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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!

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Latest reviews of Waikiki Boat & Sailing Cruises

Hilton Port Waikiki Sunset Cruise with Cocktails & Appetizers - Spirit of Aloha

Annual Family Tradition

2025/11/11 Families Docdavis4L

Captain Nick and crew showed us a great time on our fourth consecutive annual November sunset cruise. Each one is a little different vibe. Sunday appears to be the best day for a more peaceful vibe. Great interaction wit... more

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1-Hour Waikiki Fireworks Sail Cruise with Drinks Included - Holokai Catamaran

Beauuuutiful experience, almost perfect!

2025/11/01 Solo Travelers Honeymooners

We got married an hour before the sunset Catamaran cruise. We were so excited to finish the day with a champagne toast and the Hilton fireworks show from the boat. Great music, great group of happy passengers, the sailin... more

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

A great night out

2025/10/27 Solo Travelers Annabelle

The pick up from he hotel was seamless and boarding the cruise ship was quick. Table service was slow but the food was excellent. The sunset and following fireworks was a great experience and I would recommend this adven... more

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Star of Honolulu Dinner Cruise - Luxury Top Deck Sunset Dining Experience & Live Entertainment

Enjoyable fun night

2025/10/18 Couples Mary

A beautiful night. Great food. Great entertainment. Saw the spectacular fire works and the skyline night lights of Waikiki. Drinks included in the package was a bonus.

90-Min Maitai Waikiki Catamaran Sunset Cocktail Sail with Open-Bar

Relaxing and fun

2025/10/15 Families Drinks, Sun, and Fun

The cruise was very well organized and the staff was friendly and fun-loving. My kids and I enjoyed ourselves immensely and plan to make this a continuous part of our trip to the islands.

Na Hoku Catamaran Sunset Sail from Waikiki Beach - Fun Party Cruise with Open Bar

Lots of fun!

2025/10/11 Couples Susan

All 6 of us loved this trip! Lots of fun, great crew, awesome music. Sunset wasn't 1too great as it was a cloudy, rainy day...but that's not your fault and we had a wonderful time anyway. Good drinks, definitely not wat... 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.