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Villas near San Gimignano - Tuscany

Villa Ostignano

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Max. occupancy 12 persons

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Rental options (Size of the party):
6 12 12
Weekly prices
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Overview

Description

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This beautifully freshly-restored 14th century 84 hectars farmhouse is set within minutes of the small village of Montaione that offers all the amenities such as bars, supermarkets, restaurants, shops. It is perfectly located to explore Tuscany and in particular two of its most beautiful hill towns: Certaldo, 13km/8 miles and San Gimignano, 21km/13 miles. Florence and Siena are both reached within an hour, and in between the two, directly to the east of Villa Ostignano, lie the villages and vineyards of the Chianti Classico wine-producing region.

Getting There

Airports nearby:

Airports: Florence, 50km/31 miles; Pisa, 65km/40 miles. 

By Car:

Motorway exits at "Empoli Ovest", about 30km/18 miles, including 400m/0.3 mile of private white access road approaching the property. Ample parking.

By Train:

Railway and bus station at Castelfiorentino, 7km/4 miles.

Prices & Live availability

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Rental options (Size of the party):
6 12 12
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Booked
Available

NB. are available for parties of different sizes and priced accordingly - select your option above. For smaller parties, the unoccupied rooms or guesthouses simply remain empty or are closed and you will always have exclusive use of the villa and pool.

Prices in € are guaranteed
  • Please note that you can only book in € (EURO)
  • No booking or credit card fees (excluding AMEX)
  • No surcharges for currency fluctuations
  • Any prices listed in Pounds Sterling and US dollars are indicative only
*Your choice of currency cannot be changed after the deposit has been paid.
Live availability & exclusivity
  • All villas listed are exclusive to TN&M
  • Live availability calendar for every villa
  • Experienced sales staff who know the villas personally
We are very, very good at helping our guests choose a property to match their criteria, and we are happy to discuss any aspect of the trip, be it detailed information about the villas and their locations or general tips about travel in Italy.
Price lists
Booking Conditions

What's included and not included in your rental charge

Your rental might include some Staff & Services. Our free Concierge can help add-on any extras you require:

Included

  • Weekly rent.
  • Services included (1).
  • Credit card service charges.
  • Hot and cold tap water.
  • Garden and swimming pool maintenance.
  • VAT
  • TN&M Concierge Service
  • 24/7 Emergency Service
  • A weekly cleaning and change of bed linen on Saturdays (2).
  • A weekly change of bath towels on Saturdays (2).
  • A weekly change of swimming towels on Saturdays (2).

Not included

  • Telephone (outgoing phone calls).
  • Flights and car rental.
  • Travel insurance.
  • Transfers to/from airports.
  • Extra services available on request.
  • Use of swimming pool out of season.
  • Tourist tax.
  • Central Heating

(1) Please note that, when included in the price, maid service does not include laundry service. If you require any laundry services please advise us prior to your arrival at the villa, payable locally in Euros.

Reviews

These are collected from the feedback forms we send to all our clients.

Wonderful accommodations with everything we could have ever wanted. Perfect concierge service,chef and maid service all in the most beautiful Tuscan setting!
12-Oct-2024
What a wonderful time we had at Villa Ostignano! We shared the villa with 2 couples who are lifelong friends and created some additional wonderful memories! The villa is fantastic and is situated in the perfect location. We look forward to our return! Gary & Leona
05-Oct-2024
We have had the most incredible stay at Villa Ostignano. Everything exceeded our expectations and the staff is so wonderful (even dealing with our terrible Italian). Letizia went above and beyond in preparation for, and during, our stay. We could not have picked a better villa for our wedding reception – our guests were all incredibly impressed with both the villa and the views. We had an absolutely perfect week here, including an exceptional dinner prepared by Anna Maria and her team. We are heartbroken to be leaving, and will surely miss our morning cappuccinos, but leave with such special memories of our week here. We hope to be back one day! Letizia + team, thank you for one of the best weeks of our lives. With much love + gratitude, Kelly + Anthony
21-Sep-2024
We have had an amazing week at Villa Ostignano as a group of family and friends. The house was fantastic, and the children and the adults loved the pool! Letizia looked after us so well, before and during our trip. Annamaria cooked us both a delicious buffet at arrival, and a lovely dinner on the terrace. We made lots of lovely memories together and would love to come back some day soon! The Jackson Family, the Mee Family, the Gardener Family
27-Jul-2024
Dear Villa Ostignano, thank you for a wonderful holiday in Tuscany. What a beautiful house, everything is super. We will return soon and we look forward to seeing you in Mexico. Aziz Checa Family
18-Jul-2024
Dear Villa Ostignano, this was the perfect slice of Italian heaven for a week in Italy. We enjoyed Maria’s incredible cooking, took in the beautiful views, and delighted in exploring the wonderful towns and surrounding areas. Our trip for our family – from 4 to 63 – was full of love and laughter. The Grads & Hoermans
22-Jun-2024
The McHale Family had the most glorious time in your beautiful Villa Ostignano – thank you Roberto for sharing this little slice of heaven with us for the past 2 weeks. It was a vacation of a lifetime and we will remember it always! Your Villa is beautiful beyond words and the scenery simply mesmerizing! What a magical time in Tuscany – thanks for the memories! Ciao Tuscany! XO The McHale Family
08-Jun-2024
We’ve all had the most wonderful week here at the Villa Ostignano. The Villa was even more perfect than we imagined from the photos online – we were blown away when we arrived! The views and setting are simply breathtaking too. There are 11 of us staying here, aged 14 months to 75, here to celebrate the 75th birthday of my Mum (Angela). Letizia couldn’t have been more helpful, from the moment we booked until our last day, nothing was too much trouble – she is fabulous! Anna Mria and her team prepared us the most delicious buffet for our arrival and returned later in the week creating the most amazing special dinner for us all. Everything was perfection. We are leaving with many wonderful memories to cherish of our beautiful holiday here.
25-May-2024
We are an extended family from Iceland staying in the villa for a week. We are 14 in total and each and everyone of us had a fantastic time. Everything about the Villa is just perfect. The owners made us feel very welcome from the first minute. We enjoyed days by the pool and evening in the glass building and in other cosy parts of the villa. Thank you all! Love from Finland
18-May-2024
We had such a beautiful time here. The views, the Villa and the food were perfection. We were here to celebrate our wedding. I can not think of a place more perfect than Villa Ostignano. Everything was so beautiful. The week would never have been as perfect as it was without Letizia! Thank you so much. AND SEE YOU SOON! All our love, David, James, Gabby, Emily, Toby, Marita, Jamie, Jenny, Harry & Alessandro XXX
04-May-2024
Words can’t describe how wonderful this place is + how special it now is to me, my family + my now husband. We got married in Certaldo Alto + had the most unbelievably beautiful reception back here at this most amazing villa. Letizia was nothing short of incredible + made our stay even more spectacular. She went above + beyond for us + I’m forever grateful to her. Anna Maria + her team also played a big hole in our week being as great as it was. The cooking class was such a great experience that we will all cherish forever. She + her team even came back to cook our wedding dinner, which was the best any of us have ever had! We are already planning our next trip! See you soon Villa Ostignano! Lisa Marie O’Connor-Postiglione
21-Oct-2023
The entire team at Tuscany Now & More, regardless of who responded to our emails - Sean, Enzo, Giorgia - was prompt, friendly and very helpful. The quality of our villa (from the architecture, furnishings, amenities and views), far exceeded our expectations, and arranging extra services (such as our pasta cooking class) was a breeze. The onsite manager was quick with recommendations for the local area, although the villa was so spectacular we had days we did not want to leave. Thank you for making my sister's 50th birthday with our friends and family so memorable and one of our best vacations ever. We cannot wait to come back and stay with you again.
14-Oct-2023
What a wonderful location for our family reunion. 11 adults and 4 children including our grandson who we met for the first time. Family traveled from UK, Australia and America and the house was perfect. 6 weeks of bliss. The house has everything we needed, and we totally enjoyed Anna Maria’s cooking at our chef nights. Lots of memories made by the pool, bbq nights and lots of games. Our first time in Tuscany – we would be back. Thank you to anyone who looked after us.
19-Aug-2023
The May Family – 10 of us! We have had a wonderful time in this stunning place. Incredible countryside in every direction. We used the train from Castelfiorentino to get to Pisa and Florence. We visited many stunning medieval hill towns – Certaldo, San Miniato, Monteriggioni, + more! The bakery in town is great + open early – lovely croissants + coffee. The pool was very well tended and a perfect location with the loudest noise being the cicadas. Thank you to all the lovely staff who looked after us so well. Kate, Chris, Toby, Morven, Huw, Honor – UK Will, Maeg, Henry + Vivi - US
05-Aug-2023
We all had such a wonderful time at the Villa! We woke up most mornings to make a cafe latte and sit at the outdoor table to take in all of the views. We spotted deer, rabbits, and a boar. At night we enjoyed sitting, playing games, watching tv, and enjoying each other's company. Ping pong by the pool was also a great hit amongst our family. We played 170 times! Someone beat that! The Villa is an absolute gem being that we were able to visit so many local towns including San Gimignano, Siena, Monterigeoni, Certaldo, Vertterro, Lucca, Piccoli, and Montaione. Italy is a treasure! Thank you Villa Ostigano for welcoming us. To many more adventures filled with love and laughs. Kelly's, Oate's, Tripaolo's + Diana and Mel's
22-Jul-2023
Kelly, Oates, Di Paolos Had a wonderful week at Villa! Great food, views, and good times. Hope we can do it again. - Wonderful home with great amenities, close to many small+ charming towns. Enjoyed everything. - One of the best experiences ever! Thank you! - The gelato in town is excellent but also head to San Gimignano to try. Beautiful Villa, location, and stand. Xoxo - Great experience for the first time in Tuscany. It was amazing and the views are beautiful. Would do it all over again. Thank you for the memories of a lifetime. Ryan + Melissa"
22-Jul-2023
We are a group of 10 (6 adults, 4 children) and stayed a week in mid-July in Villa Ostignano. It was just perfect! High quality, plenty of room(s), complete privacy, astonishing view of the mountains, and great service from Letizia and her team. Of course, the great weather made it possible to enjoy all the outdoor facilities. The pool and the benches and sofa’s around it are comfortable and safe. The garden all around the house gives plenty of playroom for the children and relaxing spots, also if you want a place and time for yourself. The bedrooms are stylish, Italian, equipped with ac and good beds and bathrooms. Every morning the maids came to make the beds and clean the rooms. Hotel like! We also hired a cook, Anna Maria, for 2 evenings. Especially with children to be preferred and at least of the same quality as an above-average restaurant. Value for money! The other evenings we used the very well equipped kitchen and one of the available bbq’s. Upon arrival, we received a very much appreciated welcome package. Sets the tone! All in all, a place very much to be recommended!
15-Jul-2023
Dear Villa Ostinano, We thoroughly enjoyed your beautiful villa, the beautiful countryside, and your beautiful country. Thank you to Letizia for your assistance with reservations, you were so helpful, Your Canadian friends"
27-May-2023
Thak you for a lovely time at Villa Ostignano. The property is beautiful. We loved relaxing outside and seeing the impressive views. The landscape is gorgeous! Our children really enjoyed the pool and our entire group was very impressed by the wonderful meals prepared by Anna Maria and company. Letizia was very kind and helpful. It was the trip of our dreams. Thank you! We will be back! The Mendini's New York
27-Aug-2022
The nine of us had a wonderful week here. The house was just the right size for all of us. Lovely to have our meals outside and to enjoy the wonderful views. Everyone enjoyed the pool and the ping pong table. We had a lovely meal for our 50th wedding anniversary celebration prepared by Anna Maria and we had fun preparing the appetizers and pizzas another night. The Fitzgeralds.
13-Aug-2022
We did return in 2022 and had another lovely family holiday. Still the best Villa yet. Rowlands family 2022.
30-Jul-2022
A wonderful week with three generations of McCormicks and partners. The rolling hills of Tuscany provided a terrific vista. The pool area was a delight and the kids enjoyed it as well. Thanks to all the staff for their efficiency and present attentiveness. The family meal was splendid and well presented. The McCormicks
25-Jun-2022
We absolutely loved our time here at Villa Ostignano. The 8 of us were so relaxed while we ate amazing food and watched the gorgeous views and sunsets. Thank you to Letizia for all of her assistance. We can't wait to return. Love from Illinois and Michigan, Zitellas and Falatos
18-Jun-2022
Had the most incredible week at Villa Ostignano! Everything was more incredible than imagined. From the Villa itself to all of the staff, to the incredible wedding, this was an experience my guests and I will remember forever. A big thank you to Letizia, the Villa manager who made sure we had everything we needed and helped me arrange various reservations for us. To Elisa and Celestina who cooked us amazing breakfast every morning and who were so kind and joyful, to Anna Maria, Valentina, and Federico who taught us how to make pizza and cooked the most incredible wedding feast, complete with 12 different appetizers! And thank you to Elisabetta my amazing wedding planner who was suggested to me by Letizia. Thank you for everything, your property's incredible and if dreams come true twice, I will be back to stay here again! Grazie per tutto! Jennifer.
04-Jun-2022
Villa Ostignano is a very beautiful, spacious & secluded Villa & it was perfect for our special family holiday.  Stunning scenery & lovely pool area. We all felt instantly at home & were very sad when our holiday came to an end. We would love to return one day. Letizia was so helpful & nothing was too much trouble for her.
28-May-2022
5 Star Our stay at Villa Ostignano was simply outstanding! Letizia, Robert, and the staff were welcoming, sincere, provided great information on the villa and surrounding areas, and were so helpful that made our stay incredible. The villa was clean, comfortable, spacious (there were 9 of us), and surrounded by the beauty of Tuscany. The pool was excellent, the cook service outstanding, and a great location for our day excursions. Thank you for making our stay so memorable!
21-May-2022
We loved Villa Ostignano. We celebrated our 50th anniversary with our three children and their terrific spouses. It was an amazing and unforgettable week of cooking experiences, trips to Florence, San Gimignano, Cinque Terre, Lucca and Pisa. This was truly an unforgettable experience! Love The Garritys • Such a beautiful trip- everything was wonderful, it couldn’t have been any better! Cheers from U.S.A. • This is a wonderful Villa and the surrounding area is beautiful. Amazing experience! Lots of love, good food, good wine and beautiful Villa! Love from Virginia U.S.A. • This was my first visit to Europe at the age of 51. What a special place, special people and the beauty of Montaione I’ll never forget. Thank you for welcoming us, feeling us and making our visit very special. Love from Virginia U.S.A.
02-Oct-2021
Excellent villa, excellent service, thank you!
31-Jul-2021
We 've enjoyed it very well. Thank you for staying at your Villa
24-Jul-2021
Villa Ostignano, words cannot describe the beautiful scenic views in this gem of a Tuscan countryside destinction. We had an amazing wedding reception here on September 23rd, 2019, a night we will never forget. This place will always be special with a lot of great memories. Thank you to Letizia plus all of the staff, everyone was extremely helpful. Till the next time...
28-Sep-2019
A wonderful week at the beautiful Villa Ostignano. All of us - grandparents, parents and babies have spent very happy times in the house, garden and especially in the pool. We will leave with many happy memories of this special place. Our thanks to Letizia and the team for their kindness and efficiency!
14-Sep-2019
A Fantastic experience. We would strongly recommend the Villa to others
07-Sep-2019
Lovely house, beautifully furnished with literally everything we needed for a great two weeks.
24-Aug-2019
To Roberta and Letizia, Our families thoroughly enjoyed our stay at Villa Ostignano. There were 10 of us and the house met all our needs. From the comfortable great room to the well equipped kitchen and indoor/outdoor dining - every space is well appointed, spacious and comfortable. The whole family enjoyed the pool and lovely grounds. the kids loved exploring the property and the trails. For the adults, the welcome baskets, information binder and quick response all make the trip easy. Suggested sights, restaurants and wineries were tried and lived up to the recommendations. All-in -all, a great property, well manager and perfect for a whole family vacation. Thanks to all who made our stay so enjoyable!
15-Jun-2019
Letizia, Roberto, Gilberto and the rest of the Ostignano family were amazing! We couldn't recommend this place and this people highly enough!! Trip of a lifetime!
06-Oct-2018
The Villa is huge and well appointed very close to Montaione where you will find good Restarants. The staff in the Villa are brilliant and cannot do enough for you Just had a fabulous week , you will not be disappointed if you decide to visit Villa Ostignano
01-Sep-2018
Best villa yet. A perfect family holiday for all ages - 18 months to 70 years. We had a great time. Wonderful views, location,staff. really special villa, we hope to return
18-Aug-2018
The Villa is really beautiful and tastefully decorated. We fully enjoyed our family vacation there, with our kids and friends. The pool area is amazing and it is situated on the perfect spot, so you can enjoy the landscape. The Villa is maintained excellently and all the staff members are super nice and friendly. One week there was not enough:)
28-Jul-2018
Villa Ostignano exceeded our expectations in every way. Our family has rented numerous homes all over the world and none compare to Villa Ostignano. The home, property, amenities, views and location for those wanting a true Tuscan experience will not be disappointed. The owner Roberto and staff were truly gracious and made every effort to make our stay most comfortable and relaxing. We are looking forward to booking our next visit. Sincere Regards - Mr. Kelly Dunagan (California)
21-Oct-2017
The pool area was fabulous. All the bedrooms were very comfortable, especially with air conditioning. The lounge was lovely but we didn't really use it because the weather was so nice. Very well stocked with kitchen equipment.
19-Aug-2017
There were 8 adults and 1 child and the space was perfect for our week stay. So spacious even though most of our time was spent around the pool and the beautiful eating space overlooking the hills and towns. This beautiful villa was clean and has been looked after with loving hands. the dinner that was provided us upon our arrival was such a treat. A perfect way to kick off the holiday.
29-Jul-2017
We absolutely adored this villa and the small town close by, Montaione. We loved being on a large property, complete with farming on site and incredible views. We enjoying walking the gravel roads and exploring the land. The pool was fantastic and the ping pong/pool table were great additions. The interior of the villa had a wonderful layout. All of the bathrooms were very clean/new. The beds were comfortable and a/c worked very well. Our favorite spot was the outdoor seating area off the kitchen - we spent most of our time there. It was not pictured on the villa website but should be! There were fantastic breezes in that spot and gorgeous views.
15-Jul-2017
Dear Simon Just wanted to thank you and your staff again for helping me book the wonderful week we spent at Villa Ostignano! The Villa is truly fantastic. Everything, and I mean everything, worked perfectly. We loved the generous space which allowed the three families to be together yet have our own space when necessary. It is apparent that lots of thought has gone into the property. Roberto and the staff are very friendly and helpful. It is the first time I rent a house for a week and it certainly won’t be the last! Best regards Guido
10-Jun-2017
The property was fantastic, but the owner and property manager were even better. I can't think of anything that could have made our stay better.
27-May-2017

Verified reviews by FEEFO

A live feed of reviews collected independently from our clients by Feefo

product comment
Beautiful villa, beautiful setting, comfortable bedrooms, nice common areas. We were a group of 11 that also used a chef service to provide meals, and we all really enjoyed the stay. The location was great, close driving distance to Lucca, Pisa, Siena, and other towns.
27-Apr-2024
service comment
Lovely Tuscan Villa, Comfortable and Convenient The landlord and Tuscany Now and More were very responsive when we had some issues. The first day there were issues with the electricity due to utility company work nearby, and later issues with the internet. Issues were resolved to our saitisfaction.
27-Apr-2024
service comment
Villa Ostignano and Letizia surpassed our expectations! The Villa had everything we needed and more. The Villa is beautiful inside and out and very comfortable. The surrounding grounds are breathtaking. Our trip would not have been the same without Letizia's help and input. Letizia was kind, patient and went above and beyond to assist us with anything we asked. All in all the week was perfect and we would stay at the beautiful Villa Ostignano again!!!
02-Oct-2021
product comment
Great deal for location and size. Beautiful views, comfortable space, inviting and great for the family.
02-Oct-2021
service comment
Relaxed luxury on a hilltop. Responsive and helpful and a provided lot of great detail about the villa and the area.
22-Sep-2018
product comment
Fabulous location on top of a hill, five minutes drive from the village of Montaione. Stunning views, luxurious pool, beautifully renovated villa in top condition. Owner and his team were very friendly and helpful - nothing was too much trouble and we enjoyed their gifts of food and wine.
22-Sep-2018
product comment
This is a fabulous location! Spacious, clean, elegant, and comfortable. We enjoyed every room, and all the outdoor spaces as well. The views overlooking the countryside were incredible. It was truly something you see in a movie! We couldn't have asked for more! Magical!
23-Jun-2018
service comment
Perfection! Service was excellent. Everyone was very professional, but also warm and welcoming. The villa exceeded our expectations! The space was beautiful, comfortable, and elegant. Everything was very well maintained and clean. We thoroughly enjoyed our stay, and hope to do it again in the future. Thank you for a beautiful experience!
23-Jun-2018
product comment
Beautiful house,beautiful area,beautiful people!
23-Jun-2018
product comment
Everything about the Villa is charming and beautiful. We really loved it and would love to stay there again!
16-Jun-2018
service comment
Professional, accurate and true. We rented Villa Ostignano in June. The pictures of the house were true, the house fullfilled all our expectations. Letizia the contact person was very nice, as was the owner Roberto. They were very consious to solve all our needs and problems. We highly recommend TuscanyNow&More!
16-Jun-2018
service comment
Very good service from the team at Tuscany Now and More
02-Jun-2018
product comment
Exceptional facilities and a beautifully presented villa. The owner and his villa manager Letizia were very helpful and answered all our questions. The maid service was clean and reliable, and the cooks were perfect. Highly recommended
02-Jun-2018
product comment
Best decision we ever made. Beautiful villa and grounds. Everything was perfect. The owner and son, all staff and especially Letizia - which was an honor to work with. Highly recommend this villa!!!!
12-May-2018
service comment
The Service was outstanding. Everyone was impressed.
12-May-2018
service comment
The property is very well maintained with everything you need for a good time. Letizia is very friendly and gave all the necessary support, always available for any questions.
22-Jul-2017
product comment
The experience worth the investment
22-Jul-2017
product comment
The Villa is truly fantastic. Everything, and I mean everything, worked perfectly. We loved the generous space which allowed the three families to be together yet have our own space when necessary. It is apparent that lots of thought has gone into the property. Roberto and the staff are very friendly and helpful. It is the first time I rent a house for a week and it certainly won’t be the last!
10-Jun-2017
service comment
Tuscany Now were very helpful during the booking process and also are available during the stay for any questions.
10-Jun-2017

Services

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Services available on demand

These services are available on demand and have to be paid locally.
N.B.: Please note that prices and availability for the following services are subject to change without notice. If you wish to know more about our Extra Services, we advise you to contact our Concierge Team.
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Sample menus can be obtained by contacting Concierge Services

They do request that you pre arrange your meals prior to your arrival by contacting Concierge Services and advise us accordingly.

Remember that if any members have any allergies or food intolerances, you must advise us and of course if you have any personal preferences.

Experiences

We promised you "&More"... Our handpicked experiences show you a side of Italy that stays hidden from most visitors. TN&M's expert travel concierges work with Florence-based Taols to create customised tours and activities for two up to twenty guests. From food and wine to foraging, Florence's markets and artisans, or a guided road-trip by Fiat 500, we've got it covered. How about these three below?

Toscana Quotidiana Wine Tasting

Discover a hand-picked selection of niche yet affordable, everyday Tuscan wines from across the region in a private wine tasting from your luxury villa in Italy. An expert sommelier will guide the private tasting, offering invaluable insights into winemaking, as well as the unique flavour profiles of each Tuscan wine. 

Colle Bereto Chianti Wine Tour, Tasting & Bistecca Lunch

Experience the full flavours of Chianti at Colle Bereto, an organic, 60-hectare wine estate near Radda. Savour a niche yet diverse selection of wines from iconic reds like Chianti Classico to elegant sparkling brut Rosé. Get up close to the vines and deepen your understanding of the iconic Chianti terroir, before sitting down to an intimate lunch of Bistecca alla Fiorentina. 

Ditta Artigianale Coffee Extraction Experience

The Ditta Artigianale Coffee Extraction Experience is an introductory course for curious coffee lovers that cannot resist the flavour and feel of freshly ground espresso made the Italian way. Discover the secrets of coffee extraction in a special workshop led by head barista Simone Amenini at the Scuola del Caffè in the heart of Florence. 
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