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The Hawaiian Islands lie well north of the equator, at about the same latitude as Cuba. However, everything about them makes them true South Pacific Islands, especially from a historical and cultural perspective. The 50th state consists of over 130 islands, but most of the land mass is on the eight main islands. We will be visiting four of them on this trip. Our sailing area will also include the Hawaiian Islands Humpback Whale National Marine Sanctuary. We have reserved two forty-foot, three cabin boats from Honolulu Sailing Company, based near Waikiki Beach.

In addition to lots of sailing, we should have several opportunities for snorkeling, as well as some time on land, and to learn more about the islands and their culture.

The following itinerary is what we hope to do. Wind and waves may necessitate changes.

January 27 (Saturday)
Late afternoon, pre-board the boats at Kewalo Basin Harbor, about a mile west of Waikiki Beach. You must arrive no later than this, as we start out early the next morning.

January 28 (Sunday) - Sail to Molokai
Depart from Honolulu for the west end of Molokai. Sail past Waikiki, Diamond Head and Oahu’s “Gold Coast” to Koko Head. Between Koko Head and Molokai is the famous Kaiwi channel, the stuff of legend, and the final run in the Transpac yacht race. After a spirited sail to Molokai, we duck behind the lee of the island and sail to our first anchorage, Hale O’Lono harbor. Lono is far removed from civilization. This is the dry side of Molokai and we are a long way from the lights of civilization. The stargazing is literally “out of this world”.

January 29 (Monday) - Sail to Lanai
This morning’s sail takes us to Lanai, where we pass along sea cliffs and the site of an ancient Hawaiian fishing village. We’ll stop here for lunch and snorkeling, and, time permitting, a short hike to an overlook where you can see ruins and get a great view of the island. After lunch, we will sail to Manele Bay, our stop for the night.

January 30 (Tuesday) - Sail to Honolua Bay, Maui
Today’s sail promises to be a real treat, as we’ll head east towards Molokini (a tiny atoll off Maui) and into prime whale watching waters. At this time of year, the humpback whales have migrated down from the cold Alaska waters to mate and give birth to last year’s breeding activities. We will then continue to the north side of Maui and Honolua Bay, which has a rocky shoreline with a small beach, coral reefs in a marine preserve, and world-renowned surf break.

January 31 (Wednesday) - Sail to Lahaina
After a leisurely breakfast, and maybe a swim, it’s a short sail to Lahaina, while keeping an eye out for whales, of course. We’re in no rush, so hopefully we’ll sail for a few hours and head in after lunch sometime. The plan is to have a group dinner at the Lahaina Fish Company.

February 1 (Thursday) - Layover day in Lahaina
A full day on your own to explore parts of Maui beyond the harbor. Perhaps take an island tour, or rent a car and drive to the top of Haleakala (bring your fleece, it's over 10,000 feet, and windy!). More details about possible shore activities will be provided at a later date.

February 2 (Friday) - Sail to Kaunakakai, Molokai
Molokai is probably best known for the Leper Colony that Belgian priest Father Damien made famous. Molokai has also been called the Friendly Isle, though it sees very little tourism. The plan is to overnight in Kaunakakai, the main city on Molokai. As it’s a short sail, we should arrive in time for a few afternoon shore activities.

February 3 (Saturday) - Sail to Kalaupapa, Molokai
We sail around the east end of Molokai to the north shore. Primal is how most people describe this coast. It is like stepping back in time, and the area has an awesome presence about it. We will sail past Halawa Valley, with a view of an incredible waterfall, past many other falls, and valleys. The north shore of Molokai was revered by the Hawaiian people as a magical place. Our destination for the night lies just behind a small island at the mouth of a large and uninhabited valley, sailing between them into a protected anchorage near Kalaupapa. You can see the original church and buildings built by Father Damien to care for the afflicted who were once marooned on these shores.

February 4 (Sunday) - Sail to Papohaku Beach, Molokai
We get a late start, and set sail around Kalaupapa, headed for the western tip of Molokai. We sail past the remaining cliffs of this coast on a fast downwind run to Ilio Point. Once around the point we tuck in close to shore and enjoy sailing in the lee of the island to our next anchorage, just off a sandy beach. From here you can see Oahu silhouetted in the setting sun.

February 5 (Monday) - Return to Oahu
This is a great day's run that is on a fast tack across Hawaii's best fishing grounds. You will see the island of Oahu appear from the sea mist, and try to guess which geographical feature becomes Diamond Head. We'll sail past Koko head, past Hawaii's Gold Coast and right under Diamond Head to Waikiki. Stop for a quick swim, a chance to collect your thoughts and things, then pull into Honolulu Harbor to disembark.

February 6 (Tuesday)
This is the first day you should plan to travel home. While there are a few flights that leave Honolulu in the late evening, there is no way to predict when we will return to the charter base on Monday, because that day's sail is a long one.

The Boats

Beneteau Oceanis 393

Beneteau First 42.7

Both boats are three-cabin, two head models. As there will be a licensed captain on each boat (a charter company requirement), we will be putting just five members on each, with a Club Skipper on each serving as the first mate. If there are sufficient sign-ups, we may be able to charter a third boat.

The cost of the trip is $1725.00 per person (Skippers - no discount). Trip price includes charter fees, slip fees for two nights (Wednesday and Thursday nights), and a group dinner in Lahaina. Fuel, provisioning, other mooring fees, and other incidentals will be covered by each boat's crew. A $200.00 non-refundable deposit is required to hold your position. Please make your check payable to The Sailing Club, Inc. and mail it, along with your completed reservation and release forms, to Joel Mack at the address below. Reservations will be processed beginning April 8, 2017 with a random draw of those received by that date. All reservations received after that date are on a first-come, first-served basis. Three additional payments will be due as follows:

May 15    $500.00
July 15    $500.00
Sept. 15    $525.00

NOTE: A special cancellation policy applies for this trip. Any cancellations after October 28, 2017 will not be eligible for a refund, unless a replacement is found.

Travel insurance is not included in the trip price. Confirmed participants should make their own decisions regarding insurance that would provide coverage appropriate to their needs and that they feel best protects them in their individual situations. One useful resource for comparing plans is As always, read all policy terms and conditions carefully.

Please note that sailing conditions are dynamic, that your safety, and that of your crewmates, depends on your good physical health and agility.


Trip Leader     

Assistant Trip Leader

Steve Krakauer               
11 Clark Ct
Basking Ridge, NJ 07920        
Joel Mack        
150 Kings Highway
Middletown, NJ 07748



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OWT Trip

Rock Hall, MD
May 20-21,2017

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June 24-26, 2017

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Day Sail
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July 9, 2017

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Sept. 15-18, 2017

October Trip

Tilghman Island
Oct. 20-23, 2017