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    Maui Custom Charters

    Maalaea, HI
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    Book Maui Custom Charters

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    Sail on a Private Maui Whale Watching Cruise

    Private sailboat whale watch from Ma‘alaea Harbor (Jan–Apr), with hydrophone listening

    $2,456.18
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    Private 3-Hour Whale Watching Cruise in Maui

    Sail a private catamaran whale watch from Ma‘alaea Harbor with hydrophone listening

    $4,093.63
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    Private 4-Hour Maui Afternoon Snorkel & Sail Charter

    Snorkel and sail by private yacht to West Maui cliffs or North Kihei reefs

    $3,274.91
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    Private Whale Watch Cruise in Maui

    Cruise Maʻalaea Harbor on a private humpback whale watch for up to 13 guests

    From$1,364
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    4-Hour Shared Bottom Fishing Charter in Maalaea Harbor

    Bottom fish in a small group with bait and tackle provided

    From$284person
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    Sail a Private Sunset Charter in Maui

    Cruise Ma’alaea Bay on a private sunset sail for up to 6

    $1,637.45
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    Private Sunset Sailing Charter in Maalaea Bay

    Sail a private sunset catamaran with appetizers and room for up to 6

    $2,729.09
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    Private Morning Snorkel Charter in Maalaea Bay

    Private morning snorkel by boat from Ma’alaea Bay

    From$4,093
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    Private Bottom Fishing Charter in Maui

    Fish Maui’s bottom grounds on a private charter with captain and crew

    From$2,160
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    Private Morning Snorkel & Sail Charter in Maui

    Sail Maalaea Bay and snorkel a private spot, up to 6 guests

    From$3,274
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    Sail on a Private Charter in Maalaea Bay

    Book a private S/V Nova sailing charter for up to 6 guests

    From$1,637
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    Snorkel & Sail Full-Day Charter in Maalaea Bay

    Sail Maalaea Bay and snorkel from a private 42' monohull

    $5,731.08
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    Full-Day Snorkel & Sail Catamaran Charter In Maui

    Sail Maalaea Bay on a private catamaran with guided snorkeling and lunch

    $9,551.81
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    Fishing & Snorkeling Charter in Ma'alaea Bay

    Fish and snorkel on a private charter in Ma’alaea Bay

    From$6,140
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    Snorkel & Sail Private Morning Charter in Maui

    Private morning snorkel and sail to West Maui or North Kihei spots

    From$6,822

    Review summary

    With a perfect track record across well over a hundred reviews, this charter operation consistently delivers exceptional private sailing experiences around Maui. The crew—particularly Captain Anna, JJ, Nessa, Tim, and Marcella—earn universal praise for being knowledgeable, personable, and genuinely attentive to their guests. They regularly spot whales, dolphins, and sea turtles during tours, and their expertise about marine life adds real depth to every outing. The boats themselves (a 42-foot Catalina and 47-foot Leopard catamaran) are described as immaculate, spacious, and comfortable. What stands out is how the crew adapts to different occasions. Guests have celebrated proposals, birthdays, and even memorial services, with the team handling each event thoughtfully and professionally. They're also skilled photographers who capture beautiful moments without being asked. Whether you're snorkeling, whale watching, or simply enjoying a sunset sail, the crew creates a relaxed atmosphere while prioritizing safety and comfort. Communication from booking through the trip itself is reportedly excellent, with weather updates and helpful planning support. This is clearly a top-tier choice for anyone wanting a memorable, personalized day on the water.