Oahu · EVENING EXPERIENCES

15 Evening Experiences on Oahu Worth Booking Ahead

73 tours  ·  from $35 a head

Good evening experiences on Oahu fill up in the busy months and the best ones go first. Below: the 15 to book early, what each includes and how they differ.

Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail - Waikiki’s shore, seen from the deck
Cruises & Boat Tours, Evening Experiences, Honolulu Sunset Cruises, Oahu Sailing Tours, Tour Reviews, Tours in Oahu

Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

1.Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

★★★★★★★★★★5.0 · 2,205 reviews · 2 hours (approx.) · from $89Our pick

Set sail from Kewalo Basin Harbor for a two-hour barefoot catamaran cruise along Waikiki and past Diamond Head. The crew serves one complimentary premium drink, with additional drinks at $8 each. From November to May, you may spot humpback whales; dolphins are also possible. The boat returns to the harbor.

“Do not book this trip thru Viator. Cost less booking on your own. And DO NOT upgrade to VIP tix. A complete waste of money. All you get is on boarding first. But I am giving this cruise a 5 Star rating b/c the crew was outstanding! Very attentive and friendly. We saw whales which was a big plus since there were clouds and no sun this evening. Very relaxing and great views of Diamondhead and the coast line of Waikiki.”

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Honolulu: Three Star Deluxe Sunset Dinner Cruise and Show - A Toast, Then Five Courses
Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Evening Experiences, Honolulu Dinner Cruises, Honolulu Sunset Cruises, Show, Tour Reviews, Tours in Oahu

Honolulu: Three Star Deluxe Sunset Dinner Cruise and Show

2.Three Star Deluxe Sunset Dinner Cruise and Show

★★★★★★★★★★4.5 · 1,204 reviews · 2 hours (approx.) · from $193

Board the Star of Honolulu at Pier 8 for a roughly two-hour sunset cruise past Waikiki and Diamond Head. You’ll get a welcome toast, two premium beverages, a five-course dinner featuring lobster and tenderloin, live music, and a Hawaiian cultural show. Select hotel pickup when booking, or arrange your own ride to the pier.

“We got picked up close to our hotel by a charter bus which was comfortable and had good AC. The boat was nice with friendly and helpful staff. The (5) course meal offered a whole lobster and a decent sized piece of tenderloin. The entertainment included a jazz band w/singer, Polynesian dancers, and a duo, all very good. Very good experience over all.”

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Sunset Dinner Cruise in Honolulu, Hawaii - BYOB, the Tiki bar, and what is included
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Sunset Dinner Cruise in Honolulu, Hawaii

3.Sunset Dinner Cruise in Honolulu, Hawaii

★★★★★★★★★★4.0 · 1,023 reviews · 2 hours (approx.)

This two-hour Honolulu cruise follows the Waikiki shore toward Diamond Head Lighthouse, with sunset views from the Pacific and dinner prepared aboard the Prince Kuhio. Choose from beef short ribs or mahi-mahi, then bring your own alcohol for the upper-deck Tiki bar. Recent reports raise serious questions about cancellations, the boat’s operating status, and the meeting address, so confirm all three before booking.

“The people are very nice. The Pearl Harbor Tour was an experience. The tour was great. Thank you 💕.”

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Waikiki Signature Sunset Catamaran Sail - Turning at Diamond Head for the sunset
Cruises & Boat Tours, Evening Experiences, Honolulu Sunset Cruises, Oahu Sailing Tours, Tour Reviews, Tours in Oahu

Waikiki Signature Sunset Catamaran Sail

4.Waikiki Signature Sunset Catamaran Sail

★★★★★★★★★★4.5 · 890 reviews · 1 hour 30 minutes (approx.) · from $89

Cruise from Honolulu toward Diamond Head aboard a 53-foot catamaran, then pause for sunset views and a look for turtles, dolphins, or seasonal humpback whales. You get a light appetizer box, two alcoholic drinks, and unlimited nonalcoholic beverages. Crews have included Chris, Phil, Keoni, and Andrea, though staff can vary.

“Awesome time tonight with the captain and crew. Great sunset and great drinks. We lucked out with only 8 passengers tonight, so we got a lot of attention (thankfully, the off season)!”

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Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB - From Ala Moana Harbor toward Diamond Head
Cruises & Boat Tours, Evening Experiences, Food, Food & Drink, Oahu Food Tours, Oahu Sailing Tours, Tour Reviews, Tours in Oahu

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

5.Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

★★★★★★★★★★5.0 · 836 reviews · 2 hours (approx.) · from $44Best value

Board a 40-foot catamaran near Ala Moana Harbor for a two-hour evening sail past Diamond Head and Waikiki. Expect light appetizers, refreshments, and BYOB for adults 21 and over. Captains and crew members such as Krash, Shannon, and Lucy have been praised for a relaxed, attentive style. Wildlife and fireworks are possible, but never guaranteed.

“The sunset cruise was well worth it. Captain Krash did a wonderful job navigating and narrating along the way, and Holly was on top of her game, making sure everyone had a great time.”

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BYOB Sunset Cruise off the Waikiki Coast - BYOB makes the fare more flexible
Cruises & Boat Tours, Evening Experiences, Honolulu Sunset Cruises, Tour Reviews, Tours in Oahu

BYOB Sunset Cruise off the Waikiki Coast

6.BYOB Sunset Cruise off the Waikiki Coast

★★★★★★★★★★5.0 · 694 reviews · 1 hour 30 minutes (approx.) · from $44

Spend about 90 minutes cruising the Waikiki coast from Kewalo Basin, with views of Waikiki Beach, Diamond Head, and the sunset over the ocean. Bring your own drinks in non-glass containers; the boat has a cooler with ice, and light refreshments and snacks are included. The crew may share local stories and help with photos.

“Very nice evening on the water , the captain did a great job !!! Thanks for very good evening !!! We would recommend this sunset cruise to anyone looking for a great relaxing evening!!!”

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Honolulu: Pacific Star Sunset Dinner Cruise and Show - Finding your table and settling in
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Honolulu: Pacific Star Sunset Dinner Cruise and Show

7.Pacific Star Sunset Dinner Cruise and Show

★★★★★★★★★★4.5 · 633 reviews · 2 hours (approx.) · from $139

Board the Star of Honolulu at Aloha Tower for a two-hour sunset cruise with a Pacific Rim buffet, one signature Mai Tai, coffee and tea, and live entertainment. Head to the 60-foot wraparound decks for coastal views. Friday sailings run about three hours and include fireworks. Seating and show visibility can vary by dining package and location.

“Made everyone feel like family. Food was delicious and plentiful. The entertainment was fabulous, I think it was the best show I have seen in Hawaii. The performers really enjoy what they do and do the very best to make the audience feel included. We could not have had a better time!”

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Waikiki: Friday Night Fireworks Catamaran Cruise - The fireworks, and how to set your expectations
Cruises & Boat Tours, Evening Experiences, Oahu Sailing Tours, Tour Reviews, Tours in Oahu, Waikiki Fireworks Cruises

Waikiki: Friday Night Fireworks Catamaran Cruise

8.Friday Night Fireworks Catamaran Cruise

★★★★★★★★★★4.5 · 610 reviews · 1 hour 45 minutes (approx.) · from $67

Board Pink Sails Waikiki at Ala Wai Yacht Harbor for a 1-hour-45-minute Friday evening catamaran cruise along the Waikiki coast. Take in Diamond Head and city views, then watch the Hilton Hawaiian Village fireworks from offshore. Music and a cash bar are part of the outing; complimentary snacks are advertised, though availability may vary.

“OMG! This was the most exciting adventure! It was more like a party sailboat! The crew was so engaging and the fireworks were absolutely amazing! This is a MUST do!”

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Waikiki Sunset Cocktail Sail with Open Bar - What 90 minutes on the water feels like
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Waikiki Sunset Cocktail Sail with Open Bar

9.Waikiki Sunset Cocktail Sail with Open Bar

★★★★★★★★★★4.5 · 554 reviews · 1 hour 30 minutes (approx.) · from $84

Set sail from Waikiki aboard Holokai Catamaran for a 90-minute sunset cruise with an open bar, including wine, champagne, beer, nonalcoholic drinks, and the signature Holokai Hooch. Expect barefoot boarding through shallow water, city and Diamond Head views, and a sociable shared-boat atmosphere. Friday departures are for ages 21 and up.

“We had the best time on this beautiful cruise! Chase was an amazing bartender, the views were stunning, the music was great- highly recommend!”

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Sunset Boat Cruise: Swim and Cruise Waikiki - A swim stop makes this more than a scenic ride
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Sunset Boat Cruise: Swim and Cruise Waikiki

10.Sunset Boat Cruise: Swim and Cruise Waikiki

★★★★★★★★★★4.5 · 533 reviews · 2 hours (approx.) · from $47

Set out with Pink Sails Waikiki for a two-hour sunset cruise along the Waikiki coast. You can watch the sky change from the deck or swim during a stop in Waikiki Bay. Snacks are included; drinks are sold onboard, and snorkel gear is not provided. Crew members such as Jamie, Peter, Lexie, Brian, John, and Tyler have been praised for their help and easygoing style, though the crew may vary.

“What an awesome cruise !! Value for money, insta worthy photos 😃 spectacular sunset, swim in the ocean and whale spotting all in one !! Teenagers loved it ! Fantastic crew made the experience even more fun - thank you captain Jamie, Xavier , Ryan and the rest of your crew !”

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Oahu: Waikiki Sunset Catamaran Sail and Swim - Diamond Head from the water
Cruises & Boat Tours, Evening Experiences, Honolulu Sunset Cruises, Oahu Sailing Tours, Tour Reviews, Tours in Honolulu

Oahu: Waikiki Sunset Catamaran Sail and Swim

11.Waikiki Sunset Catamaran Sail and Swim

★★★★★★★★★★4.7 · 519 reviews · from $44

Pink Sails Waikiki runs a two-hour evening sail from the Waikiki waterfront, with sunset views of Diamond Head and time for an ocean swim when conditions allow. The crew speaks English and has included Jamie, Alex, John, and Tyler on past trips, though crew assignments vary. Boat type may also change with availability and conditions.

“Great price, good jokes, fun swimming, great guides and sunset was amazing. Definitely will do it again.”

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Oahu: Waikiki Glass Bottom Boat Sunset Cruise - Waikiki from the water
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Oahu: Waikiki Glass Bottom Boat Sunset Cruise

12.Waikiki Glass Bottom Boat Sunset Cruise

★★★★★★★★★★4.6 · 518 reviews · 1h 30m · from $60

Board the 50-foot Haleiwa Queen at Honolulu’s Ala Moana Harbor for a 90-minute cruise along Waikiki’s south shore. The crew shares local stories as you look toward Diamond Head and the city skyline at sunset. Bottled water is provided, and you can bring your own food and drinks, including alcohol. Crew members have included Courtney and Tristan, though the team may vary.

“This was such a nice, relaxing short cruise with a beautiful sunset. It was a really chill atmosphere with good music and laid-back, easy going guides. We even got lucky and saw a couple of whales!”

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Waikiki Beach Sunset Sail - What the onboard mood is really like
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Waikiki Beach Sunset Sail

13.Waikiki Beach Sunset Sail

★★★★★★★★★★5.0 · 378 reviews · 1 hour 30 minutes (approx.) · from $70

Board the Ke Kai catamaran on Waikiki Beach for a roughly 90-minute sail through Mamala Bay, with views of Diamond Head and Oahu’s south shore. Soft drinks and alcoholic beverages are included, and crew members such as Kyle, Johnny, Justin, and Aiden have helped make the trip lively. Expect music, open-air seating, and a chance of getting splashed near the bow.

“What can I say? This boat ride was EVERYTHING and more! Kyle, Johnny, and Justin made sure everyone felt welcomed and included throughout the whole time. I beat cancer last year, and for them to go above and beyond to make me feel special was life-changing. Justin driving the boat was phenomenal! Don’t waste anytime just BOOK!”

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Oahu: Waikiki Sunset Catamaran Cocktail Cruise - Finding your spot on the catamaran
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Oahu: Waikiki Sunset Catamaran Cocktail Cruise

14.Waikiki Sunset Catamaran Cocktail Cruise

★★★★★★★★★★4.7 · 348 reviews · 1h 30m · from $99

Sail the Waikīkī coast for 90 minutes aboard the Hanu Lani, with views of Diamond Head, a premium bar, light bites, and shaded or open-air seating. The crew changes, though past sailings have included staff such as Clay and Captain Mark. Bring a light layer, and ask ahead about dietary needs and drink limits.

“We had a great time on the boat cruise and highly recommend this sunset cruise! The crew was fantastic and made it a really fun experience for everyone on board. They made sure we had the perfect sunset views and there was more food than expected.”

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Premier Waikiki Sunset Party Cruise with Live DJ and Full Bar - Waikiki’s coastline as the light fades
Cruises & Boat Tours, Drinking Tours, Evening Experiences, Tour Reviews, Tours in Oahu

Premier Waikiki Sunset Party Cruise with Live DJ and Full Bar

15.Premier Waikiki Sunset Party Cruise with Live DJ and Full Bar

★★★★★★★★★★5.0 · 322 reviews · 2 hours (approx.) · from $72

Set sail from Kewalo Basin Harbor at 5:30 pm for a roughly two-hour, 21-and-over cruise along Waikiki and Diamond Head. Expect a live DJ, LED lights, one included adult drink, a full bar for additional purchases, and wraparound seating on a two-deck powerboat. The boat can rock, and shoes are not allowed onboard.

“We had a wonderful time, the crew was very energetic & fun, the DJ (sorry forgot his name) had us dancing the entire time. The bartender Rachel was great & nice. Ryan was dancing get everybody in the mood. Zack was a great captain & I can’t remember the other crew guys name but he was also great & fun. Our entire boat was a rocking in the good way!!!”

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