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    Best results for

    Sailing in Kailua, HI

    Showing 49-71 of 71 results
    Private Waikiki Fireworks Sailing Catamaran Cruise

    Private Waikiki Fireworks Sailing Catamaran Cruise

    Sail aboard Sea Scape for private ocean views and Friday night fireworks

    Sail aboard Sea Scape for private ocean views and Friday night fireworks
    4.7 • 164 reviews
    $2,041& up
    Honolulu Sunset Sail

    Honolulu Sunset Sail

    Sail past Waikiki and Honolulu as Hawaii's sunset colors the horizon

    Sail past Waikiki and Honolulu as Hawaii's sunset colors the horizon
    $84/ person
    Sunset Sail In Waikiki With Complimentary Drinks

    Sunset Sail In Waikiki With Complimentary Drinks

    90-minute Waikiki sunset sail with complimentary drinks

    90-minute Waikiki sunset sail with complimentary drinks
    $69/ person
    Cultural Sail Charter on O'ahu

    Cultural Sail Charter on O'ahu

    Sail O'ahu's Kona coast with Hawaiian stories, activities, and deckside relaxation

    Sail O'ahu's Kona coast with Hawaiian stories, activities, and deckside relaxation
    4.9 • 107 reviews
    $1,107
    Private Daytime Sailing Charter in Honolulu

    Private Daytime Sailing Charter in Honolulu

    Sail Waikiki’s coast privately with a captain and room to relax on deck

    Sail Waikiki’s coast privately with a captain and room to relax on deck
    4.7 • 164 reviews
    $949& up
    Private Sailing Charter in Honolulu

    Private Sailing Charter in Honolulu

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

    Set your own course for a private sail along Oahu's south shore
    $449& up
    Waikiki Friday Night Fireworks Sail

    Waikiki Friday Night Fireworks Sail

    Sail off Waikiki for Friday night fireworks with complimentary drinks

    Sail off Waikiki for Friday night fireworks with complimentary drinks
    $69/ person
    90-Minute Honolulu South Shore Sail

    90-Minute Honolulu South Shore Sail

    Cruise Oahu’s south shore with complimentary drinks and Diamond Head views

    Cruise Oahu’s south shore with complimentary drinks and Diamond Head views
    $46/ person
    Honolulu Sunset Sail

    Honolulu Sunset Sail

    A lively sunset catamaran sail with complimentary drinks

    A lively sunset catamaran sail with complimentary drinks
    $57/ person
    Sunset Sail in Honolulu from Kewalo Basin Harbor

    Sunset Sail in Honolulu from Kewalo Basin Harbor

    Sunset sailing, sightseeing, and complimentary drinks aboard Manu Kai

    Sunset sailing, sightseeing, and complimentary drinks aboard Manu Kai
    $60/ person
    Waikiki 1-Hour Diamond Head Sail

    Waikiki 1-Hour Diamond Head Sail

    Sail Waikiki’s coastline with music, ocean views, and complimentary drinks

    Sail Waikiki’s coastline with music, ocean views, and complimentary drinks
    $40/ person
    Waikiki 1-Hour Sailing Cruise

    Waikiki 1-Hour Sailing Cruise

    Sail Waikiki’s coast with ocean views and complimentary drinks

    Sail Waikiki’s coast with ocean views and complimentary drinks
    $46/ person
    Private Ash Scattering & Ceremony Sail in Honolulu

    Private Ash Scattering & Ceremony Sail in Honolulu

    Private morning sail for memorials, ash scatterings, and meaningful ceremonies

    Private morning sail for memorials, ash scatterings, and meaningful ceremonies
    $999
    Waikiki Sunset Catamaran Sail

    Waikiki Sunset Catamaran Sail

    Sail Waikīkī at sunset with drinks and light bites included

    Sail Waikīkī at sunset with drinks and light bites included
    4.9 • 926 reviews
    $115/ person
    Diamond Head Sail & Swim From Waikiki

    Diamond Head Sail & Swim From Waikiki

    Sail past Diamond Head, then anchor off Waikiki for a swim

    Sail past Diamond Head, then anchor off Waikiki for a swim
    5.0 • 121 reviews
    $110/ person
    Private 1.5-Hour Sunset Sail in Honolulu

    Private 1.5-Hour Sunset Sail in Honolulu

    1.5-hour private sunset sail with wine, beer, and non-alcoholic drinks

    1.5-hour private sunset sail with wine, beer, and non-alcoholic drinks
    4.9 • 917 reviews
    $4,314
    Sunset Swim & Sail Cruise in Waikiki

    Sunset Swim & Sail Cruise in Waikiki

    Sail Waikīkī’s Gold Coast at sunset with optional swim time

    Sail Waikīkī’s Gold Coast at sunset with optional swim time
    4.9 • 169 reviews
    $74/ person
    Waikiki Friday Fireworks Cruise

    Waikiki Friday Fireworks Cruise

    Sail at sunset for Waikiki Beach fireworks views

    Sail at sunset for Waikiki Beach fireworks views
    4.8 • 1.6K reviews
    $87/ person
    Private 2-Hour Sailing Lesson in Honolulu

    Private 2-Hour Sailing Lesson in Honolulu

    Build sailing skills with hands-on instruction from Captain Al

    Build sailing skills with hands-on instruction from Captain Al
    $424& up
    Waikiki Friday Night Fireworks Sail with Drinks and Bento

    Waikiki Friday Night Fireworks Sail with Drinks and Bento

    Sail at sunset for front-row views of Waikiki’s Friday fireworks, with drinks and a bento included

    Sail at sunset for front-row views of Waikiki’s Friday fireworks, with drinks and a bento included
    4.9 • 926 reviews
    $183/ person
    Private Afternoon Sail in Waikiki

    Private Afternoon Sail in Waikiki

    Private beach-boarded sail with Diamond Head Lighthouse views

    Private beach-boarded sail with Diamond Head Lighthouse views
    4.9 • 917 reviews
    $2,259
    Afternoon Waikiki Coast Sail

    Afternoon Waikiki Coast Sail

    Relax along Oʻahu’s south shore with Waikiki views, Diamond Head, snacks, and drinks

    Relax along Oʻahu’s south shore with Waikiki views, Diamond Head, snacks, and drinks
    4.9 • 926 reviews
    $86/ person
    1-Hour Fireworks Sail in Honolulu

    1-Hour Fireworks Sail in Honolulu

    Watch Honolulu’s Friday-night fireworks from a private sail

    Watch Honolulu’s Friday-night fireworks from a private sail
    4.9 • 917 reviews
    $3,514
    123
    Kailua Things To Do
    Sailing71Snorkeling134Surfing Lessons104Scuba Diving95Boat Tours60
    More
    • Bus Van and Limo Tours57
    • Stand Up Paddle Boarding57
    • Historical Tours44
    • Whale Watching43
    • Yacht Charters39
    • Day Trips34
    • Fishing Charters31
    Guided Tours
    27
  1. Kayaking Tours26
  2. Guided Hikes23
  3. Bike Tours20
  4. Dance Performances19
  5. Helicopter Tours19
  6. Sightseeing19
  7. Theater Musicals and Shows17
  8. Themed Dinners17
  9. Sunrise and Sunset Tours15
  10. Waterfalls12
  11. Yoga12
  12. Zip Lining12