12 Honolulu Sailing Tours to Get on the Water

1.Waikiki Beach: Turtle Snorkeling and Sailing on Hāwea

★★★★★★★★★★4.7 · 656 reviews · 2h 30m · from $84Our pick

Board Hāwea behind the Duke Kahanamoku Statue for a 2.5-hour Turtle Canyon trip. You’ll snorkel with green sea turtles and reef fish, then sail along Waikiki with Diamond Head views. The crew provides gear, safety help, non-alcoholic drinks, and morning cold brew with Anahola Granola.

“Wonderful crew made for a very relaxing and exciting time snorkelling. Felt safe and saw plenty of fish and luckily had a large turtle surface right next to us and watched young ones being cleaned by the local fish. Great time and worth the money. Highly recommended.”

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2.Waikiki Sunset Catamaran Sail and Swim

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

Spend two hours on Pink Sails Waikiki’s catamaran, leaving Waikiki for a sunset cruise with views of Diamond Head and the shoreline lights. You can jump into the ocean before sunset or stay aboard. English-speaking crew members such as Jamie, Alexio, Peter, and Morgan have earned praise for friendly service, music, photos, and good humor.

“AWESOME! best thing i did in waikiki!!!!! the crew (alex, nici and mo) was amazing and the vibes were GREAT!”

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3.Board from Waikiki Beach: Scenic Sunset Sail on the Hāwea

★★★★★★★★★★4.9 · 217 reviews · 1h 30m · from $68

Board the 50-foot Hāwea near the Duke Paoa Kahanamoku Statue for a 90-minute sunset sail along Waikiki. Expect Diamond Head views, island music, nonalcoholic drinks, and an onboard bar with cocktails, beer, wine, and seltzers for purchase. Hawea Premium adds unlimited cocktails. Arrive 30 minutes early.

“The best activity we booked during our entire stay! Relaxing, clean, welcoming.”

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4.Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

★★★★★★★★★★5.0 · 191 reviews · 2 hours (approx.) · from $71Top rated

Spend about two hours sailing from Honolulu past Diamond Head, the Royal Hawaiian Hotel, and Magic Island, then swim off Waikiki as the sun sets. Three Tiki Sailing keeps the boat to a maximum of 35 people, plays music, and lets you bring your own drinks. Bring cups, ice, and a towel.

“We had a great time with our teenage kids and parents. Great for family or couples. The crew was welcoming and fun.”

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5.Board from Waikiki Beach: Friday Night Fireworks sail

★★★★★★★★★★4.8 · 70 reviews · 1 hour · from $71

Board behind the Duke Kahanamoku Statue for a one-hour Friday night sail along Waikiki. You’ll watch the coast brighten after sunset, order beer, wine, seltzers, or a Signature Sip at the onboard bar, then face the fireworks from the water. Crew members, including bartender and guide Cameron, help with safety and boarding.

“Best way to see the fireworks and the lights of the city. So pretty. Had the best time.”

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6.Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

★★★★★★★★★★4.5 · 68 reviews · 5 hours 30 minutes (approx.) · from $196

Start with a guided five-mile downhill bike ride on Tantalus Mountain, stopping for views from Diamond Head to the Waiʻanae Mountains. Then sail from Kewalo Basin on a 38.6-foot catamaran and snorkel in deeper water with reef fish and turtles. Guides such as Terry, Rudolph, and Captain Crash may lead different parts of the day.

“We spend this great time enjoying the pristine nature of Hawaii close to the view of the beautiful Waikiki beach area”

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7.90 Minute Catamaran Sunset Sail

★★★★★★★★★★4.8 · 64 reviews · 1h 30m · from $56

Board the 45-foot yellow-and-red Na Hoku 2 at Kewalo Basin Harbor for a 90-minute sunset sail. You’ll pass views of Ala Moana Beach, Kaka‘ako, Waikiki, and Honolulu’s skyline while the crew serves soda, juice, water, beer, Mai Tais, and mixed drinks. Expect music and a social, party-style setting rather than a quiet cruise.

“The crew was amazing and did an great job taking pictures and catering to all guest, I will definitely be back.”

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8.Full Day Oahu Bike, Hike, Sail and Snorkel Combo

★★★★★★★★★★4.5 · 33 reviews · 8 hours (approx.) · from $292

Spend about eight hours moving from sacred rainforest to reef on Oahu. You’ll hike two miles with a local guide, coast five paved miles downhill by bike, then sail a 38-foot boat near Diamond Head and snorkel with provided gear. Guides such as Terii, Daniel, Michael, and Jeremy are known for strong island stories and careful help.

“Wonderful knowledgable guide! Terri knew all kinds of interesting facts about Hawaii. Very safe and very accommodating. Loved every minute of my day!!!”

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9.Board from Waikiki Beach for our Aloha Hour Sail

★★★★★★★★★★4.4 · 15 reviews · 1h 30m · from $52

Board the hand-built 50-foot catamaran Hawea behind the Duke Kahanamoku Statue for a 90-minute Waikiki sail. You’ll cruise toward Diamond Head with included alcoholic and nonalcoholic drinks, including mai tais, tropical cocktails, local beer, wine, seltzers, and soft options. Bring sunscreen, sunglasses, and a camera.

“Great trip and we saw flying fish!! Was beautiful”

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10.Sunset sailing in small intimate groups

★★★★★★★★★★5.0 · 7 reviews · 2 hours · from $103

Join Captain Tony aboard The Universe for a two-hour sunset sail from Honolulu’s Ala Wai Harbor. With only six people aboard, you’ll cruise toward Diamond Head, hear stories about Waikiki, enjoy snacks and soft drinks, and watch the coastline shift from golden light to city sparkle. Bring food and alcohol if you wish, but no glass bottles.

“By far the best way to enjoy an Oahu sunset. Thank you Captain Tony for a wonderful experience. The whole family loved it!”

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11.BYOB Weekend Sightseeing Sail towards Diamond Head

★★★★★★★★★★3.0 · 4 reviews · 1 hour · from $23Best value

Join the certified English-speaking crew aboard Island Magic for a one-hour sail from Prince Waikiki toward Waikiki, Turtle Canyon, and Diamond Head. Bring your own drinks, snacks, and camera, then enjoy South Shore views without a snorkeling stop or swimming. The boat returns to 1 Holomoana St.

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12.Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles

★★★★★★★★★★5.0 · 3 reviews · 8 hours (approx.) · from $1,100 whole boat, up to 5

Spend about eight hours with Custom Island Tours, combining a private Oahu drive with a two-hour sail to Turtle Canyon. Guides Carey or JP can adjust the five-hour road portion to your interests. Expect hotel valet pickup, east-coast viewpoints, local food stops, Honolulu views from Tantalus, and a chance to see sea turtles.

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