Waikiki Sailing at a glance
- Our pick: Waikiki Sunset Sail: Cocktails on the Moana Catamaran, US$ 90 per person (2h, 4.87★ · 2,477).
- Top rated: Waikiki: Turtle Canyon Snorkeling & Sunrise Sail Small Group, US$ 99 per person (2h, 5.00★ · 109).
- Best value: Waikiki Catamaran Sail with Open Bar: Afternoon Trade Winds, US$ 45 per person (1h 30m, 4.83★ · 263).
Price per person across the 20 options priced per person: US$ 45–US$ 284 (median US$ 72). With 100+ reviews: 18 of 21.
Of the 21 options: 18 with live guides in English, 21 with free cancellation, 21 with instant confirmation, 20 kid-friendly, 1 private and 17 bookable last-minute.
How we rank: quality, number of reviews, availability, booking conditions and relevance to the topic. In the comparison table, our top 3 comes first. Price per person. “Top rated” = the highest score among options with at least 100 reviews.
Waikiki Sailing
Based on each operator's calendar. Confirmed when you book.
21 options
The 15 best
Ranked by quality, reviews, availability and booking conditions.
Waikiki Sunset Sail: Cocktails on the Moana Catamaran Sail 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. Every day · 17:00 · All ages ★ 4.87 (2,477 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 90 per person
Oahu: Waikiki Catamaran Snorkel & Sea Turtles with Lunch Snorkel with Hawaiian green sea turtles on a 65-foot catamaran from Waikiki. Includes gear, local beer, lunch option, and free re-ride if turtles aren't spotted. Every day · 10:30 · All ages ★ 4.68 (2,136 reviews) Duration: 2h–3h Live guide: EN ✓ Free cancellation. from US$ 170 per person
Oahu Sunset Catamaran: Diamond Head & Waikiki with BYOB Rated 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. Every day · 17:15 · All ages ★ 4.92 (1,031 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 55 per person
Oahu Turtle Canyon: 2-Hour Snorkeling with Sea Turtles 2-hour snorkeling tour at Turtle Canyon, Oahu with guaranteed sea turtle sightings, gear included, small groups. Departs Waikiki daily, families welcome. Every day · 08:00, 11:00, 13:30 and 14:00 · Up to age 70 ★ 4.71 (1,519 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 81 per person
Waikiki Sunset Cruise with Open Bar: Barefoot Beach Boarding Board directly from Waikiki Beach on a 45-foot catamaran with unlimited beer, wine and cocktails included: no harbor shuttle, no waiting around. Every day · 17:00 · All ages ★ 4.75 (630 reviews) Duration: 1h 30m ✓ Free cancellation. from US$ 85 per person
Waikiki Sunset Sailing: 2-Hour Catamaran Swim & Sail Sail 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. Every day except Friday · 16:30 and 17:00 · All ages ★ 4.74 (629 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 47 per person
Waikiki Sunset Sail on Catamaran: 90-Minute Cruise with Drinks Sail off Waikiki Beach at sunset on a 49-passenger catamaran with complimentary cocktails, beer and soft drinks included. Every day · 17:30 · All ages ★ 4.79 (488 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 70 per person
Waikiki: Turtle Canyon Snorkel & Sail at Noon Noon snorkel at Turtle Canyon from Waikiki beach with professional guide, catamaran sail toward Diamond Head, gear and drinks included. Travelers' Choice award. Every day · 12:00 · All ages ★ 4.77 (330 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 72 per person
Waikiki: Sunset Catamaran Sail with Drinks & Diamond Head Views Feel the ocean breeze on a Waikiki sunset catamaran sail. Sip drinks, snap Diamond Head photos, and relax with music: includes bar and crew stories. Every day · 17:00 and 17:30 · All ages ★ 4.83 (329 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 58 per person
Waikiki Sunset Cocktail Cruise: Live Music & Open-Air Decks Sail the Waikiki coast at sunset aboard the Majestic, a three-deck yacht with an open-air top level and full bar: one complimentary drink included. Every day · 17:15 and 19:00 · All ages ★ 4.49 (265 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 85 per person
Waikiki Catamaran Sail with Open Bar: Afternoon Trade Winds Sail 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. Every day · 15:00 · Season until 30 Nov · All ages ★ 4.83 (263 reviews) Duration: 1h 30m ✓ Free cancellation. from US$ 45 per person
Honolulu: Waikiki Sunset Sail & Swimming with BYOB Sailing trimaran Hokulani departs Waikiki for Diamond Head and Magic Island with sunset swim. 41-foot vessel, 1,000 sq ft deck. Bring your own drinks (no glass). Every day · 16:30 and 18:00 ★ 4.91 (222 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 79 per person
Waikiki Sunset Boat Cruise: Dolphins, Whales & Diamond Head Ninety minutes on the water watching the sunset over Waikiki and Diamond Head, with snacks and local beverages included. Every day · 17:00 · From age 3 ★ 4.89 (284 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 51 per person
Oahu: Waikiki Catamaran Swim & Sail with Diamond Head Catamaran swim and sail off Waikiki with Diamond Head views, cocktails, and netted lounges. Includes all fees. Half-day cruise, small groups. Every day · 14:00 · All ages ★ 4.89 (266 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 50 per person
Waikiki: Turtle Canyon Snorkeling & Sunrise Sail Small Group Wake 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. Every day · 07:00 · From age 4 ★ 5.00 (109 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 99 per person
Also popular with travelers
The ones most travelers have taken, by number of reviews.
Waikiki: 1-Hour Catamaran Sail with Diamond Head & Drinks One-hour catamaran sail from Waikiki Beach with complimentary drinks, Diamond Head views, and a yellow-red boat. Departs daily, all ages welcome, arrive 30 minutes early. Every day · 10:00, 11:30, 13:00, 14:30 and 16:00 · All ages ★ 4.73 (124 reviews) Duration: 1h ✓ Free cancellation. from US$ 46 per person
Waikiki Sunset Sailing Tour: Small Group, Diamond Head Views Every day · 16:30 ★ 4.88 (121 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 99 per person
Waikiki & Diamond Head: Catamaran Sail with Drinks Sail from Waikiki Beach on a lively catamaran, sip complimentary drinks, and catch unique views of Diamond Head. Includes check-in, local crew, and all ages welcome. Every day · 14:30 and 16:00 · All ages ★ 4.91 (87 reviews) Duration: 1h Live guide: EN ✓ Free cancellation. from US$ 53 per person
Compare 3 more options for Waikiki Sailing
From US$ 225 per person · 2 h to 3 h
Waikiki: Polynesian Canoe Sunset Sail & Cultural Dinner Feel 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. Next departure: 9 Feb 2027 · All ages ★ 4.90 (130 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 225 per person
Snorkeling in Waikiki: Private Yacht with Lunch Snorkel from a 43-foot yacht in Waikiki with a maximum of six guests, professional gear, lunch and drinks included. Tue, Thu and Sun · 10:00 · All ages ★ 5.00 (21 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 284 per person
Waikiki Private Sunset Cruise & Diamond Head with Dolphins Private yacht sunset cruise in Waikiki for up to 6 guests. See Diamond Head, dolphins, turtles & whales. Includes drinks, snacks & attentive crew. Every day except Friday · 17:30 Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 950 per group
The top 12 of 21 options, side by side
✓ 2026-11-14| Option | Price | Duration | Rating | Days and times | Guide languages |
|---|---|---|---|---|---|
| Waikiki Sunset Sail: Cocktails on the Moana CatamaranOur pick | US$ 90 per person | 2h | 4.87★ · 2,477 | Every day · 17:00 | English |
| Waikiki: Turtle Canyon Snorkeling & Sunrise Sail Small GroupTop ratedGroup of up to 6 | US$ 99 per person | 2h | 5.00★ · 109 | Every day · 07:00 | English |
| Waikiki Catamaran Sail with Open Bar: Afternoon Trade WindsBest value | US$ 45 per person | 1h 30m | 4.83★ · 263 | Every day · 15:00 · Season until 30 Nov | — |
| Oahu: Waikiki Catamaran Snorkel & Sea Turtles with Lunch | US$ 170 per person | 2h–3h | 4.68★ · 2,136 | Every day · 10:30 | English |
| Oahu Sunset Catamaran: Diamond Head & Waikiki with BYOB | US$ 55 per person | 2h | 4.92★ · 1,031 | Every day · 17:15 | English |
| Oahu Turtle Canyon: 2-Hour Snorkeling with Sea Turtles | US$ 81 per person | 2h 30m | 4.71★ · 1,519 | Every day · 08:00, 11:00, 13:30 and 14:00 | English |
| Waikiki Sunset Cruise with Open Bar: Barefoot Beach Boarding | US$ 85 per person | 1h 30m | 4.75★ · 630 | Every day · 17:00 | — |
| Waikiki Sunset Sailing: 2-Hour Catamaran Swim & Sail | US$ 47 per person | 2h | 4.74★ · 629 | Every day except Friday · 16:30 and 17:00 | English |
| Waikiki Sunset Sail on Catamaran: 90-Minute Cruise with Drinks | US$ 70 per person | 1h 30m | 4.79★ · 488 | Every day · 17:30 | English |
| Waikiki: Turtle Canyon Snorkel & Sail at Noon | US$ 72 per person | 2h 30m | 4.77★ · 330 | Every day · 12:00 | English |
| Waikiki: Sunset Catamaran Sail with Drinks & Diamond Head Views | US$ 58 per person | 1h 30m | 4.83★ · 329 | Every day · 17:00 and 17:30 | English |
| Waikiki Sunset Cocktail Cruise: Live Music & Open-Air Decks | US$ 85 per person | 1h 30m | 4.49★ · 265 | Every day · 17:15 and 19:00 | English |
By what you need
- Private (1): Waikiki Private Sunset Cruise & Diamond Head with Dolphins (US$ 950 per group)
- Small groups (up to 15) (4): Waikiki: Turtle Canyon Snorkeling & Sunrise Sail Small Group (US$ 99 per person) · Waikiki Sunset Sailing Tour: Small Group, Diamond Head Views (US$ 99 per person) · Waikiki: Polynesian Canoe Sunset Sail & Cultural Dinner (US$ 225 per person)
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