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What to expect


Our Mission is simply to hear all our clients say: "That was the best holiday we've ever had, we'll be back".

Our values
The finest villas, exclusive to The Thinking Traveller
Informed advice, local expertise, flexibility and financial security 
Support and peace of mind on holiday
Comprehensive, joined-up service


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Our values

The words below describe our values. They are the things that get us out of bed in the morning, and the beliefs we turn to when we need guidance.

Quality through exclusivity

Because the villas in our portfolios are only available through us, we are able to create enduring partnerships with owners, invest directly in our product, and maximize each villa’s potential and quality.

Superior product and local knowledge

Our London staff visit our regions and stay at our properties regularly. Their passion and superior product knowledge allow us to give practical advice enabling clients to identify the perfect villa and location for their holiday.

On-the-ground support – we’re with you all the way

As several of us live and work in our regions, we know what’s going on, who’s who, how things work and where to get the best pizza! Part problem-solvers, part talking guidebooks and part concierges, we provide privileged access to things most visitors never hear about.

Passion, dynamism and innovation

We are a pioneering company: the first to develop the quality rental market in Sicily, to produce and publish its own guidebooks, to offer a fully integrated in-villa wine delivery service. And we are benchmark-raisers in Puglia and the Ionian Islands. But we don’t rest on our laurels - there’s much more to be done!

We always go the extra mile

We are a team and each of us will always go the extra mile to ensure we exceed expectations.

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The finest villas

Expect the finest properties: The Thinking Traveller is the point of reference for the owners of the finest villas in Sicily, Puglia and the Ionian Islands who wish to open their doors to paying guests, and those seeking the unique experience of staying in such properties. There are hundreds of villas and apartments available for rent in all of our destinations through a myriad of locally and foreign owned companies but the best are only available exclusively through The Thinking Traveller. We only take on villas that are made available to us on an exclusive basis, and we reject far more properties than we accept. That’s how we are able to guarantee that The Thinking Traveller's exacting standards are met.

Expect luxury and authenticity: our properties range in style from the downright luxurious to the quirky and authentic. Traditional “star ratings” are not easy to apply to such properties. Several (such as those in our Think Exquisite range) offer the service and comfort of a five star hotel, with the added advantage of being totally private. Others have made it into the Thinking Traveller ranges because of their unique qualities: they might not be luxurious, but they certainly have their own peculiar charm. These differences in character make it very important that you tell us what is important to you and allow us to advise you.

Expect cooks and maids: experiencing the local cuisine is an important part of any trip, and having a local cook for you at home is a great way of doing it. Being able to put your feet up and let someone else get on with the housework is also a high priority for many people. Some of The Thinking Traveller's villas come with both cook and maid service included in the price. At virtually all others we will be happy to organise a cook or maid for you.

Expect built in sustainability: much is written about sustainability and carbon footprints, and we think that The Thinking Traveller scores excellently on both fronts. You will stay in private houses. The building and restoration work done preparing them for you is carried out by local, family run contractors, as are the cleaning, cooking and other services you may use during your stay. Foodstuffs are overwhelmingly seasonal and locally produced. In addition to having a low carbon footprint, this model contributes directly to developing local economies and helps make Sicily, Puglia and the Ionian Islands better places in which to live.



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Informed advice, local expertise, flexibility and financial security


Expect us to listen to you: understanding your requirements is the first and most vital stage in our relationship with you. Please tell us as much as possible about what you like. Tell us about your past holiday experiences, what you enjoyed and what you didn’t. Tell us about yourself and the people travelling with you. And although email is a great tool, please talk to us. Our phone lines are open for business, and we are longing to talk to you about your holiday.

Expect local expertise: most “specialist” operators spread themselves too broadly to give genuinely specialist advice. We have incomparable local knowledge. Our London team visits Sicily, Puglia and the Ionian Islands regularly, so you’ll always be able to speak to someone who has spent time at the villa you will stay in, seen the areas you will visit, and done the things you’d like to do. Rossella, Huw and the local teams spend their time on the road meeting people, visiting properties and cultivating a large and growing network to provide you with an access to Sicily, Puglia and the Ionian Islands that the casual tourist or less focused operator simply won’t find.

Expect honesty, accuracy and straight talking: we know how precious your holiday is and want to make sure you go to the place that suits you best. We will work with you, and apply all our extensive knowledge, training and experience to find the best combination for you. We will never try to fit you into something we don’t think you will enjoy.

Expect exceptional value for money: it is reassuring to know that with The Thinking Traveller you can book luxury holiday accommodation at very reasonable rates. In terms of pricing per person per night, The Thinking Traveller's villas offer exceptional value for money compared to hotels.

Expect guaranteed prices: the prices on our website are guaranteed and the prices you see are what you will pay. Indeed, unlike many tour operators, The Thinking Traveller's unique pricing structure means that you will never be asked to pay currency surcharges if the exchange rate changes.

Expect peace of mind: back in 2002 The Thinking Traveller practically "invented" the villa rental business in Sicily and have been the undisputed market leaders ever since, constantly raising standards and setting new benchmarks. This raising of standards has been fundamental in our subsequent moves to Puglia and The Ionian Islands, and so by booking with The Thinking Traveller you can be sure of getting the best villas (all exclusive to The Thinking Traveller), the best service, the best information and the peace of mind guaranteed by travelling with one of the most respected villa rental companies in the world. The Thinking Traveller is a member of ABTOI (the Association of British Travel Organisers to Italy), ASTA (The American Society of Travel Agents) and ATOL. Many of the flights and flight-inclusive holidays on this website are financially protected by the ATOL scheme. But ATOL protection does not apply to all holiday and travel services listed on this website. Please ask us to confirm what protection may apply to your booking. If you do not receive an ATOL Certificate then the booking will not be ATOL protected. If you do receive an ATOL Certificate but all the parts of your trip are not listed on it, those parts will not be ATOL protected. Please see our booking conditions for information, or for more information about financial protection and the ATOL Certificate go to


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Support and peace of mind while on holiday

Expect support whilst you’re away: our network of villa owners and caretakers is supported by our expert team of locally based Sicily, Puglia and Ionian Islands team members, who are available 24/7 to ensure that your holiday runs smoothly. Between 2011 and 2015, readers of Condé Nast Traveller have consistently voted The Thinking Traveller as one of the Top Three Villa Rental Companies in the World, specifically mentioning our superb on-the-ground support.

Expect comprehensive information: The Thinking Traveller's support starts even before you leave! In fact, several weeks before departure, you will receive an exhaustive information pack designed to help you get the most out of your trip and to ensure that everything runs perfectly to plan. This pack includes:

  •  a House Guide, complete with detailed directions to your villa, useful tips about how to get the most from the property and information about the surrounding area, including local restaurants, beaches, shops and leisure activities
  • a detailed Thinking Traveller map of Sicily, Puglia or your island in the Ionian or Sporades archipelagos. 

Expect a safe and enjoyable holiday: all reasonable steps have been taken to ensure you have an enjoyable and safe holiday with The Thinking Traveller. Safety standards and regulations vary from country to country. The Thinking Traveller has its own set of standards, and safety levels in all our properties are assessed in accordance with these. We also work very closely with our suppliers to ensure that safety levels are maintained. Please see our dedicated Health and Safety page for more information.


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Comprehensive, joined-up service 

The Thinking Traveller’s joined-up team of passionate specialists work hand-in-hand to ensure your holiday is a complete success. Here’s a little summary of who you will be in contact with and when:

1. Villa Specialists
Your first contact with The Thinking Traveller’s team will most likely be with one of our Villa Specialists. Their aim is to help you identify the perfect villa(s) and destination for you and your group. They have personal, first-hand knowledge of our properties, which they visit and stay at regularly. They will have the answer to all your questions and will offer transparent, tailored advice in a proactive, thoughtful way. If you book online without speaking to us, one of our Villa Specialists will be in touch just to check that you haven’t missed any important details about your chosen property.

2. Experience Specialists
Once your booking is confirmed, you will be contacted by one of our Experience Specialists, who will have been briefed by your Villa Specialist. The aim of our Experience Specialists is to make your holiday both a logistical breeze and the experience of a lifetime. They’ll do the paddling while you glide across calm waters, assisting you with practical details (check-in times, rooming arrangements, transfers, car hire, maid service, pre-arrival hampers and in-villa wine deliveries), and organising any holiday-enhancing activities – our Think Experiences - that might have caught your eye. These range from cultural and culinary activities (special interest guided tours, cookery lessons, in-villa dinners, wine-tastings, etc.) to thrilling adventures (helicopter rides, yacht and boat charters, 4x4 excursions on Mount Etna and much more beside).

3. Local Managers
From the eve of your holiday until the day of your return home, you’ll be looked after by one of our Local Managers. They too will have been briefed about all elements of your holiday. Part concierges, part trouble-shooters, they’ll be on hand 24/7 for the entire duration of your stay, always at the end of the phone and always ready to meet you at your villa. Whether you need a good restaurant recommendation, a ticket for the opera, help planning excursions, or assistance with some aspect of your villa, they’ll always come up with a winning solution.