Sunset Sails

Sunset sails are smaller, sailing-focused trips, usually on a catamaran, that head out from Waikiki in the late afternoon. Many include a swim stop before the sun goes down, and they tend to be more relaxed than larger sunset cruise boats.

Showing all 6 results

  • Hawaii Nautical Ko Olina Signature Sunset Sail Oahu

    Original price was: $99.00.Current price is: $94.95.

    ✓ Secure booking • Instant confirmation

    Hawaii Nautical Ko Olina Signature Sunset Sail Oahu Set sail from Waianae for a breathtaking...

    Book Now

  • Hawaii Nautical Waikiki Kewalo Basin Sunset Cocktail Sail Oahu

    Original price was: $99.00.Current price is: $94.95.

    ✓ Secure booking • Instant confirmation

    Waikiki Kewalo Basin Signature Sunset Cocktail Sail with Hawaii Nautical Relax and unwind on a...

    Book Now

  • Pink Sails Waikiki – Sunset Swim & Sail

    Original price was: $56.00.Current price is: $49.95.

    ✓ Secure booking • Instant confirmation

    Enjoy the Beauty of a Hawaii Sunset Cruise There’s no better way to watch the...

    Book Now

  • Pink Sails Waikiki – Sunset Whale Watching

    $114.14

    ✓ Secure booking • Instant confirmation

    Sunset Whale Watching in Waikiki Experience the thrill of whale watching in paradise! Join our...

    Book Now

  • Three Tiki Sailing Sunset Swim & Sail Oahu

    Original price was: $79.00.Current price is: $74.95.

    ✓ Secure booking • Instant confirmation

    Three Tiki Sailing Sunset Swim & Sail Oahu Embark on an amazing BYOB Sunset Sail...

    Book Now

  • Waikiki Sailing Tours – Oahu Sunset Tour

    Original price was: $99.00.Current price is: $94.95.

    ✓ Secure booking • Instant confirmation

    Waikiki Sailing Tours - Oahu Sunset Tour 2 Hours Hawaii is well known for its...

    Book Now

Choosing a sunset sail

Sunset sails are on sailing catamarans, so you get the wind, the quiet and a closer feel to the water than on a big cruise boat. Options include:

  • Swim & sail trips (Three Tiki, Pink Sails) with a swim stop before sunset.
  • Cocktail sails from Kewalo Basin (Hawaii Nautical) and the Waikiki Sailing Tours sunset sail.
  • Ko Olina’s Signature Sunset Sail on the calmer west side.
  • Sunset whale watching sails in winter.

Waikiki catamarans often board right from the beach, so wear clothes you don’t mind getting wet. For larger boats, see sunset cruises; on Fridays, see fireworks sails.

Frequently asked questions

Do Waikiki sunset sails board from the beach?

Several Waikiki catamarans load directly from the sand, so expect to wade in ankle-deep water. Other sails leave from Kewalo Basin harbor.

Can I swim on a sunset sail?

Swim & sail trips include a swim stop. Standard sunset sails stay on board.

Are sunset sails good for kids?

Yes, many sails welcome families, though cocktail-focused sails can be adults only. Check each listing.