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Best greek itinerary and amazing views in Cyclades on a big 50 ft boat

Greece:

Cyclades

Duration:

7 days - 7 nights

Max number of passengers:

10 people

Available:

-

Boarding from:

Naxos, Greece

What's included

Cancellation policy

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Organised by:

Greg & Aga

Member since 2016 -

Organisation

English

Polish

This experience, in a nutshell

Looking for an active rest this summer? There is no better plan than to join our sailing holidays! All routes are individually prepared for each crew, depending on the weather conditions, your preferences and mood. Your safety and comfort are our priority!

Round cruises from Naxos are definitely our favorites! After 15 years of sailing in Greece we prepared for you the best possible sailing route in Greece.
Starting and ending in Naxos - in the heart of Cyclades, enables us to not waste time on long sailing from Athens and exploring amazing Cyclades from the first moment of your sailing holiday!

Small Cyclades are the pearl of this area - far less touristic and commercial than other islands. Crystal clear blue water (the most beautiful we saw in Greece), desert islands, small villages with our favorite tavernas on the hill, friendly local people, lots of great food and wine! Among others on our way beautiful Iraklia which is empty even in the middle of the season, Kufonissi with its amazing caves and blue water, Schinoussa - truly local and greek small village, beautiful yet unspoiled Amorgos with breathtaking monastery carved in the rock, where the monks are waiting for you to climb the stairs with delicious psimeni raki and loukoumi :)

From there we may go to Ios - more busy but worth visiting because of its old town which is said to be the most scenic Chora in Cyclades. On the way back we have Paros - one of the most beautiful islands in the Cyclades with its quieter sister Antiparos, where if you are lucky enough we may meet Tom Hanks :)

You have a chance to visit and feel the real Greece with its unspoiled local atmosphere. We love it so much that we have sailed there each year for more than 15 years now :) Relaxed sailing, lots of time to explore Greece both in the sea and on land.

This is how our typical sailing day looks like:

- We wake up, eat breakfast, have some coffee in the village or a little walk and we sail away.
- We sail for a few hours and then we reach some beautifull bay with a lovely and deserted beach. Then we have time for snorkelling, swimming, sunbathing, exploring the island / bay, reading books and so on.
Together we prepare some lunch (greek salad seems to be perfect for the hot day!), have some rest - maybe a little nap won't hurt :) and we sail away.
- We sail for a few hours - for volunteers chance to learn how to steer, tie a knot and other sailing activities :) For others time to relax and sunbathe on deck.
- We reach a new island, moor in a lovely small village and explore the new place.
In the evening we go to the Taverna to try some awesome local food as well as the delicious greek wine, dance some Zorba, listen to live music and relax! "No hurry" - that's our main theme :) On Amorgos we also have a possibility to explore the islands by car/scooter/quad.
Nothing is better on a hot summer’s day than being on the water, swimming in crystal clear sea and feeling the wind in your hair.

Bringing your loved ones on board and experiencing all this together is an adventure of a lifetime. Unplug yourself and spend some quality time together.
Be close to nature and feel the freedom that only sailing can offer you :)

We know what we do! We have been organizing sailing cruises for more than 15 years now, having thousands of happy crews on our board.
If you have questions, doubts or just wish to talk with us - don't hesitate!
We will be more than happy to help you and provide all the necessary info!

During all our cruises Aga will be your guide. She takes care of our crews and helps solve all the issues that might come up. With Aga you will know where to do the shopping, where is the best Moussaka, fish or calamari and which place serves the best coffee. She will tell you what each island has to offer, as well as indicate the best view points and local spots :)

No Departures available

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5+

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Boat & Classes of Service

Beneteau Cyclades 50.5 - 2007

Type

Sailboat

Length

15.24 m.

Toilets

3

Cabins

5

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21+

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Our itinerary

Our trip starts here:

Naxos, Greece.

Check-in: 5:00 PM

Our trip ends here:

Naxos, Greece.

Check-out: 8:00 AM

The organiser reviews

avatar image

Organised by:

Greg & Aga

Member since 2016 -

Organisation

English

Polish

4.8/5

out of

48

reviews

Skipper

Boat

Destination

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Sailing paradise in Greece on a big 50 ft boat: the best local experience

09/13/2025

Stefano S.

-

Italy

An unforgettable experience from start to finish, and I can’t recommend it enough! First of all, our skipper Arnon was absolutely fantastic. Calm, professional, and with a great sense of humor, he made everyone feel safe and relaxed from the moment we stepped on board. His deep knowledge of the area meant that every stop was better than the last. He also involved us in the sailing, which made the experience even more fun! A huge shoutout as well to our wonderful hostess, Agatka. Her cooking was simply incredible — every meal was fresh, flavorful, and beautifully presented. She had an amazing way of making the boat feel like home, always with a smile, and was invaluable in organizing our land expeditions. You can tell she really loves what she does, and it shows in every detail. The itinerary was perfectly paced — a mix of sailing, swimming, exploring on land, and many nice little seaside restaurants. I left the boat with new friends, a camera full of memories, and a heart full of gratitude. If you’re considering this trip — go for it. You won’t regret it.
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Sailing paradise in Greece on a big 50 ft boat: the best local experience

09/9/2025

ANNA V.

-

Italy

Wonderful, relaxing as well as interesting holiday... sea and enchanting places, rich breakfasts and tasty lunches lovingly prepared by Aga, visit to archaeological sites and a family-run winery with excellent dinner and wine tasting, various dinners in taverns or characteristic restaurants where you can taste fresh fish or exquisite traditional dishes of Greek cuisine, all organized with precision and professionalism by Aga (who is also very nice). In short, I was really good, what more could you want? To come back, yes I really think you have to come back! :-)
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Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

08/31/2025

Michele L.

-

Portugal

Amazing adventure. Aga, Aja and Greg are supportive and dedicated. Notwithstanding the weather conditions have been challenging for sailing beginners they managed to make our trip amazing. Aga and Aja’s breakfasts and lunchs are healthy, tasty and creative!
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Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

08/18/2025

Francesco P.

-

Italy

Amazing adventure holidaying across the most beautiful seas Aga & Greg loving and caring hosts Incredible local vegetarian and healthy food experience on board And tavern selection for the nights on the ground A must try experience!

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