Inter-island and Multi-day Adventures

Pre-covid, a multi-day sailing charter in Hawaii was the best adventure to sign up for. It still looks like it will be a while before I will have the opportunity to safely 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.

Sail Blue Hawaii                                (808) 347-0235


“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.

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

Oahu possiblities:

  • A wonderful downwind sail to the west end (Makaha) where there is beautiful snorkeling and possible dolphin encounters.
  • Kaneohe Bay, windward side Oahu.  When you wake up here in the morning you will think you have reached nirvana.

sunrise over Chinaman’s Hat:

           view from the top of Chinaman’s Hat:

Molokai possibilities:

  • Overnight at Hale o Lono…a quiet non-descript anchorage but a walk ashore will find you on your own beautiful, private beach.
  • Kaunakakai: the island’s only town. Guests often rent a car to drive the island perimeter and see the beauty of Molokai from the land perspective.
  • Take a mule ride down to the Kalaupapa Peninsula.  You’ll experience an incredible lesson in history and human endurance. Extended trip required.
    Suggested reading: “Molokai” by Alan Brennert.
    Also, visit “,_Hawaii“.
  • Papohaku Beach:  beautiful!
  • North shore Molokai:  the highest sea cliffs in the world rise 3,000 ft above sea level…awesome. Summer only.

sunset while sailing Molokai’s north shore: 

Day time; Molokai’s north shore  

Lanai possibilities:

  • Anchor on the remote “backside” at Nanahoa (Five Needles) and enjoy fabulous snorkeling.
  • Manele Bay: beautiful beach with 5-star resort. Dolphins often come into the bay in the morning. After days on the boat, our guests love the feel of luxury if they wander up to the resort treating themselves to an evening at the pool bar or restaurant.
  • If you’d like to visit “Garden of the Gods”, old Lanai town, or do some 4-wheel driving to remote Shipwreck Bay, this can all be arranged. Extended trip required.

Maui possibilities:

  •  Lahaina, an historic whaling village, is the stop for guests to do a little shopping, browse classy art galleries, enjoy a restaurant and/or a cold beer at the historic Pioneer Inn.  This is also the jumping off place for any touring you’d like to do:  again, rental car is the way to go if you want to venture inland.  Or, how about a HOG ride to the top of Haleakala (“House of the Sun”)!    Extended trip required.
  •     During the winter months, you’ll be delighted and astounded by up-close-and-personal humpback whale watching in these waters.

  • Honolua Bay on Maui’s northwest coast is a wonderful anchorage with more great snorkeling.  Can you say:”humuhumunukunukuapua’a”???

So, come on sailor, LET’S GO SAILING!

Sign up for your Hawaii sailing adventure today!

Contact us for rates and schedules