Waikiki Sailing & Cruises | Book Waikiki Tours, Activities & Things to Do with HawaiiActivities.com
Waikiki Beach Things to Do

Waikiki Boat & Sailing Cruises

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Set sail on unforgettable Waikiki boat and sailing cruises with breathtaking views of Diamond Head and Honolulu’s skyline. Choose from relaxing daytime sails, romantic sunset cruises, or lively cocktail catamaran trips right off Waikiki Beach. Many tours include snorkeling at Turtle Canyon, seasonal whale watching, or private charter options for families and groups. With convenient departures from Waikiki, these sailing adventures offer the perfect way to enjoy Oahu’s ocean beauty.
Your Guide to Waikiki Sails & Cruises
If you're looking for a fun way to explore Waikiki, then there is no better way than on a Waikiki sail or cruise! From snorkeling tours to day sails and sunset cruises, there's something for everyone.

Many of the snorkeling tours go to Turtle Canyon off the coast of Waikiki, so you can enjoy a beautiful underwater world surrounded by green sea turtles, or honu in Hawaiian, while you are out on the ocean. During the winter months, you might even be lucky enough to spot some whales in the distance, and if you take one of the morning sails, you'll likely be treated to a show by some of Hawaii's spinner dolphins. Don't forget to keep an eye out for that iconic view of Diamond Head, and have your phones and cameras ready for the best views of this amazing natural landmark.

For those looking for an extra special evening out, there are plenty of sunset dinner cruises and sunset booze cruises available too. The dinner cruises offer delicious food options that range from multi-course steak and lobster dinner, to a yummy plate of Hawaiian-style garlic shrimp from a popular local restaurant. The booze cruises will also often come with complimentary drinks for all guests, have the best drink prices in Hawaii, and for the boats without a bar, you can always BYOB and enjoy your favorite drinks while out on he best sails and cruises in Waikiki.

On your next visit to Hawaii, check out the Waikiki sailing and cruising option, and with so many tour options, there is sure to be a sail or cruise for any budget, group, and age. Don't miss out on an unforgettable experience, and book your Waikiki sail or cruise today!

Top-Rated Activities for Waikiki

Latest reviews of Waikiki Boat & Sailing Cruises

Waikiki Sunset Cocktail Sail with Open Bar Included - Holokai Catamaran

Great

2026/03/07 Couples Alex

Very friendly team. Highly recommend. Thank you very much

90-Min Waikiki Beach Sunset Cocktail Sail Cruise with FREE Drinks Included - Ke Kai Catamaran

Lots of fun snd good drinks

2026/03/07 Friends CJ

Friendly staff. Good drinks. Clear directions and information.

Pink Sails Waikiki Whale Watching Tour - Morning & Sunset Cruise [Dec-Apr]

Pink sails whale watching was a fantastic!

2026/03/02 Friends LP & LS

Capt Jamie and the crew were amazing and very knowledgable! We got to see a pod of whales pop up 4 times or more, we saw flying fish, and a pid of dolphins with babies! Great cruise!

Waikiki Sunset Cocktail Sail with Open Bar Included - Holokai Catamaran

Fun evening cruise

2026/02/06 Couples Mike

Fun crew- free flowing drinks. Hooch ok could have been stronger. Overall a good experience

90-Min Waikiki Beach Sunset Cocktail Sail Cruise with FREE Drinks Included - Ke Kai Catamaran

Guaranteed good time!

2026/02/04 Couples Deb

We went on this cruise for our anniversary… Had so much fun. We booked it for a few days later. The crew is always awesome and so much fun. We do this every time we are in Hawaii.

90-Min Waikiki Beach Sunset Cocktail Sail Cruise with FREE Drinks Included - Ke Kai Catamaran

So fun we booked twice!

2026/02/04 Couples Deb

We have done this cruise every time we go to Hawaii. We had so much fun a few days prior that we booked it again! The crew always shows you a good time!

Waikiki Sailing & Cruises | Book Waikiki Tours, Activities & Things to Do with HawaiiActivities.com
Set sail on unforgettable Waikiki boat and sailing cruises with breathtaking views of Diamond Head and Honolulu’s skyline. Choose from relaxing daytime sails, romantic sunset cruises, or lively cocktail catamaran trips right off Waikiki Beach. Many tours include snorkeling at Turtle Canyon, seasonal whale watching, or private charter options for families and groups. With convenient departures from Waikiki, these sailing adventures offer the perfect way to enjoy Oahu’s ocean beauty.