Gaiole in Chianti Vacations from ￥326,508
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The Latest Gaiole in Chianti Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa
Historic Centre of Florence
￥343,231
per person
Dec 27 - Dec 30
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Florence (FLR)
9.6/10 Exceptional! (605 reviews)
Very clean room with cold ac . Well thought out bathroom . Nice size room for Europe . And for the ladies the lighting in the bathroom was excellent .
Reviewed on Oct 13, 2026
The Hoxton, Florence
Historic Centre of Florence
￥329,056
per person
Dec 27 - Dec 30
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Florence (FLR)
9.4/10 Exceptional! (358 reviews)
We stayed at the Hoxton before we headed out to Tuscany for our wedding weekend. The staff was very accommodating and helpful, and the property itself was beautiful with a great location, it was a little bit more on the outskirts of the city center, which we are used to staying in when we travel to Florence, but we liked how quiet and secluded it was and the design of the property was really well done. We enjoyed the coffee bar downstairs and the Photo Booth in the lobby and the outdoor courtyard/bar area was a great meeting point for us and friends who were getting into town for wedding festivities.
We would recommend staying at the Hoxton and look forward to future stays in other cities and hopefully Florence again.
Reviewed on Oct 13, 2026
Find the Best Gaiole in Chianti Vacation Packages
Gaiole in Chianti Hotel Deals
Castello di Spaltenna- Small Luxury Hotels of the World
Via Spaltenna 13 Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
￥52,023
￥58,991 total
Oct 30 - Oct 31
includes taxes & fees
9.6/10 Exceptional! (295 reviews)
"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."
Reviewed on Oct 11, 2026
Castello di Tornano Wine Resort
Loc. Tornano Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
￥24,063
￥27,887 total
Oct 25 - Oct 26
includes taxes & fees
Italiana Hotels Florence
Viale Europa 205 Florence FI
Fully refundableReserve now, pay when you stay
￥14,327
￥18,233 total
Nov 8 - Nov 9
includes taxes & fees
7.6/10 Good! (1,001 reviews)
"Was our second time there so it must be good for that alone."
Reviewed on Oct 15, 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 theater 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 savor 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 savoring 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.
Castello di Meleto Cantina
This 11th-century castle invites you to explore noble rooms, ancient cellars, and an 18th-century theater. Conclude your visit with a guided tasting of their renowned Chianti Classico wines in the atmospheric enoteca.
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 savor panoramic countryside views from its strategic hilltop position.
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.
What to do in Gaiole in Chianti
SMALL-GROUP Wine Safari: Tuscany Wine Tasting Tour from Florence
￥23,423
per adult
100% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
￥11,712
per adult
88% of travellers recommend
Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting
￥8,387
per adult
88% of travellers recommend
Frequently asked questions
How much does a Gaiole in Chianti vacation package cost?
You'll find cheap prices from ￥326,508 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 vacation 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 vacation 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 neighborhoods such as Badia Coltibuono and Vertine during your Gaiole in Chianti vacation. 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 vacation 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 vacation.
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 vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights separately. Better still, you can customize 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 vacation 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 favorite 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 vacation. 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 vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
