Gaiole in Chianti Vacations from $1,398

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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.
Alfieri9

Alfieri9

3 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,153, price is now $1,398 per person
$1,398
per person
Oct 6 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (170 reviews)
More quiet residential area of Firenze in walking distance of center but away from the crowds. No elevator and two flight of stairs.

Reviewed on Jul 5, 2026

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was $2,093, price is now $1,488 per person
$1,488
per person
Oct 19 - Oct 24
found 3 hours ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (1,000 reviews)
Location Location Location

Reviewed on Aug 2, 2026

L'Andana

L'Andana

5 out of 5
Save 100% on your flight
Price was $3,505, price is now $2,385 per person
$2,385
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (91 reviews)
Breathtaking views of the Tuscan countryside, as well as incredibly attentive staff.

Reviewed on Jun 9, 2026

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Price was $2,035, price is now $1,422 per person
$1,422
per person
Oct 6 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (422 reviews)
Wonderful property, amazing hosts. 20 minutes outside of Florence center-easy to get a taxi. My family loved everything about our stay here!

Reviewed on Jul 7, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was $4,137, price is now $2,903 per person
$2,903
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (154 reviews)
The place it’s an Amazing. Very clean. Is more beautiful than the pictures.

Reviewed on Aug 2, 2026

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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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What to do in Gaiole in Chianti

Siena: Cathedral Complex Pass with Audio Guide

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

$21
per adult
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$59
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Florence Day Trip: Medieval Villages & Cooking Class

Florence Day Trip: Medieval Villages & Cooking Class

$158
per adult
86% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
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
$396 nightly
The price is $447 total per night from Aug 4 to Aug 5
$447 total
Aug 4 - Aug 5
Total with taxes and fees
9.6/10 Exceptional! (280 reviews)
"A truly remarkable place. The staff made the stay even better. I highly recommend this hotel if you’re looking for a place in Chianti."

Reviewed on Aug 1, 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
$214 nightly
The price is $245 total per night from Aug 6 to Aug 7
$245 total
Aug 6 - Aug 7
Total with taxes and fees
9/10 Wonderful! (117 reviews)
"We had lizard in our room. Apart of that room was clean. Property has unpaved one way road so driving is not easy. Breakfast was delicious!"

Reviewed on Jul 22, 2026

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
$151 nightly
The price is $175 total per night from Sep 1 to Sep 2
$175 total
Sep 1 - Sep 2
Total with taxes and fees
8.8/10 Excellent! (161 reviews)
"Not only is it far out .. when you get there they are quite rude at the reception areas ..quite disappointing in the dining area as well, as we were told to shush our kids that were there watching to soccer finals.. they do not go out of the way to keep the customer happy .. we had noo working air, ..."

Reviewed on Jul 28, 2026

Ultimo Mulino Wellness Country Hotel
See all 8,652 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 $1,398 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.

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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.