The Pacific Offshore Challenge is a one week cruise and learn sailing experience around the Hawaiian islands on the 35 ft classic sailing yacht s/v Gemini. On this live aboard sailing experience with 2 to 4 student/crew plus instructor/ Captain Greg, the voyage takes you from our homeport of Ala Wai Harbor to a few of our neighbor islands and back. The exact itinerary is determined and planned by the crew on the first morning, depending on the weather and boat’s range limitations, but under generally expected conditions we follow our favorite itinerary:
Day 1 – Planning/ familiarization with boat, local sail training, maneuvering and MOB drills and first night moored in Keehi Lagoon, the next harbor over, dinner at La Mariana.
Day 2 – Sail upwind against the Trades (or if we’re lucky, reach with Kona winds) across the Kaiwi Channel to Lono Harbor on Molokai, anchor for the night, dinner served aboard.
Day 3 – Sail to Lanai, anchor off Pinnacles, sail around the south end to Manele Bay, moor in a guest slip, swim on Hulopo’e beach, dinner at Four Seasons.
Day 4 – Sail to Lahaina Maui, anchor offshore or if we’re lucky get a guest slip in the harbor, anchor or take an LYC buoy and dinghy in to explore the fun historic Lahaina town, dinner at Lahaina Yacht Club or wherever the crew decides.
Day 5 – Sail downwind across the Pailolo Channel back to Molokai, moor in Kaunakakai, either side tie to the guest dock or anchor out and dinghy in to explore Kaunakakai, dinner at Paddler’s Inn!
Day 6 – Land exploration of Molokai, rent a U Haul truck from Rawlins and drive east to Halawa Bay, north to Kalapapa lookout and west to Papahaku/ Kepuhi beaches, end up at Paddler’s again or maybe Hiro’s Ohana grill at Hotel Molokai.
Day 7 – Sail back down the Kaiwi channel to Oahu, sail around Diamond Head around sunset.
* Variations on this itinerary: If the Trades aren’t too strong or we have Kona winds, we might decide to return from Maui and sail the north shore of Molokai, maybe skip Lono Harbor and go to Kaunakakai instead. Or if we can’t get a guest slip in Manele Bay, we can stay at anchor off the Pinnacles and have a longer sail to Lahaina. The weather always determines the best route and we might spend an extra day on land, maybe explore Lanai one full day instead of Molokai.
* While sailing is the main event, the places we’re sailing to are really worth exploring too so this is about balancing learning to sail and exploring Hawaii off the beaten path. On this one week voyage we cover all the theory discussion and practice all the skills for two ASA intermediate cruising levels (ASA 103 Basic Coastal Cruising and ASA 104 Bareboat Cruising) ASA 101 Basic Keelboat is a prerequisite for this course and the Pacific Offshore Challenge is always scheduled after an ASA 101 Basic Keelboat course, so you can plan a 9 day learn to sail trip to Hawaii.
The Pacific Offshore Challenge is scheduled about once per month or whenever there is interest, so please check us out and contact us for more information!
Update: June 2022 – Sail Hawaii has been sold to and is managed now by Pink Sails Waikiki. Please contact them for more information.
