TAILOR-MADE TOURS OF THE CYCLADES
Do you want to travel to Greece and visit its Cyclades Islands?
Since 2023, at Trinakria Tours we have been inviting travellers to discover the Cyclades in a different way: slowly, with personally selected accommodation and tailor-made itineraries, away —as far as possible— from the most crowded side of Greece.
We have travelled through these islands ourselves: their villages, beaches, paths and tavernas, in order to design trips that preserve the authentic spirit of the Aegean.
Our selection began with Naxos, Tinos and Syros, three islands with their own character, local life and a more unhurried way of experiencing the Greek summer. We are now expanding the proposal with Milos, Sifnos and Paros, which add unique landscapes, excellent gastronomy, sea, culture and that very Greek balance between rest and discovery.
We can also include nights in Mykonos or Santorini when needed for flights or connections, or simply for travellers who wish to experience them, always looking for the most balanced way to include them in the journey.
Because of the nature of these islands —small territories with limited capacity and very sensitive to tourism pressure— we do not usually recommend travelling in July and August. During quieter months, the Cyclades can be enjoyed at their best: the beaches breathe, the villages recover their rhythm, and the journey comes much closer to what we seek when we think of Greece.
Travelling to the Cyclades with Trinakria Tours means travelling in a slow, genuine and carefully designed way, just as we believe the Greek summer should be experienced.
OUR TAILOR-MADE TOURS OF THE CYCLADES
Charming Cyclades
FROM € 920,00 per person
A customisable 8- to 15-day island-hopping journey through the Cyclades, combining ferry connections with locally arranged car hire. Stay in exclusive boutique hotels located in historic houses and charming villas, carefully selected for their authenticity on the islands of Syros, Tinos, and Naxos. Ideal for those seeking a sophisticated and genuine experience, in touch with the true essence of the Aegean Sea.
Cyclades at your pace
FROM € 800,00 per person
A flexible 8- to 15-day island-hopping journey through the Cyclades, planned around ferry connections and your preferred pace. Stay in charming rural and urban bed and breakfasts, run by local families that reflect the essence of the islands. Ideal for those seeking an authentic experience, connecting with the local culture and enjoying the diversity of Syros, Tinos, and Naxos in their own way.
WHY TRAVEL WITH US TO THE CYCLADES?
Choosing the right combination of islands is central to a well-planned Cyclades journey. Syros, Tinos and Naxos have very different characters, and not every route works equally well for every set of travel dates. We organise the itinerary around ferry connections, your arrival point and enough time on each island, avoiding a succession of short stays.
Our tailor-made island-hopping tours combine selected accommodation, hire car arrangements and a route that allows you to explore independently. You might experience the neoclassical atmosphere of Syros, the villages and marble traditions of Tinos, or the inland landscapes and beaches of Naxos. Local guides, food experiences, walks and boat trips can be added according to your interests.
We favour boutique hotels, family-run guesthouses and small properties that reflect the character of each island. The journeys shown on this page are starting points, which we adapt to ferry schedules, travel dates, preferred pace and choice of accommodation.
Tell us which Cyclades islands you would like to discover and we will prepare a personalised proposal.
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.
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.