15 Oahu Sailing Tours, Best Day First

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

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

Board the Hawaii-built Moana Catamaran at Kewalo Basin Harbor for a two-hour sunset sail along Waikiki and past Diamond Head. Your captain and crew serve a complimentary first drink from the premium bar, with more available for $8. Look for dolphins, and humpback whales from November through May. Shoes are collected before boarding.

“A really wonderful expierence, we did the VIP which we liked to board early and get the free drinks included. Lovely hosts and weather was amazing!”

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2.Waikiki Turtle Snorkel and Sail on Hawea Catamaran

★★★★★★★★★★5.0 · 1,655 reviews · 2 hours 30 minutes (approx.) · from $89

Meet at the Duke Paoa Kahanamoku Statue for a 2.5-hour catamaran trip to Turtle Canyon. The crew provides snorkel gear and guides you to turtles, tropical fish, reefs, octopus, and starfish. Morning and afternoon departures are available, with snacks, drinks, and a sailing ride along Waikiki included.

“The crew made this an awesome, safe, and fun experience! The bar onboard was a great bonus after snorkeling :-)”

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3.Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

★★★★★★★★★★4.5 · 936 reviews · 2 hours 30 minutes (approx.) · from $76

Sail from Kewalo Harbor to Turtle Canyon for a guided family snorkel with provided gear, certified lifeguards, and a secured raft for children and beginners. You may see turtles, tropical fish, starfish, octopuses, dolphins, or even a monk seal. The first drink from the premium bar is included.

“Such a great experience even with 2 kids.We saw 2 turtles and tons of fish. Everyone who worked the boat was very knowledgeable and sweet. One even swam down and brought up a sea urchin for my son to hold. Great adventure!!”

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4.Ko Olina Catamaran Sail and Snorkel with Lunch

★★★★★★★★★★5.0 · 630 reviews · 3 hours (approx.) · from $195

Sail Oahu’s west coast aboard a 53-foot catamaran, then snorkel over a reef known for tropical fish and possible sea turtles, dolphins, and whales. The 3-hour trip includes gear, a turkey or vegetarian sandwich lunch, three complimentary cocktails for adults, and juice or soda. Ko Olina pickup is easy, while Waikiki transport costs extra.

“This excursion was by far the best experience we had. For the price it is so worth it. They gave us three free drinks, an amazing sandwich for lunch, and let us snorkel and jump off the boat. We saw wildlife and lots of fish. You won’t regret booking!”

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5.Waikiki Sunset Cocktail Sail with Open Bar

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

Join Holokai Catamaran for a 90-minute sunset sail from Waikiki. Drinks include wine, champagne, Maui Brewing beers, rum punch, sodas, juices, and the signature Holokai Hooch. Crew members such as Ryan, Chase, Kevin, Kayla, Bridget, and Alec are known for keeping the mood social. Expect barefoot boarding through shallow water and possible spray.

“Beautiful scenery and vibes !! ✨️ Good drinks at open bar !! Very relaxing, smooth ride to see the sunset 😎 🌺🌇”

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6.Waikiki Beach Sunset Sail

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

Sail from Waikiki Beach aboard Ke Kai for about 90 minutes, with Diamond Head, Mamala Bay, music, soft drinks, and alcoholic beverages included. Crew members including Kyle, Johnny, Justin, and Aiden have been praised for their friendly service and fun energy. Expect an upbeat boat ride, ocean spray near the bow, and a party atmosphere more than a quiet sunset cruise.

“Beautiful cruise. Party atmosphere with bar and places to congregate. We enjoyed the sunset and the lights on the shore.”

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7.West Oahu Dolphin Watch and Snorkel Sail with Lunch

★★★★★★★★★★4.5 · 320 reviews · 3 hours (approx.) · from $125

Cruise Oahu’s Leeward Coast aboard a catamaran with Hawaii Nautical, watching for spinner dolphins, turtles, and seasonal whales before snorkeling over coral reefs. Captain Jessie, Ian, Nick, Nicole, and other crew members have earned praise for helping families and nervous swimmers. Breakfast, lunch, drinks, gear, restrooms, and optional pickup are included.

“No breakfast, but fun trip just got sea sick. In the description it said there would be breakfast with fruit and a biscuit but there was none, couldn’t wear shoes so deck was hot, fun trip though”

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8.Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

★★★★★★★★★★5.0 · 277 reviews · 1 hour 30 minutes (approx.) · from $72

Sail from Waikiki Beach aboard the 50-foot Hāwea for about 90 minutes, with one included drink, music, local stories, and views of Diamond Head and the Honolulu coast. Crew members such as Cameron, Dez, and Kapono help create a friendly, relaxed mood. You will board barefoot through shallow surf, so wear shorts and keep bags light.

“All crews are nice and took photos for us. The tour was amazing and definitely would come back next time.”

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9.Waikiki 3pm Tradewind Sail – Open Bar Included

★★★★★★★★★★5.0 · 246 reviews · 1 hour 30 minutes (approx.) · from $53

Sail from Waikiki for about 90 minutes aboard the Holokai catamaran. You may see Diamond Head Lighthouse, sea turtles, dolphins, or humpback whales in winter. Captains and crew may include Ryan, Mitch, Austin, and Marc. Expect beach boarding, wind, some boat movement, and a relaxed rather than fast-paced cruise.

“Worth it!!! We had 7 people and everyone enjoyed it a lot. Beautiful scenery and people working were so personable!”

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10.Sail and Turtle Snorkeling Tour in Waikiki

★★★★★★★★★★5.0 · 242 reviews · from $99

Spend two hours aboard Three Tiki Sailing’s stable trimaran, cruising from Waikiki to a turtle-snorkeling site. Swim with fish and honu when conditions allow, or relax under the large shaded canopy. Crew members including Chad, Jack, and Austin focus on safety, comfort, and friendly help for first-time snorkelers.

“My family's first time snorkeling and it was a great experience. We saw turtles and all sorts of different fishes. It was like being in the Nemo movie is what my family kept saying.”

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11.Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

★★★★★★★★★★5.0 · 236 reviews · 2 hours (approx.) · from $34Best value

You’ll spend about two hours sailing from Kewalo Basin toward Diamond Head, with time to swim from the catamaran or stay aboard for coastal views. The friendly English-speaking crew serves cocktails for purchase, provides float belts, and keeps the mood relaxed. This is a swim-and-sail outing, not a snorkeling tour.

“Love the all women crew. Very friendly to talk to and very helpful. 10 out of 10 would recommend again. Very worth the money. Great drinks for great price.”

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12.Honolulu Sunset Sail from Kewalo Harbor Including Drinks

★★★★★★★★★★5.0 · 169 reviews · 1 hour 30 minutes (approx.) · from $61

Board the Na Hoku 2 at Kewalo Basin Harbor for a 90-minute sunset sail toward Waikiki. Expect Diamond Head views, included alcoholic and non-alcoholic drinks, music, and a social party-boat mood. Crew members such as Ricki and Jeff have helped make past sailings especially fun, but check your confirmation for the current departure point.

“What a Fun crew we had! They kept us laughing, played great music, the drinks were just as good. They came around and checked on us, helped take pictures if needed. The only downside I might say is my husband doesn’t drink, but drinks non alcohol beer and I wish more activities like these would have that option, it truly is not fun to not feel included on a booze cruise that you are graciously doing with your wife and daughters. The sail it self was gorgeous, the timing was perfect for the peek of the sunset and the glow bouncing off mountains and pacific. The price was very reasonable…”

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13.Board from Waikiki Beach for Aloha Hour Sail on Hāwea Catamaran

★★★★★★★★★★5.0 · 134 reviews · 1 hour 30 minutes (approx.) · from $55

Board the 50-foot Hāwea catamaran near the Duke Kahanamoku Statue at 3:00 pm for a 90-minute sail along Waikiki toward Leahi, better known as Diamond Head. Enjoy included alcoholic drinks, mocktails, music, ocean breezes, and a relaxed crew. Sightings may include dolphins, turtles, flying fish, or seasonal humpback whales.

“Very enjoyable experience. The crew is very friendly and works hard to ensure all passengers are comfortable. I also felt very safe in their care.”

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14.2-Hour Oahu Sunset Catamaran Sail

★★★★★★★★★★5.0 · 122 reviews · 2 hours (approx.) · from $130

Sail from Ko Olina Marina on a 53-foot catamaran for two hours of ocean views, sunset light, complimentary cocktails, soda, juice, shrimp cocktail, and charcuterie. The crew, including names such as Jackie, Ethan, Todd, Brittany, and Captain Tamika on some departures, handles drinks and snacks while you relax offshore.

“We loved our sunset sail. The staff were great, the ship was beautiful and the snacks and drinks were great. I highly recommend this trip to anyone looking for a comfortable and relaxing sunset cruise.”

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15.Waikiki Turtle Snorkel Sail

★★★★★★★★★★4.7 · 103 reviews · 2 - 3 hours · from $99

Sail from Kewalo Harbor on the 65-foot Honu Lani, then snorkel Waikiki reefs where Hawaiian green sea turtles and tropical fish often gather. The crew helps beginners, supplies sanitized gear, and serves drinks, snacks, and island views. Past sailings featured Captain Greg, Julia, and Kiara.

“We had a great time and the crew was very friendly and hopeful.”

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