Cyclades at your pace
Type of accommodation:
Carefully curated boutique Bed & Breakfasts
Duration:
8–15 days
Recommended for:
Ideal for travellers seeking a genuine, locally rooted experience, where true luxury lies in simplicity and in reconnecting with the islands’ purest essence. Perfect for those who value independence, cultural depth, and meaningful encounters.
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.
Cyclades at your pace: explore the islands from the coast to traditional villages
Cyclades at Your Pace offers the freedom to explore the archipelago independently, balancing the vibrant energy of ports and towns with the tranquillity and charm of traditional villages.
Dramatic landscapes, whitewashed settlements, hidden beaches, and the warm hospitality of locals define the itinerary. Each stop highlights the distinctive character of Syros, Tinos, and Naxos, revealing these breathtaking islands well beyond their postcard image.
Boutique Bed & Breakfasts and intimate island hotels have been attentively selected for their character and authenticity. Locally managed, these residences reflect the craft and passion of hosts devoted to genuine hospitality.
Designed for travellers who value independence and cultural authenticity, this bespoke itinerary allows exploration at a relaxed pace while staying in places of true character.
By choosing Cyclades at Your Pace, the islands will be experienced through curiosity, discovery, and meaningful encounters — in their most genuine form.
Small, intimate boutique hotels along the route
On this route, we seek out simple accommodations that are close to local life: small B&Bs, guesthouses, and family-run hotels that allow you to explore the Cyclades freely, while still experiencing the hospitality and daily rhythm of the islands.
Welcoming, intimate, and well-located spaces, selected for their connection to the villages, ports, and Aegean landscape, so you can discover Syros, Tinos, and Naxos at your own pace.
-
1
Ploes Seaside Houses
Ploes Seaside Houses is located on Plaka Beach, one of the island’s most pristine stretches of sand, just 50 metres from the sea and approximately 4 km from the airport.Its setting provides a relaxed and understated island atmosphere, perfect for exploring the coastline at a leisurely pace.
Type of accommodation: Apartments
Feature: 50 metres from the beach
Number of units: 9
Highlights: Peaceful atmosphere, beachfront
Services
- Hotel parking
- Pets allowed
- Kitchen use
- Television
- Air Conditioning
- Towels
- Mini-Bar or Fridge
- Internet / Wi-Fi zone
-
2
5 Hermoupolis Concept Sites
5 Hermoupolis Concept Sites is an intimate guesthouse located in the heart of Hermoupolis, just beside the renowned Apollon Theatre and within easy walking distance of the city’s main attractions.Its central location offers the perfect base to experience the cultural pace and vibrant character of Syros.
Type of accommodation: Bed & Breakfast
Feature: Centre of Hermoupolis
Number of rooms: 5
Highlights: Warm and attentive hospitality, with Christos – the owner – always happy to provide guidance and share local insights throughout the stay of his guests.
Services
- Pets allowed
- Television
- Air Conditioning
- Heating
- Safe
- Towels
- Shower gel
- Mini-Bar or Fridge
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.
Cyclades at your pace: price, inclusions, and details
This tailor-made tour has been designed for travellers wishing to explore the Cyclades while staying in carefully curated, family-run boutique Bed & Breakfasts and intimate island hotels that offer an authentic and locally rooted island experience. 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.
