Hawaii · SUNSET CRUISES IN WAIKIKI
Every trip has one free day too few. These 15 sunset cruises in Waikiki justify the slot, priced and timed so you can decide in minutes and get back to the fun part.
Sail the Waikiki coast for about two hours aboard the Hawaii-built Moana Catamaran. You’ll pass Diamond Head, watch the sunset, and may spot dolphins or humpback whales from November to May. The first premium drink is included, with more available for $8.
“The entire staff was very friendly and outgoing and welcoming. This would include Viv, and the little puppy dog Jeffrey.”
Sail from Honolulu toward Diamond Head on a 53-foot catamaran with a bento box, two alcoholic drinks, and unlimited soft drinks. The crew, including captains Chris and Flynn on some departures, shares local wildlife information while you watch for turtles, dolphins, and seasonal whales.
“What a wonderful sunset. The crew and catamaran were top-notch. I definitely would do this again. Very friendly and a perfect way to end our trip to Hawaii! I would recommend this to all.”
Board Living Ocean Tours at Kewalo Basin for a 90-minute BYOB sunset cruise past Waikiki Beach and Diamond Head. Bring sealed, non-glass drinks, use the onboard cooler with ice, and enjoy snacks, city lights, music, and a friendly crew in a group of up to 40 people.
“Great sunset cruise. Had originally booked sunset dinner cruise but got cancelled due to mechanical issues. Rained most us cruise but still great”
Join Holokai Catamaran in Waikiki for a 90-minute sunset sail with unlimited wine, champagne, Maui Brewing beer, rum punch, soda, juice, and the signature Holokai Hooch. Crew members including Ryan, Chase, Kevin, Kayla, Bridget, and Alec help keep the mood social and the drinks moving.
“I had a friend who suggested it to back in Australia. It was beautiful & better than what I had expected. Highly recommended 👍🏾😎. Everyone was approachable, helpful & easygoing.”
Join Pink Sails Waikiki for a relaxed two-hour catamaran cruise from 1 Holomoana Street. Captain Jamie, Peter, Lexie, and other crew members may host the trip, with time to swim, music, snacks, drinks for purchase, and sunset views toward Waikiki and Diamond Head.
“Great sunset, great views , the captain and crewmen’s were very helpful and nice … awesome swim.. chill and relaxing sail”
Join Pink Sails Waikiki for a two-hour afternoon or evening cruise with a friendly English-speaking crew. Expect Diamond Head views, music, Waikiki lights, and time to jump into the ocean before sunset. Boat assignments can change, so the ride may not always use a catamaran.
“The activity itself is fun. We get to swim whilst we were waiting for the sun to set. We even saw a whale! The other tourists i was with were super awesome. Love the vibes. The staffs are friendly, accommodating and just amazing! They made the time out there fun and engaging. Too bad i cant remember their names but i think the captains name was nick. Anyways, to the crew who sailed us on the 6th of February 2005 departing at 1700 for the sunset swim and sail, thank you very much!!! ♡ ♡ ♡ ♡ ♡”
Sail from Ala Moana toward Waikiki and Diamond Head aboard the 50-foot Haleiwa Queen. You get a shaded deck, restroom, live English commentary, city views, and sunset photos. The relaxed crew, including names such as Courtney, Tristan, Jim, and Lorenzo, adds local color.
“Courtney and Tristen are the best crew and the main reason we keep coming back!!!! 6 trips with them over the course of 2 years and we will be back soon to go on another one!!!”
Set sail from Waikiki Beach on Ke Kai with captains and crew members including Justin, Kyle, Johnny, and Aiden. This 90-minute catamaran trip offers Diamond Head views, music, soft drinks, alcoholic beverages, and a chance to get wet on the front nets.
“The Brandon’s were so sweet. They made the experience extra special. They catered to you’re needs. Very informative”
Board the Hanu Lani at Kewalo Basin Harbor for a 90-minute sunset sail along Waikiki. You’ll have open-air and shaded seating, a full bar, light bites, restrooms, and views of Diamond Head and Honolulu. The casual crew, including captains and bartenders such as Clay, Greg, and Mark, keeps the mood easy and social.
“This my favorite tour/activity that my wife and I did while in Waikiki. The drinks were strong and the appetizers were filling. The boat was nice and the crew and captain were so down to earth and fun to be around. Highly recommend!!”
Board the Hāwea near the Duke Paoa Kahanamoku Statue for a 90-minute sunset sail from Waikiki. You will wade barefoot through shallow surf to reach the catamaran, then enjoy Diamond Head views, music, one included drink, and a cash bar. Crew members such as Cameron, Dez, and Kapono have helped create a lively, welcoming ride.
“The crew was amazing—fun, friendly, knowledgeable, and helpful. The amount of time on this nice boat was just right to enjoy an experience on the ocean and take lots of photos of the sunset and Diamondhead without buildings in the way.”
Spend about 90 minutes aboard the Majestic by Atlantis, a modern three-level yacht leaving from Honolulu’s Aloha Tower. You’ll get a welcome drink, Waikiki Coast views, air-conditioned lounges, an open-air upper deck, live music on some sailings, and a full bar for extra drinks and snacks.
“Great view of sunset, but I was expecting better experience on the boat. Food was minimal so make sure not to board hungry. Cocktails reasonably priced. This could have been elevated experience if they would have offered better food like fruit and cheese tray, shrimp cocktail. Entertainment was minimal with one solo musician. No photographer on board. For next time I would look for a more specialized and elevated experience for a sunset cruise.”
Spend 90 minutes sailing Waikiki aboard Hāwea, a hand-built 50-foot catamaran. You’ll see Diamond Head in changing evening light, enjoy onboard music and nonalcoholic drinks, and may purchase cocktails, beer, wine, or seltzers. Hawea Premium includes cocktails throughout the sail.
“we did the unlimited cocktail package for our anniversary. value for money. the staff were friendly and amazing and great at what they do. thoroughly recommend.”
Set sail from Honolulu for a two-hour BYOB cruise past Diamond Head, the Royal Hawaiian, and Magic Island. Swim off Waikiki, enjoy music, and watch the sunset from a boat limited to 35 people. Bring your own drinks, cups, ice, and towel.
“I had such a great time on this sail, I did it again the following night. The crew is friendly and fantastic. They were a pleasure to get to know and talk to. Also very entertaining. I chose to do this on my solo trip to Oahu. It was just what I needed. Very relaxing.”
Set out from Kewalo Basin for a 90-minute Waikiki sunset cruise with views of Diamond Head, Honolulu’s shoreline, and evening city lights. Choose a BYOB boat or a separate cash-bar option with a welcome beverage. Captain Sean, Kevin, Nick, and Carlos are among the crew members praised for their friendly hosting.
“Definitely worth the money! My friends get nauseous on Catamaran’s so this was a great option. They have seating at the front/back/ middle and upper deck which made it amazing for photos & views. Staff was extremely friendly”
You’ll board a comfortable sailboat near Hilton Pier for a 90-minute barefoot cruise along Waikiki toward Diamond Head. Enjoy chicken or vegetarian bento dishes, two alcoholic drinks, unlimited non-alcoholic beverages, and a chance to spot the green flash.
“Grundsätzlich ganz solide Veranstaltung, aber schon um 19:00 Uhr vorbei statt um 22:00 Uhr.”
Pick a coast, a reef or a ridge.
