This overview of sailing the Hawaiian Islands is intended for those contemplating sailing there or even those planning to charter once there. Despite those nay sayers who say Hawaii is not great cruising, we loved it. Each island had its own character, providing lots of variety. You do have to be prepared to anchor out, which we prefer anyway, but there are occasional marinas as well.

We spent less than three weeks in Hawaii in August 2008 and visited Big Island, 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, have the reputation of being quite tricky at times. The tradewinds funnel between the islands and can create large swells and high winds. Although we always treat unfamiliar waters with respect, we didn’t find anything particularly daunting during our visit. However the topography definitely could create serious seas, so please be careful or cross evenings or early mornings. These are the major channels that we crossed:
Location | Channel Name | Distance (nm) |
---|---|---|
Big Island to Maui | Alenuihana | 30 |
Maui to Molokai | Pailolo | 20 |
Molokai to Oahu | Kaiwi | 20 |
Oahu to Kauai | Kauai | 80 |
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 the process must be started months before you leave, it is possible to comply and once we arrived they were very pleasant to deal with. Our dog was inspected at the marina on our arrival and did not spend any 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, click the links to read about each area:
- Big Island – Hilo / Radio Bay
- Maui – Lahaina
- Molokai – Kaunakaukai Harbor
- Oahu – Kaneohe Bay
- Kauai – Hanalei Bay and Nawiliwili Harbor
Other Resources (by other people)
- Cruising Guide to the Hawaiian Islands – Carolyn and Bob Mehaffy (updated 1998)
- Cruising Hawaii by Endless Summer (August 2006)