The verdict
Our pick
Waikiki Sunset Sail: Cocktails on the Moana Catamaran★ 4.86 (2,429) · 2h
Best value
Oahu: Waikiki Catamaran Swim & Sail with Diamond Head★ 4.89 (265) · 2h
Top rated
Waikiki: Turtle Canyon Snorkeling & Sunrise Sail Small Group★ 5.00 (105) · 2h
The 12 best-value of 13 options, side by side
✓ 2026-09-28Real price per person across the 13 options: US$ 50–US$ 250 (median US$ 73).
Default order: price per person.
Sort
Oahu Sunset Catamaran: Diamond Head & Waikiki with BYOBYou board a 40-foot catamaran limited to 28 passengers and sail toward Diamond Head as the sun drops. You get complimentary pupus, water, and juice, plus free ice and Yeti coolers if you bring your own drinks. The boat stays out long enough to watch Waikiki light up at night before heading back, and the whole experience takes about two and a half hours without any of the crowding or upsell pressure of bigger sunset cruises.Is it for me?Book this if you want a sunset experience on the water without the crowding or the markup on drinks — the 28-person limit and BYOB setup are what make it feel less like a tour and more like a private evening with people who know what they're doing.
Waikiki Sunset Cruise with Open Bar: Barefoot Beach BoardingA sunset cruise on Oahu's Holokai Catamaran departs directly from Waikiki Beach with a fully stocked open bar, no harbor transfers, and a 1.5-hour sail timed to catch the golden hour. Beer, wine, cocktails and motion sickness aid are included; parking validation covers four hours at Embassy Suites valet. Friday sails are adults 21+ only; Saturday through Thursday welcome all ages, with discounted rates for children 4–12 and infants sailing free.Is it for me?This is a social sail built for groups and solo travelers who want to mingle in a fun crowd—not a private charter or a quiet family outing. Friday nights are adults only; if you're bringing kids or want a mixed-age group, book Saturday through Thursday instead.
Waikiki Sunset Sailing: 2-Hour Catamaran Swim & SailA 2-hour sunset sailing activity on a catamaran in Waikiki where you swim in the ocean and watch the sunset from the water with an experienced guide. The boat departs as the sun begins to set, so timing is fixed around that window. Swimming is optional, and you'll want a camera—the light changes fast and the colors are the whole point.Is it for me?Book this one if you want to watch the Waikiki sunset from the water instead of the beach, with the option to swim in the open ocean as the light changes—the catamaran puts you in the middle of it instead of watching from shore.
Waikiki: Sunset Catamaran Sail with Drinks & Diamond Head ViewsYou’ll board right from Waikiki Beach for a relaxed sunset sail with drinks included, music playing in the background, and Diamond Head views glowing in evening light. Sit on the net if you’re up for a splash or chat with locals from the crew as you sip something cold. Expect laughter and that easy island feeling long after you step back onto sand.
Waikiki: Sunset Cocktail Cruise Majestic Yacht & City LightsYou’ll board the Majestic yacht in Waikiki for a sunset cocktail cruise with city skyline views and a complimentary welcome drink. Enjoy both open-air decks and an air-conditioned lounge while live music plays in the background. Whether you’re outside feeling the breeze or relaxing by panoramic windows, this evening leaves you with more than just photos.
Waikiki Catamaran Sail with Open Bar: Afternoon Trade WindsAn afternoon catamaran sail from Waikiki Beach on Oahu with a fully stocked open bar, departing at 3pm for a 1.5-hour voyage toward Diamond Head. You board directly from the sand—no shuttle, no harbor, no wasted time—and the boat carries near 360-degree views from a spacious 45-foot hull. Beer, wine, cocktails and non-alcoholic drinks are included in the ticket price, along with reef-safe sunscreen, motion sickness aid and parking validation.Is it for me?This works best for afternoon visitors who want to be on the water without eating up the whole day—the 3pm departure and 4:30pm return fit between lunch and dinner, and the direct beach boarding means you skip the usual harbor shuffle. Small groups and families travel together on the same boat, so it's social without being crowded.
Waikiki Sunset Boat Cruise: Dolphins, Whales & Diamond HeadA 90-minute sunset boat cruise departing from Waikiki that sails the coastline toward Diamond Head Crater as the sun sets over the water. The tour includes snacks and local beverages; dolphins and Hawaiian green sea turtles are frequently spotted, and humpback whales appear in winter months. Children from age 3 are welcome, and infants sit on an adult's lap.Is it for me?The boat departs from Waikiki, so if you're staying in the area or without a rental car, you skip the drive to a distant harbor—the sunset happens on the water where you already are, and you're back before dark.
Honolulu: Waikiki Sunset Sail & Swimming with BYOBYou board a three-hulled sailing trimaran and spend the evening moving past Diamond Head, Magic Island, and the Royal Hawaiian Hotel as the light changes. You get a swim off Waikiki during the golden hour, a full 1,000-square-foot deck to move around on, and the option to bring your own drinks (no glass). The smooth hull design keeps the ride stable even in rougher conditions, and you're back on shore by nightfall.Is it for me?Book this if you want a sunset on the water without the crowded beach scene—the boat moves you past the landmarks instead of anchoring, and you control what you drink and how long you stay in the water.
Waikiki: Polynesian Canoe Sunset Sail & Cultural DinnerYou’ll step aboard a traditional Polynesian canoe in Waikiki, sail at sunset with local guides sharing stories and chants, try your hand at poi pounding or lei making, and share a dinner of Hawaiian dishes as music drifts across the deck. This is one of those evenings where you’ll feel part of something—maybe even long after you’re back on land.
Waikiki Sunset Sailing Tour: Small Group, Diamond Head ViewsYou’ll feel the ocean breeze as you sail from Honolulu with just a handful of fellow travelers, watching Waikiki and Diamond Head shift colors at sunset. With snacks and soft drinks included—and a local captain steering—the evening feels easy and real. It’s less about perfect photos and more about letting go for an hour or two.
Frequently asked questions
Can I book with free cancellation?
Yes: 13 of the 13 options offer free cancellation, so you can book now and confirm your plans later.
How long do these experiences last?
Most options last up to 2 hours.
Which one is the travelers' favorite?
Waikiki Sunset Sail: Cocktails on the Moana Catamaran is the travelers' favorite, rated 4.86 out of 5 across 2,429 reviews.
More things to do in Oahu
Parasailing Waikiki116 optionsSnorkel Oahu55 optionsOahu Luaus6 optionsHiking Oahu6 optionsOahu Whale Watching8 optionsBoat Tours in Oahu42 optionsSurf Lessons in Waikiki10 optionsUSS Arizona Memorial Tours9 optionsOahu Helicopter Tour9 optionsOahu Ziplines5 optionsNorth Shore Tours40 optionsOahu Catamaran Cruises34 optionsSnorkeling in Waikiki29 optionsFishing in Oahu9 optionsWaterfalls in Oahu6 optionsScuba Diving Oahu17 optionsOahu Sunset Cruise19 optionsGlass Bottom Boat Tours in Oahu9 optionsDiamond Head Tours40 optionsByodo in Temple Tours9 optionsSurfing Lessons in Oahu20 optionsParasailing in Oahu6 optionsOahu Turtle Tour41 optionsKo Olina Luaus5 optionsStand Up Paddleboarding in Oahu6 optionsNorth Shore Snorkeling8 optionsOahu Day Trips9 optionsKayaking in Oahu8 optionsDolphin Tour in Oahu15 optionsPolynesian Cultural Center Tours6 optionsE-Bike Tours in Oahu5 optionsOahu Food Tours6 optionsTurtles at North Shore5 optionsOahu Airport Shuttle7 optionsDiamond Head Hiking Tour12 optionsDiamond Head Helicopter Tour7 optionsDiamond Head Sunset Cruises5 options
