Oahu Cruises, Sailing & Water Tours

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Oahu Activities

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Waikiki Beach Whale Watching: Catamaran Sail & Open Bar
5.0 (13)

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (13)
from
$53
Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu
4.7 (1,265)

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.7 (1,265)
from
$53
1-Hour Diamond Head Sail from Waikiki Beach on Ke Kai Catamaran
5.0 (80)

1-Hour Diamond Head Sail from Waikiki Beach on Ke Kai Catamaran

Join us for a 1-hour fun-filled sail departing directly off of Waikiki Beach! Enjoy a breezy midday diamond head sail with complimentary drinks on YELLOW...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
5.0 (80)
from
$53
Ko Olina Glass Bottom Boat Tour - 1 Hour Reef Adventure
Likely to Sell Out
Likely to Sell Out
5.0 (1)

Ko Olina Glass Bottom Boat Tour - 1 Hour Reef Adventure

Discover one of the top-rated ocean experiences in Ko Olina on this exciting 1-hour Glass Bottom Boat Reef Adventure along Oahu’s beautiful West Side. Departing...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
5.0 (1)
from
$51
Waikiki Sunset Boat Cruise
Likely to Sell Out
Likely to Sell Out
5.0 (228)

Waikiki Sunset Boat Cruise

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (228)
from
$50
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
4.9 (259)

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (259)
from
$50
Sunset sail Aboard Manakai Catamaran
Likely to Sell Out
Likely to Sell Out
5.0 (24)

Sunset sail Aboard Manakai Catamaran

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (24)
from
$50
Oahu 5-in-1 Deluxe Cruise: Turtle Snorkeling & Ocean Activities
4.7 (291)

Oahu 5-in-1 Deluxe Cruise: Turtle Snorkeling & Ocean Activities

In addition to the amazing turtle snorkeling in the beautiful waters of Waikiki, our 135-passenger boat offers a unique selection of activities that set us...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.7 (291)
from
$49
Waikiki Sunset Boat Cruise
5.0 (40)

Waikiki Sunset Boat Cruise

Witness Waikiki's iconic sunset from the water while we take you along the beautiful coastline of Honolulu. Cruise by the beautiful Diamond Head and the...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (40)
from
$49
South Shore Open Sail from Kewalo Harbor Including Drinks
4.8 (26)

South Shore Open Sail from Kewalo Harbor Including Drinks

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (26)
from
$48
Waikiki Glass Bottom Boat Cruise
4.7 (2,356)

Waikiki Glass Bottom Boat Cruise

Experience the beauty of Oʻahu South Shore as we sail toward Lēʻahi (Diamond Head) aboard the spacious Haleiwa Queen, a 50ft power catamaran, with 49...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
4.7 (2,356)
from
$46
Waikiki Beach Glass Bottom Boat Tour
4.7 (949)

Waikiki Beach Glass Bottom Boat Tour

Enjoy the beauty of Oahu’s South Shore! Depart from the Kewalo Basin Harbor and head toward Lē’ahi (Diamond Head). While aboard the Haleiwa Queen, enjoy...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
4.7 (949)
from
$46
Waikiki Beach Glass Bottom Boat Cruise
4.7 (330)

Waikiki Beach Glass Bottom Boat Cruise

Enjoy the beauty of Oahu’s South Shore as we cruise from the Kewalo Basin Harbor toward Lē’ahi (Diamond Head). Enjoy the clear view of the...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
4.7 (330)
from
$46
Waikiki Glass Bottom Boat Tour
4.5 (156)

Waikiki Glass Bottom Boat Tour

Experience the beauty of Oʻahu South Shore as we sail toward Lēʻahi (Diamond Head) aboard the spacious Haleiwa Queen, a 50ft power catamaran, with 49...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
4.5 (156)
from
$46
Sea Safari, Dolphins, Turtles and Waikiki Cruise
3.9 (116)

Sea Safari, Dolphins, Turtles and Waikiki Cruise

Experience the beauty of Oʻahu South Shore as we sail toward Lēʻahi (Diamond Head) aboard the spacious Haleiwa Queen, a 50ft power catamaran, with 49...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
3.9 (116)
from
$46
1 Hour Waikiki Sail on Na Hoku 3 Catamaran
4.7 (49)

1 Hour Waikiki Sail on Na Hoku 3 Catamaran

Join us on NA HOKU 3 for a 1-hour fun-filled sail departing directly off of Waikiki Beach! Enjoy a breezy midday diamond head sail with...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
4.7 (49)
from
$46

Frequently Asked Questions

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

Recent activity reviews
Sunset
New York City
Waikiki Sunset Boat Cruise
daniac323, Sep 2026
Sunset
Abby and Bain were extremely inviting and were great guides. Super fun!
Read more
Best Sunset Boat Cruise
New York City
Waikiki Sunset Boat Cruise
Jasmeet_T, Sep 2026
Best Sunset Boat Cruise
We had such an amazing experience on the sunset boat cruise with Oahu Charter! I would 100% recommend doing a sunset tour if you’re in Hawaii. The whole experience was such a vibe, and the views were absolutely beautiful.The captain and staff were incredibly kind and welcoming. A special shoutout to Aleiah, who made us feel so welcome right from the moment we arrived. She was so friendly, took the time to chat with us, brought around chips and fruit, and even helped us with ice for our drinks. She also took some amazing pictures of my husband and me, which we really appreciated!The hospitality was honestly top-notch, and we had such a great time from start to finish. I would definitely book with Oahu Charter again! 🌅🌺
Read more
seriously the best...
New York City
1-Hour Diamond Head Sail from Waikiki Beach on Ke Kai Catamaran
Jena_M, Sep 2026
seriously the best...
seriously the best experience! It’s the perfect amount of time to cruise around the beautiful Hawaiian waters. The crew is so friendly and sweet. The drinks were awesome! 10/10
Read more
Great time!!!
New York City
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
Q7130NUnicolec, Sep 2026
Great time!!!
So fun!!!!! Great crew. Great energy.
Read more
Good vibes and some fish too
New York City
Waikiki Beach Glass Bottom Boat Tour
370shellyq, Sep 2026
Good vibes and some fish too
Had such a great time ! Ian and Brandon made our experience very special. We did the early trip out at 815 and it was clear with a little mist once we were out. We saw turtles and different fish on the side of the boat. Saw a few small fish through the panels and the reef but most of the fish we saw from the side of the boat. Good music, good vibes and they helped us take pictures. Overall enjoyed the trip.
Read more
Cool, educational and refreshing boat ride
New York City
Waikiki Beach Glass Bottom Boat Tour
Y1914KYsallyh, Sep 2026
Cool, educational and refreshing boat ride
Great value and fun trip! The tour guide and his co-pilot were fun and informative and caring. My hat blew off and they turned around and retrieved it from the ocean.
Read more
Great time on the high sea
New York City
South Shore Open Sail from Kewalo Harbor Including Drinks
Johnathan_W, Aug 2026
Great time on the high sea
It was fun and the crew is great, the boat is beautiful. The captain dropped the sails and we took off like a rocket.
Read more
Great time.
New York City
1-Hour Diamond Head Sail from Waikiki Beach on Ke Kai Catamaran
Lauren W, Aug 2026
Great time.
We had an awesome time. The crew were fun, friendly and attentive. I would do this again. Thank you.
Read more
Great choice!
New York City
Waikiki Glass Bottom Boat Tour
betsymC4289JB, Aug 2026
Great choice!
Had a great time. Glad to have gone.
Read more
Awesome Experience thank you
New York City
Waikiki Glass Bottom Boat Tour
552sallyanneb, Aug 2026
Awesome Experience thank you
Our guides were Jim and Ian and they were great , telling us where to see the dolphins and we seen some Turtles the weather was lovey was a awesome trip the staff were very safety conscious I would recommend this adventure
Read more
Super good vibes loved the music choices loved everything about it
New York City
1 Hour Waikiki Sail on Na Hoku 3 Catamaran
Itzel_N, Aug 2026
Super good vibes loved the music choices loved everything about it
You don’t really get off the boat to swim since it is a cruise on the boat. No shoes on the boat so bring flip flops
Read more
free refillable alcoholic...
New York City
1 Hour Waikiki Sail on Na Hoku 3 Catamaran
Jan_R, Aug 2026
free refillable alcoholic...
free refillable alcoholic drink and beers. cool music. spacious boat. nice crew members. nice views from the ocean.
Read more
Amazing experience. We...
New York City
Waikiki Glass Bottom Boat Cruise
John_M, Aug 2026
Amazing experience. We...
Amazing experience. We were a family of 3 the baby was happy too watching the fish. We enjoyed our time.
Read more
Amazing Experience
New York City
Oahu 5-in-1 Deluxe Cruise: Turtle Snorkeling & Ocean Activities
Julie_T, Aug 2026
Amazing Experience
Our crew was amazing! They gave lots of tips and we meet some amazing people during our few hours with everyone. Just an FYI that you are going with other groups. Everything is provided for you; all you need is your own towel.
Read more
Amazing tour!
New York City
Waikiki Glass Bottom Boat Cruise
Mariah_G, Aug 2026
Amazing tour!
Tour guide and crew were very welcoming and knowledgeable, keeping the guest entertained. Tour was kid/family friendly!
Read more
Great Sunset Cruise
New York City
Sunset sail Aboard Manakai Catamaran
Kathie_L, Aug 2026
Great Sunset Cruise
We did this sunset cruise to celebrate our daughter’s birthday and it was wonderful. There are 10 in our family and everyone had a great time. All the crew members were very well trained and friendly.
Read more
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  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
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On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Hawaii over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

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