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Sailboat sailing in Greece


The Bear sailing Family experience

Sail in peace of mind with Dubi, Seagal and Yam Or Klein

The Bear sailing Family Experience Cruises is owned by Dubi Klein, a professional skipper with over 25 years of experience sailing around the world.

You just pack a bathing suit and come sail with us at ease.

Sailing dates 27/4-4/5



*Participation in the cruise.

* 2 available cabins.

* General organization.

* Renting of the yacht.

* Linens and towels. (1 set for each participant)

* Professional Skippers services - ( 1500 euro value )

* Yacht insurance.

* Service boat with outboard motor -  ( 150 euro value )

* Wireless internet on the yacht -  ( 100 euro value )

* Snorkeling gear.

* S.U.P. -  ( 150 euro value )

* End cleaning of the yacht -  ( 150 euro value )

Available with Additional Fee:
* Docking in marinas - ( around 50 - 250 euro per week )  

* Entrance to tourist sites.

Naoussa Paros.jpeg

Not included


* Flights, shuttles and transfers.

* Personal travel insurance.

* Food and drinks - ( around €30 per person per day ) 


The basics like spices and cleaning products, some extra food and drinks will be onboard, the rest we buy together.

Breakfast and lunch will usually be prepared together on the yacht.

Dinner at anchorages is usually eaten in taverns, but not mandatory. Of course, the expenses depend on the expenses in the restaurants in the evening and on the daily consumer goods.

Here's a suggested itinerary Milos to Paros and the Islands around:

Day 1: Milos


  • Meet At Adhamas Port and welcome onboard.

  • Arrive at the Yacht where We get to know our home for the week.

  • Provisioning for the next days in the Town and a night in the village.


Day 2: Milos

  • Sailing to the Stunning landscapes in the south of the island for a whole day of relaxing and watersports.

Day 3: Kimolos

  • Discover a beautiful unspoiled Gem in the Aegean sea.

  • Sail to the quaint village of Kimolos, dine, rest and stock on provisions.

Day 4:Sifnos

  • Sailing Kimolos to Sifnos island. Stop in Prasonisi on the NE of kimolos for a lunch stop.

  • Sail to Plati Gialos, on the south of Sifnos island.

  • Enjoy the local tavernas, the beach bars, the beach and much more  in this beautiful anchorage.


Day 5: Despotiko

  • Sail to Despotiko island. We can stop in Antiparos sea cave for snorkeling and for cliff diving for those who want to.

  • sleep in Despotiko bay, the best pirates cove in the Cycladic islands. We can walk ashore to Apollo's temple and maybe we get lucky and see a sea turtle here.


Day 6: Paros

  • Late morning sail to Fira, a small islet North of Antiparos island.

  • Anchor in this beautiful bay and treat yourself to a mud bath.

  • Sail back to Paroikia, Paros for dining, Party or just take a stroll around.


Day 7: Paros


*Routes will be determined in real-time based on weather forecasts, the skipper's decision, and the participants' desire.

We plan for a calm and pleasant sail as much as possible.

Why you should sail with us:

We organize a yacht sailing week for you where everything is planned, just come. We will take care of the safety on board, Give advice on what is there to see/do, take you to our favorite places and make your sailing adventure easy and hassle free. Come take it easy, sail for fun and meet like-minded people. The yacht is our home so we keep it up to date, clean and comfy and ready for you to feel at home.


You will get a safe and fun sailing experience, yacht cleaning at the end of the voyage, planning a route and trips to the islands, recommendations and closing a place in restaurants, organizing special tours of the islands from personal acquaintances and other experiences. Just sail and enjoy.

Greek Paradise

* Insurance and deposit - our yachts are insured with full insurance that covers the participants in the voyage against injuries, accidents or breakdowns and negligence of the skipper. However, the fittings and equipment of the yacht are insured up to an amount of 750 euros. That is, we take a deposit of 750 euros for each voyage in which we guarantee the integrity of the boat's furniture and accessories - if any damage occurs we will repair it at the expense of the deposit and return the balance to you.

*The number of cruises is limited.

Welcome Aboard

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