Stay in attractive hotels and villas handpicked by us throughout your trip.
We’ll help you structuring an itinerary that match you expectations from climbing volcanoes to where is the best beach to lay down or where to eat the best cannoli.
Although it takes little more than four hours to drive from one side of Sicily to the other, there is huge amount to see in between! A tailor made holiday that combines several destinations in Sicily is a great way to explore different cities, to experience the countryside or grab a few days by the beach.
Several of our multi-centre holidays are more suited to those who prefer not to drive, staying in towns and cities where cars are not needed, and transferring to other locations by train or by private chauffeur.
If you enjoy the freedom of having a rental car, then we can work out an itinerary that best suits your needs with recommended accommodation and route plans.
Multi-centre car-free holidays
Palermo, The Aeolian Islands And Taormina
Sicily three ways is a bustling city break, an island retreat and a chic hilltop town, all rolled into one car-free holiday.
- 14 nights
Palermo, The Aeolian Islands And Taormina
Sicily three ways is a bustling city break, an island retreat and a chic hilltop town, all rolled into one car-free holiday.
- 14 nights
Car-Free Holidays
Taormina And Siracusa: Sicily Twin-Centre
Keep it coastal and cultural on this two-centre holiday to two of eastern Sicily's hotspots.
- 7 nights
Taormina And Siracusa: Sicily Twin-Centre
Keep it coastal and cultural on this two-centre holiday to two of eastern Sicily's hotspots.
- 7 nights
Car-Free Holidays
Multi-centre fly drive holidays
Western Sicily: Palermo And A Vineyard Stay
An ideal late summer break the Sicilian capital with the pristine beaches and vineyards of southwestern Sicily.
- 7 nights
Western Sicily: Palermo And A Vineyard Stay
An ideal late summer break the Sicilian capital with the pristine beaches and vineyards of southwestern Sicily.
- 7 nights
Sicily Discovery: a 2-week fly-drive holiday
A whistle stop tour that combines the best of Sicily's culture, gastronomy and beach and city life.
- 14 nights
Sicily Discovery: a 2-week fly-drive holiday
A whistle stop tour that combines the best of Sicily's culture, gastronomy and beach and city life.
- 14 nights
Eastern Sicily: Taormina and the Val Di Noto
Combine the glamour and glitz of Taormina with the captivating rural landscape of South East Sicily.
- 10 nights
Eastern Sicily: Taormina and the Val Di Noto
Combine the glamour and glitz of Taormina with the captivating rural landscape of South East Sicily.
- 10 nights
Baroque Beauty In Sicily
A brief snapshot of the best of Sicily's baroque treasures in Siracusa and Modica.
- 7 nights
Baroque Beauty In Sicily
A brief snapshot of the best of Sicily's baroque treasures in Siracusa and Modica.
- 7 nights
Sicily Tailor Made Holidays
Car-free or fly and drive?
Once you arrive, the best way to visit Sicily is by car.
If you don’t feel like driving, don’t rely on trains. If anything, there are bus companies that connect the main cities to each other (Sais, Etna Trasporti and Interbus, but there are also others).
We can help you navigate the timetables and create an itinerary around, but keep in mind that, compared to a car, buses only travel between town centres.
For connections to the Aeolian, Ustica and Egadi islands, you are spoiled for choice between ferries and hydrofoils.
How long should I spend in Sicily?
If you want to tour around from Palermo to Catania, and also hit up Trapani, Ragusa and the smaller islands, you should consider taking at least three weeks. If you only have two weeks, you’ll have to cut something out, but you can still make a nice itinerary.
A week and a bit
If you can’t strecth it to two weeks, we suggest you only devote yourself to one area. You could opt for a tour of the east coast between Catania and Siracusa. Or, again in a week, you could choose to visit the west coast between Palermo and Trapani.
Another idea on what to visit in Sicily within a week could be the area of the Val di Noto with Ragusa, Modica and Siracusa.
When to go?
If swimming in the sea is not one of your objective, you can holiday in Sicily pretty much any time of the year. For example, on the 13 of December, when its celebrate its Patron Saint Lucy, Siracusa makes an excellent Christmas breaks.
Of course, being able to choose, one would exclude January to March because of the rain and, arguably, August because of the summer full house.
In August, beaches and resorts are overcrowded, it is difficult to find some space (and relax) at the sea. Not to mention August’s central week when, almost everywhere, total chaos reigns.
June and September are two excellent months for holidays in Sicily, not only for a more limited crowding issue but also for the temperature, hot but not sultry and gently breeze. Some showers can always happen, especially in September, but they are phenomena that usually do not last long. September is also when the sea is at its best: calm, flat, warm and, above all, unfrequented.
Even July could be fine if you do not suffer too much from the high temperatures: in Sicily in July, it is usually warmer than in August, but there is not the same confusion.
May is another excellent period to visit Sicily, as temperatures remain around 25-26 degrees during the day but that drops a lot in the evening, specially, if you are away from the coast.
Personalise your stay
Like what you see? Tell us your wishes and we’ll create the perfect holiday for you and your loved ones, at the time of year you prefer, and make you live the experiences you’ve always dreamed of.
What are our customers saying?
We had an amazing honeymoon, thank you so much for organising a great break!We were in Rome, Naples and the Amalfi Coast. Everything went according to plan.Our driver was waiting at the airport on arrival and got us to Leon's Place in good time. What a beautiful hotel with amazing decor, we really enjoyed our stay and used an open top bus to get round for three days!The high speed train to Naples was great. We got a cab at Naples to Chiaja de Charme, which was a good thing, as the drivers are mad, especially those on scooters! The location of Chiaja de Charme was ideal, not as grand as Leon's Place, but a perfect base for a short stay. We wandered up the main shopping street and also had a lovely evening meal down by the harbour/castle. We also took advantage of the open top tours for the best part of half a day, and enjoyed the complimentary pastries in the late afternoon/evening at Chiaja de Charme!Picking up the car at the airport was stress free, and the drive down to Relais Blu through Sorrento was straight forward, although we wondered if we'd ever reach Relais Blu. When we did - wow - stunning, spectacular views, amazing place, and even the photos on their website which were fantastic don't do the place justice. By far the best hotel we have ever stayed at - helped by great weather for the first three days there and the amazing backdrop and view of Capri (which we visited and enjoyed). They looked after us, a bottle of bubbly in our room on arrival, chef's specials lined up on silver spoons on a slate plate, along with great advice where to go, where to eat and how to make the best of our stay. We spent a lot of time in Sorrento, which is lovely, and also visited Pompei, took a drive over to Positano and Amalfi, and left with a sad heart.All in all, a truly memorable experience, fantastic memories (plus over 1500 photos) and unforgettable, a perfect honeymoon break, so a massive thank you for organising and advising. We've already decided to return to Rome and Relais Blu in the future, and would not hesitate to come back to you to help with our itinerary.
Antonio booked our honeymoon in 2012 and we had an amazing visit to Rome, Naples and Sorrento. He was the obvious choice to organise our 10th wedding anniversary and came up absolute trumps with an itinerary including Naples and Ischia.Two amazing hotels, the Caruso Place bang in the heart of Naples with shops, restaurants, attractions within very close walking distance. On the stunningly beautiful island of Ischia the Botania Relais Hotel and Spa was amazing and exceptional on every level. Beautiful setting and great facilities, wonderful pool, restaurants on site, food excellent and very helpful staff (as were the team at Caruso Place). Grazie mille Antonio!
We have just returned from a holiday in Sorrento and Ischia, organised by Antonio/ExpertoItaly.We went away to celebrate our 40th wedding anniversary, so although we have spent many family vacations in and around Sorrento and know the area very well, we sought Antonio’s help to arrange something really special. He succeeded!Antonio listened carefully to our objectives, carefully steered us away from ideas that wouldn’t have worked and suggested things that we would not have thought of ourselves - from attending a wonderfully entertaining Three Tenors concert in Sorrento to staying at the enchanting Botania Relais & Spa on Ischia.He was always readily available before and during the holiday to discuss and adjust details. For example, when we decided - at late notice - to spend the final day of the holiday in Naples, en route from Ischia to the airport, Antonio arranged for us to leave our luggage in storage at a hotel there while we explored the city.Congratulazioni, Antonio - hai colpito la palla fuori dal parco!
Antonio and Expert to Italy planned, organised and executed a truly excellent and magical holiday experience for us. They understood our brief, suggested a wonderful itinerary that met our brief completely and all of the destinations exceeded our already high expectations (this was our 3rd holiday with Expert to Italy). We particularly appreciated the following:- Local insight and understanding to suggest places we had never heard of and that gave us a real taste of Italy- Commitment to proactively suggest and amend details of our holiday even when it was fully booked and paid for- The personal relationship Antonio clearly has with the hotels we visited- Attention to detail and all arrangements considered to ensure we could relax to the maximumWe thank you for a wonderful holiday experience.
Outstanding service from Antonio and his team. Thank you for a holiday we will never forget.
Antonio is the best travel agent we have ever worked with. without question. He helped to plan our somewhat complicated Italian road trip and really took on board what we wanted (in terms of itinerary, type of hotels, etc). He did a fantastic job at rearranging our trip twice as a result of the Covid pandemic and, when the time finally came that we could go ahead, he was full of great suggestions for places to visit, scenic routes to take, things not to miss, places to eat, etc. He was also in touch with us while we were away and was incredibly proactive, re-booking a restaurant that he had previously booked for us when he found out it was going to be closed, and proactively booking 3 (excellent!) restaurants at Lake Como when he realised that everywhere was getting booked up quickly. We can't thank him enough for providing such a great service and ensuring we had a really marvellous holiday.
We have been on three lovely holidays arranged by ExpertoItaly. Our hotels have always been well-chosen and we get great advice about where to stay and places to visit. Antonio listens carefully to our requirements and reacts positively to questions and comments.
An intriguing part of a much loved country that I had undiscovered.ExpertoItaly - Antonio was attentive, helpful and meticulous at every turn. A fabulous support in navigating new territories. Truly an expert and nothing is ever too much trouble. Appreciated and highly recommended.
Antonio was a huge help in planning our big trip to Italy. He listened to what we wanted, what was important to us and factored it all into the plan. We had the best trip. The hotels were lovely and well located. Throughout our trip Antonio was available on WhatsApp if we had any queries or needed advice. We definitely had a better holiday because of his support. If you want to experience Italy and get great inside tips speak to Antonio!
My friend and I have just had a stunning holiday in Italy, all organised by Antonio. All the travel arrangements (we went by train from London to Paris, Turin, Florence, Siena and further south to Foligno) went like clockwork, and we stayed in simply beautiful palazzos, with glorious comfortable rooms , conveniently situated for the sightseeing we had planned. The palazzo staff/owners were very welcoming, extremely helpful in booking restaurants and taxis, printing entry tickets for cathedrals etc . Having Antonio make the arrangements took all the stress out of the holiday planning, and he remained in contact in case any difficulties were to arise. This was my second holiday organised by Antonio, the first being equally successful taking my 90 year old mother in 2017 to Venice and Florence, and my friend and I are now starting to think about the next one!
Being a single woman, traveling the globe for trade fairs in my industry, and never quite knowing where to stay and how to attain the best experience, ExpertoItaly was recommended to me by a colleague in the UK and I am thrilled to share that this was the best investment I could have made.To my amazement, this company spent countless hours supporting my travels, mapping out my routes, train stops, airlines, restaurants, shops, and more to inspire the most remarkable trip! Always available, with the most dedicated support, I can't begin to tell you how this made my travels the most remarkable experience~!I was abroad for 13 days for both business and pleasure and I could have never had the experience I did without the support, patience, kindness, and knowledge of this company. As I traveled, I spoke with innkeepers, restaurant owners, and many who knew this company from previous engagements and always smiled when I mentioned their company. This to me is stellar as I knew that I was in the right care.I will certainly refer and promote EXPERTOITALY to many of my colleagues, friends, and family because everyone deserves to travel the world and feel safe, and secure and have the best itinerary to explore as they travel! Much gratitude to EXPERTOITALY, I will be forever grateful and you can count on my business in the future!For corporate or family travel, this company will ensure your best experience. BRAVO!!!
We loved our week in Villa Lighea booked through Expertoitaly. If you are looking for a romantic, water-front cottage, this is it. We swam in the sea every day.It’s a bit remote from the major cities of Sicily but we hadn’t planned a lot of sightseeing. We ate at a few great restaurants but mostly cooked at the villa. Great weather and warm water in September.Antonio was easy to work with and flexible when we had to reschedule due to COVID. We would book with him again.
Antonio arranged a great two weeks in Campania for us this year. It was excellent to get to places that were quiet, smart and friendly. Everything worked just right, even this crazy year. Previously he has sorted us out a car tour of Sicily, two return visits to that lovely island, and breaks in the bay of Naples. We had done quite a lot of Italy under our own steam, but ExpertoItaly really are experts with a fantastic set of choices , and you get a great personal service. We will be back again next year.
Outstanding service, advice and organisation of our holiday combined with an intimate understanding and knowledge of places to stay and see.go no further.
Expertoitaly (and Antonio) first came to our attention in 2014 when we were planning a celebratory trip to Italy for 2015. Although we approached a number of household names about our plans and itinerary by e-mail Antonio immediately stood out. He phoned back almost straight away to get to know something about us and what we liked to do.On the back of that discussion he quickly put together a trip and budget. Given his obvious knowledge of the country and his quick grasp of what we were looking for together with the attention to detail it was a 'no brainer' to put our trust in this company. As a consequence we duly enjoyed a 3 week multi-stop trip in July 2015 tailored to suit us perfectly!On return we almost immediately booked to return in October for a short break to 2 of the locations in Tuscany we particularly enjoyed - Lucca and Montepulciano both of which are delightful.We fell in love with Italy and have returned several times since then all courtesy of Antonio:2016 - A short break to attend the Opera in Verona.2017 - 2 weeks in Sicily2018 - the same - we love Sicily and would urge anyone to go. (where we finally got to meet Antonio in Ragusa which was great)We were due to return to Italy this year for a 3 week road trip - albeit with private transfers rather than actual driving - from Verona to just south of Naples - all immaculately put together by Antonio of course. Alas Covid-19 had different ideas.We can only say that Expertoitaly have dealt with this professionally and as speedily as circumstances allowed and have refunded all the monies. We have no reservations about using them again in the future. In fact Antonio is already on standby to reprise the 'lost' trip as soon as this madness ends and unhindered travel becomes possible again - just extended an improved.Andrew & Susan SmithTadworthSurrey
If you are looking to go to Italy for a holiday, Antonio at Experto Italy is amazing. We have just come back from our fourth holiday he has arranged for us. He sent us to places that days of googling would never have found.He also has a knack of keeping to budget even with my numerous demands!Fabulous fabulous!!
Just returned from a fab trip to Italy - all organised by Antonio. His time and effort to get what was just right for us was amazing.. he had a lot to put up with! We have used Expertoitaly before and will do again.We visited Ischia and Naples. Both very different and wonderful. Ischia is perfect for a good rest (visits to the Giardini La Mortella and the Ravino Gardens are a must). The Gardens & Villas Resort is a beautiful setting, very private, calm with amazing staff. Also the little town of Lacco Ameno has some really nice restaurants. Naples was very HOT! but we still managed to spend 7 hours walking about just soaking up the atmosphere and visiting some of the fantastic historic sights. Visit to the underground roman town is well worth it - it is mind boggling to think it was built thousands of years ago.
This is the third occasion that Antonio has organised an Italian holiday for me. As it was a Birthday celebration involving a party of 10, the arrangements were complex, involving a villa, guides and attendance at the Palio on July 2nd. Without exception everything went exactly as planned. The recommended villa on the Montestigliano Estate, south west of Siena, was wonderful. Our guide made sure we had a full understanding of the history and culture of the Palio which meant that, with a spectacular view over the Campo from the apartment booked by Antonio, we were able to appreciate the event that much more.We shall certainly be going back to Italy with Expertoitaly.
We had an amazing trip organised by Antonio, we visited Naples for a few days then stayed in Sant’ Agata. Both hotels had fabulous amenities and restaurants. The trip was effortless and everything was meticulously arranged. Antonio was also on had for anything we needed during the trip.I would definitely recommend Expert to Italy and we will definitely use this company again in the future
Antonio with his meticulous planning and caring service has been solely responsible for the best Italian holidays we have had. His ability to offer excellent hotel accommodation which provides for every need and requirement is second to none . Hotels that are not main stream , that provide high quality of service in excellent locations are one of Antonio’s strength. It’s great to have a provider that know and understands his market. Grant B Stupart
July 2018_________________________________Have just completed another 10 day holiday arranged by Antonio at Expert to Italy. We went with Antonio's suggestion and spent 2 days at Matera and then the remainder in Pisciotta in the Cilento. Matera was amazing and felt completely different to anywhere else we have been in Italy. We loved Pisciotta and the hotel was wonderful with lovely owners who were great at suggesting things to do. We visited a buffalo farm, a vinyard and tooks boats to isolated coves with lovely clear water. All arrangements were absolutely faultless. We would never have found such lovely places without Antonio!2016_________________________________We have just returned from a fantastic holiday suggested no arranged by ExpertTo Italy. Once again the organisation by Antonio was flawless and everything worked perfectly. We spent 5 nights by lake Maggiore and 3 in Cogne in the Italian Alps. Both hotels and locations were fantastic - particularly the Bellvue in Cogne. Please see trip advisor if interested in the hotels as I will give a more specific review there - I'm not a fanatic reviewer but both really deserve it. We have used this company for the past 5 years and Antonio seems to have a real gift for finding fantastic hotels and matching locations to his clients. I would not usually put the level of trust in anyone to arrange holidays for me that I have with Antonio but he has delivered every time and I can unreservedly recommend his services. Italy is a beautiful country with huge variety - if you describe what you like to Antonio and let him make suggestions then you will not be disappointed. Very definitely 5 stars from me. So - Antonio and team, please keep it up!Jon
Antonio delivered more than expected! Our family of four stayed at two beautiful villa's on the Amalfi Coast. Both of the locations were top class. Antonio provided excellent service and was always available if we had questions about the details of our trip. He was easy to work with and we would recommend his services to others traveling to Italy.
This was our second holiday with ExpertoItaly, and it was just as good as the first! Antonio provided us with fast, efficient and personal attention. His choice of hotels was first class. Real attention to detail means that you get a holiday that really suits your personal requirements. Brilliant!
We have just made an amazing journey by train, taxi, boat and bus through France, a night in Paris, then a night on a mountain in Switzerland, train across the alps on the Bernina Express, 5 days on Lake Como and 6 days on Lake Maggiore. We stayed in the most glorious quality hotels. We made visits to local towns and attractions using buses and boats. Every connection on the journey was planned and executed wonderfully.This is 5 star planning, 5 star service, 5 star experience all personally organised by Antonio at ExpertoItaly. We must never forget the James Bond moment of being whisked across Como by Luca in his luxury Taxiboat from Varenna to the Hotel Filario in Lezzeno with Pavarotti as our musical accompaniment then met on the jetty by a lovely suited receptionist. A dream. Thanks Antonio.See views from our rooms Como then Maggiore.
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Package holidays are sold by ExpertoItaly Ltd (Reg. 12035194)
TTA membership Q8055
Email us on holidays@expertoitaly.com
Call us on +44 (0) 77 3838 5790
Registered office: 33 Miles Close, London, SE28 0NJ
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Friday 9am to 5:30pm
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