Charming Cyclades
Type of accommodation:
Carefully selected boutique and 4-star hotels
Duration:
8–15 days
Recommended for:
Ideal for romantic escapes and honeymoons, as well as for travellers seeking a sophisticated island experience, where landscape, heritage, and understated elegance define it all.
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 itinerary aligned with your expectations.
Charming Cyclades: a unique and unforgettable journey
Imagine waking in a traditional villa overlooking the Aegean Sea, or in an elegant boutique hotel tucked within a whitewashed village of cobbled lanes. Charming Cyclades is designed for travellers wishing to discover the genuine spirit of Syros, Tinos, and Naxos through lovingly selected boutique hotels.
Intimate hotels and rural residences full of local character have been chosen thanks to their respectful integration into their surroundings, combining contemporary comfort with the warm, authentic hospitality of the Cyclades. From refined boutique hotels in historic buildings in Syros to magnificent countryside houses in Naxos, each stay becomes a distinctive retreat — a place to connect with the quiet magic of island life.
This bespoke tour is ideal for travellers seeking tranquillity, authenticity, and understated sophistication. Explore crystalline beaches, mountain landscapes, and fertile valleys, and wander through villages where life unfolds at a timeless pace shaped by tradition.
Perfect for honeymoons, romantic escapes, or travellers wishing to disconnect with intention, the itinerary invites discovery of the rich heritage, culture, and flavours of this unique corner of the Mediterranean.
Small, intimate boutique hotels along the route
On this route, we’ve selected charming accommodations with Cycladic character: boutique hotels, traditional villas, and small historic houses where white architecture, the Aegean light, and local hospitality are essential parts of the journey.
Intimate spaces, carefully curated and seamlessly integrated into their surroundings, chosen for their location, tranquility, and ability to complement a more serene and sophisticated experience among Syros, Tinos, and Naxos.
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1
Ploes Boutique Hotel
Boutique Hotel Ploes is housed in a 19th-century neoclassical mansion in an excellent location, just a few steps from the centre of scenic Hermoupolis.Once a private residence, it now offers an elegant and intimate island retreat. Its historic architecture and elegant atmosphere evoke the aristocratic heritage of Syros.
Type of accommodation: Boutique hotel
Feature: Former private mansion
Number of rooms: 7
Highlights: Beautiful outdoor terrace and elegant historic setting.
Services
- Jacuzzi
- Pets allowed
- Television
- Air Conditioning
- Heating
- Safe
- Towels
- Shower gel
- Mini-Bar or Fridge
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2
18 Grapes Hotel
18 Grapes is a distinctive boutique hotel located just 200 metres from the stunning beach of Agios Prokopios in Naxos.Designed with passionate attention to detail, it blends contemporary elegance with a relaxed island atmosphere. Its graceful setting provides an ideal base for enjoying both the coastline and the island’s natural beauty.
Type of accommodation: Boutique hotel
Location: Very close to Agios Prokopios Beach
Number of rooms: 18
Highlights: High-quality design and services; inviting pool area; and a chic, stylish bar.
Services
- Hotel parking
- Swimming pool
- Children's area
- Jacuzzi
- Pets allowed
- Television
- Air Conditioning
- Heating
- Safe
- Towels
- Shower gel
- Mini-Bar or Fridge
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3
Porto Raphael Residences & Suites
Porto Raphael is a traditionally built seaside complex comprising 25 residences and suites, each featuring fully equipped kitchens and modern comforts for a relaxed island stay.Overlooking the Aegean Sea, it offers generous space and a tranquil atmosphere just steps from the water.
Type of accommodation: Hotel
Feature: Overlooking the Aegean Sea
Number of units: 25
Highlights: Spacious suites and residences with stunning sea views.
Services
- Hotel parking
- Children's area
- Pets allowed
- Television
- Air Conditioning
- Safe
- Internet / Wi-Fi zone
July and August: minimum stay of 3 nights per boutique hotel
*This island-hopping tour involves ferry connections between the islands. Ferry tickets and port transfers are not included in the “from” price, but can be added to your personalised proposal. A separate Category B rental car is included on each island featured in the final itinerary.
Charming Cyclades: price, inclusions, and details
This tour has been designed for travellers wishing to discover the Cyclades while staying in exclusive boutique hotels housed in restored Cycladic heritage buildings. 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.
Discover what our travellers think…
All our tours of 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.
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.
