Gaiole in Chianti Vacations from $907
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Your Gaiole in Chianti Vacation
When a city getaway is calling, answer it with a Gaiole in Chianti vacation package. The neighborhood of Badia Coltibuono, which is great for families, nature and walking, makes an excellent base for your adventures. Any trip to Gaiole in Chianti needs a well-crafted itinerary. Fill yours with famous sights like Castle of Brolio, Meleto Castle and Castello di Albola. Whoever you're going away with and whether your budget is big or small, your dream Gaiole in Chianti vacation is only clicks away with Expedia.
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
$1,129
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (600 reviews)
Extremely clean, breakfast service was awesome. Absolutely beautiful room . Shower with steam and jacuzzi settings was wonderful.
Reviewed on Oct 2, 2026
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
$1,087
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9/10 Wonderful! (1,004 reviews)
Hotel La Scaletta exceeded our expectations! Everything about the property - location, amenities, breakfast, room, and helpful staff - was excellent. I had stayed in the hotel (and loved it) decades before but it has ascended from a pensione to a true hotel. I hope to return one day!
Reviewed on Oct 2, 2026
Donati Luxury Tower Suites
Historic Centre of Florence
$1,805
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (77 reviews)
Excellent lodging option very close to the Duomo and central to Florence. It is a terrific location in that it is close to everything but secluded off a very small road that only gets traffic for people checking in or leaving the property. The lodging is in a very old tower that has been converted to about 10 rooms. The front desk is excellent and surprised us when we checked in by telling us they would deliver an assortment of pastries to our room every day for breakfast. We had the Gemma suite which was not large but well laid out with a very comfortable bed and furniture and a very nice bathroom.
Reviewed on Oct 4, 2026
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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.
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.
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.
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
Siena, San Gimignano, Monteriggioni & Chianti from Florence
$75
per adult
88% of travellers recommend
From Siena: Chianti and Castles Tour with Wine Tastings
$98
per adult
90% of travellers recommend
Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting
$54
per adult
88% of travellers recommend
Gaiole in Chianti Hotel Deals
Castello di Spaltenna- Small Luxury Hotels of the World
Via Spaltenna 13 Gaiole in Chianti SI
$332 nightly
$376 total
Oct 30 - Oct 31
Total with taxes and fees
9.6/10 Exceptional! (291 reviews)
"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."
Reviewed on Oct 2, 2026
Castello di Tornano Wine Resort
Loc. Tornano Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
$142 nightly
$165 total
Oct 26 - Oct 27
Total with taxes and fees
9.2/10 Wonderful! (128 reviews)
"This was a magical place!!! Has a working farm mentality but all the nice touches of an upscale place. Modern bathrooms, updated AC, a pool that was wonderful to relax in after touring some local wineries. Gorgeous terrace area, a bar and some wonderful wines, delicious buffet breakfast, and superb ..."
Reviewed on Oct 3, 2026
Radisson Blu Hotel, Florence
Via Giovanni Agnelli 33 Florence FI
Fully refundableReserve now, pay when you stay
$107 nightly
$134 total
Nov 1 - Nov 2
Total with taxes and fees
8.8/10 Excellent! (170 reviews)
"Great hotel and knowledgeable staff. We had a front desk person, which is from the Philippines and recommended great restaurant and helped us on our extended stay."
Reviewed on Oct 2, 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 Gaiole in Chianti Vacation Packages
Gaiole in Chianti Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Closest Airport | Peretola Airport (FLR) |
Population | 1,100 |
Max Temp Winter | 50ºF |
Max Temp Summer | 85ºF |
Top Sights | Siena Cathedral, Monteriggioni Castle and Castle of Brolio |
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Frequently asked questions
How much does a Gaiole in Chianti vacation package cost?
You'll find cheap prices from $907 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?
August, October and November are great times to look for cheap Gaiole in Chianti vacation packages. Choosing to travel in less busy months means you can usually find lower prices on hotels and flights.
How many days is enough for Gaiole in Chianti?
Gaiole in Chianti vacations come in many shapes and sizes, but to get a true feel for this destination, we think 3 days is a good ballpark. This will mean you can fit in top sights like Badia a Coltibuono and Cantalici Winery and track down some lesser-known spots. Don't miss out on neighborhoods such as Badia Coltibuono and Lecchi in Chianti either. If you plan wisely, you can even schedule a day trip or two from Gaiole in Chianti too.
Is it worth booking a vacation package to Gaiole in Chianti?
Popular for its bars and pubs, views and walking trails, a Gaiole in Chianti vacation has something for everyone. Be sure to check out key sights like Meleto Castle and Church of San Sigismondo, and consider renting a set of wheels for day trips to discover even more.
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?
- Choose your dates: The things you want to do in Gaiole in Chianti and your favorite season can help you decide when to get away.
- Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to experiences and flights. Your accommodations will likely be the biggest expense during your trip to Gaiole in Chianti.
- Organize your Gaiole in Chianti escape with Expedia's trip planning tool: Look for and book accommodations and experiences all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Gaiole in Chianti together.
- Set the duration of your trip: Start by listing all the activities and sights you want to get to in Gaiole in Chianti. Then, estimate how long you'll need for each, including any travel time.
- Bundle your accommodations and airfare: After you've nailed down your travel dates and duration, book the right Gaiole in Chianti vacation package for you.
- Book any activities or day trips: Now to the fun part — locking in everything you want to do and see. Check out some of the exciting things to do in Gaiole in Chianti and book your tickets in advance to save time (and maybe some dollars too!).
Does Expedia offer Book Now, Pay Later Gaiole in Chianti vacation packages?
Your Gaiole in Chianti trip is meant to be a relaxing escape from your busy life, not a source of money worries. So to allow you extra flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no 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.