Gaiole in Chianti Vacations from $989

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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.
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,001 reviews)
Convenient location, walkable, and pleasant staff. Only downside was the wifi was not working the whole 4 nights we were there. We used up all of our data and didnt have any left for the rest of our trip.

Reviewed on Jul 14, 2025

Villa Olmi Firenze

Villa Olmi Firenze

4 out of 5
Save 100% on your flight
per person
Oct 1 - Oct 6
just found
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (723 reviews)
Beautiful property & amazing staff

Reviewed on Jul 8, 2025

Glance Hotel In Florence

Glance Hotel In Florence

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 1 - Oct 6
just found
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (1,003 reviews)
Great location and super friendly staff

Reviewed on Jul 11, 2025

Tenuta di Artimino Member of Meliá Collection

Tenuta di Artimino Member of Meliá Collection

4 out of 5
per person
Sep 8 - Sep 11
just found
Roundtrip non-stop flight included
Los Angeles (LAX) to Florence (FLR)
9.4/10 Exceptional! (116 reviews)
Rural area, quiet and quaint

Reviewed on Jul 10, 2025

Via Roma 33 Tuscany Boutique Hotel & Spa - Adults Only

Via Roma 33 Tuscany Boutique Hotel & Spa - Adults Only

4 out of 5
per person
Sep 8 - Sep 11
just found
Roundtrip non-stop flight included
Los Angeles (LAX) to Florence (FLR)
9.8/10 Exceptional! (26 reviews)
Overall a lovely stay. The staff is very welcoming and accommodating. Rooms are very clean. Pool too cold to swim in even though they said that it was heated. Wirlpool/hot-tub was on the cool side too. Couldn’t get sauna to work properly -however, I should have asked. Restaurant food was very good.

Reviewed on May 12, 2025

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Discover the most popular places to visit in Gaiole in Chianti

Castello di Meleto, Gaiole in Chianti, Tuscany

Meleto Castle

Find out about the history of Gaiole in Chianti when you spend time at Meleto Castle. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Meleto Castle

Castle of Brolio

5/5(21 reviews)

You can find out about the history of Gaiole in Chianti with a stop at Castle of Brolio. Discover the beautiful countryside and charming coffeehouses in this walkable area.

Castle of Brolio

Cantalici Winery

You can enjoy a tasting or tour at Cantalici Winery during your travels to Gaiole in Chianti. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Cantalici Winery

What to do in Gaiole in Chianti

Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

$58
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

$89
per adult
88% of travellers recommend
From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting
Chianti Colours and Flavours from Florence

Chianti Wineries Tour with 7 Wine Tastings from Florence

$100
per adult
Chianti Wineries Tour with 7 Wine Tastings from Florence
See all activities in Gaiole in Chianti

Gaiole in Chianti Hotel Deals

Castello di Spaltenna- Small Luxury Hotels of the World
Castello di Spaltenna- Small Luxury Hotels of the World
5 out of 5
Via Spaltenna 13, Gaiole in Chianti, SI
Fully refundableReserve now, pay when you stay
$392 nightly
The price is $443 total per night from Aug 12 to Aug 13
$443 total
Aug 12 - Aug 13
Total includes taxes and fees
9.4/10 Exceptional! (233 reviews)
"We stayed here as a family of six, including our two 3-year-olds, and it was by far our favorite place during our time in Italy! The kids absolutely loved swimming in the pools and running around the beautiful property. It felt peaceful, safe, and perfect. The breakfast was lovely each morning—fresh, ..."

Reviewed on Jun 28, 2025

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
$204 nightly
The price is $234 total per night from Aug 8 to Aug 9
$234 total
Aug 8 - Aug 9
Total includes taxes and fees
8.8/10 Excellent! (87 reviews)
"Beautiful property in a stunning location! Would have been nice to have some sort of gathering area indoors as we were multiple pe"

Reviewed on May 29, 2025

Castello di Tornano Wine Resort
Hotel Le Pozze Di Lecchi
Hotel Le Pozze Di Lecchi
4 out of 5
Loc. Molinaccio, Gaiole in Chianti, SI
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $148 total per night from Jul 19 to Jul 20
$148 total
Jul 19 - Jul 20
Total includes taxes and fees
9.2/10 Wonderful! (56 reviews)
"This is a beautiful hotel! Everything was perfect except the pillows. They are hard as rocks and flat. Other than that very small flaw our stay was perfection and authentically Italian."

Reviewed on Jun 11, 2025

Hotel Le Pozze Di Lecchi
See all 8,771 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.

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 $989 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.