Hawaii Itineraries: Day Charters and Multi-Day Routes

Hawaii’s cruising ground centres on the sheltered waters between Maui, Lanai and Molokai – the triangle that offers the calmest conditions, the richest marine life and the most varied anchorages. The itineraries below are designed to be combined: a guest looking at the 3-day Maui–Lanai route and the 4-day Maui–Big Island itinerary can stitch them together into a comprehensive 7-day voyage covering four islands without repeating a single stop. Every itinerary is fully customisable – your Boatcrowd charter specialist and onboard captain tailor stops, pacing and activities to your group’s interests and the conditions on the day.

Day Charter Routes

Molokini Crater and South Maui

Depart Maalaea Harbour on Maui’s south coast at first light and cruise three miles offshore to Molokini Crater. Arrive before the tour boats and snorkel the inner crescent in visibility that regularly exceeds 45 metres – butterflyfish, parrotfish, moray eels and whitetip reef sharks in a marine reserve of extraordinary clarity. Your chef serves breakfast on the aft deck with the crater glowing in the morning sun. Continue south along Maui’s coast to Makena (Big Beach) for a late-morning swim, then cruise to the old fishing village of Kihei for lunch. Return to Maalaea by mid-afternoon.

Maui to Lanai – Hulopoe Bay

Cross the Au’au Channel from Lahaina – just 9 miles, roughly 45 minutes at cruising speed. During whale season (December–April), this short crossing is one of the best whale-watching passages in the Pacific, with humpback mothers and calves visible from the flybridge. Arrive at Hulopoe Bay on Lanai’s south coast, a marine preserve with calm, clear water, excellent snorkelling and spinner dolphins that often enter the bay in the early morning. Spend the morning swimming and exploring the tide pools, then enjoy lunch on the beach or aboard. Return to Lahaina in the late afternoon with the setting sun behind you.

Kona Coast and Kealakekua Bay (Big Island)

Depart Honokohau Harbour and cruise south along the Big Island’s Kona coast to Kealakekua Bay – roughly 12 miles, a 45-minute run past black lava fields meeting turquoise water. Anchor in the marine sanctuary and snorkel above pristine coral reef, with spinner dolphins, green sea turtles and clouds of tropical fish. The white Captain Cook Monument stands on the far shore, marking the spot where the British explorer was killed in 1779. Your chef prepares lunch aboard, then cruise back north along the coast, stopping at a sheltered cove for an afternoon swim. Return to Honokohau by late afternoon, with an optional night manta-ray dive arranged for after dinner.

Multi-Day Itineraries

3-Day Hawaii Yacht Charter Itinerary: Maui, Lanai and Molokai

Day 1: Lahaina, Au’au Channel and Lanai

Board your yacht at Lahaina Harbour on Maui’s western coast by mid-morning. After a welcome briefing and champagne toast on the flybridge, cruise west across the Au’au Channel toward Lanai. During whale season, your captain slows for whale encounters – humpback mothers with calves, breaching males and travelling pods are all common in this 9-mile channel. Arrive at Hulopoe Bay by late morning, anchor in the marine preserve and spend the afternoon snorkelling, swimming and exploring the tide pools. Spinner dolphins may make an appearance in the bay’s shallow waters. Dinner aboard as the sun sets behind Lanai’s western cliffs.

Day 2: Lanai’s South Coast to Molokai

Cruise north from Lanai along its sheltered western coast, watching for spinner dolphins and sea turtles. Cross the Kalohi Channel to Molokai – roughly 25 nautical miles, about 1.5 hours at cruising speed. Molokai is the least developed of Hawaii’s main islands, with no traffic lights, no buildings taller than a coconut palm, and a fierce pride in traditional Hawaiian culture. Anchor off the island’s south coast and explore the fringing reef by snorkel – Molokai’s reef system is the longest in Hawaii, stretching nearly 25 miles. In the afternoon, tender ashore to visit Kaunakakai, the island’s main town, for fresh bread from Kanemitsu’s Bakery (a local institution since 1922). Dinner aboard in a calm anchorage as the Milky Way appears overhead – Molokai has some of the darkest skies in Hawaii.

Day 3: Molokai’s West Coast to Maui

Spend the morning cruising along Molokai’s dramatic north coast by tender or from the yacht’s flybridge (conditions permitting) – this stretch of coastline features the tallest sea cliffs in the world, rising over 1,000 metres from the ocean. Waterfalls cascade down the green cliffs, and the scale is almost beyond comprehension from sea level. Return to the yacht and cross back to Maui, arriving at Maalaea by early afternoon. Cruise to Molokini Crater for a late-afternoon snorkel in the crystal-clear crater, then return to Lahaina Harbour by early evening.

Guests looking for a longer voyage can combine this 3-day itinerary with the 4-day Maui–Big Island route below for a 7-day charter covering four islands, world-class snorkelling, whale watching, night manta-ray encounters, and some of the most varied scenery in the Pacific – without repeating a single stop.

4-Day Hawaii Yacht Charter Itinerary: Maui to the Big Island

Day 1: Molokini Crater and South Maui

Board your yacht at Maalaea Harbour by mid-morning. Cruise three miles offshore to Molokini Crater and drop anchor outside the crescent for a morning of world-class snorkelling in the marine reserve. Visibility routinely exceeds 45 metres, and the 250-plus fish species and 38 hard-coral species make this one of Hawaii’s top underwater experiences. Your chef lays out lunch on the aft deck, then cruise south along Maui’s coast to the Ahihi-Kinau Natural Area Reserve – a lava-field coastline with sheltered coves and outstanding snorkelling over fresh lava reef. Anchor off south Maui for the evening, with dinner aboard as the last light catches the summit of Haleakala.

Day 2: Maui to the Big Island – Kohala Coast

Depart south Maui at first light and set course for the Big Island – roughly 30 nautical miles across the Alenuihaha Channel, a 2–3 hour crossing that your captain times for the calmest conditions (typically early morning). Arrive on the Big Island’s Kohala Coast by late morning and anchor off one of the beautiful white-sand bays along this dry, sun-drenched stretch of coastline. Snorkel over volcanic reef, swim from the yacht’s platform, and enjoy a leisurely lunch as the Big Island’s volcanic peaks – Mauna Kea (4,207 metres) and Mauna Loa (4,169 metres) – tower above you. In the afternoon, cruise south to Honokohau Harbour for provisioning. Dinner aboard in the harbour, with an optional sunset walk along the ancient fishponds at Kaloko-Honokohau National Historical Park.

Day 3: Kealakekua Bay and Night Manta Rays

Cruise south from Honokohau to Kealakekua Bay – roughly 12 miles along the Kona coast. Anchor in this protected marine sanctuary and spend the morning snorkelling above pristine coral reef, with spinner dolphins, green sea turtles and hundreds of reef fish species. The Captain Cook Monument stands white against the green hillside on the far shore. After lunch aboard, visit Pu’uhonua o Hōnaunau National Historical Park (the Place of Refuge), a 180-acre sacred site with reconstructed temples, royal fishponds, and a stone wall 12 feet high and 18 feet thick that once offered sanctuary to those who broke the ancient kapu laws. Return to the yacht and cruise back to Keauhou Bay for the evening’s highlight: a night manta-ray snorkel. Float at the surface as mantas with 5-metre wingspans glide beneath you, barrel-rolling through plankton illuminated by underwater lights.

Day 4: Kona Coast and Return to Maui

Spend the morning exploring the Big Island’s Kona coast by tender – lava-rock tide pools, hidden coves, and one final snorkelling stop at a sheltered bay of your captain’s choosing. An optional helicopter tour over Kilauea volcano can be arranged for the morning (roughly 45 minutes, departing from the Kona coast). Enjoy a farewell brunch on the aft deck, then set course north-east for Maui – arriving at Lahaina or Maalaea by late afternoon for disembarkation.

Combine this 4-day Maui–Big Island itinerary with the 3-day Maui–Lanai–Molokai route above for a 7-day charter that covers four islands and offers an unmatched breadth of Hawaiian experiences – from the towering sea cliffs of Molokai to the manta rays of Kona, with whale watching, volcanic landscapes and world-class snorkelling along the way.

5-Day Hawaii Yacht Charter Itinerary: Maui, Lanai, Big Island and Kona Coast

Day 1: Lahaina and Lanai’s Hulopoe Bay

Board at Lahaina Harbour and cross the Au’au Channel to Lanai. Arrive at Hulopoe Bay by late morning for snorkelling, swimming and spinner-dolphin watching in this sheltered marine preserve. Explore the tide pools and beach through the afternoon. Dinner aboard with Lanai’s quiet shoreline and star-filled sky as your backdrop.

Day 2: Lanai to Molokini Crater

Cruise east from Lanai back toward Maui, stopping at Molokini Crater for a morning snorkel in the marine reserve. The 45-metre visibility and 250-plus fish species make this a world-class underwater experience. After lunch aboard, cruise south along Maui’s coast to the Ahihi-Kinau lava coastline for a late-afternoon swim over volcanic reef. Anchor off south Maui for the evening.

Day 3: Maui to the Big Island – Kohala and Kona

Depart at dawn for the Alenuihaha Channel crossing to the Big Island – roughly 30 nautical miles, timed for the calm early-morning conditions. Arrive on the Kohala Coast by late morning and anchor off a white-sand bay for swimming and snorkelling. Continue south to Honokohau Harbour for provisioning, then cruise to a sheltered cove along the Kona coast for the evening. Dinner aboard as the sun sets behind the Pacific.

Day 4: Kealakekua Bay, Place of Refuge and Night Mantas

Cruise south to Kealakekua Bay for a morning of snorkelling in the marine sanctuary. Visit Pu’uhonua o Hōnaunau National Historical Park after lunch, then return to Keauhou Bay for the evening’s manta-ray night snorkel – an experience found nowhere else on Earth.

Day 5: Kona Coast and Return to Maui

A final morning on the Big Island – an optional helicopter tour over Kilauea, a last snorkel at a hidden Kona cove, or a deep-sea fishing excursion in waters famous for marlin and yellowfin tuna. Farewell brunch on the aft deck, then cruise back to Maui for late-afternoon disembarkation at Lahaina or Maalaea.