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  • Best results for

    Sailing in Kaaawa, HI

    Showing 25-48 of 74 results
    Sunset Catamaran Sail with Open Bar in Waikiki

    Sunset Catamaran Sail with Open Bar in Waikiki

    Sail Waikiki at sunset with drinks included on a 1.5-hour happy hour cruise

    4.9 • 917 reviews
    $90/ person
    Waikiki Sunset Catamaran Sail

    Waikiki Sunset Catamaran Sail

    Sail off Waikiki at sunset with a pupu platter and skyline views

    4.8 • 160 reviews
    $95/ person
    Private Event Sailing Charter in Honolulu

    Private Event Sailing Charter in Honolulu

    Customize your private Waikiki charter for groups up to 40

    4.9 • 790 reviews
    $1,826& up
    Full-Day Private Sailing Charter to Waimea Bay

    Full-Day Private Sailing Charter to Waimea Bay

    Private 6-hour sail to Waimea Bay for up to 6 people

    5.0 • 59 reviews
    $1,937
    Watch Friday Night Fireworks on a Waikiki Sail

    Watch Friday Night Fireworks on a Waikiki Sail

    Friday fireworks sail with front-row views from the water

    4.9 • 169 reviews
    $117/ person
    Morning Sail on Oahu's Kona Coast

    Morning Sail on Oahu's Kona Coast

    A weekday sail with Hawaiian cultural activities and refreshments

    4.9 • 107 reviews
    $221/ person
    Private Sailing Charter in Honolulu

    Private Sailing Charter in Honolulu

    Set your own course for a private sail along Oahu's south shore

    5.0 • 176 reviews
    $449& up
    Friday Night Fireworks Cruise in Waikiki

    Friday Night Fireworks Cruise in Waikiki

    Watch Waikiki's Friday fireworks from a 55-foot catamaran

    4.8 • 5.6K reviews
    $90/ person
    Catamaran Sail in Honolulu with Diamond Head Views

    Catamaran Sail in Honolulu with Diamond Head Views

    Sail past Waikiki and Diamond Head with a full bar onboard

    4.8 • 2.4K reviews
    $98/ person
    Honolulu Sunset Sailing Charter

    Honolulu Sunset Sailing Charter

    Private sailing with Waikiki views, swimming, and snorkeling options

    4.9 • 28 reviews
    $663
    90-Minute Waikiki Sailing Cruise

    90-Minute Waikiki Sailing Cruise

    Sail off Waikiki with ocean views, splashy fun, and drinks available onboard

    4.8 • 1.6K reviews
    $53/ person
    Ko Olina Sunset Sail With Hawaiian Music

    Ko Olina Sunset Sail With Hawaiian Music

    Toast the evening with coastal views and a full open bar

    4.9 • 1K reviews
    $160/ person
    Watch Friday Night Fireworks on a Honolulu Sail

    Watch Friday Night Fireworks on a Honolulu Sail

    Sail Friday night and watch Honolulu fireworks from the water

    4.9 • 917 reviews
    $96& up
    Honolulu Sunrise Private Cruise

    Honolulu Sunrise Private Cruise

    Private morning sailing with mimosas and open-water views

    4.7 • 164 reviews
    $2,041& up
    Private Sunset Cruise in Honolulu with Diamond Head Views

    Private Sunset Cruise in Honolulu with Diamond Head Views

    Golden-hour views of Waikiki and Diamond Head

    4.7 • 52 reviews
    $341
    Half-Day Private Sailing Charter on Oahu's North Shore

    Half-Day Private Sailing Charter on Oahu's North Shore

    Sail the North Shore with a naturalist and seasonal whale listening

    5.0 • 59 reviews
    $1,661
    Ko Olina Sunset Sail & Luau

    Ko Olina Sunset Sail & Luau

    Sail Oʻahu’s coast before an evening of island dining and culture

    4.9 • 1K reviews
    $342/ person
    Hawaiian Cultural Sail on O'ahu's Kona Coast

    Hawaiian Cultural Sail on O'ahu's Kona Coast

    Sail into Hawaiian culture with music, activities, and refreshments

    4.9 • 107 reviews
    $221/ person
    Morning Sail Charter on O'ahu's Kona Coast

    Morning Sail Charter on O'ahu's Kona Coast

    Explore Hawaiian culture and ocean landscapes on a family-friendly morning sail

    4.9 • 107 reviews
    $1,107
    Sunset Cruise in Waikiki

    Sunset Cruise in Waikiki

    Open-bar Mai Tais and coastal views as the sun sets

    4.8 • 1.6K reviews
    $90/ person
    3-Hour Sailing Lesson in Honolulu

    3-Hour Sailing Lesson in Honolulu

    Learn foundational sailing skills with professional captains in Hawaii

    4.9 • 28 reviews
    $663/ person
    Honolulu 3-Hour Sailing Lesson

    Honolulu 3-Hour Sailing Lesson

    Take the Helm With Private Sailing Instruction

    4.7 • 164 reviews
    $1,358
    Waikiki Afternoon Sail

    Waikiki Afternoon Sail

    Afternoon catamaran sail with included drinks and Waikiki views

    4.8 • 1.6K reviews
    $90/ person
    Sunset Sail In Waikiki With Complimentary Drinks

    Sunset Sail In Waikiki With Complimentary Drinks

    90-minute Waikiki sunset sail with complimentary drinks

    $69/ person
    1234
    Kaaawa Things To Do
    SailingSurfing Lessons146Snorkeling144Scuba Diving115Bus Van and Limo Tours82
    More
    • Boat Tours73
    • Stand Up Paddle Boarding65
    • Fishing Charters59
    • Historical Tours55
    • Sightseeing49
    • Whale Watching47
    • Yacht Charters41
    Day Trips
    36
  • Guided Tours33
  • Guided Hikes29
  • Kayaking Tours26
  • Theater Musicals and Shows22
  • Dance Performances21
  • Bike Tours20
  • Helicopter Tours20
  • Themed Dinners19
  • National Parks16
  • Sunrise and Sunset Tours15
  • Waterfalls12
  • Yoga12