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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 Oahu

Latest reviews of Waikiki Boat & Sailing Cruises

Star of Honolulu Whale Watching Cruise with Banana Bread & Coffee | 2-Hour Morning Tour [Jan-Mar]

Morning whale watch was incredible!

2026/01/22 Couples Eric Y

My wife and I booked the morning 2hr whale watch cruise and it was breathtaking. The views all the way throughout the cruise was the highlight. Not to mention the whales we spotted in the distance. The cruise staff were ... more

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Star of Honolulu Sunset Buffet Dinner Cruise & Polynesian Show

Such a wonderful night

2026/01/21 Friends Mama bear

The food was good and plentiful the entertainment was awesome

2-Hour Moana Sailing Waikiki Sunset Cruise with Drink Included

The All Female Crew Rocked!!!

2026/01/21 Families with Young Children Sinem

We had such a wonderful time on our sunset cruise while in Oahu. Lost track of how many whales we saw while out there. And the staff were so incredibly nice. Special shout out to Vivian who spent some extra time with my ... more

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Star of Honolulu Sunset Dinner Cruise – 5-Course Steak & Lobster Menu, Polynesian Show & Live Music

Such a shame that the offering has changed

2026/01/18 Couples Simon

We were so disappointed with our Sunset Dinner Cruise this week.
Why oh why, when a company has it just right, do they get greedy and take away the finesse?
Having taken the steak & lobster package last year, we were so ... more

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Spirit of Aloha Waikiki Morning Adventure Sail from Hilton Pier

Satisfied

2026/01/10 Couples Danah

Convenient, smooth, friendly staff. Easy to book and reserve. Perfect way to start your morning on this sunrise cruise

Afternoon Whale Watch Sail from Hilton Waikiki Pier - Spirit of Aloha [Dec-Mar]

A “whale” of a time!

2025/12/29 Friends Scott and Amy

We had an incredible experience. It was early in the season so we didn’t think we were going to see anything. The crew told us to hurry and board as some other boats had said they saw some whales out there. We had been o... more

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Waikiki Sailing & Cruises | Book Oahu 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.