayed at the Eurostar Barcelona an outstanding hotel. This Eurostar hotel should be demolished!

Reviewed on 30 Sept 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence
Save 100% on your flight
€572
per person
27 Nov - 1 Dec
found 5 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9/10 Wonderful! (1,004 reviews)
Excellent location, beautiful, clean and comfortable rooms - excellent staff and the rooftop has stunning views. Highly recommended.

Reviewed on 26 Sept 2026

Bernini Palace

Bernini Palace

Historic Centre of Florence
Save 100% on your flight
€767
per person
27 Nov - 1 Dec
found 4 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.8/10 Exceptional! (1,006 reviews)
Palazzo Montebello

Palazzo Montebello

Historic Centre of Florence
€525
per person
27 Nov - 1 Dec
found 4 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
.

Reviewed on 30 Sept 2026

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

Oltrarno
€545
per person
27 Nov - 1 Dec
found 4 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.8/10 Excellent! (436 reviews)
Our stay was beautiful. We went in September so it was nice weather. Good was a bit expensive for dinner but we realized we could order something by the pool up to 6:30 and then it was about 8-10 euro cheaper than the sit down restaurant. Pool is beautiful but very cold. I like it cold but my friends not so much

Reviewed on 30 Sept 2026

Top hotels in Gaiole in Chianti

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
€334
30 Oct - 31 Oct
includes taxes & fees
9.6/10 Exceptional! (290 reviews)
"From the moment we checked in, This place was a Gem. From the friendly and helpful staff to the beautiful grounds, we were so impressed. Its hard to put into words how wonderful this Hotel is. The food, and drinks were incredible. We also celebrated my wife's birthday at this resort and they did ..."

Reviewed on 1 Oct 2026

Castello di Spaltenna- Small Luxury Hotels of the World
Castello di Tornano Wine Resort

Castello di Tornano Wine Resort

Loc. Tornano Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
€147
29 Oct - 30 Oct
includes taxes & fees
9.2/10 Wonderful! (127 reviews)
"This is a special place. A welcome tranquil rest that is renewing. The grounds are large and lovely. You can find everything you need plus! It offers the winery, the restaurant and lounge options, comfortable rooms, a helpful staff, swimming and more."

Reviewed on 29 Sept 2026

Castello di Tornano Wine Resort
Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

Via Giovanni Agnelli 33 Florence FI
Fully refundableReserve now, pay when you stay
€119
1 Nov - 2 Nov
includes taxes & fees
8.6/10 Excellent! (168 reviews)
"Everything was great, staff were helpful. A couple comments I do have are: One of the staff let themselves into our room in the morning while I was still sleeping then saw me and said “sorry” and turned around and walked out. Weird. Also the room had a lot of thick cob webs and didn’t seem that they ..."

Reviewed on 29 Sept 2026

Radisson Blu Hotel, Florence
See all 8,598 properties in Gaiole in Chianti
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.
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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.
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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.
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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.
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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.
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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.
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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.
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Church of San Sigismondo

This 1930s stone church houses a remarkable 1699 marble altar featuring the Madonna del Rosario. Visit in morning light to appreciate its medieval-inspired artworks and tranquil atmosphere.
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What to do in Gaiole in Chianti

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

€79
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting

€47
per adult
90% of travellers recommend
Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

€65
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
See all activities in Gaiole in Chianti

Frequently asked questions

How much does a Gaiole in Chianti holiday package cost?
You'll find cheap prices from €476 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?
  1. 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.
  2. 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.
  3. 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.
  4. 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.