Sailing Oahu 16 options
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Waikiki Sunset Sail: Cocktails on the Moana CatamaranSail the Waikiki coast at sunset on the Moana Catamaran with a complimentary first cocktail, live captain, and views of Diamond Head and the city lights.★ 4.87 (2,451)2h✓ Free cancellationfromUS$ 90per person
Oahu: Turtle Snorkel & Sailing with Luxury Catamaran & BarSnorkel Turtle Canyon on Oahu's largest catamaran with certified lifeguards, premium gear, and complimentary cocktails. Diamond Head backdrop, small groups.★ 4.70 (976)2h 30m✓ Free cancellationfromUS$ 85per person
Oahu: Makani Catamaran Sunset Cruise & Waikiki PickupSail the Oahu coast on a 65-foot catamaran with Diamond Head views, dolphins, and optional round-trip transport from Waikiki. Two-hour sunset cruises with one drink included.★ 4.55 (696)2h✓ Free cancellationfromUS$ 89per person
Waikiki Sunset Sailing: 2-Hour Catamaran Swim & SailSail the Waikiki coastline at sunset on a 2-hour catamaran, swim in the open ocean, and watch the sky turn gold and purple from the water: an experienced guide leads the way.★ 4.73 (625)2h✓ Free cancellationfromUS$ 59per person
Oahu Sunset Catamaran: Diamond Head & Waikiki with BYOBRated top sunset cruise in the US. 40-foot catamaran, Diamond Head views, complimentary pupus and drinks. BYOB welcome, free Yeti coolers. Max 28 guests, 2.5 hours.★ 4.92 (1,014)2h✓ Free cancellationfromUS$ 55per person
Waikiki Sunset Cruise with Open Bar: Barefoot Beach BoardingBoard directly from Waikiki Beach on a 45-foot catamaran with unlimited beer, wine and cocktails included: no harbor shuttle, no waiting around.★ 4.75 (625)1h 30m✓ Free cancellationfromUS$ 85per person
Waikiki: Sunset Catamaran Sail with Drinks & Diamond Head ViewsFeel the ocean breeze on a Waikiki sunset catamaran sail. Sip drinks, snap Diamond Head photos, and relax with music: includes bar and crew stories.★ 4.83 (326)1h 30m✓ Free cancellationfromUS$ 73per person
Ko Olina Sunset Cruise: Small Group Yacht Prosecco TastingYacht sunset cruise from Ko Olina on Oahu with a maximum of 6 passengers, bottomless bar, and Captain's Tasting Menu prepared onboard as you watch the sun.★ 4.96 (144)2h–2h 30m✓ Free cancellationfromUS$ 236per person
Oahu: Waikiki Catamaran Swim & Sail with Diamond HeadCatamaran swim and sail off Waikiki with Diamond Head views, cocktails, and netted lounges. Includes all fees. Half-day cruise, small groups.★ 4.89 (266)2h✓ Free cancellationfromUS$ 50per person
Waikiki Sunset Boat Cruise: Dolphins, Whales & Diamond HeadNinety minutes on the water watching the sunset over Waikiki and Diamond Head, with snacks and local beverages included.★ 4.90 (262)1h 30m✓ Free cancellationfromUS$ 50per person
Waikiki Catamaran Sail with Open Bar: Afternoon Trade WindsSail Waikiki's coastline on a 45-foot catamaran with beer, wine and cocktails included. Board straight from the beach at 3pm and be back by 4:30pm.★ 4.83 (261)1h 30m✓ Free cancellationfromUS$ 53per person
Waikiki Sunset Sailing Tour: Small Group, Diamond Head ViewsFeel the breeze off Waikiki Beach as you sail past Diamond Head in a small group at sunset: includes drinks, snacks, and a friendly local captain. Book your spot now.★ 4.88 (118)2h✓ Free cancellationfromUS$ 99per person
Oahu Sportfishing Charter: Luxury Yacht, All Gear IncludedPrivate deep-sea sportfishing charter on Oahu aboard a luxury Post 50 yacht with captain, first mate, all tackle and ice storage.★ 4.90 (106)4h✓ Free cancellationfromUS$ 1,399per group
Waikiki: Turtle Canyon Snorkeling & Sunrise Sail Small GroupWake up early in Waikiki for a sunrise sail, snorkel with turtles at Turtle Canyon, and spot dolphins near Diamond Head. Includes gear, snacks, and guide.★ 5.00 (105)2h✓ Free cancellationfromUS$ 99per person
Oahu: Small Group Yacht Snorkel Tour with Lunch & DrinksFeel the ocean breeze on a small group yacht cruise from Ko Olina, snorkel West Oahu’s reefs, spot dolphins, and enjoy lunch with drinks included.★ 4.97 (74)3h✓ Free cancellationfromUS$ 338per person
Waikiki: Polynesian Canoe Sunset Sail & Cultural DinnerFeel the ocean breeze on a traditional Polynesian canoe off Waikiki, join hands-on Hawaiian activities, and enjoy a local dinner with music: includes all food and drinks.★ 4.90 (129)2h✓ Free cancellationfromUS$ 250per person
The 12 best of 16 options, side by side
✓ 2026-10-17Sailing Oahu at a glance
- Our pick: Oahu: Turtle Snorkel & Sailing with Luxury Catamaran & Bar, US$ 85 (2h 30m, 4.70★ · 976).
- Best value: Oahu: Waikiki Catamaran Swim & Sail with Diamond Head, US$ 50 (2h, 4.89★ · 266).
- Top rated: Waikiki: Turtle Canyon Snorkeling & Sunrise Sail Small Group, US$ 99 (2h, 5.00★ · 105).
Real price per person across the 16 options: US$ 50–US$ 338 (median US$ 85). With 100+ reviews: 15 of 16.
Of the 16 options: 16 with free cancellation, 14 with instant confirmation, 16 kid-friendly, 1 private and 13 last-minute.
How we rank: quality, number of reviews and relevance to the topic. In the comparison table, our top 3 comes first. Real price per person: the group price divided by the seats it includes.
Frequently asked questions
Can I book with free cancellation?
Yes: 16 of the 16 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. There are also shorter and longer formats to fit your itinerary.
Which one is the travelers' favorite?
Oahu: Turtle Snorkel & Sailing with Luxury Catamaran & Bar is the travelers' favorite, rated 4.70 out of 5 across 976 reviews.
More things to do in Oahu
Waikiki Tours119 optionsSnorkel Oahu57 optionsOahu Luaus6 optionsWaikiki Trolley6 optionsHiking Oahu6 optionsOahu Whale Watching8 optionsNorth Shore Tours38 optionsBoat Tours in Oahu40 optionsSurf Lessons in Waikiki10 optionsUSS Arizona Memorial Tours11 optionsOahu Helicopter Tour9 optionsOahu Ziplines5 optionsOahu Catamaran Cruises33 optionsSnorkeling in Waikiki31 optionsFishing in Oahu9 optionsWaterfalls in Oahu6 optionsScuba Diving Oahu17 optionsOahu Sunset Cruise18 optionsWaikiki Sunset Cruise15 optionsGlass Bottom Boat Tours in Oahu10 optionsDiamond Head Tours37 optionsByodo in Temple Tours8 optionsSurfing Lessons in Oahu20 optionsParasailing in Oahu6 optionsKo Olina Tours8 optionsOahu Turtle Tour42 optionsOahu Food Tours6 optionsStand Up Paddleboarding in Oahu7 optionsNorth Shore Snorkeling8 optionsOahu Day Trips7 optionsWaikiki Whale Watching5 optionsKayaking in Oahu8 optionsWaikiki Glass Bottom Boat Tours7 optionsPolynesian Cultural Center Tours6 optionsDolphin Tour in Oahu16 optionsE-Bike Tours in Oahu5 optionsTurtles at North Shore5 optionsAirport Waikiki8 optionsOahu Airport Shuttle7 optionsWaikiki Sailing12 optionsDiamond Head Hiking Tour12 optionsWaikiki Turtle Tours27 optionsWaikiki Boat Tours24 optionsDiamond Head Helicopter Tour7 options