LUXURY SICILY TOURS
For us, luxury in Sicily means having enough time for each place and the freedom to shape the journey around what interests you. Our luxury Sicily tours combine distinctive places to stay, local experiences and a carefully paced itinerary.
LUXURY TOURS OF SICILY, DESIGNED WITH FIRST-HAND KNOWLEDGE
Sicily offers an extraordinary variety of experiences within a single island. Wander through the historic streets of Palermo, explore the Baroque towns of the south-east, taste wines on the slopes of Mount Etna or slow down among the landscapes and villages of the Sicilian countryside.
A luxury tour of Sicily allows you to bring these different worlds together in a route that works naturally, without trying to fit too much into each day. Drawing on our direct knowledge of the island, we consider distances, travel times and the character of each place when designing every itinerary. You can explore independently by rental car, with private transfers and local guides included when they suit the route.
Accommodation and experiences are then chosen to complement the route, from properties we know personally to local guides and activities that genuinely add to the trip. The result is not a fixed luxury package, but a well-balanced way to experience Sicily, with the flexibility to adapt it to your interests.
A DIFFERENT WAY TO EXPERIENCE LUXURY IN SICILY
For us, luxury is not simply about stars or labels. Travelling well means having time, staying in memorable places and choosing experiences that offer a deeper understanding of Sicily.
EXCEPTIONAL PLACES TO STAY
Small boutique hotels, historic residences, countryside estates and refined properties with their own sense of place. We personally select the accommodation we recommend, looking beyond category or labels to properties we value for their character, location, atmosphere and connection to their surroundings.
CURATED EXPERIENCES
A private visit, a wine tasting at a local estate, a cooking experience or time spent discovering a place with someone who knows it intimately. We include these experiences when they fit the route and reflect your interests, rather than simply filling the itinerary with activities.
TIME TO EXPERIENCE SICILY
There is no need to see everything. For us, luxury also means allowing enough time for each place, avoiding rushed itineraries and unnecessary kilometres. We design balanced routes that leave space to enjoy Sicily rather than simply move through it.
LUXURY SICILY TOURS TO INSPIRE YOUR TRIP
Every itinerary we create is different, but our existing tours can be a useful starting point. These routes reflect different sides of Sicily and can be refined or combined when creating your own itinerary.
CHARMING SICILY
Discover Sicily through personally selectedboutique hotels, historic residences and characterful countryside stays, combining heritage, landscapes and the island’s understated elegance.
THE AEOLIAN ISLANDS
Experience another rhythm of Mediterranean life between Palermo, Stromboli, Salina and Mount Etna, with volcanic landscapes, sea journeys and time to experience the distinctive character of the islands.
RURAL SICILY
Travel through a quieter Sicily of vineyards, countryside, small towns and agriturismi(farm-stays), staying close to the landscape and the traditions that continue to shape it.
CULTURE, FOOD AND LANDSCAPES ACROSS SICILY
CULTURE & HERITAGE
From Palermo’s layered architecture and Agrigento’s Greek temples to the Baroque towns of south-eastern Sicily, each region reveals a different layer of the island’s Mediterranean history.
NATURE & LANDSCAPES
Explore Mount Etna, the Madonie and Nebrodi mountains, nature reserves and the quieter landscapes of rural Sicily, balancing cultural visits with time outdoors.
FOOD & WINE
Meet local producers, discover Sicilian wines and enjoy a cuisine shaped by the island’s landscapes and many cultures. Tastings and gastronomic experiences can be woven naturally into the route, connecting you with the places and people behind Sicily’s food traditions.
ISLANDS & MEDITERRANEA
Add the Aeolian Islands or time by the sea to experience Sicily from a different perspective. Depending on the season, island stays and experiences on the water can bring a slower Mediterranean dimension to the itinerary.
WHY CHOOSE TRINAKRIA FOR YOUR LUXURY SICILY TOUR?
Sicily is where Trinakria Tours began, and our first-hand knowledge of the island helps us understand how places, distances and experiences can work together naturally within an itinerary.
For us, a luxury tour is not about adding more, but making the right choices. We combine realistic travel times with personally selected accommodation and experiences that complement the route, leaving enough time to enjoy each place without turning the trip into a succession of stops.
You develop the proposal directly with us. From the first ideas to your time in Sicily, our team takes care of the arrangements and provides a real point of contact when you need us.
EXPLORE MORE WAYS TO DISCOVER SICILY
There is more than one way to experience the island. Explore our different travel styles, each offering a distinct approach to discovering Sicily.
PRIVATE SICILY TOURS
Travel exclusively with your partner, family or friends, with an itinerary and services organised for your own private party.
SICILY FOOD & WINE TOURS
Discover the island through its vineyards, producers, markets, culinary traditions and local flavours.
SICILY SELF DRIVE TOURS
Enjoy the freedom of exploring Sicily by car, with a well-planned route, accommodation and rental car arranged before you travel.
START PLANNING YOUR LUXURY TOUR OF SICILY
Tell us when you would like to travel, how much time you have and the kind of Sicily you would like to discover. Drawing on our knowledge of the island, we will create a considered proposal bringing together the route, places to stay and experiences that make sense for your trip.
Discover what our travellers think…
Hello!!! Your interest in the outcome of our bespoke journey speaks volumes about your way of working. Sardinia truly lived up to our desires and expectations. Visiting this fantastic island away from the beaten path of tourists and getting away from the typical “canned and standard” vacation… has been a real pleasure.
We have just returned from a wonderful vacation booked with you, where everything was perfect. Later on, if you’re interested, I can send you another email with more details about the places we visited. In short, EVERYTHING WAS PERFECT… the people, the landscapes, the food, the beaches, the nature… The only minor issue, which was no one’s fault, was the EXCESSIVE HEAT we endured, but we did our best to cope with it. Overall, a 9-10 vacation!
I wanted to thank you for your great availability and excellent service: our vacation was fantastic. We loved the accommodations, and although they were very different from each other, both seemed wonderful to us.
We also want to highlight the kindness of the ladies at Muto di Gallura—so charming and warm. We bothered them quite a bit, making full use of their facilities, yet we were always greeted with a big smile and kind words.
Additionally, we loved the agriturismo, the surroundings, and, above all, the amazing meals and dinners.
We can’t wait to book another vacation with you! We just hope we can find a way to visit Sicily next year.
FREQUENTLY ASKED QUESTIONS
Our private tours are tailor-made journeys created exclusively for you and the people travelling with you. They are not group departures and do not follow a fixed programme.
Most of our travellers choose a self-drive journey: you travel independently in a hire car, following a route designed around your interests, your pace and the time you have available. Flights are booked separately, while we arrange the accommodation, car hire and other services included in your proposal.
Where it adds value, we can include private local guides, transfers, wine tastings, cooking classes and other experiences. A private guide does not normally accompany you throughout the journey unless this has been specifically requested and included.
The itineraries shown on our website are starting points. Every journey is adapted to the traveller, drawing on our first-hand knowledge of Sicily, Sardinia, Puglia, Tuscany and Greece.
All our journeys are fully tailor-made.
We don’t work with fixed programmes or pre-designed packages. Every itinerary is created from scratch, based on your travel style, your interests and the time you have available.
Of course, our experience allows us to suggest routes and ideas that have proven to work well, but these are always adapted and refined for each traveller. No two journeys are exactly the same.
This approach gives you the flexibility to shape the trip around what matters most to you — whether that means a slower pace, specific locations, particular types of accommodation or selected experiences along the way.
In the end, the goal is not to fit you into an itinerary, but to design an itinerary that fits you.
We primarily work with boutique hotels, small historic properties and charming independent stays.
These are places with a strong sense of identity — where architecture, atmosphere and local hospitality reflect the character of the destination. Rather than large resorts or standardised hotels, we look for accommodations that feel authentic, personal and connected to their surroundings.
Depending on the journey, this can include countryside estates, agriturismi, coastal hideaways or small town hotels, always selected for their quality, location and overall experience.
Our goal is not simply to provide a place to stay, but to ensure that each accommodation becomes a natural and meaningful part of the journey.
The planning and booking process is straightforward, with our team supporting you at every stage.
It usually starts with a first contact, where we learn about your travel plans, preferences and timing. Based on this, we prepare a tailor-made proposal, including a suggested route, selected accommodations and any experiences you may wish to include.
Once the proposal is ready, you will receive it in a digital itinerary format, accessible through a private link. This allows you to explore your journey in a clear and structured way — including the route, accommodations, experiences and practical details — all in one place, at your own pace.
You can review the proposal and we refine it together until everything feels right — in terms of itinerary, style and overall experience. When you are ready to proceed, you can confirm the trip by completing a short booking form directly within the itinerary.
Once confirmed, we take care of all the arrangements. Before departure, you will receive all the necessary documents and practical information for your trip.
Throughout the process, you are supported by one dedicated team, ensuring clarity, continuity and a smooth experience from start to finish.
Our car rentals are designed to offer maximum peace of mind and simplicity.
They typically include comprehensive insurance with no excess, so you can travel without worrying about unexpected costs in case of damage. We also include practical elements such as an additional driver and clear, straightforward conditions whenever possible.
Our aim is to avoid the complexity often associated with car rentals, ensuring that everything is easy to understand, well covered and adapted to the journey.
Full details are always provided in your travel documents, so you know exactly what is included before you travel.
Our booking conditions are designed to be clear, transparent and fair.
Once your journey is confirmed, we typically require a deposit to secure the arrangements, with the balance due closer to the departure date. The exact details are always shared with you in advance, so you know exactly what to expect at each stage.
In terms of cancellations, conditions may vary depending on the services included in your itinerary, as many of the accommodations and providers we work with have their own policies.
For this reason, we always explain the applicable terms clearly before confirmation, so you can make your decision with full confidence
We also recommend considering travel insurance, which can provide additional protection in case of unforeseen changes.
Yes — we can include travel insurance in your trip if you wish.
We usually offer comprehensive policies covering both medical assistance and cancellation, tailored to the type of journey you are planning.
We work with trusted providers such as AXA, and occasionally others, selecting options that offer a good balance of coverage, flexibility and price.
As with any insurance, it is important to review the policy conditions carefully, as specific terms and exclusions may apply. We will always provide you with the full details in advance so you can choose the option that best suits your needs.