Honokohau Harbor, Big Island
Hanalei Bay, Kauai
Lahaina Roadstead, Maui
Kaneohe Bay, Oahu
Manele Bay, Lanai
Snorkel Molokini Crater’s protected waters
Watch humpback whales in the Auau Channel
Hike to Hanakapiai Falls on the Napali Coast
Explore Hawai’i Volcanoes National Park
Paddle an outrigger canoe with a local crew
Napali Coast, Kauai
Hawai’i Volcanoes National Park
Lahaina, Maui
Waikiki, Oahu
Hilo, Big Island
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April through October offers the calmest seas and least rain across most islands, though Hawaii’s climate stays mild enough for chartering nearly year-round. Winter brings humpback whales to the channels between Maui, Lanai and Molokai from roughly December through April, alongside bigger surf on Oahu’s North Shore. Guests chasing calmer water for swimming and snorkelling generally do best in the summer months, when trade winds are steadier and rainfall lowest.
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Honolulu International Airport (HNL) on Oahu handles the most international traffic and connects onward to each island’s own airport: Kahului (OGG) on Maui, Kona (KOA) on the Big Island and Lihue (LIH) on Kauai. Many charter guests fly directly into whichever island their itinerary starts from rather than routing through Honolulu, since inter-island flights add time. Direct long-haul flights reach Honolulu from the US mainland, Japan, Australia and several other Pacific and Asian cities.
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Honokohau Harbor on the Big Island offers reliable shelter close to Kailua-Kona’s restaurants, while Hanalei Bay on Kauai’s north shore sits beneath dramatic green cliffs, though it’s only comfortable outside winter’s north swell. Lahaina Roadstead off Maui puts guests within reach of the old whaling town, and Kaneohe Bay on Oahu’s windward side is the island’s largest and most sheltered natural harbour. Conditions shift seasonally, so most captains plan a flexible route rather than a fixed anchorage each night.
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Ten to fourteen days allow a charter to properly cover two or three islands rather than rushing a single coastline, since the open channels between islands can bring rougher water than the sheltered leeward coasts themselves. A week is enough to explore one island in depth, such as Kauai’s Napali Coast or the Big Island’s volcanic south shore. Many guests pair Maui and Lanai, connected by the calm Auau Channel, for an easier multi-island route.
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Only by boat, since no road reaches this roughly 26-kilometre stretch of Kauai’s northwest shore, and its cliffs make it one of the most dramatic coastal approaches in the Pacific. Landing at beaches such as Nualolo Kai is possible in calm conditions, though anyone hiking inland beyond Hanakapiai on the Kalalau Trail needs a permit booked months ahead through Hawaii’s state parks system. Most charter guests are content simply admiring the coastline from the water.
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