Charming Sicily
Type of accommodation:
All rooms feature a private en-suite bathroom.
Duration:
8–15 days
Recommended for:
Travellers who value beauty, exclusive experiences, and the art of travelling with style. Ideal for couples seeking a romantic escape in characterful accommodation — boutique hotels, historic estates, and charming residences — where every detail reflects Sicily’s noble past. Perfect for those wishing to combine culture, landscapes, and authenticity within an atmosphere of understated sophistication.
Best time to travel:
Spring and autumn offer the most rewarding conditions. If summer is your only option, do get in touch with us—we will craft a thoughtfully balanced, tailor-made journey aligned with your expectations.
Tailor-made Sicily tours: elegance, heritage and lush landscapes
Charming Sicily reveals the island’s noble and refined side, while preserving the pleasure of its lush and distinctive natural landscapes.
The agroturism (local farm stays) along the route have been carefully selected to reflect the aristocratic, time-honoured style once associated with Sicily’s great families. The itinerary offers a unique and authentic atmosphere, with characterful accommodations that embody this elegant tradition. Charming Sicily is one expression of the approach behind our Luxury Sicily Tours, where quality is defined by distinctive places to stay, meaningful experiences and time to enjoy the island.
Important: Our bespoke itineraries are presented as 15-day journeys. Each can be fully tailored — from duration and accommodations to destinations and nights spent — to suit your personal preferences and travel style.
Small, intimate boutique hotels along the route
Staying along this route means discovering small boutique hotels, historic residences, and charming 4-star accommodations where every space reflects the elegance and unique character of Sicily. Traditional architecture, carefully curated interiors, and a tranquil atmosphere complement a trip designed to enjoy the island with a more relaxed and sophisticated approach.
Places with their own distinct personality, selected for their beauty, their location in historic settings, and their attention to detail. Spaces that combine comfort, authenticity, and romance, ideal for experiencing some of Sicily’s most evocative corners in style.
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1
Resort Fontes Episcopi
Resort Fontes Episcopi dates back to 19th-century Sicily, when it served as the country residence of the future Bishop Gerlando Genuardi.Today, the former estate has been transformed into an intimate boutique property in the Sicilian countryside. The atmosphere is rural and full of character, offering a peaceful and authentic stay. Exquisite details enhance the charm of this cosy hotel.
Type of accommodation: Boutique Hotel
Feature: Small, charming hotel
Number of rooms: 7
Highlights: Charming rural atmosphere, perfect for couples and lovers of outstanding cuisine, with a small pool for cooling off and a peaceful setting just outside the village of Aragona.
Services
- Hotel parking
- Swimming pool
- Barbecue
- Pets allowed
- Restaurant
- Bicycle rental
- Relax area
- Television
- Air Conditioning
- Heating
- Safe
- Towels
- Shower gel
- Mini-Bar or Fridge
- Internet / Wi-Fi zone
- Washing machine
- Disabled access
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2
Pietra d'acqua
Pietra d’Acqua is a boutique hotel belonging to the luxury Geocharme collection.Nestled by nature just 2 km from the beautiful beaches of Sampieri and within easy reach of the surrounding Baroque towns. This refined retreat combines comfort and tranquillity, offering an intimate atmosphere close to the sea.
Type of accommodation: Boutique Hotel
Feature: Near the sea
Number of rooms:
Highlights: Charming setting near the beach, ideal for couples and honeymoon escapes.
Services
- Hotel parking
- Swimming pool
- Pets allowed
- Relax area
- Television
- Air Conditioning
- Heating
- Safe
- Towels
- Shower gel
- Mini-Bar or Fridge
- Internet / Wi-Fi zone
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3
Relais San Giuliano
Relais San Giuliano is a perfect choice for travellers seeking an authentic and relaxing Sicilian stay.Set within a historic village, it combines cultural heritage with high-quality services in a serene natural environment. The atmosphere blends tradition and contemporary comfort, offering a welcoming and refined countryside retreat.
Type of accommodation: Rural boutique hotel
Feature: Located in the village, natural surroundings
Number of rooms: 12
Highlights: Warm and welcoming atmosphere, harmonious mix of tradition and modernity, wellness facilities including swimming pool, spa and gym. Excellent base for exploring eastern Sicily and enjoying outdoor activities.
Services
- Hotel parking
- Swimming pool
- Relax area
- Television
- Air Conditioning
- Heating
- Fan
- Safe
- Towels
- Shower gel
- Mini-Bar or Fridge
- Internet / Wi-Fi zone
- Disabled access
July and August: a minimum stay of 3 nights per hotel generally applies. For shorter trips, we will adapt the route and select fewer bases.*
*This tour has been designed assuming arrival and departure via Catania Airport. The route can be reversed in case of arrival at or departure from Palermo Airport, and can also be adapted for arrivals at other airports.
Charming Sicily: price, inclusions, and details
This tour has been designed for travellers wishing to explore Sicily at its most refined, while staying in carefully selected boutique hotels across the region. To receive a personalised proposal, please submit your request via the form below. *The “from” price refers to a standard double room, based on 7 nights in low season (from January to Easter, and from 15 October to 20 December).
Book with peace of mind.
Flexible conditions and expert advice before and during your trip.
All our fares include flexible change or refund conditions thanks to our Trinakria Flexible Fee policy.
If your plans change, you can modify or reschedule your trip according to applicable conditions.
Our team will be available to help you before and during your trip.
What's included in your trip
Accommodation, rental car, custom itinerary design, and pricing details.
This trip includes:
- Daily breakfast
- Category B rental car
- Custom itinerary design
- Trip management fees
- VAT and taxes
Car rental includes: unlimited mileage, comprehensive damage and theft insurance, second driver, airport fees, and local taxes.
See our pricing policy here.
Personalize your experience
Add select activities and unique local experiences.
We can also add:
- Travel insurance – Cancellation insurance and medical assistance (AXA).
- Local experiences – Wine tastings, gastronomy, hiking and cultural visits.
- Higher category vehicles – Possibility of reserving cars of higher categories.
- Flights – We will advise you on the best options to reach your destination.
Regenerative tourism in the Mediterranean
Trips that contribute to caring for the land and local communities.
At Trinakria, we believe that travel can leave a place better than we found it.we found it.
Our itineraries support local economies, landscapes, and cultural traditionsin the Mediterranean.
We collaborate with small accommodations, local producers, and guides, creating authentic experiences connected to the land.
A portion of each trip contributes to funding local regeneration projects related to the conservation of the landscape, cultural heritage, and Mediterranean communities.
Because travel can also be a way to care for the places we visit.
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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.
