Hawaii multi-day sailing charter

Pre-covid, a multi-day sailing charter in Hawaii was the best adventure to sign up for. It still looks like a while before I have the opportunity to safety re-start these amazing sailing adventures. In the meantime, do book a private sailing charter for the day. A day-sail can be just the adventure you want.

Why chose a multi-day sailing charter?

“DON’T DREAM YOUR LIFE, LIVE YOUR DREAM”

“So, where are we going?”

“We are going sailing.”

… with island-stops and remote anchorages, sailing Oahu and Maui county from home-base, Oahu.  Where we go between day-one and journey’s end will depend on wind and weather. If you want to take time to have a day here and there to just hang out “on the hook” or at the beach, we can also accommodate this.

To understand Hawaii sailing is to understand her geography:  remote islands in the middle of the Pacific Ocean, shallow channels between these islands, high mountain peaks on each of these islands. This combination can brew very windy and high-sea-state conditions, especially in the channels.

Please understand this is NOT A CRUISE. IT IS adventure sailing…some call it “extreme” sailing…from easy light air and downwind runs to upwind sailing in strong winds and big seas.  Yes, on some days, conditions will be challenging. Rest assured: your USCG-licensed captain has sailed these waters for years and the boat is a sturdy workhorse in these conditions. This is blue water sailing at its best as only Hawaii can offer.

A multi-day charter in the Hawaiian Islands is perfect for adult sailors who have some ocean in their veins.  That being said, if you are sailing as a newbie, all you need is a sense of adventure, love of the outdoors and “roughing it”, and your cheery disposition.

Inter-island trips are offered as multi-day sailing vacations for adults only, (max four adults) not ferry services.  In other words, if all you want is a quick delivery from one island to another, this is not offered.  While land-time can be arranged, please understand that your destinations are weather-permitting and it is best to keep the sailing vacation schedule as loose as possible. Land-based activities can be arranged within an extended trip. Our inter-island sailing grounds are off Oahu, Molokai, Lanai and Maui.  They do not include passage to Big Island or Kauai.

sailing Oahu’s west end

Overnight adventures (minimum 2 nights, 3 days) are also available, Oahu-based. This is a wonderful way to enjoy tradewind sailing if the idea of channel crossing sounds more than your idea of “fun”.