Montisi Magica

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June 11, 2013 by Christina Hamlett

Ann Alexander

A Conversation with Ann Alexander

Once upon a time, a successful attorney from the 21st century stepped into a Medieval village in Southern Tuscany and knew from the start that this would not only be the place of happily-ever-afters for herself but also for anyone she invited to join her. Ann Alexander, the heroine of this real-life fairy tale, is the Founder/Owner of Montisi Magica and the imaginative planner behind creative getaways with an accent on fun.


Q: For most of your adult life you’ve not only been a lawyer in the specialized field of medical negligence but also devoted your off-hours to charitable causes and cultural activities. Aside from the obvious question of when did you have time to add yet another passion to your resume as a modern Renaissance woman, what was the catalyst that led you to launch your own travel business in 2012?

A: It was really a string of events that began with my decision to sell my law firm. My two wonderful children were grown up (if children ever are!), I had had a wonderful career growing a very well respected business, helping many vulnerable people and contributing to real improvements in patient safety in the UK and I just felt it was time for a change. I started my career and my family quite young, was something of a workaholic and just felt I needed to slow down and try something completely different. As a consequence I merged my law firm and decided to do two of the things I had always wanted to do – make a documentary for BBC Radio 4 and learn to speak Italian.

I had holidayed and taken a cookery course in Tuscany and had simply fallen in love with all things Italian. In 2010 I rented a house for a month in Southern Tuscany and it was on this visit that I came to the Medieval village of Montisi for the first time totally by chance. In the village bar I met a local artist, an Englishwoman, Elizabeth Cochrane who had lived in the village for 13 years. Chatting to her, one thing led to another and it turned out we had been brought up 7 houses apart in the same road in the small village in Cheshire where I still live – and I knew her parents. Not only that, when I told my son the story – he was living in California at the time – he told me he had ‘met a guy from Harrop Rd too’ – it was in fact Liz’s brother!

I am a great believer in fate – things are meant to be. And the next day I made some enquiries and discovered there was a house for sale in need of considerable restoration right in the middle of the village on the main street. From the moment I stepped over the doorstep I knew I wanted it, even before I had seen the stunning views from the overgrown garden. And even though it had virtually no kitchen and bathroom – simply a sink and a toilet – and there were dangerous looking wires everywhere, I knew I had to have it.

I managed to buy it and began to spend an increasing amount of time in the village while I was restoring it, getting to know the area and entertaining my family and friends who came to visit. And as someone who is naturally friendly I began to talk to the occasional tourists who found their way to the local bar – even though Montisi isn’t on the tourist map.

And that gave me the idea to start a small travel business.

Q: What were your first impressions about the town, the landscape and the people who lived there?

A: Rolling hills, huge amounts of sky, cypress trees and olive groves – this is the stunningly beautiful scenery of southern Tuscany and as we drove along the winding road there was this very beautiful village perched on a small hill – breathtaking. The first thing I saw when we drove in was the narrow main street, the tall terraces of houses which were been built around the medieval castle walls and the profusion of flowers from every doorway. And everywhere was spotlessly clean – not even a cigarette end in the road. The village itself is quite small with a population of 400, and yet there was a bakery, a general store and a florist, and a part time post office. I just couldn’t believe how friendly everyone was even from that first day and even though my Italian was quite shocking. Just walking down the street after parking the car everyone said “Buongiorno”. And it is really like that still.

Q: I’m assuming it’s no coincidence that the enchanting name speaks to the spell which the village casts on all who visit, yourself included?

A: Indeed – it is just magical. I kept a guest book in the house for my family and friends to write their memories of their visit and the one word which kept cropping up was ‘magical’. Every morning when I wake up I can’t quite believe how beautiful it is here. And it’s not just the scenery – it’s the people, the food, the atmosphere – just everything.

Q: Tell us about the thought process that went into defining your target market, acquiring the necessary licenses and permits, and starting a marketing buzz?

A: I spend half the year in Montisi now from April til November. The winters are very quiet and can be very cold. July and August can be very hot. I decided to try out my idea on a pilot group so I contacted a number of my connections on LinkedIn and invited them to spend a week here in October 2012 on the basis that they would enjoy a week of cooking, painting, touring historic towns, tasting wonderful wines and eating delicious food. The deal was that they would pay just the cost price in return for giving me feedback. I wanted a group of 8 people and very soon I had my group – 3 couple and 2 single women. Although they were my ‘connections’, I didn’t know them well; none of them knew each other, even the single women, and their ages ranged from early 30’s to mid 60’s.

It was the most incredible week, the more so because they ‘bonded’ by the end of dinner on the first night at my house. There was so much laughter and fun that week and they have all met up since. Importantly though they gave me very valuable feedback and using that I was able to define my target market and the plan for the week of activities.

I identified that my target market was 30’s to 60’s, couples and singles, people who were ready to try something different. I began to pass the word around, using social media such as LinkedIn, Facebook and Twitter and I set up a website. My pilot group kindly allowed me to use the photos and it is such a pleasure to see their smiling faces every time I visit the site. I am now progressing with my marketing strategy and hopefully will make the delights of Montisi Magica known to a wider audience.

I have set the business up as a Limited Company in the UK which I am allowed to do as I spend half the year there – and as such there is relatively little ‘red tape’.  I am not offering flights although I can advise on travel and this avoids the need to be ABTA registered.

Q: What aspects of your legal background, leadership skills and community activism contributed to this transition to a completely different field?

A: I think the community activism helped enormously. I have always been a good communicator and I have always been very well connected. Indeed one of my business interests has been to teach the benefits of networking. This has really helped both in terms of spreading the word, talking to prospective guests and dealing with group dynamics. The leadership skills have also helped – I have been described as the ‘glue’ that holds the whole thing together. In terms of the legal background, this has helped generally but has hindered me slightly in that only now am I learning to write creatively! 

Q: You also have extensive experience in the world of broadcasting. Any plans to make a documentary someday about the history of the region, the castle, and the Cacciaconti family?

A: I would love to. I have no plans as yet – my focus is getting this business well and truly established. It would be an interesting opportunity as I have seen wonderful old photographs and heard quite a few interesting stories but I think I will have to wait until my Italian is rather more fluent so that I can converse properly with the older villagers!

Q: Were you fluent in Italian when you first arrived or is this still a work-in-progress?

A: My Italian was still fairly poor when I first arrived, and is definitely improving although it isn’t yet fluent. However, I am no longer nervous about having a conversation on the phone in Italian which for me is a great achievement.

Q: How did you go about finding your first guests for the Montisi Magica experience?

A: After the pilot week, I spent a lot of time contacting everyone I knew, passing on the information about what I was doing and I even had a piece in my local evening newspaper. Interestingly I set up a website for my law firm back in the days when lawyers didn’t have websites and although it was incredibly successful, I have had to learn a lot of new skills around the use of social media – and it is that which is now starting to work and generate the interest.

Q: What do you know now about running a travel business that you didn’t know when you started?

A: It’s very different from being a lawyer! Firstly I am having to spend a great deal of time marketing and it is time consuming although I am enjoying it. And the guests need a lot of looking after – it is very much a question of anticipating their every need – even before they know it. I didn’t think I would be so exhausted when they left, it really is a 24/7 job when they are here, but the pleasure I get from seeing everyone enjoying themselves so much makes it all worth while.

Q: What types of enrichment activities and holiday packages are the most popular with your guests?

A: So far the guests have been enjoying a range of activities – painting, cooking, touring historic towns, wine tasting, cheese tasting, olive oil tastings, walking and much more. They have been delighted with everything! The most surprising thing has been that few have wanted to paint and have painted because it was included – and then said that was the activity they most enjoyed!

I think what has proved most popular has been the opportunity to have a very varied week of activity – the chance to experience life in a real Tuscan village and try something completely different.

Q: Living in Southern Tuscany sounds like a dream come true! What have your guests had to say about this blissful lifestyle (besides, perhaps, that they never want to leave)?

A: They certainly haven’t wanted to leave! They have been quite envious too and they have all said they will be coming back. One of the original pilot group members has even decided to take a few months out of her professional life and try her hand at something less stressful and more life style too!

Q: For the first-time visitor to this part of Italy, what’s the best time of year to plan a trip?

A: Either the early summer May and June or later say September/October. It is very hot in July and August and Siena for example is very busy. So for an activity holiday the heat of these months is best avoided.

Q: If they could see/experience only three things during a one week stay, what are your top recommendations?

A: Definitely a guided tour of Siena, one of the most beautiful places in the world and a chance to understand its history. Seeing the beautiful countryside and some of the historic towns and villages in this part of Tuscany. And experiencing a real Tuscan food and wine experience!

Q: What would readers be the most surprised to learn about you?

A: Probably that I have had such a complete career change – from a high flying, high profile workaholic lawyer to a very contented individual with a lifestyle business whose job is to make people have fun and be happy!

Q: Anything else you’d like to add?

A: Just that I hope you will come over and sample the magic for yourself!

Readers can learn more by visiting




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