Waikiki Sailing & Cruises(Page 2) | Book Oahu Tours, Activities & Things to Do with HawaiiActivities.com
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Waikiki Boat & Sailing Cruises

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Ride on the winds and waves of Hawaii as you set out on the best Oahu sailing and cruising adventures along Waikiki Beach! Take your pick from a variety of ocean activities, and begin your day early with a visit to your captain's favorite snorkeling spots, take a scenic boat tour at twilight and watch the beautiful sunset as you sip on tropical cocktails, and even dine on a delicious Pacific-Rim inspired feast. Then simply relax and enjoy amazing views of the Waikiki coastline and Diamond Head.
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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31 Activities Availability varies by date for all activities.
Enjoy a fun and affordable one hour Happy Hour sail aboard the Ke Kai Catamaran
Includes complimentary soda, juice, water, and 3 alcoholic beverages like beer and mai tai cocktails
Pick-up Not Provided
Meal Not Provided
Afternoon
1.5 hour(s)
Daily
Enjoy a fun 90-min daytime cruise. Daily afternoon departures at 11:00 AM & 1:00 PM
Mai Tais, beer, champagne, wine, juices and soft drinks are available for purchase onboard
Pick-up Not Provided
Meal Not Provided
Afternoon
2 hour(s)
Daily
Have the best seats in the house to see the popular Friday Night Fireworks on a 90-min cocktail sail
Set out on this family-friendly Waikiki catamaran sail with the amazing views of the fireworks
Pick-up Not Provided
Meal Not Provided
Evening
2 - 2.5 hour(s)
Fri Only
Join Ocean & You on a 2-hour morning or afternoon whale watching cruise with free transportation
Includes snacks, beverages, hula entertainment & underwater hydrophone to listen to the whales
Pick-up Provided
Meal Not Provided
Morning / Afternoon
2.5 - 4.5 hour(s)
Daily
Set sail on an affordable 1-hour morning cruise to Diamond Head
See marine wildlife in their natural environment. Includes non-alcohol beverages
Pick-up Not Provided
Meal Not Provided
Morning
1.5 hour(s)
Sun / Thu Only
Get ready for a night of fun and excitement on a 90-minute private sunset sail
Sit back, relax, and enjoy three complimentary cocktails and beers, and unlimited soft drinks
Pick-up Not Provided
Meal Not Provided
Evening
2 hour(s)
Daily
Join Hawaii Nautical on a 2.5-hour cruise to one of the most popular spots to see turtles on Oahu
Book the morning turtle snorkel cruise for a delicious lunch and two free cocktails
Pick-up Not Provided
Meal Not Provided
Morning / Afternoon
3 - 3.5 hour(s)
Daily
Join Makani Catamaran on a 2-Hour sail along the Oahu's scenic South Shore
Full service cash bar! Drinks are available for purchase
Pick-up Provided
Meal Not Provided
Morning / Afternoon
2.5 - 4 hour(s)
Daily
Enjoy a scenic 90-minute private afternoon sail aboard Manu Kai Catamaran
Raise your glass and enjoy three complimentary cocktails and beers, and unlimited soft drinks
Pick-up Not Provided
Meal Not Provided
Afternoon
2 hour(s)
Sun / Fri / Sat Only
Head out on a 2-hour private sailing adventure, and take the plunge for an ocean swim
Includes complimentary soft drinks and cocktails, as well as snorkel gear and a floating lounger
Pick-up Not Provided
Meal Not Provided
Afternoon
2.5 - 3.5 hour(s)
Sun / Fri / Sat Only
Enjoy a relaxing 90-min scenic sail along Waikiki coastline. Includes 2 complimentary bar drinks
Includes bar snacks, unlimited nonalcohol drinks & 2 free cocktails
Pick-up Provided
Meal Not Provided
Afternoon
2 - 3 hour(s)
Daily
12

Top-Rated Activities for Oahu

Latest reviews of Waikiki Boat & Sailing Cruises

Maitai Catamaran Waikiki Fireworks & Moonlight Sail with Open Bar

Perfect !

2025/03/30 Couples Brianna

Our tour was perfect. Bartender and crew were all very friendly and kept our drinks full the entire trip. Great views of the fireworks and downtown. Would recommend!

Star of Honolulu Morning Whale Watch Tour with Banana Bread & Coffee [Jan-Mar]

The best time ever!!

2025/03/29 Families with Young Children Sandy

It was very organized. The staff were all helpful and happy. I’ve always wanted to see whales and this tour made it all possible. Didn’t want the tour to end!

Waikiki Submarine Tour - Descend to 100ft, See Shipwrecks & Sunken Airplanes

Clear conditions

2025/03/27 Couples Kara

We had a greast day, we got to see a ton of sea life including a few turtles!

Waikiki Snorkel with Turtles Cruise with Beers & Cocktails - Ke Kai Catamaran

Loved our experience

2025/03/26 Families with Young Children OG

The crew was great, very friendly and helpful. Such beautiful views. The current was strong during our snorkel time which was tough, I’d definitely like to do it again when it’s calmer (obviously nothing we can control).... more

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

Amazing everything

2025/03/26 Couples TA Melanie

The crew was very knowledgeable and attentive.
We had a perfect day and saw several whales.
The pod that passed us gave a great show of surfacing and waving their flukes.
The boat was clean and safe. It was the best e... more

Close
Waikiki Sunset Booze Cruise with FREE Drinks Included - Ke Kai Catamaran

Booze Cruise

2025/03/26 Couples Nanners

Great boat!
Great crew!
Great views!
Great drinks!
Great experience!

Waikiki Sailing & Cruises | Book Oahu Tours, Activities & Things to Do with HawaiiActivities.com
Ride on the winds and waves of Hawaii as you set out on the best Oahu sailing and cruising adventures along Waikiki Beach! Take your pick from a variety of ocean activities, and begin your day early with a visit to your captain's favorite snorkeling spots, take a scenic boat tour at twilight and watch the beautiful sunset as you sip on tropical cocktails, and even dine on a delicious Pacific-Rim inspired feast. Then simply relax and enjoy amazing views of the Waikiki coastline and Diamond Head.
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