Gaiole in Chianti Vacations from $643

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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.
Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was $882, price is now $643 per person
$643
per person
Jan 18 - Jan 23
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (931 reviews)
Amazing property & the staff is incredible.Love this place.

Reviewed on Oct 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
Price was $1,213, price is now $779 per person
$779
per person
Jan 18 - Jan 23
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (485 reviews)
My husband Felix and I had the pleasure of celebrating both our wedding anniversary and my birthday at The Moon Boutique Hotel in Florence, and we couldn’t have asked for a more perfect experience. From the moment we arrived, the warmth and professionalism of the staff made us feel truly welcomed. A special mention goes to the tall gentleman with glasses from Calabria—his courteous demeanor and exceptional customer service stood out throughout our stay. He went above and beyond to ensure we were comfortable and well-informed, adding a personal touch that made our visit even more special. The housekeeping team deserves equal praise. Their attention to detail was remarkable, and our room was consistently immaculate, creating a serene and luxurious atmosphere that enhanced our celebration. The Moon Boutique Hotel is more than just a place to stay—it’s a haven of elegance, comfort, and genuine hospitality. We left with beautiful memories and deep appreciation for the team that made our milestone moments unforgettable.

Reviewed on Nov 12, 2025

Collegio alla Querce, Auberge Collection

Collegio alla Querce, Auberge Collection

5 out of 5
Le Cure
Save 100% on your flight
Price was $3,675, price is now $2,534 per person
$2,534
per person
Jan 14 - Jan 20
found 21 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Florence (FLR)
10/10 Exceptional! (3 reviews)
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $924, price is now $644 per person
$644
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,015 reviews)
This hotel is all about location… close to everything about 10-15 mins by walking. The entrance of the hotel is a bit scary at night time on my personal view. The room is big and clean. Don’t expect much on breakfast … it’s enough for you to start the day.

Reviewed on Nov 11, 2025

The Excelsior, a Luxury Collection Hotel, Florence

The Excelsior, a Luxury Collection Hotel, Florence

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,394, price is now $1,731 per person
$1,731
per person
Jan 14 - Jan 20
found 21 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Florence (FLR)
9.4/10 Exceptional! (352 reviews)
We had a nice 5 night stay. The hotel and staff are all wonderful. Only slight i

Reviewed on Oct 25, 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 wineries in this walkable area.

Castle of Brolio

Badia a Coltibuono

5/5(4 reviews)

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

Monteriggioni fortress

Tuscany Hiking Tour from Siena Including Wine Tasting

$64
per adult
Tuscany Hiking Tour from Siena Including Wine Tasting
Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

$57
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$76
per adult
86% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
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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
9.4/10 Exceptional! (260 reviews)
All good

Reviewed on Oct 20, 2025

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Castello di Spaltenna- Small Luxury Hotels of the World
Hu Firenze Camping In Town

Hu Firenze Camping In Town

Via Generale Dalla Chiesa, 1-3, Florence, FI
Fully refundableReserve now, pay when you stay
$49 nightly
The price is $62 total per night from Nov 23 to Nov 24
$62 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (1,591 reviews)
Room and set up was good. I think the rooms need one more desk for luggage and organizing things.

Reviewed on Nov 11, 2025

Hu Firenze Camping In Town
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $93 total per night from Dec 10 to Dec 11
$93 total
Dec 10 - Dec 11
Total with taxes and fees
9.2/10 Wonderful! (999 reviews)
All clean. Great room. Good breakfast. Nice bar.

Reviewed on Nov 6, 2025

Hotel Athena
See all 8,493 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 $643 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.