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When the Club’s last trip to Hawaii ended in February 2018, and crews arrived at the airport for the flight home, many vowed to return. Sailing between the islands had far exceeded our expectations. The large number of whales sighted, hearing the whale songs while snorkeling, the food, the people, the knowledge and skill of the hired captains, the great sailing, the varied landscape and the culture of the citizens of Hawaii who actively protect their land and all people who live there, were all factors in our decision. Hawaii roughly translates to water and life force supreme. We agree.

The plan is for ten days of sailing, starting at the charter base in Honolulu. We'll sail to Molokai, Lanai, Molokini and Maui, before heading back to Oahu. We'll board the boats on Saturday, January 28th, but not leave port until the next morning. This will allow time for boat check-outs, after which gear can be stowed and provisions procured.

January 28 (Saturday)
Late afternoon, board the boats. Boat checkout and provisioning

January 29 (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 sailing 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.” Plan on an appetizer beach party as we watch the sun set.

January 30 (Monday) - Sail to Lanai
Today's sail takes us to Lanai, where we pass along sea cliffs and the site of an ancient Hawaiian fishing village. Our destination for the night is Hulopoe Bay. Located on Lanai's southern coast, Hulopoe Bay will greet us with a pearl-white sand beach and crystal blue waters. There is a Four Seasons resort nearby for dining, otherwise it's likely dinner aboard.

January 31 (Tuesday) - Sail to Molokini
The sail to the tiny atoll of Molokini promises to be a real treat, as we’ll head east 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. At the anchorage, there should be time to get in some excellent snorkeling before having dinner aboard.

February 1 (Wednesday) - Sail to Lahaina
After breakfast, and maybe a swim, it’s a northerly sail to Lahaina, while keeping an eye out for whales, of course. Along the way, we'll stop for lunch and some snorkeling at Coral Gardens, on the west side of Maui. Here you will see natural reef formations where specimen coral abound.

February 2 (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. This would also be a good opportunity to re-provision. A group dinner at Lahaina Fish Co. is planned.

February 3 (Friday) - Sail to Kaunakakai, Molokai
Molokai 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, as well as dinner at Paddlers Restaurant. Afterwards, you might want to stop for loaded bread - a pillowy loaf stuffed with your favorite fillings.

February 4 (Saturday) - Sail to Honoloa, Maui
We set sail east, back to the north coast of Maui, and anchor in Honoloa Bay, which has a rocky shoreline with a small beach, coral reefs in a marine preserve, and world-renown surf break. There should be plenty of time for snorkeling (listen for the whales!) before dinner aboard.

February 5 (Sunday) - Sail to Molokai
We'll aim for Molokai's west end in preparation for the next day's crossing back to Oahu. If conditions are favorable, we will sail across the primeval northern coast of the island, past the Halawa valley with its magnificent waterfall. 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.

February 6 (Monday) - Return to Oahu
This is a great day's sail that is on a fast tack across Hawaii's best fishing grounds. We'll return to the charter base and either have dinner ashore or a must-go party. For those who desire, it will be possible to stay on the boats and disembark on Tuesday morning.

February 7 (Tuesday)
We'll need to be off the boats by mid-morning, after the usual clean-up. 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 float plan can and may well be adjusted. Skippers will meet each morning to agree on the day's course based upon wind and weather. We have planned for many stops for snorkeling and land touring. But there are eight major islands that make up the Hawaiian Islands and we’re only visiting four of them. If you plan to arrive early or stay after the trip, plan and reserve a car well in advance. You can explore some options at Hawaii Travel

We have planned the layover day at just about the midpoint of the trip, February 2nd, in Lahaina. Lahaina was the capital city for the Hawaiian Kingdom from 1820 to 1845 and the museum there is worth the visit. It’s a charming old town and there are taxis and tours of the island, or you can just wander the town, but whatever you do, you must include a visit to the ancient banyan tree in the center of town.

Maui is one of the top whale watching destinations in the world. And it’s no wonder since it is estimated that over 10,000 humpback whales migrate to the waters off Maui each year. For more information about whales, visit the Maui Whale Watching Guide website.

Our final evening will be back at Honolulu base to allow time to pack, clean out refrigerators and perhaps enjoy a must-go dinner.


The Boats

Three monohulls have been chartered from Honolulu Sailing Company:

Beneteau 43
three cabins and two heads

Beneteau Sense 50
two cabins and two heads

Jeanneau 46
three cabins and three heads.

Each boat will be skippered by a local US Coast Guard licensed Captain provided by Honolulu Sailing. Each boat will have a Club-qualified skipper on board who will act as First Mate. On this trip, Club skippers will not receive a discount and the trip leader and assistant trip leader will each receive only a 25% discount for their trip planning efforts in an effort to keep trip costs down.

The cost of the trip is $2,650.00 per person (Skippers - no discount, Trip and Assistant Trip Leaders - $1,993.00). The trip price includes charter fees, licensed Captain, dinghies, and some slip fees. Fuel, provisioning, other mooring fees, the group dinner in Lahaina, gratuities to the Captain, and other incidentals will be covered by each boat's crew. A $500.00 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 form, to Mary Ann Gordon at the address below. Reservations will be processed beginning June 8, 2022 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:

July 1    $730.00          September 16    $710.00          November 15    $710.00


NOTE: A special cancellation policy applies for this trip. Any cancellations before November 28, 2022 will receive a full refund. Cancellations between November 29 and December 28 will receive a full refund only if a replacement is found. Cancellations from December 29th on will receive a full refund, less a $75 cancellation fee, only if a replacement is found.

Travel insurance

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. Two useful resources for comparing plans are and As always, read all policy terms and conditions carefully.

Pre-trip Meeting

A pre-trip meeting will be held about a month before the trip, at a time and place to be announced. All crewmembers should make every effort to attend in order to meet your crewmates, plan your meals, and/or to make car pool plans to airport.

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

Mary Ann Gordon
2714 Packer Ct.
Bridgewater, NJ 08807        
Bob Rainey        
2006 South Branch Dr.
Whitehouse Station, NJ 08889


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Rock Hall, MD
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