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Cyclades sailboat charter with or without skipper

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197 boats found within a 100 km radius of your search.
  1. Oceanis 37

    7,9

    2010 11.8 meters

    3 Cabins 8 Berths

    Fully battened mainsail, Maneuverability, Versatility

    from $1,451

    See the boat
  2. Hanse 418

    Hanse 418

    Lavrion (26 km from Cyclades Islands)

    8,6

    2020 12.4 meters

    3 Cabins 8 Berths

    Mainsail on furler, Spacious deck, Habitability

    from $2,121

    See the boat
  3. Sun Odyssey 490

    Sun Odyssey 490

    Paros - Zakynthos - Nea Peramos in the Saronic Gulf

    8,4

    2021 14.45 meters

    4 Cabins 10 Berths

    Semi-battened mainsail, Spacious deck, Habitability

    from $2,456

    See the boat
  4. Dufour 430 GL

    7,2

    2020 13.24 meters

    4 Cabins 10 Berths

    Barbecue, Bimini, Fully battened mainsail

    from $2,345

    See the boat
  5. Need some advice?
    Pierre
    Pierre your cruise expert
    Pierre is a French-American sailing expert living between San Francisco and Barcelona, he regularly meets with our European partners to guarantee you the best service and the most reliable boats.
    • Let's find the best cruise together thanks to our 30 years of experience
    • Best price guaranteed: If you find a lower price somewhere else, we commit to matching it.
  6. Sun Odyssey 440

    Sun Odyssey 440

    Lavrion (26 km from Cyclades Islands)

    8,7

    2021 13.39 meters

    4 Cabins 10 Berths

    Semi-battened mainsail, Spacious deck, Habitability

    from $2,121

    See the boat
  7. Oceanis 40.1

    Oceanis 40.1

    Lavrion (26 km from Cyclades Islands)

    8,6

    2022 12.87 meters

    4 Cabins 10 Berths

    Desalination system, Bimini, Electric windlass

    from $2,121

    See the boat
  8. Sun Loft 47

    7,8

    2020 14 meters

    7 Cabins 12 Berths

    Mainsail on furler, Spacious deck, Habitability

    Departures possible every day

    from $3,283

    See the boat
  9. Sun Odyssey 49 DS

    Sun Odyssey 49 DS

    Lavrion (26 km from Cyclades Islands)

    8,2

    2006 14.98 meters

    4 Cabins 10 Berths

    Teak deck, Bimini, Electric windlass

    from $2,791

    See the boat
  10. Bavaria Cruiser 46

    Bavaria Cruiser 46

    Lavrion (26 km from Cyclades Islands)

    8,8

    2016 13.6 meters

    4 Cabins 9 Berths

    Bimini, Electric windlass, Solar panels

    from $2,121

    See the boat
  11. Sun Odyssey 479

    Sun Odyssey 479

    Kos - Paros

    7,3

    2016 14.33 meters

    4 Cabins 10 Berths

    Mainsail on furler, Spacious deck, Habitability

    from $2,233

    See the boat
  12. Need some advice?
    Pierre
    Pierre your cruise expert
    Pierre is a French-American sailing expert living between San Francisco and Barcelona, he regularly meets with our European partners to guarantee you the best service and the most reliable boats.
    • Let's find the best cruise together thanks to our 30 years of experience
    • Best price guaranteed: If you find a lower price somewhere else, we commit to matching it.
  13. Sun Odyssey 380

    Sun Odyssey 380

    Lavrion (26 km from Cyclades Islands)

    8,4

    2022 11.22 meters

    3 Cabins 8 Berths

    Semi-battened mainsail, Maneuverability, Versatility

    from $1,786

    See the boat
  14. Sun Odyssey 410

    Sun Odyssey 410

    Paros - Platanias - Nea Peramos in the Saronic Gulf

    8,4

    2019 12.35 meters

    3 Cabins 8 Berths

    Semi-battened mainsail, Spacious deck, Habitability

    from $2,010

    See the boat
  15. Oceanis 40.1

    Oceanis 40.1

    Zakynthos - Lavrion

    8,4

    2021 12.87 meters

    4 Cabins 8 Berths

    Mainsail on furler, Spacious deck, Habitability

    from $2,010

    See the boat
  16. Sun Odyssey 410

    Sun Odyssey 410

    Lefkas - Lavrion - Nea Peramos in the Saronic Gulf

    8,4

    2023 12.35 meters

    3 Cabins 8 Berths

    Semi-battened mainsail, Spacious deck, Habitability

    from $2,121

    See the boat
  17. Sun Odyssey 415

    Sun Odyssey 415

    Paros - Nea Peramos in the Saronic Gulf

    8,4

    2026 12.35 meters

    3 Cabins 8 Berths

    Semi-battened mainsail, Spacious deck, Habitability

    from $2,345

    See the boat
  18. Sun Odyssey 490

    Sun Odyssey 490

    Lavrion (26 km from Cyclades Islands)

    8,4

    2020 14.45 meters

    4 Cabins 10 Berths

    Mainsail on furler, Spacious deck, Habitability

    from $2,456

    See the boat
  19. Dufour 530 GL

    Dufour 530 GL

    Kos - Paros

    8,1

    2022 16.35 meters

    5 Cabins 11 Berths

    Generator, Barbecue, Bimini

    from $3,740

    See the boat
  20. Dufour 530 GL

    Dufour 530 GL

    Lavrion - Athens - Lefkas

    8,1

    2023 16.35 meters

    6 Cabins 12 Berths

    Generator, Desalination system, Barbecue

    from $3,740

    See the boat
  21. Sun Odyssey 440

    Sun Odyssey 440

    Lavrion (26 km from Cyclades Islands)

    7,7

    2018 13.39 meters

    4 Cabins 10 Berths

    Fully battened mainsail, Spacious deck, Habitability

    from $2,791

    See the boat
  22. Bavaria Cruiser 46

    Bavaria Cruiser 46

    Lavrion (26 km from Cyclades Islands)

    7,6

    2020 13.6 meters

    4 Cabins 10 Berths

    Mainsail on furler, Spacious deck, Habitability

    Departures possible every day

    from $2,322

    See the boat
Sailboat: 197 boats available

Cyclades sailboat charter with or without skipper

Last updated on 8 April 2025

Why rent a sailboat in the Cyclades?

The Cyclades archipelago is a true paradise with picture-postcard landscapes, which you will enjoy discovering as you approach by sea. A sailboat charter in the Cyclades will allow you to freely visit the best of this archipelago, which extends into the Aegean Sea. On its 24 inhabited islands, you will recognize this enchanting panorama, typical of the Greek islands: villages on the side of the cliff, full of white houses shining in the sun, topped with azure blue domes. A feeling of freedom will certainly come over you as you sail through this archipelago of long beaches and rocky coasts.

 

The best places to sail in the Cyclades

The 250 islets that make up the Cyclades archipelago are home to rich nature and authentic landscapes. A sailboat charter in the Cyclades will allow you to coast from island to island and discover the magnificent panoramas that some of them offer. Mykonos is probably the best known and most popular with tourists of all: famous for its white houses, Mykonos is above all the destination for party animals and nightclubs. Then coast over to the island of Santorini, which will probably offer you the best panoramas of the archipelago from the top of its mountains, and also has beautiful white sandy beaches for lounging. Naxos, the largest island in the Cyclades, is a perfect anchorage for shelter from the wind and for fans of old buildings. Discover picturesque villages on the island of Paros, before stopping off in the wildernessof Amaros, the island famous for the filming of the movie The Big Blue.

 

Useful advice for sailing

The best time for a sailboat charter in the Cyclades is from May to October. The temperatures will be warm and the sailing pleasant. This will enable you to avoid the terrible Meltemi, an summer wind that makes sailing much more challenging, particularly in the Cyclades area. It can blow in gusts of between 35 and 50 knots during the months of July and August. A good solution may be to rent your boat with a skipper, so as to benefit from the experience and advice of a professional navigator in the area.

Need some advice?
Pierre
Pierre your cruise expert
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