Hawaii private sailing charter

Your custom private sailing charter can sail any time of day. Whatever length of time you wish. Our islands are most consistently graced with trade winds so any time is a good time to go sailing…✨SUNRISE, morning, afternoon, SUNSET. ✨ It is all good.

5 best private sailing ideas

  • A private sunrise cruise will set your day right, especially if you have just flown in from the east coast and your internal clock is not yet on Hawaii time.
  • Choose the one night of the month (or, the famous “blue moon” second night of the month) to sail from sunset to full moon. It is truly magical to see the full moon rise over Diamond Head after sailing into the sunset. 
  • There’s nothing more special than saying “I do” under a tropical sky  while sailing into the sunset.  Your captain will marry you with a personalized  service on your own private yacht.
  • Hawaii private sailing lesson: help set the sails and take the helm if you like as you learn the “ropes” of sailing.  The first thing you learn: they are not ropes.  They are “lines.” Captain Gaelyn will assist you to build your skills and confidence. For all levels of sailing experience.
  • Just for the joy of it. Choose a private sailing charter and it could well be the highlight of your Hawaii vacation.