Experience a sunset cocktail sail or booze cruise & drift away with the fading sun while sipping on tropical cocktails and nibbling on delicious appetizers. Sit back and let the cool ocean breeze carry away your stress & relax to the sound of the ocean waves (or perhaps live Hawaiian music!) as your sailboat or catamaran drifts just off-shore, giving you beautiful panoramic views of beaches, mountains & the Pacific ocean.
23Activities
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  1. Set sail on the popular Holokai Catamaran, direct from Waikiki Beach. Relax on board with a drink and let your cares fade with the sun.

    USD55.00

    Daily
    2 hour(s) (evening)
  2. Set sail from Waikiki Beach on a laid-back cruise, with views of Waikiki, filled with cocktails, a brilliant sunset and local crew, plus Fireworks on Fridays.

    USD45.00

    Daily
    2 hour(s) (evening)
  3. Set sail from Waikiki's Hilton Pier on a coastal cruise along Waikiki and witness the stunning beauty of the perfect Hawaiian sunset aboard a luxury catamaran.

    USD82.72

    Sun, Mon, Tue, Wed, Thu, Sat
    2 hour(s) (evening)
  4. A pirate themed sunset dance cruise for adults only! Sip some grog and sail Waikiki with a crew of swashbuckling pirates and a live DJ with fireworks on Fridays!
    Pick-up Provided

    USD64.73

    Fri, Sat
    2 - 3.5 hour(s) (evening)
  5. Experience 5-star service on this luxury sunset sail featuring the beautiful and unique west Oahu coast and sunset! Free pick-up from from Ko Olina hotels.
    Pick-up Provided

    USD85.88

    Mon, Wed, Thu, Fri
    (evening)
  6. Get ready for a relaxing sunset sail with Holo Holo Charters along Kauai's breathtaking Na Pali Coast with refreshing cocktails and delicious appetizers.
    Meal Provided
    Special

    From USD121.60

    12%
    OFF
    Daily
    3.5 hour(s) (afternoon)
  7. Take an unforgettable cocktail and appetizer sail across the crystal clear waters of Kohala as you sip on cocktails while Big Island sun dips below the horizon.
    Pick-up Provided
    Accessible

    USD138.25

    Mon, Wed, Fri, Sat
    (afternoon, evening)
  8. Set sail aboard this open-bar catamaran cruiser and chase the sun as it sinks into the distant horizon. Alii Nui is Maui at her finest!
    Pick-up Provided
    Special

    USD134.80

    10%
    OFF
    Sun, Mon, Wed, Fri
    2.5 - 5.5 hour(s) (evening)
  9. North Shore Sunset Catamaran Sailing (from Haleiwa) Oahu / Waikiki
    Instant Confirmation
    A casual BYOB (Bring-your-own-beverages) sunset sail from Oahu's North Shore, where the aloha spirit is strong, everyone is family and the sunset is extra special!

    From USD64.63

    Daily
    2.5 hour(s) (afternoon, evening)
  10. Relax on a glass bottom boat over the clear waters of Hawaii as the sunset lights up the Hawaiian sky, and view the ocean below with fish, turtles and more.

    USD57.59

    Sun, Mon, Tue, Wed, Thu, Sat
    2 hour(s) (evening)
  11. Have an evening to remember as you set out on a semi-private sunset cruise with delicious fruit and sushi, and then snorkel among the majestic giant manta rays.

    USD115.00

    Daily
    2 hour(s) (evening)
  12. The Leila, a 50' authentic sailing catamaran, is waiting to spirit you off to the Poipu Coast, where you can watch the sun fade over the rim of a mai tai glass.
    Meal Provided

    USD90.67

    Daily
    2.5 hour(s) (afternoon)
  13. Set sail from Lahaina along Maui's west coast, watching the sky break into an array of colors at sunset while enjoying open bar drinks and tasty island snacks.

    From USD75.88

    2%
    OFF
    Daily
    2.5 hour(s) (afternoon, evening)
  14. Watch as the sky and sea illuminate every Friday night with a glass bottom boat cruise and fireworks show. A fantastic evening with lights above and below!

    USD52.36

    Fri
    2 hour(s) (evening)
  15. With a convenient Kaanapali departure, sip on a cocktail from the open-bar, nibble on tasty appetizers and relax as you watch the sun dip below Maui's horizon.

    From USD68.59

    Daily
    2.5 hour(s) (afternoon, evening)
  16. Sail along the Waikiki Coastline and enjoy the brilliant colors of a Hawaiian sunset and scenic city views on this elegant sailing catamaran!
    Pick-up Provided

    USD85.88

    Sun, Mon, Tue, Wed, Thu, Sat
    2 - 3 hour(s) (evening)
  17. Hawaiian Canoe Sunset Sailing Cruise (from Keauhou Bay) Hawaii, Big Island
    Instant Confirmation
    Sail into the Kona sunset on a Hawaiian double-hulled sailing canoe! Experience Keauhou Bay, relax and enjoy the beautiful sunset at sea.

    USD80.38

    Daily
    1.5 hour(s) (evening)
  18. Set sail into the sunset along the romantic Kaanapali coast of West Maui and enjoy a few cocktails and an intimate moment with that special someone.
    Special

    USD99.83

    Mon, Tue, Wed, Thu, Sat
    2.5 hour(s) (afternoon, evening)
  19. Enjoy an unforgettable sail along the beautiful Garden Isle coastline with Captain Andy and enjoy tropical cocktails as the sun dips below the Pacific Ocean.

    USD73.60

    13%
    OFF
    Sat
    2.5 hour(s) (afternoon, evening)
  20. Board the Alala, a powered catamaran that holds up to 76 passengers! An open bar, snorkeling equipment & meal options make this an ideal large group setting.
    Pick-up Provided
    Meal Provided
    Accessible

    From USD6,670.15

    Daily
    2.5 - 6 hour(s) (morning, afternoon, evening)