tailor-made tours to 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 Islands:
CHARMING CYCLADES
FROM 880 € per person
Cyclades with charm is designed to enjoy the islands in boutique and exclusive accommodations.
CYCLADES AT YOUR OWN PACE
FROM 750 € per person
Cyclades at your own pace is a fantastic trip that will help you discover all the hidden spots of the islands.
Why travel to the Cyclade Islands with us?
On our website, you’ll find some of the best sustainable tourism and bespoke travel offers to explore the Greek islands. Choose between a self-guided road trip with a rental car or a stay at one of our handpicked boutique hotels and Bed and Breakfast located across the island.
We avoid mass tourism and specialize in alternative and high-quality travel services.
Each handpicked boutique hotel and bed & breakfast on the Cyclades has been personally inspected by a local manager from our team and then chosen as optimal to include in our holiday proposals.
The proposals that you will see here are examples of the personalized trips we can offer to meet your particular needs. After you contact us, we will eventually match with the Cyclades travel offer that you were looking for.
Come discover the Cyclades on an unforgettable Greek-style holiday!!!
WHAT OUR CUSTOMERS SAY
When trying to describe our impressions of our trip to Sardinia, we realized how difficult it is to find the right adjective for an island with such unique characteristics. In our case, I think the most suitable adjective would be… Surprising? Yes, surprising.
Surprising because, although we noticed in the guidebook you recommended that there were many diverse activities to do—mainly cultural—the true possibilities that Sardinia offers can only be fully understood once you’re there.
When you first start researching this destination, what stands out most are the specialized travel magazines from agencies and tour operators, which primarily market Sardinia as a sun-and-beach destination. But that wasn’t what we were looking for in a vacation spot—we already have plenty of sun and beaches on our own coasts.
During the 15 days we spent in Sardinia, we discovered that sun and beach tourism is just a small fraction of what this Mediterranean destination has to offer. Its historical and cultural tourism offerings are immense. Additionally, it provides opportunities for a wide range of niche tourism activities, including sports (both maritime and mountain-related), archaeology, gastronomy, anthropology, ethnology, and more.
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!
Hello Boris and Giovanni, on saturday, our vacation came to an end, and we returned home. I’m writing this email to thank you for the wonderful treatment we received and to share that everything went perfectly. It was an amazing trip!
We absolutely loved the accommodations. We were a bit tired of overcrowded hotels, so this was a refreshing change. Everyone who welcomed us at the different lodgings was delightful, but the family at the rural house in Baratili San Pietro was especially kind. They treated us as if we were part of their own family.
Hello Giovanni, how are you? We’re back from our trip to Sardinia, and I just wanted to thank you for organizing everything so well—from the car rental (they even gave us an upgrade) to the selection of agriturismos, all of which were fantastic.
If it weren’t for you, we would have kept thinking that Sardinia was just about beaches, but that’s not the case at all. We absolutely loved the inland areas and the mountains.
Truly, thank you for everything. We’ll definitely keep traveling with you!
Hello Boris, although we usually don’t write on forums or blogs due to our busy schedules, we’re making an exception this time because we truly believe you deserve it.
The trip was carefully structured at a reasonable price. On top of that, you provided numerous details and recommendations that clearly show your firsthand knowledge of the destination. The agriturismos and B&Bs were fantastic, each with its own unique charm.
In short, the trip was absolutely perfect thanks to your expertise and the thoughtful approach you took. We are very grateful and recommend you to everyone who will listen—even to locals in Sardinia! We will definitely count on you for future trips.
The trip was AMAZING! The island truly exceeded our expectations, especially its beaches and Cagliari. Everything was perfect in terms of accommodations and the car rental. We really noticed a big difference between the lodgings you arranged and the ones we booked ourselves in the north—a shame we didn’t reserve everything with you from the start!
We especially loved the agriturismo S’Omu. The owners were wonderful, and the hostess was an incredible cook. The whole Oristano area and its beaches were a fantastic discovery—not as well-known as the north, but absolutely worth it.
We also met several Spanish travelers at our accommodation, and everyone was really happy with their stay. The B&B Kastrum was also perfect, both for its location and thanks to Michele—such a charming host! He provided us with all the information we needed on what to visit.
I just got back to work, which is why I hadn’t contacted you yet, but I had planned to call and congratulate you.
The trip was wonderful and far exceeded my expectations. Kastrum, Lu Pastruccialeddu, and Guthiddai are all in fantastic locations and offer excellent cleanliness and comfort.
If I had to pick a favorite, Lu Pastruccialeddu would take first place for the warm and familiar hospitality of the lady who runs it and the incredible breakfasts she prepared. We even nicknamed her “nonna” because of her kindness and her exceptional skills in the kitchen and pastry-making.
The places we visited—quite a few, given the number of kilometers we covered—were amazing, with just a couple of exceptions. But of course, not everything can be perfect; that’s part of traveling, right?
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.
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
We design tailor-made journeys across the Mediterranean, shaped around the way you like to travel.
Our itineraries typically combine boutique accommodations, scenic routes and carefully selected local experiences, all connected into a journey that feels natural and well paced. Rather than offering fixed programmes, each trip is created from scratch, adapting to your interests, your rhythm and the time you have available.
Most of our travellers opt for fly & drive itineraries, which offer the freedom to explore independently while following a route that has been thoughtfully designed in advance.
Along the way, we can include experiences such as wine tastings, cooking classes, guided visits or outdoor activities — always chosen for their authenticity and their connection to the destination.
We focus on places we know deeply — including Sicily, Sardinia, Puglia, Tuscany and Greece — which allows us to create journeys that are both well organised and genuinely connected to local life.
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 process is simple and fully guided.
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.