Oahu Cruises, Sailing & Water Tours

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Oahu Activities

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Whale Watching Catamaran Sail
4.7 (22)

Whale Watching Catamaran Sail

2hr whale watching sail aboard the Ho'oNaea Catamaran. Enjoy Oahu's majestic North Shore and encounter the Hawaiian Humpback whales up-close from the of the decks...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.7 (22)
from
$105
Oahu Custom Private Circle Island and Mini Circle Island Tours
Likely to Sell Out
Likely to Sell Out
5.0 (20)

Oahu Custom Private Circle Island and Mini Circle Island Tours

See all O`ahu has to offer and enjoy a ride around the Ko`olau Mountain Range.  Visit the South or North Shore on a Mini Circle...

6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (20)
from
$699
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
Likely to Sell Out
Likely to Sell Out
4.8 (14)

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (14)
from
$1,150
Oahu: Private North Shore Boat Charter
Likely to Sell Out
Likely to Sell Out
5.0 (7)

Oahu: Private North Shore Boat Charter

Our North Shore adventure tours are perfect for people of all ages. Bring your family or friends and create new memories. Turn the tour into...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (7)
from
$1,200
Private Boat Charter in Waikiki for Snorkeling and Events
Likely to Sell Out
Likely to Sell Out
5.0 (6)

Private Boat Charter in Waikiki for Snorkeling and Events

Discover the beauty of Waikiki with a private boat day charter, perfect for snorkeling, coastal cruising, events, and seasonal whale watching from January to March....

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (6)
from
$1,300
Whale Watching on "The World Famous North Shore of Oahu", Hawaii
Likely to Sell Out
Likely to Sell Out
4.8 (5)

Whale Watching on "The World Famous North Shore of Oahu", Hawaii

Our company is uniquely owned by Native-Hawaiian watermen. As the only company of its kind on the island, we hope you'll support local. Our owners,...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (5)
from
$135
Private Oahu Pearl Harbor and Island Sightseeing Combination Tour
Likely to Sell Out
Likely to Sell Out
5.0 (15)

Private Oahu Pearl Harbor and Island Sightseeing Combination Tour

Combine any route or tour into one incredible, unforgettable day.  Visit Pearl Harbor, then head up to the North Shore, or even cruise around the...

6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (15)
from
$699
Private Sunset Luxury Cruise of Oahu
Likely to Sell Out
Likely to Sell Out
5.0 (3)

Private Sunset Luxury Cruise of Oahu

Enjoy a relaxing cruise along the North Shore of Oahu. Take in the breathtaking views of Oahu from the water where you can see Mt....

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (3)
from
$400
Custom Private Multi Day Tours on the island of Oahu Hawaii
Likely to Sell Out
Likely to Sell Out
5.0 (5)

Custom Private Multi Day Tours on the island of Oahu Hawaii

Your Multi-Day Tours make sure you have the most fun possible, see everything you want, as well as have a driver for things like dinner, golf,...

3 days • Hotel pickup offered
3 days • Hotel pickup offered
3 days • Hotel pickup offered
5.0 (5)
from
$1,998
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
Likely to Sell Out
Likely to Sell Out
5.0 (2)

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (2)
from
$1,595
Private Whale Watching and Coastal Swimming Tour Honolulu
Likely to Sell Out
Likely to Sell Out
5.0 (4)

Private Whale Watching and Coastal Swimming Tour Honolulu

Our experienced crew are masters of Hawaii's ocean, ensuring your safety and best possible experience. This tour is on a power catamaran, a boat design...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (4)
from
$749
Oahu Personalized Private North Shore Highlight Custom Tour
Likely to Sell Out
Likely to Sell Out
5.0 (7)

Oahu Personalized Private North Shore Highlight Custom Tour

Explore the Seven Mile Miracle known as O`ahuʻs North Shore.  Winter brings big waves and world-class surfing, while the summer is calm and perfect for visiting...

6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (7)
from
$699
Private Group SUP Lessons for 4 by Waikiki Beachboys at the Royal
Likely to Sell Out
Likely to Sell Out
4.7 (6)

Private Group SUP Lessons for 4 by Waikiki Beachboys at the Royal

Learn how to stand up paddle with your own Waikiki Beachboy in the birth place of surfing.  We are located in the heart of Waikiki, just...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
4.7 (6)
from
$101
Waikiki to Diamondhead: Sunset BYOB Cruise
Likely to Sell Out
Likely to Sell Out
5.0 (2)

Waikiki to Diamondhead: Sunset BYOB Cruise

Want a spectacular sunset cruise? Our cruise offers multi level viewing of the dramatic Waikiki coastline and spectacular sunset on the water views. We offer...

2 to 190 minutes • Free Cancellation
2 to 190 minutes • Free Cancellation
2 to 190 minutes • Free Cancellation
5.0 (2)
from
$139
Mokulua Islands Self-Guided Kayak Adventure
Likely to Sell Out
Likely to Sell Out
4.2 (5)

Mokulua Islands Self-Guided Kayak Adventure

Explore the Mokolua Islands on this adventurous self-guided tour. The island is a seabird sanctuary and the beach is also a resting spot for monk...

4 hours • Free Cancellation
4 hours • Free Cancellation
4 hours • Free Cancellation
4.2 (5)
from
$82
Offshore Fishing Adventures With Ohana Deep Sea Fishing
Likely to Sell Out
Likely to Sell Out
5.0 (1)

Offshore Fishing Adventures With Ohana Deep Sea Fishing

-Welcome aboard our well-equipped fishing charter boat and set off into the open seas with our expert captain and crew. - Explore prime fishing spots...

4 hours • Free Cancellation
4 hours • Free Cancellation
4 hours • Free Cancellation
5.0 (1)
from
$1,360

Frequently Asked Questions

These answers are based on answers previously given to Cool Hawaii customers' questions.

Recent activity reviews
Self guided tandem kayak to Mokulua Islands.
New York City
Mokulua Islands Self-Guided Kayak Adventure
F5777TAstevena, Aug 2026
Self guided tandem kayak to Mokulua Islands.
We had a great time kayaking! The whole setup and rental process was really easy. Mario, who rented us our gear, was extremely helpful and kind. He was easy to work with, very knowledgeable, and gave us some great tips before we started, especially since I had never kayaked before.Mario even gave us a map showing the recommended route to the islands, which was really helpful. I would highly recommend following the route they give you. There are a lot of rocks between the shoreline and the islands, which is why they recommend staying close to the shoreline for most of the way before heading out toward the islands.We parked at the nearest beach, and the walk from there to the kayak launch point really wasn’t too bad, even with the gear.It took us about 1.5 hours to kayak out because we were going against the current and wind, but the paddle back only took about an hour. I would recommend having at least a moderate level of fitness for this activity, especially if it’s windy that day.We were lucky enough to see manta rays along the way, which was awesome! The monk seals were sunbathing when we arrived, so we weren’t able to do the trail, but it was still well worth the trip.Definitely wear LOTS of sunscreen! You’re exposed to the sun for quite a while, and it’s easy to underestimate how much sun you’re getting while you’re out on the water.Overall, we had a really fun experience and I would definitely recommend it!
Read more
Amazing experience- great staff and easy to work with! Highly recommended!
New York City
Oahu: Private North Shore Boat Charter
kaliblumen, Aug 2026
Amazing experience- great staff and easy to work with! Highly recommended!
AMAZING experience!! My family of 4 just returned from a 8 night O'ahu trip and the absolute HIGHLIGHT was when we went out on the boat with Kevin last Wednesday! I will also say the person who booked us prior to our trip was friendly and super knowledgeable and helpful - really set the tone for our excursion. Parking was easy to find, and Kevin went above and beyond turning what was supposed to be a snorkeling excursion into the best marine tour ever! Thanks to Lala, the water was too murky for us to snorkel but our kiddos still had a blast being out on the boat, ending up in the middle of a pod of 200+ spinner dolphins and watching the babies attempt spins with their mamas by their side! We also were lucky enough to see a honu in the open waters and then attempted to see sharks! Overall, can't recommend this enough- Kevin was so great!! We will definitely be back!!
Read more
Awesome experience
New York City
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
Climber19817325401, Aug 2026
Awesome experience
The crew took excellent care of us. The small and private experience provided a more intimate setting, allowing for more personalized attention. We had the opportunity to see dolphins and even go snorkeling. The experience was highly customizable, making it an ideal choice for those seeking a private and memorable adventure.
Read more
Fantastic experience
New York City
Oahu Personalized Private North Shore Highlight Custom Tour
Resort14330456578, Jul 2026
Fantastic experience
An amazing experience and our tour guide was fantastic. I wouldn’t hesitate to recommend any tour with him.
Read more
Amazing
New York City
Private Boat Charter in Waikiki for Snorkeling and Events
M8293EIandrews, Jul 2026
Amazing
This was our third time using Hawai’i Ocean Tours for a private outing. We love these guys! We saw dolphin, turtles, and even a shark! Hailey, the first mate, even found an octopus! The best experience every time, and a highlight to our trip.
Read more
Worth the money, wonderful time!
New York City
Private Boat Charter in Waikiki for Snorkeling and Events
JoMaLa, Jun 2026
Worth the money, wonderful time!
Our family group of 31 had a wonderful time with Captain Carlos, Erika and sorry, forgot the 2nd gal’s name. We went to a great snorkeling spot with lots of fish and turtles and many of us loved jumping off the upper level of the boat into the ocean. Everyone enjoyed our time on the boat and with the staff who were friendly and knowledgeable.
Read more
Book with Michael and you’ll be glad you did
New York City
Custom Private Multi Day Tours on the island of Oahu Hawaii
mikewN5960QF, Jun 2026
Book with Michael and you’ll be glad you did
If you want a tour in Oahu do yourself a favor and book with Michael. He’s extremely knowledgable, fun, accommodating, and responsive. Our family of 10 did 2 custom tours and both were top notch. The stories he told, the local food spots, and activity recommendations were invaluable to making our first time Hawaii experience unforgettable.
Read more
First Time in Hawaii
New York City
Oahu Custom Private Circle Island and Mini Circle Island Tours
vanessacE3361BT, Jun 2026
First Time in Hawaii
This was the first time my husband and I had been to to Oahu and were excited to see much of the island. We booked a peivate Oahu circle tour with Michael and had a great time. He was very knowledgeable and friendly and provided a lot of flexibility based on out personal interests and preferences. This day trip was definitely a highlight of our trip and would absolutely recommend to others.
Read more
Very cool
New York City
Whale Watching on “The World Famous North Shore of Oahu”, Hawaii
kellybZ9167UR, May 2026
Very cool
The tour guides that are brothers are incredible! My bf wanted to go and loved it so much. I was terrified and they helped me with my snorkels feel comfortable and were cheering me on. Saw many sharks. This is NOT for anyone who gets sea sick. You’re in open ocean with massive waves and the cage is slamming against the boat too that you go in. Amazing people though dealing with sea sick passengers
Read more
Kayaking Awesome Adventure!
New York City
Mokulua Islands Self-Guided Kayak Adventure
Chase_P, Apr 2026
Kayaking Awesome Adventure!
It was a great adventure! For a novice kayaker. We were able to manage the trip. Would definitely tell more people to do the same as us!
Read more
A great day
New York City
Offshore Fishing Adventures With Ohana Deep Sea Fishing
robdL7517GH, Apr 2026
A great day
Mike and Kahi are a fantastic crew. We have been fishing with them before and enjoy there company, the care they give to the sea, the boat and us. The waters were very challenging this year with the amount of rain they received the weeks prior, but they worked the water and birds to help my son catch his first MahiMahi. We had a great day on the water and will absolutely reach out for a fishing trip next time we’re visiting Oahu.
Read more
Whales & Sunset, the boat tour on Oahu
New York City
Whale Watching on “The World Famous North Shore of Oahu”, Hawaii
kahelelanic2026, Feb 2026
Whales & Sunset, the boat tour on Oahu
Amazing experience from start to finish!Even though we are a local family, this was our first time on the whale watch sunset tour with Haleiwa Shark Tours, and it completely exceeded our expectations. As far as location, it is always better out on the North Shore away from overcrowded Waikiki. We are glad to support a Hawaiian-owned company. Their connection to Hawaii made the experience much more meaningful. The boat was comfortable, with great viewing spots—and we were lucky enough to see humpback whales breaching, blowing spouts, and slapping their tails just offshore. Truly breathtaking.The crew was friendly, professional, and very knowledgeable, sharing interesting facts about the whales, their behavior and connection to Hawaii. You could tell they genuinely care about the ocean and the wildlife.Ending the tour with a sunset near Haleiwa was perfect. Watching the sunset on the ocean is pure magic and an unforgettable way to wrap up the day.This was our first whale watch tour with them, I’ve also done their shark tour, which was just as incredible—so I can confidently say Haleiwa Shark Tours delivers amazing experiences all around. Highly recommend if you’re looking for something special on Oahu.
Read more
Best company to book with!
New York City
Private Whale Watching and Coastal Swimming Tour Honolulu
Q5832VPannam, Feb 2026
Best company to book with!
We had the best day Saturday! We booked a 4 hour private trip with a group of 16 and it was amazing! We snorkeling with turtles and a large variety of fish, and checked out a starfish. Then saw some whales and finished with book cruising with the dolphins! To make it even better; the crew was absolutely amazing! Kind, knowledgeable and very accommodating. The boat was clean and had a perfect layout to accommodate our group! You can’t go wrong with this company!!! We had an 8 year old to a 68 year old!
Read more
Magical family excursion
New York City
Private Oahu Pearl Harbor and Island Sightseeing Combination Tour
Kelly B, Dec 2025
Magical family excursion
This was truly an unforgettable experience and worth every moment. Arriving to Pearl Harbor before the crowds made the experience personal. Throughout the day our guide Michael was absolutely amazing: incredibly knowledgeable, genuinely kind, and so welcoming. From the very beginning, he made both me and my kids feel completely comfortable and included, which made the experience even more special. He was patient, engaging, and wonderful with the kids, making history come alive in a way that held everyone’s attention. This felt less like a tour and more like being shown around by a local friend. If you’re looking for an exclusive, meaningful, and memorable way to experience Pearl Harbor and Hawaii, I can’t recommend this enough.
Read more
Michael did an...
New York City
Oahu Custom Private Circle Island and Mini Circle Island Tours
Mary_H, Dec 2025
Michael did an...
Michael did an exceptional job on doing a circle tour of the island. He above and beyond to make certain we had a wonderful time. Not only was he knowledgeable, but he also had a sense of humor while driving us around and showing us the various locations. It was the best tour of our vacation. If we ever came back to the island again, I would want to do another tour with him.
Read more
Mana Cruise
New York City
Private Sunset Luxury Cruise of Oahu
Regina299, Nov 2025
Mana Cruise
What a fabulous cruise it was. The food was great. Captain Austin and Marco kept us entertained. The sunset cruise was amazing. To top of our cruise Austin and Marco caught their fish for Thanksgiving. Anyone not doing this cruise would be amiss of a spectacular ride in a catamaran which was immaculately clean and comfortable. Even drinks were non stop. Food was expertly created and served. Thank you Mana Cruise of Oahu.
Read more
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