Top Oahu Cruises & Sailing - page 2
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rei_z, Jun 2026
Amazing!
Such wonderful memories! The boat was brand new, and the colors of the sails were absolutely beautiful. The best part was that the meeting point was incredibly easy to find—right downstairs from my hotel, so there was no way to miss it. The boarding spot was also just a few minutes' walk away. Everything was so convenient.
We hit some big waves during the tour, and standing at the bow completely soaked my clothes! But it was incredibly thrilling and a blast! Such a unique memory!
If I had to pick a downside, the cocktails weren't great, but they also had beer and wine available to choose from.
Ernie_M, Jun 2026
Nice Sunset Cruise
Captain Crash and Margaret were great hosts. This is a great value excursion for the experience and memories. Friendly reminder is that there are no shoes, but the flooring is very comfortable and makes for an enjoyable trip. You can't control the weather but if you get motion sickness easy then I would prepare for it. We were blessed with good weather for the evening our family went. Many blessings to you and your business.
Anthony_S, Jun 2026
Mai Tais, Maritime Chaos, And Questionable Life Choices
I booked the Waikiki Sunset Cruise expecting a relaxing evening on the water. What I got instead was three straight hours of tropical chaos, public intoxication, emotional instability, and one of the best nights of my life.
The second we boarded, the deck hands immediately set the tone by roasting people with the precision of professional comedians who just happened to also know maritime safety regulations.
One guy walked on carrying six drinks and a mountain of free chips while balancing two sodas and a Mai Tai, and a deckhand hit him with:
“Sir, you either trust yourself way too much or not enough.”
Another crew member somehow spent the entire cruise simultaneously:
* pouring drinks,
* hyping up the crowd,
* giving safety instructions,
* taking photos for strangers,
* and bullying a guy named Steve for wearing socks with sandals.
Absolute elite multitasking.
Meanwhile the actual cruise itself felt like a fever dream sponsored by rum.
There were at least seven separate birthday parties happening at once. A woman lost a flip flop to the Pacific and everyone held a brief memorial service for it. A guy absolutely annihilated the free chips like he was training for a national championship.
The bartender was making Mai Tais strong enough to make you temporarily forget your PIN number.
At one point, the music shifted from smooth island vibes into full blown “middle school dance in the best possible way” energy and suddenly fifty strangers were screaming the lyrics to Sweet Caroline while the boat bounced around like a shopping cart with one bad wheel.
And somehow… the sunset still stole the show.
The sky looked fake. Like one of those motivational desktop wallpapers your aunt posts on Facebook with a quote about blessings. People were stopping conversations mid-sentence just staring at the horizon like they’d collectively seen a UFO.
Meanwhile the deck hands were still running around cracking jokes and keeping the energy going like caffeinated cruise goblins.
One of them looked directly at our group while we were trying to take a photo and yelled:
“Don’t worry, I can tell from here this one’s going on Facebook.”
He was right.
By the end of the cruise:
* I had made temporary best friends with at least four strangers,
* my hair contained 40% ocean air and 60% Mai Tai vapor,
* and I was fully convinced that every sunset back home is now personally insulting me.
10/10 experience.
If you’re looking for a quiet, dignified evening, absolutely do not do this.
If you want tropical nonsense, beautiful views, hilarious crew members, and the exact kind of vacation memory that gets louder and more exaggerated every time you retell it — this is the move.
akparkin, Jun 2026
Sunset cruise
It was lovely to be out on the water, and to enjoy the late afternoon. Our group did not go swimming, but those who did seem to really have fun. The crew was very efficient and accommodating for the passengers.
This is a good, low key activity that can be enjoyed by most age groups.
Hailee_A, Jun 2026
Best sunset cruise
The experience was amazing to say the least! We had the all girl crew and they were so sweet and cool. They were very informative about the island and took pictures for us which was awesome. Also the drinks were very good and a lot cheaper than back on the island lol, HUGE PLUS! They also helped a man propose to his wife which was very sweet!! :)
Marvella_M, May 2026
Sunset dinner cruise
My husband and I went. The accommodations were very nice and comfortable. The food was very good I especially liked the chicken it was juicy and very flavorful. After dinner we went outside walked around the bow then went up to the upper deck and sat outside just to watch the water and look at Honolulu from the water it was very pretty I hoped we would have seen some dolphins but we did not. Overall it was a good tim
Tracey_H, May 2026
This was one of my...
This was one of my absolute highlights of my trip to Hawaii, the crew on the catamaran were amazing, my partner proposed to me on here and the crew even put the song he requested on and recorded the moment for us . Highly recommend doing this tour with this company 10/10 . Tracey QLD Australia
S_M, May 2026
Hawaiian Sunsets done right - Pink Sails Never Disappoints
Wow! A sunset in Hawaii is so much more than a cliché, it’s absolutely magnificent! The Pink Sails Waikiki team delivered above and beyond service and attention from start to finish.
There are many companies offering sunset cruises, but if you’re looking for a more relaxed and less crowded experience, this is the one. The catamaran holds a maximum of 80 people, and the vessel is spacious enough that you can comfortably move around and enjoy the views without feeling cramped.
On this particular cruise, the combination of current hits and ‘90s music had everyone singing along and enjoying the moment together. The charcuterie snack box was just enough, and the two included drinks were a nice touch.
I thoroughly enjoyed every moment and every view. Sunset cruises are always a favorite of mine, and I continue to choose Pink Sails because their sailings never disappoint.
TanyaM, May 2026
Beautiful ride
Booking was quick and easy. When you meet at the pier be sure to look for their trailer and hang out there. Someone will greet you and give QR code to sign waiver for each person in your party. We had an all female crew which was cool. They were so friendly and compassionate. I truly was grateful when they realized I am legally blind based on my cane (not many are aware) but they gently guided and even described where I needed to place my hands in order to board the boat on and off. They check on their passengers throughout the ride. Beverages and light snacks were offered and you can BYO alcohol if you choose. The ride was great to see the Waikiki coast and Diamond head and even watch the sunset on the ride home. I got lots of great pictures and videos. Great crew, ride and time on the ocean. We didn’t see any wild life in the ocean but I still enjoyed it.
Lynne_S, Apr 2026
Chill, fun vibes
Ian and Stone were the captains for our tour and they brought the vibes. They had seen some whales while out on the tour before ours and knew exactly where to get us to see them for ourselves. Did not disappoint! I think there were 4 whales and we saw them multiple times moving around. It was so fun, especially for our kids (11 & 12) to see them for the first time. Music was great, Ian and Stone were fun, plus it was just a chill ride and a laid back way to see the island. Definitely recommend this one. (Bring a couple drinks to enjoy since it’s BYOB)
Danielle_C, Oct 2025
So fun!!
I booked this boat ride to go with my family that was coming into town. It was very easy to book and they sent me a lot of information on how to get to the meeting spot to fill out the waiver before hand. When we got on the boat the crew members were really nice and they offered to take pictures for us. The boat ride was beautiful and it was all around. Great experience.
Robin_H, Oct 2025
Amazing
We had a great time. Food was incredible as were the sights. Ty to captain Travis and chef Taylor!! They were so awesome and knowledgeable about the area. Great service and even tried to find whales and dolphins. Would definitely recommend. Beautiful yacht too.
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