Oahu Cruises, Sailing & Water Tours

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Oahu Activities

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Private Gondola Cruise Waikiki with cute tour guide & he sings!
4.9 (21)

Private Gondola Cruise Waikiki with cute tour guide & he sings!

Explore the Polynesian Riviera of Waikiki in small groups of 1 to 4 people per gondola and immerse your senses in this gentle, calm activity....

45 to 60 minutes • Free Cancellation
45 to 60 minutes • Free Cancellation
45 to 60 minutes • Free Cancellation
4.9 (21)
from
$670
Private cruise Gondola waikiki with cute tour guide & he sings!
5.0 (2)

Private cruise Gondola waikiki with cute tour guide & he sings!

Drift and relax under the starlight as you glide effortlessly on the tranquil waters of Waikiki. Gaze in awe under romantic moonlight while interacting with...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
5.0 (2)
from
$670
Uniquely Personalized Private Island Tour on Oahu, Hawaii
Likely to Sell Out
Likely to Sell Out
5.0 (46)

Uniquely Personalized Private Island Tour on Oahu, Hawaii

Plan Your Personalized Private Tours around any activity or event that you want.  You can even combine this option with other activities you find on...

6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (46)
from
$699
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
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
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
Personalized Private Pearl Harbor National Memorial Oahu Tours
Likely to Sell Out
Likely to Sell Out
5.0 (2)

Personalized Private Pearl Harbor National Memorial Oahu Tours

Visit the World War II Valor in the Pacific National Monument at Pearl Harbor to reflect, remember and understand the tragic events of December 7,...

6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (2)
from
$699
Private Snorkeling and Wildlife on The Adventure Boat
5.0 (89)

Private Snorkeling and Wildlife on The Adventure Boat

**Private boat tour for up to 6 people** Larger group? Call for options. Fast and fun adventure sightseeing tours in Hawaii. Escape the crowds and...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (89)
from
$726
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
Private Whale Watching Trip from Oahu
5.0 (2)

Private Whale Watching Trip from Oahu

6 Guests Maximum Private + Exclusive Unlike large group tours, this experience is limited to just 6 guests aboard a 32-foot World Cat, ensuring a...

90 to 150 minutes • Free Cancellation
90 to 150 minutes • Free Cancellation
90 to 150 minutes • Free Cancellation
5.0 (2)
from
$750
Private Tiki Bar Sunset Cruise in Honolulu
5.0 (1)

Private Tiki Bar Sunset Cruise in Honolulu

**Private boat tour for up to 6 people** Larger group? Call for options. Escape the crowds and traffic of the city and jump on amazing...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (1)
from
$758
Oahu Private First, Last and Transfer Day Tours with Luggage
Likely to Sell Out
Likely to Sell Out
5.0 (2)

Oahu Private First, Last and Transfer Day Tours with Luggage

Make the first or last day of your vacation the best one, without any hassle or wasted time.  We all know the feeling of an early...

6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (2)
from
$799
Private Whale Watching Adventure
4.9 (25)

Private Whale Watching Adventure

**Private boat tour for up to 6 people.** Larger group? Call for options. Escape the crowds and join us on 2-hour private whale watching cruise...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (25)
from
$831
Private Catamaran Charter in Waikiki (1-6 Guests)
Likely to Sell Out
Likely to Sell Out
5.0 (25)

Private Catamaran Charter in Waikiki (1-6 Guests)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (25)
from
$900
Private Catamaran Sunset Sail in Waikiki
Likely to Sell Out
Likely to Sell Out
5.0 (11)

Private Catamaran Sunset Sail in Waikiki

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (11)
from
$900
Private Luxury Sunset Cruise in Waikiki

Private Luxury Sunset Cruise in Waikiki

Experience the ultimate luxury and exclusivity with a private yacht cruise in Waikiki, where you can bask in the breathtaking beauty of the Hawaiian sunset...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
from
$950

Frequently Asked Questions

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

Recent activity reviews
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
Better than advertised!
New York City
Private Catamaran Charter in Waikiki (1-6 Guests)
derickg967, Jul 2026
Better than advertised!
Captain Steve and Bella were amazing! They made the trip so enjoyable and were so easy going. I would highly recommend you book with them now!
Read more
Hali'a Tours is the best private tour for Oahu
New York City
Uniquely Personalized Private Island Tour on Oahu, Hawaii
Curiosity08643877030, Jun 2026
Hali'a Tours is the best private tour for Oahu
Booking our 2 tours was very easy and Michael was very accommodating. He is an amazing tour guide and made us feel like family. Our tours were totally customized to what we wanted to do. Michael went above and beyond in every aspect. He is very knowledgeable and kind. 100% recommend Michael for any tour needs you may have in Oahu.
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
A wonderful 3 hours with family on the water at Waikiki
New York City
Private Catamaran Sunset Sail in Waikiki
Burleya13, May 2026
A wonderful 3 hours with family on the water at Waikiki
A great day on the water with Tom, Savannah and Bella celebrating Alicia’s 70th birthday with our children and grandchildren. Swimming off the catamaran with dolphins and turtles. We also saw a seal in the harbour before sailing. A great birthday present and memories. Highly recommend the professional expertise of the crew.
Read more
Great Sailing Trip
New York City
Private Catamaran Charter in Waikiki (1-6 Guests)
Dave1151a, May 2026
Great Sailing Trip
My entire family had a fantastic experience. Captain Tom , Savanah, Hailey were great hosts. We went to a quiet swim/snorkeling area. Saw plenty of fish. A very peaceful tranquil outing.
Read more
What a day for a day dream
New York City
Uniquely Personalized Private Island Tour on Oahu, Hawaii
normanb838, Feb 2026
What a day for a day dream
Michael was fantastic Great service excellent decisions on where to go. It was an absolute perfect day. He was very knowledgeable about the island and its history. If you are considering a tour guide for the island, you need Michael as your guide. You won't be disappointed.
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
A perfect private catamaran sunset tour
New York City
Private Catamaran Sunset Sail in Waikiki
DebbyL71, Feb 2026
A perfect private catamaran sunset tour
I booked the private catamaran sunset tour for my family and I and we were not disappointed. It was a fantastic tour. The waters were a bit choppy that day, but we all laughed when a couple of the waves got some of us a bit wet!! All fun!! The trip back was so spectacular…..even though it was too overcast for a proper sunset, the suns rays poked through the clouds and made up for it (and the warm blanket for the ride back was the ‘icing on the cake’). Our ‘captain’ and ‘crew member’ were so friendly it made the trip very enjoyable. Thank you so much!!!
Read more
Whale Watching tour w/JJ
New York City
Private Whale Watching Trip from Oahu
Catie H, Feb 2026
Whale Watching tour w/JJ
We did a private whale watching tour with Mana Cruises and had a fantastic experience. There were six of us, and JJ was our captain—he did an excellent job finding whales, especially considering it was toward the end of the whale season in Oahu. We were really grateful to still get such great sightings. JJ was knowledgeable, professional, and clearly knew where to look. The boat had water and juice available, but honestly, we didn’t even try the snacks because we were too busy watching for whales the entire time. Overall, a memorable experience and a great way to see whales up close in a more personal setting. Highly recommend Mana Cruises and JJ if you’re looking for a quality whale watching tour.
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
Great company, great experience!
New York City
Private Tiki Bar Sunset Cruise in Honolulu
deboralbtravels, Dec 2025
Great company, great experience!
We booked with this company for a group of five. Professional and fun staff who communicated well throughout the evening. Really fun experience overall and highly recommend booking with them!
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
Highly recommend
New York City
Private Snorkeling and Wildlife on The Adventure Boat
Travelbugfamily75, Nov 2025
Highly recommend
These 2 guys were great! Friendly, funny and engaging with a relaxed attitude towards the activities of the day without compromising on the important aspects of the trip. We saw Dolphins and swam with Turtles then cruised around the water sightseeing landmarks. Well worth the booking. Totally recommend.
Read more
Our guide Michael Water...
New York City
Personalized Private Pearl Harbor National Memorial Oahu Tours
Bob_K, Oct 2025
Our guide Michael Water...
Our guide Michael Water was excellent. Extremely knowledgeable about the entire Pearl Harbor sites. !!
Read more
Great travels
New York City
Oahu Personalized Private North Shore Highlight Custom Tour
helengW5980AL, Jun 2025
Great travels
What a great experience! We brought our granddaughter for her first trip to Hawaii and wanted to make sure she had a great experience. Mike took us wherever we wanted to go, but he was very knowledgeable about Hawaii we had him take us where he felt would be fun for our granddaughter. We all enjoyed the places he took us! The Waimea waterfalls were great. We went to the old sugar cane factory and had delicious shaved ice, the Dole Pineapple plantation. As we drove around Mike would explain about the different areas we were at. He also let us take our time visiting each site. Highly recommending this tour! Thank you Mike and Halia Tours!
Read more
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