Our Greek Island “Sailing Holiday Charters” are custom designed and personalized for you our customers. You nominate the start and end dates of the charter, as well as any particular Greek Islands you would like to visit. Our skipper does the rest and with over 10 years experience in the Greek Islands, our skippers and crew are not only the most sought after charter captains in the Greek Islands, but they have a real love for the Dodecanese and Cyclades and know the best routes, landmarks and activities on the way. To give you some examples of our sailing holiday charters here are four very different but equally charming examples:

Sail Kos to Patmos

The “northerly” trip to Patmos and return combines not only wonderful sailing but an opportunity to face off against Kalymnos (if you dare) and a  chance to experience a diverse collection of island lifestyles and cultures. Pserimos and Marathis are remote Greek Islands with pristine beaches and landscapes.

Sail Kos to Rhodes

A southerly charter from Kos includes sailing to Tilos then visiting the picturesque island of Alki, a stop in Rhodes, on to Simi and then the picturesque island of Nisyros. Pristine waters, great island hiking, a dormant volcano, fishing and archaeological ruins plus restaurants and beaches and deserted bays. 

Sail Mykonos to Santorini

This is a gem whether you start in Naxos, Mykonos or Santorini. There are so many options and islands to explore on your Greek island sailing holiday including the best that the Cyclades Islands have to offer. 

Sail Rhodes to Kastelorizo

This is off the beaten track but a one way sailing charter crammed with adventure and sites to see on the Turkish Coast. Your chance to do almost any activity from exploring ruins to paragliding on your sailing charter 

Wildside’s sailing holiday charters utilize “Kool”, our high performance Catamaran (Catana 381). While any Wildside “Sailing Holiday Charter” can be fully customized (both in terms of location and focus), you may wish to view a few sample itineraries for Sailing Holidays in Greece offered up by our skippers. We have one way sailing holiday charters and charters that start and finish from very interesting islands.

Greek Island Sailing Holiday Charters from Wildside – Life is Now!