Gaiole in Chianti Vacations from $845

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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 Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 15 - Oct 20
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,007 reviews)
Air conditioner was excellent!!!

Reviewed on Aug 11, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 15 - Oct 21
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Great location and very clean

Reviewed on Aug 12, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 15 - Oct 21
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (230 reviews)
I VERY MUCH ENJOYED THE STAY

Reviewed on Jul 18, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 15 - Oct 21
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
The hotel is located a 25 min walk away from the heart of Florence so very easy to access the main attractions within the city. The hotel itself is immaculate and the staff are extremely helpful with dealing with any questions you may have. Being able to access the spa everyday for 1 and 30 minutes is an excellent perk as the facilities are well worth a visit, you are also able to book massages for an extra fee. The breakfast also gives a variety of options to start each day and the room itself is spacious, with the shower particularly being very comfortable.

Reviewed on Aug 13, 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
Save 100% on your flight
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
10/10 Exceptional! (1 review)
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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

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

Badia a Coltibuono

You can enjoy a tasting or tour at Badia a Coltibuono during your travels to Badia Coltibuono. Discover the beautiful countryside in this relaxing area, or enjoy its local tours.

Badia a Coltibuono

What to do in Gaiole in Chianti

Brolio Castle

Small-Group Chianti Trip with Wine Tasting from Siena

$211
per adult
Small-Group Chianti Trip with Wine Tasting from Siena
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

Siena & San Gimignano Day Trip from Florence with Chianti Views

$89
per adult
88% of travellers recommend
Siena & San Gimignano Day Trip from Florence with Chianti Views
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
$430 nightly
The price is $485 total per night from Aug 25 to Aug 26
$485 total
Aug 25 - Aug 26
Total includes taxes and fees
9.4/10 Exceptional! (243 reviews)
"Beautiful hotal located in such a paradise location amazing view very good food. The staff was very nice. The service was amazing. I definitely recommend the place. It’s a beautiful relaxing, gorgeous."

Reviewed on Aug 13, 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
$253 nightly
The price is $288 total per night from Aug 24 to Aug 25
$288 total
Aug 24 - Aug 25
Total includes taxes and fees
9/10 Wonderful! (88 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
Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel

4 out of 5
Localita La Ripresa di Vistareni, Gaiole in Chianti, SI
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $191 total per night from Aug 28 to Aug 29
$191 total
Aug 28 - Aug 29
Total includes taxes and fees
8.6/10 Excellent! (130 reviews)
"Such a classic Tuscany location. Beautiful old Watermill turned into a hotel so it is very rustic. Cell phone service on the area is not good but WiFi seemed fine. Pools were nice but not too big and not a lot of space to accommodate all guests. Enjoyed the breakfast. Staff were helpful."

Reviewed on Jul 30, 2025

Ultimo Mulino Wellness Country Hotel
See all 8,791 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.

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Frequently asked questions

How much does a Gaiole in Chianti vacation package cost?
You'll find cheap prices from $845 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.