Rent a Sailboat in Cyclades With Skipper

Sailboat Hire in Cyclades With Skipper

With over 200 islands to explore you can’t simply fly into one of the three main airports in the Cyclades and hope to appreciate what these islands have to offer. You need to rent a sailboat in Cyclades with a skipper.

Of course, if you’re an experienced sailor you may want to skip the skipper. You should be aware that despite having a Mediterranean climate, these waters can be tricky. Because of the lack of mainland around these islands, the wind can pick up Its known as the Meltemi and often blows at force 5-7, even sometimes hitting force 8.

The wind generally starts to pick up in June, making May an ideal time for less experienced sailors. The Meltemi is generally weaker in June and September, while the weather is around 20-25 degrees, making this a great option for those with a little experience. Renting a sailboat in the Cyclades with a skipper could be in this case the best solution for you. 

In fact, this is also a great time to visit the islands as they are not in their peak season, they’ll be less people around.

If you’ve got plenty of experience sailing and like a challenge then you may want to try the peak season and rent a sailboat without a skipper.

Having a skipper isn’t just going to make it easier to navigate the waters and find the sights that you may otherwise miss. It also means you can relax and enjoy the vacation while appreciating some of the most beautiful coastlines in the world.

A great starting point is Santorini, the largest island and one that has an abundance of sun-kissed beaches with traditional Greek architecture. You’ll also want to sail into Mykonos to check out the modern, cosmopolitan feel and drift through the waters to the center of these islands, Delos.

Delos is steeped in mythology dating from the times of Greek gods, it has a Sacred Lake which is intentionally kept dry to avoid disease spreading and the famous Minoan fountain. You will definitely have to visit the Temple of the Delians, fully restored.  

These ancient buildings and monuments will give you a sense of the importance of this small island throughout history. You’ll also be amazed at what could be achieved before the arrival of machines! With just 14 inhabitants you may feel that you’ve discovered the lost world, just don’t get lost yourself!

You’ll want to take your time exploring this fascinating place and you’ll be grateful to have the boat to return to. 

Other delights in the Cyclades include Karthaia, a remote twin cove where the ancient city of Karthaia stood, one of the most important cities in the world, in its day. Take a look at the Vallindras Distillery on Halki’s main square and sample the kitron liqueur which has been made in the same traditional way since the 19th century.

If you fancy some time onshore you should try the walking trails in Paros Park, there are an abundance of hidden coves and stunning beaches for you to find from land and by sea. You’ll also need check out the monastery, museum, and ancient architecture.

It’s also worth looking at the cave of Antiparos, just 10km south of the port, visit by land or by sea and admire the massive cave with impressive acoustics. It has to be seen to be believed.

Rent a sailboat in Cyclades with skipper and you’ll get to see a host of other amazing sights, they’ll remind you of how many things humans have achieved, how we’ve developed, and what we’re capable of.

It’s awe-inspiring and deeply satisfying as you sail from island to island enjoying the summer sun.

70 boats
  • Sailing boat
  • 2019
  • 47 ft

Jeanneau Sun Odyssey 490

Paros, Cyclades Islands

  • 9 berths
  • 4+1 cabins
  • 4 WC
  • Included Outboard Engine
  • Bow thruster
  • GPS Plotter in cockpit
Starting from€4,131

Boat price + skipper cost

  • Sailing boat
  • 2017
  • 45 ft

Jeanneau Sun Odyssey 449

Paros, Cyclades Islands

  • 10 berths
  • 3+1 cabins
  • 2 WC
  • Included Outboard Engine
  • Bow thruster
Starting from€3,410

Boat price + skipper cost

  • Sailing boat
  • 2016
  • 42 ft

Jeanneau Sun Odyssey 419

Paros, Cyclades Islands

  • 8 berths
  • 3 cabins
  • 2 WC
  • Included Outboard Engine
  • Bow thruster
  • GPS Plotter in cockpit
Starting from€3,030

Boat price + skipper cost

  • Sailing boat
  • 2016
  • 52 ft

Jeanneau Sun Odyssey 519

Paros, Cyclades IslandsKalamaki, Athens

  • 10 berths
  • 4+2 cabins
  • 3 WC
  • Included Outboard Engine
  • Bow thruster
  • Air conditioning
  • Generator
Starting from€6,860

Boat price + skipper cost

  • Sailing boat
  • 2017
  • 71 ft

Hanse 675

Mykonos, Cyclades IslandsKalamaki, Athens

  • Skipper on board
  • 6 berths
  • 3 cabins
  • 3 WC
  • No security deposit
  • Included Outboard Engine
  • Bow thruster
  • Air conditioning
Starting from€18,000

Boat price + skipper cost

  • Sailing boat
  • 2006
  • 51 ft

Bavaria 50 Cruiser

Paros, Cyclades Islands

  • 10 berths
  • 3+2 cabins
  • 3 WC
  • Bow thruster
  • GPS Plotter in cockpit
Starting from€2,853

Boat price + skipper cost

  • Sailing boat
  • 2018
  • 44 ft

Jeanneau Sun Odyssey 440

Paros, Cyclades IslandsLavrion, Athens

  • 10 berths
  • 4 cabins
  • 2 WC
  • Included Outboard Engine
  • Bow thruster
  • GPS Plotter in cockpit
Starting from€4,250

Boat price + skipper cost

  • Sailing boat
  • 2002 (refit 2014)
  • 46 ft

Beneteau Oceanis 473

Mykonos, Cyclades Islands

  • 10 berths
  • 4+1 cabins
  • 2 WC
  • Included Outboard Engine
  • Optional Gennaker
  • Bow thruster
  • GPS Plotter in cockpit
Starting from€2,585

Boat price + skipper cost

  • Sailing boat
  • 2020
  • 51 ft

Hanse 508

Mykonos, Cyclades IslandsKalamaki, Athens

  • 12 berths
  • 4+2 cabins
  • 3 WC
  • New boat
  • Optional Gennaker
  • Bow thruster
  • Self taking jib
Starting from€6,230

Boat price + skipper cost

  • Sailing boat
  • 2021
  • 39 ft

Dufour 390 Grand Large

Paros, Cyclades Islands

  • 6 berths
  • 3 cabins
  • 3 WC
  • New boat
  • Included Outboard Engine
  • Bow thruster
Starting from€2,891

Boat price + skipper cost

  • Sailing boat
  • 2018
  • 44 ft

Jeanneau Sun Odyssey 440

Paros, Cyclades IslandsLavrion, Athens

  • 8 berths
  • 4 cabins
  • 2 WC
  • GPS Plotter in cockpit
Up to-24%
Starting from€3,494

Boat price + skipper cost

  • Sailing boat
  • 2018
  • 46 ft

Dufour 460 Grand Large

Paros, Cyclades Islands

  • 8 berths
  • 4 cabins
  • 4 WC
  • Included Outboard Engine
  • Bow thruster
  • Air conditioning
  • Watermaker
Starting from€3,161

Boat price + skipper cost

  • Sailing boat
  • 2020
  • 46 ft

Dufour 460 Grand Large

Mykonos, Cyclades Islands

  • 10 berths
  • 4 cabins
  • 4 WC
  • New boat
  • Included Outboard Engine
  • Bow thruster
  • GPS Plotter in cockpit
Starting from€3,170

Boat price + skipper cost

  • Sailing boat
  • 2019
  • 46 ft

Bavaria Cruiser 45

Paros, Cyclades Islands

  • 10 berths
  • 4+1 cabins
  • 2 WC
  • Bow thruster
Starting from€3,680

Boat price + skipper cost

  • Sailing boat
  • 2020
  • 44 ft

Dufour 430 Grand Large

Paros, Cyclades Islands

  • Skipper on board
  • 10 berths
  • 3+1 cabins
  • 2 WC
  • New boat
  • Included Outboard Engine
  • Bow thruster
  • GPS Plotter in cockpit
Starting from€2,950

Boat price + skipper cost

  • Sailing boat
  • 2018-2021
  • 42 ft

Jeanneau Sun Odyssey 419

Paros, Cyclades Islands

  • 8 berths
  • 3 cabins
  • 2 WC
  • Bow thruster
  • GPS Plotter in cockpit
Starting from€3,169

Boat price + skipper cost

  • Sailing boat
  • 2020
  • 51 ft

Hanse 508

Mykonos, Cyclades IslandsKalamaki, Athens

  • 12 berths
  • 6 cabins
  • 4 WC
  • New boat
  • Bow thruster
  • GPS Plotter in cockpit
  • Self taking jib
Starting from€6,770

Boat price + skipper cost

  • Sailing boat
  • 2018
  • 51 ft

Bavaria Cruiser 51

Mykonos, Cyclades Islands

  • 10 berths
  • 4+1 cabins
  • 3 WC
  • Bow thruster
  • GPS Plotter in cockpit
Starting from€4,610

Boat price + skipper cost

  • Sailing boat
  • 2021
  • 46 ft

Bavaria Cruiser 45

Mykonos, Cyclades IslandsKalamaki, Athens

  • 12 berths
  • 4+1 cabins
  • 2 WC
  • New boat
  • Bow thruster
Starting from€3,629

Boat price + skipper cost

  • Sailing boat
  • 2012
  • 55 ft

Beneteau Oceanis 54

Mykonos, Cyclades Islands

  • 12 berths
  • 4+1 cabins
  • 3 WC
  • Bow thruster
  • GPS Plotter in cockpit
Starting from€4,076

Boat price + skipper cost

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