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Two Humans and a Dog sail Mexico on a Sea Maid Ketch

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Cruising Notes: Overview of Sailing the Hawaii Islands

Sailing the Hawaii Islands is a wonderful experience if you don’t need luxurious marinas. The people are lovely, each island has its own character for variety, and the weather and wind are usually magnificent. If you proceed up the island chain from southeast to northwest as we did you will often have perfect trade wind conditions.

Overview | Hawaii | Maui | Molokai | Oahu | Kaua’i

Northwest and Downwind through the island chain
Northwest and Downwind through the island chain

Overview

We arrived in Hilo in late August 2008 and spent the next three weeks sailing the Hawaii Islands from Big Island to Maui, Molokai, Oahu and Kauai. Since all the anchorages we visited except Hanalei Bay in Kauai were protected from NW swells that predominate in winter, these notes may also be useful in winter.

Due to a law passed in the 1960s, public marinas in Hawaii are strictly limited to what they can charge. For our 40′ boat, this was free to $10/night. Anchorages charged up to $7 per night but were often free for less than 3 nights. The one marina we stayed in charged $10/night. As a result of these limited charges, anchorages and public marinas in Hawaii are not maintained to standards found in most of the US. However, if you’re careful and take responsibility for what you tie to and how you anchor, Hawaii is a delightful and inexpensive destination.

The passages between islands, especially the narrower ones, are reputed to be very tricky at times. The trade winds funnel between the islands and can create large swells and high winds. Although we always treat unfamiliar waters with respect, we were lucky and just found great winds and a bit of chop. However the topography could create serious seas, so please be careful or cross evenings or early mornings. These are the major channels that we crossed:

LocationChannel NameDistance (nm)
Big Island to MauiAlenuihana30
Maui to MolokaiPailolo20
Molokai to OahuKaiwi20
Oahu to KauaiKauai80

Dogs in Hawaii

We brought our dog to Hawaii with us, following the rules set up by the Department of Agriculture for importation of pets. Although the form is daunting and you must start the process months before you leave, it is possible to comply. Once we arrived they were very pleasant to deal with. The vet inspected our dog at the dock on our arrival and immediately approved her for the visit, so she spent no time in quarantine . See full details on pet importation here.

Destinations

We started in Hilo, Big Island and travelled downwind (northwest) to Kauai. We visited these locations along the way:

  • Big Island  – Hilo
  • Maui – Lahaina
  • Molokai – Kaunakakai
  • Oahu – Kaneohe Bay
  • Kauai – Hanalei Bay and Nawiliwili

Other Resources (by other people)

  • Cruising Guide to the Hawaiian Islands – Carolyn and Bob Mehaffy (updated 1998)
  • Cruising Hawaii by Endless Summer (August 2006)

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