Oahu Cruises, Sailing & Water Tours

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Oahu Activities

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Private South Shore Sail Charter
5.0 (2)

Private South Shore Sail Charter

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze,...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (2)
from
$1,000
Discover Popoia Island and Kailua Bay by Kayak Guided Tour
5.0 (4)

Discover Popoia Island and Kailua Bay by Kayak Guided Tour

Kayak in the crystal clear waters of Kailua Bay with one of our guides and visit one of Oahu's smallest offshore islands. It's only a...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (4)
from
$169
Aloha Gondola Cruise with Drinks & Pastries
5.0 (4)

Aloha Gondola Cruise with Drinks & Pastries

Impress your family with the very Best Waikiki has to offer. This is the only commercial cruise experience that tours within the tranquil waters of...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
5.0 (4)
from
$250
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
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
Venture Wildlife Snorkel Charter from Ko Olina
5.0 (4)

Venture Wildlife Snorkel Charter from Ko Olina

6 Guests Maximum **From December 15th to March 31st,** join us for our seasonal favorite Whale Watch + Snorkel, where your experience can be as...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (4)
from
$995
Snorkel and Catamaran Sail
4.7 (7)

Snorkel and Catamaran Sail

Board a catamaran from Haleiwa harbor to snorkel and sail the beautiful waters of Oahu's famous North Shore. Offered throughout the summer months, this tour explores the northern coastline...

4 hours • Free Cancellation
4 hours • Free Cancellation
4 hours • Free Cancellation
4.7 (7)
from
$142
Oahu Whale Watching Catamaran Sail Experience
Likely to Sell Out
Likely to Sell Out
3.0 (1)

Oahu Whale Watching Catamaran Sail Experience

Join an intimate whale watching adventure aboard open-deck sailing catamaran, limited to just 35 guests for a more personal experience. Every winter, humpback whales migrate...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
3.0 (1)
from
$55
#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson
5.0 (4)

#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (4)
from
$450
Battleships of WWII at Pearl Harbor from Maui
5.0 (1)

Battleships of WWII at Pearl Harbor from Maui

Join us on a powerful historic journey starting with the surprise Japanese attack on Pearl Harbor December 7, 1941 that catapulted the U.S. into World...

7 to 9 hours • Free Cancellation
7 to 9 hours • Free Cancellation
7 to 9 hours • Free Cancellation
5.0 (1)
from
$460
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
Whale and Dolphin Watch Boat Cruise in Oahu
5.0 (1)

Whale and Dolphin Watch Boat Cruise in Oahu

Experience this sensational opportunity aboard our semi-private charter. We have limited our tours to just 6 guest per excursion to offer the most personalized adventure....

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (1)
from
$125
Affordable Afternoon Sail in Waikiki
3.7 (3)

Affordable Afternoon Sail in Waikiki

Looking for an unforgettable experience that won’t break the bank? Join us aboard Island Magic for the Aloha Hour a scenic, one hour sail offering...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
3.7 (3)
from
$30
Oahu: Ko Olina Kaula Kai Sunset Sail and Luau Experience
3.0 (1)

Oahu: Ko Olina Kaula Kai Sunset Sail and Luau Experience

Set sail on the stunning leeward coast of Oʻahu during the Kaula Kai experience, combining a breathtaking sunset sail with a vibrant luau. Start your...

90 to 180 minutes • Free Cancellation
90 to 180 minutes • Free Cancellation
90 to 180 minutes • Free Cancellation
3.0 (1)
from
$139
3 Hour Luxury Private Sailing Catamaran for 7-12 People
Likely to Sell Out
Likely to Sell Out

3 Hour Luxury Private Sailing Catamaran for 7-12 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
from
$1,995
Private Luxury Sunset Cruise Aboard Limitless
Likely to Sell Out
Likely to Sell Out

Private Luxury Sunset Cruise Aboard Limitless

Set sail with on a private 2-hour sunset cruise, the perfect way to wind down your day in Hawaii. As the sun sinks toward the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
from
$1,199

Frequently Asked Questions

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

Recent activity reviews
Kayaking
New York City
Discover Popoia Island and Kailua Bay by Kayak Guided Tour
Erik_W, Aug 2026
Kayaking
Mario was very knowledgeable and friendly. Getting to ocean was fun on electric bikes. Kayaking was great. It was a beautiful day.
Read more
Great snorkeling.
New York City
Snorkel and Catamaran Sail
E3390QVss, Jul 2026
Great snorkeling.
A better snorkel experience than I expected having spent last summer on the Belize reef. Saw many schools of fish and several turtles. Had a solid hour in the water and a nice ride to and from Shark Cove (about 45 minutes each way). I recognized the sandwiches they served from foodland- they weren’t bad but I wouldn’t expect “lunch” more of a “snack,” but appreciated post-snorkel. One tip: 9:00 am snorkel tour is actually 8:30. We arrived at 8:40 and everyone was on board and waiting for us to leave. Should call it the 8:30 tour.
Read more
Amazing snorkel and lunch trip!
New York City
Venture Wildlife Snorkel Charter from Ko Olina
knkwelsh5, Jun 2026
Amazing snorkel and lunch trip!
Our cruise was absolutely amazing! Captain and first mate Lyndsey went above and beyond to make our snorkel trip an experience of a lifetime! We saw so many fish and turtles! Lunch was delicious and the boat was beautiful! Would definitely highly recommend!! Thanks guys for helping us make lasting memories for our 40th anniversary!!
Read more
Chill and Affordable
New York City
Affordable Afternoon Sail in Waikiki
kendraf415, May 2026
Chill and Affordable
We had a fantastic experience. The boat isn't too big and it isn't crowded. There are fun nets in the front that you can sit on. The captain also found some whales for us to watch and adjusted the trip so we could see the whales. We also could bring our own drinks and there weren't any further gimicks to make us spend more money.
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
Perfect afternoon.
New York City
Discover Popoia Island and Kailua Bay by Kayak Guided Tour
Mark C, Jan 2026
Perfect afternoon.
Excellent experience. Kyle was our guide. He was very sensitive to our needs. He seemed knowledgeable on local history, culture species of fish, birds,etc. We really enjoyed the experience and would recommend it to anyone. We did the half day excursion.
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
Book This ASAP
New York City
Venture Wildlife Snorkel Charter from Ko Olina
Glendalys_S, Oct 2025
Book This ASAP
Captain Mark & First Mate Marco gave us an experience of a lifetime. Our party had overlapped activities, and they thankfully accommodated us to fit this experience into our schedule. It's always been my dream to rent a boat to go swimming, and they made it come true. Not to mention, their patience with our children was incredible. My nephew wanted to fish and we almost caught a huge fish. If not for the fact that we had reservations for another experience, we would've extended our time happily.If you're looking for an intimate excursion with friendly experts, look no further.Thank you, MANA, Capt. Mark and Marco for memories we'll cherish for a lifetime.
Read more
Great way to experience the Waikiki shoreline!
New York City
Affordable Afternoon Sail in Waikiki
Josie_M, Jul 2025
Great way to experience the Waikiki shoreline!
What a fun activity for families! Captain and crew were awesome! Highly recommend! Our 11 and 5 year olds love it!
Read more
Not long enough
New York City
Battleships of WWII at Pearl Harbor from Maui
teresasingleton915, May 2025
Not long enough
The site is somber and uplifting at the same time. Well maintained and beautiful. We bought a tour package so our time was EXTREMELY limited. I would love to go back but I will take my chances with a taxi or something. $925 for just a couple hours at the site isn't my idea of a good deal.
Read more
Private Marriage proposal
New York City
Aloha Gondola Cruise with Drinks & Pastries
Shakhan_S, Apr 2025
Private Marriage proposal
This turned out better than I could have ever planned. They go above and beyond to make your experience be as great as it can be. Mines was a wedding proposal, and Elliot gave us all the bells and whistles. Small Family owned so they care about the details. 5 star, if you want a special memory and a beautiful evening with the city lights book this at night..glad I made that choice.
Read more
Breaching Whales and Dolphins!
New York City
Private Whale Watching Trip from Oahu
Jeff215, Apr 2025
Breaching Whales and Dolphins!
We booked a whale watch charter knowing that the end of the season was upon us. We were prepared for the possibility that we wouldn't see any whales but thanks to the expertise, experience and knowledge of Captain Mark, above all odds, he found several northbound whales that put on a wonderful show for us. He also introduced us to a few Hawaiian Green Sea Turtles and several pods of Hawaiian Spinner Dolphins. He mentioned he does fishing charters, dolphin cruises and evening sunset charters too.
Read more
Amazing time!
New York City
Whale and Dolphin Watch Boat Cruise in Oahu
Alexa_M, Feb 2025
Amazing time!
What a great experience! We saw whales and dolphins on a beautiful morning. Great service and worth the price. Great option for those who don’t want to be stuck with 50 other people. We got lucky and were the only ones who booked the tour so it turned into a private tour! 10/10 recommend!
Read more
Efoil and kite with Ray best day ever !!!!
New York City
#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson
maximilianm475, Dec 2024
Efoil and kite with Ray best day ever !!!!
I had a lot of fun with Ray he told me how to foil in one lesson I even took a kite boarding lesson after one of the best days of my life.
Read more
Great teacher with local knowledge
New York City
#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson
723tarynl, Sep 2024
Great teacher with local knowledge
Josh is awesome to work with. His equipment is great and well taken care of. He matches the equipment to your needs and has many options. He is a long time Kailua local and knows the spots and conditions. Foiling was fun and he made it easy. Two way radio helmet meant no need to return to him for coaching just spend all your minutes having fun with Coaching as you to. Josh is safety focused and a very patient teacher. Highly recommend.
Read more
100% Great Time!
New York City
Private South Shore Sail Charter
Lorrieann_U, Dec 2023
100% Great Time!
We really enjoyed the whole trip sailing Waikiki with South Shore Sail. From the moment we walked up to the greeters they made us feel very special and welcome. The whole crew was very professional and friendly. One and half hours was just right to get a little outing on the water and the free drinks was a plus! I will reccomend this sailing company to everyone! The cost is very reasonable and was so much FUN!
Read more
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