Calzaiolo Holidays from £413
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Your Calzaiolo Holiday
Book a Calzaiolo holiday package and get ready to experience everything this city has to offer. Consider staying in the neighbourhood of Lastra a Signa, which is good for walking, nature and bars and pubs. If your trip to Calzaiolo includes a little sightseeing, don't miss famous attractions like Antinori nel Chianti Classico, Monastary of Sorelle Clarisse and Torre Del Chianti. Browse Expedia's wide range of travel options and begin planning your ultimate holiday to Calzaiolo now.
Top Calzaiolo Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Certosa Di Maggiano
£413
per person
13 Dec - 18 Dec
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
10/10 Exceptional! (217 reviews)
Our stay for our honeymoon was amazing. We loved our room and we were upgraded to a suite because they had it available. All the staff were kind and helpful. They carried our luggage up two flights of stairs to our room, helped make reservations, called taxis for us, etc.
The property was beautiful, maintained nicely, and was very quiet.
Really have no complaints. To note it is outside of city Centre of Siena so you will need taxis back and forth to the city for meals etc. which can get quite pricey so just plan ahead. Our room could’ve been cleaned a little better in between each day but overall it was still very clean. We would definitely stay there again!!
Reviewed on 28 Sept 2026
Hotel Casale la Sterpaia Pisa
£487
per person
23 Dec - 30 Dec
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
7.8/10 Good! (74 reviews)
It's a beautiful place in national park very close to Pisa, easy to cycle to see tower . From
Your window you can see a large stable (previously used for the king's horses)
Little magic place
Reviewed on 25 Aug 2025
Monastero di Cortona Hotel & Spa
Cortona Old Town
£514
per person
13 Dec - 18 Dec
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
10/10 Exceptional! (337 reviews)
From the moment we arrived at Monastero di Cortona, everything was wonderful. We were welcomed with a cold, delicious drink and invited to sit and relax while the staff took care of everything else for us. Anna then gave us a lovely tour of the hotel, which was such a nice way to begin our stay. When we walked into our room, there was a beautiful welcome table waiting for us with waters, chocolates, and even a lovely necklace charm, which was such a thoughtful touch. The room smelled absolutely amazing, and the view was stunning. Even the shower felt like a spa experience, with chromotherapy lighting and water that left our skin feeling incredibly soft. The complimentary breakfast was amazing, beautifully presented, and the staff was so attentive and made sure we had everything we needed. We also spent time at the spa and absolutely loved it. The Turkish bath, sauna, and massaging pool were all incredibly relaxing, and we also had massages that were absolutely amazing. Even as we were leaving, the thoughtfulness continued—the housekeeping staff left us a departing gift, which was such a sweet and unexpected touch and made us feel special right up until the end. From the beautiful surroundings to all the thoughtful little details and wonderful service, our stay felt luxurious, peaceful, and very special. We truly felt taken care of from the moment we arrived until the moment we left.
Reviewed on 5 Oct 2026
Castello di Velona Resort Thermal SPA & Winery
£872
per person
13 Dec - 18 Dec
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9/10 Wonderful! (377 reviews)
Amazing views. Relaxing stay! A very romantic hotel, though I was surprised by the number of families there; given its location and amenities, I had assumed it was geared towards couples. That isn't a negative comment, though—it was simply a case of my own mistaken perception.
Reviewed on 27 Sept 2026
Calzaiolo Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Closest Airport | Peretola Airport (FLR) |
Max Temp Winter | 10ºC |
Max Temp Summer | 29ºC |
Top Sights | Cantina Antinori, San Casciano Museum and Monastary of Sorelle Clarisse |
Top hotels in Calzaiolo
Plus Florence - Hostel
Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
£76
1 Nov - 2 Nov
includes taxes & fees
The Social Hub Florence Belfiore
Viale Belfiore, 55 Florence FI
Fully refundableReserve now, pay when you stay
£77
1 Nov - 2 Nov
includes taxes & fees
9.4/10 Exceptional! (770 reviews)
"A little walk from the city center, but an amazing space with lots of amenities, clean rooms and tons of great vibes"
Reviewed on 5 Oct 2026
Hotel Paris
Via Banchi 2 Florence FI
£130
4 Nov - 5 Nov
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"It was a nice comfortable room for our last night in Florence"
Reviewed on 4 Oct 2026
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.
What to do in Calzaiolo
Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine
£15
per adult
94% of travellers recommend
Florence: Pasta Cooking Class with Unlimited Wine
£15
per adult
94% of travellers recommend
Accademia timed-entry Ticket with App Guide
£33
per adult
90% of travellers recommend
Frequently asked questions
How much does a Calzaiolo travel package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Calzaiolo from just £413. And the more you bundle, the more money you save. Your dream holiday has never been more affordable.
If I'm not able to travel, can I cancel my Calzaiolo travel package?
Your situation can change without warning, so yes, you can. You may be able to cancel and rebook your Calzaiolo travel package for free if you've booked in the last 24 hours. For bookings older than that, you can still make changes, but your airline, hotel or car rental company may charge a fee. Want more information? Take a look at our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Calzaiolo?
Our Calzaiolo travel packages promise plenty of savings for the savvy traveller. For the best deals, simply bundle your flights, hotels and extras (including activities) into a neat and tidy package. But bargain prices are only the start of your next awesome adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 hotel options throughout the world to pick from. No matter your style, there's a travel package that's perfect for you.
Does Expedia offer Book Now, Pay Later Calzaiolo holidays?
Yes. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in instalments. Simply pick the payment plan that suits best during the checkout process and take away the stress of budgeting for your trip. Don't forget to bundle your accommodation, car hire and flights with Expedia to get the biggest bang for your travel buck. Take a look at our flexible payment options below:
- Pay monthly holidays: If paying bite-sized amounts each month works for you, Klarna can help. Paying in convenient monthly instalments will make that dream getaway possible.
- Pay in instalments holidays: If you want to pay for your escape across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: Hitting the "book now" button is much easier with this option. Put down a small deposit on your booking and then start working on your travel plans.
Where should I stay in Calzaiolo?
With interesting attractions like Cantina Antinori and Monastary of Sorelle Clarisse in this neighbourhood, look for a hotel positioned near either one. Torre Del Chianti is another sight that draws the crowds.
What are the top hotels in Calzaiolo?
Book a stay at Villa I Barronci Resort & Spa. It's one of this area's most in-demand properties. Another great option in Calzaiolo is Villa Il Fedino.
How far in advance should I book my Calzaiolo holiday?
Savvy travellers often book early. You can usually compare international airfares on Expedia up to 12 months before your flight. If you've left things to the last minute, don't stress. Low prices occasionally appear in the last weeks before departure.
What does an Expedia Calzaiolo travel package include?
Flights, hotels and a cool car for all your fun road trip adventures. Simply mix and match your preferred bundle and get access to incredible deals. Once you've made your booking, add on some activities and tours and watch your savings grow. When it comes to organising your Calzaiolo getaway, the choice is all yours!
What should I know before booking a Calzaiolo travel package?
Whether it's relaxation or adventure you're seeking, a Calzaiolo travel package lets you organise your escape your way. Plus, you'll score great discounts when you combine your accommodation with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Calzaiolo Expedia travel package?
Expedia has access to more than 550 airline partners globally, so you sure can! Simply select the carrier that suits you and put together the perfect Calzaiolo trip.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
