Gaiole in Chianti Vacation Packages

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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.

Top Gaiole in Chianti Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
per person
Sep 27 - Sep 30
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on Jun. 6, 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 21 - Sep 27
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Great location and lovely breakfast.

Reviewed on Jul. 9, 2025

The St. Regis Florence

The St. Regis Florence

5 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Aug 18 - Aug 24
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (259 reviews)
Nice property in a great location.

Reviewed on Jun. 29, 2025

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 17 - Sep 23
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (464 reviews)
Breakfast was very good and the staff were excellent. Expresso in the morning was on point.

Reviewed on Jul. 5, 2025

Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 17 - Sep 23
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (42 reviews)
The staff went out of their way to be helpful with all queries

Reviewed on Jun. 21, 2025

Ready to book your vacation to Gaiole in Chianti?

 

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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
Fully refundableReserve now, pay when you stay
The price is CA $537 per night from Aug 12 to Aug 13
CA $537
CA $607 total
Aug 12 - Aug 13
includes taxes & fees
9.4/10 Exceptional! (232 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
The price is CA $279 per night from Aug 8 to Aug 9
CA $279
CA $320 total
Aug 8 - Aug 9
includes taxes & 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
The price is CA $173 per night from Jul 17 to Jul 18
CA $173
CA $203 total
Jul 17 - Jul 18
includes taxes & 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.

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Discover the most popular places to visit in Gaiole in Chianti

Medieval Tower of Barbischio

Find out about the history of Gaiole in Chianti when you take a trip to Medieval Tower of Barbischio. Discover the beautiful countryside in this walkable area, or enjoy its local tours.

Medieval Tower of Barbischio

Church of San Sigismondo

You can find out about the history of Gaiole in Chianti with a stop at Church of San Sigismondo. Discover the beautiful countryside and charming coffeehouses in this quaint area.

Church of San Sigismondo

What to do in Gaiole in Chianti

Wine tasting in the historic Cantalici winery

Wine tasting in the historical Cantalici winery

CA $24
per adult
100% of travellers recommend
Wine tasting in the historical Cantalici winery
Tour of the cellar and tasting of 6 wines

Tour of the cellar and tasting of 6 wines

CA $48
per adult
Tour of the cellar and tasting of 6 wines
Large cutting board, 6 wine tasting and Guided tour

Large cutting board, 6 wine tasting and Guided tour

CA $96
per adult
Large cutting board, 6 wine tasting and Guided tour
See all activities in Gaiole in Chianti

Frequently asked questions

How much does a Gaiole in Chianti vacation package cost?
You can grab a vacation package to this popular destination from CA $1,529 on Expedia. But how much your vacation to Gaiole in Chianti costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Gaiole in Chianti?
The off-season is the best time to head to Gaiole in Chianti if you're on a budget. Another tip for scoring cheap Gaiole in Chianti vacation packages? Avoid visiting during public holidays and any major festivals.
How many days is enough for Gaiole in Chianti?
Gaiole in Chianti vacations can be short or long, but to really get a feel for this destination, we think 3 days is about right. In this timeframe, you can fit in headline attractions like Badia a Coltibuono and Castello di Radda Winery as well as hidden gems. Don't miss out on cool neighbourhoods such as Badia Coltibuono and Vertine either. If you're clever with your time, you may even be able to take a day trip or two from Gaiole in Chianti too.
Is it worth booking a vacation package to Gaiole in Chianti?
Well known for its walking trails, cycling and bars and pubs, a Gaiole in Chianti vacation is a hit with all kinds of visitors. Be sure to visit key sights like Meleto Castle and Badia a Coltibuono, and consider renting some 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 preferred travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Gaiole in Chianti package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Gaiole in Chianti escape underway.
Is it cheaper to book a Gaiole in Chianti vacation as a package?
You can enjoy significant savings on your Gaiole in Chianti getaway by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Gaiole in Chianti?
If you're considering a spontaneous Gaiole in Chianti trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Gaiole in Chianti?

  1. Pick your travel dates: The things you want to do in Gaiole in Chianti and your favourite season can help you decide when to go.
  2. Budget wisely: As well as the price of your hotel, you'll need to consider other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that may come up during your trip to Gaiole in Chianti.
  3. Decide your trip length: Think about how long you want to spend discovering Gaiole in Chianti. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a personalized Gaiole in Chianti vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.