Oahu
Sailing Trips & Tours

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Our most recommended Oahu Sailing Trips & Tours

Waikiki: Turtle Canyons Snorkel Excursion

1. Waikiki: Turtle Canyons Snorkel Excursion

Experience the magical underwater world of sea turtles. Dive under the waves with a snorkel and see the rainbow of tropical fish. Connect with the wide array of stunning marine life on this two-hour tour. Start off with a cruise along the coast, where you can potentially spot spinner dolphins and humpback whales during the wither months. Once at the Turtle Canyons, you’ll get a brief lesson on snorkeling and your snorkeling equipment.  Snorkel alongside the sea turtles and tropical sea life under the supervision of a certified lifeguard, returning to the boat whenever you please to relax with complimentary refreshments.

From Honolulu: Waikiki Glass Bottom Boat Sunset Cruise

2. From Honolulu: Waikiki Glass Bottom Boat Sunset Cruise

Experience the beauty of Oahu's south shore as you sail towards the volcanic tuff cone of Lēʻahi (Diamond Head) as the sun dips below the horizon on this tour from Honolulu. Hear about Waikīkī with facinating commentary from the local crew. Climb aboard the spacious Haleiwa Queen, a 50-foot catamaran with 49 seats, an onboard restroom, and shaded deck for your comfort. Have the chance to bring your own food and drink to enjoy while you sail. Enjoy a comfortable ride as the crew shares their knowledge about Waikīkī, the thriving farm productions, and royalty that have frequented the area throughout history. Learn about its transition into an urban society. Leave with a newfound appreciation for the people and marine life of Hawaii, and then gaze in awe as the sun reflects off the city skyline, overlooked by the towering peak of Diamond Head, at magical sunset hour.

Oahu: North Shore Snorkeling Tour from Haleiwa

3. Oahu: North Shore Snorkeling Tour from Haleiwa

Head out to Waimea Bay on Ocean Outfitters Hawaiian rollercoaster ride. This ocean adventure off the North Shore of Oahu lets you snorkel up close and personal with our marine friends. This tour operates from May 1st to Oct 31 and is closed during the high surf winter months. Dolphins, rays, turtles, and native Hawaiian reef fish are known to frequent the area. Some of the reef fish are found nowhere else in the world. Humpback whales make their annual journey to Hawaii between the months of November to April, so you can really see them strut their stuff in the pristine blue waters.

Honolulu: Diamond Head Cruise with Drinks and Appetizers

4. Honolulu: Diamond Head Cruise with Drinks and Appetizers

Discover the beauty of the Diamond Head volcanic cone from the water on this sailing catamaran cruise from Honolulu. Watch the sunset and delight your senses with fresh, local cuisine, unlimited non-alcoholic beverages, and 2 bar drinks. Treat yourself to an evening on the Honi Olani, a 53- by 30-foot sailing vessel. Try authentic Hawaiian appetizers such as avocado poke, pipikaula (Hawaiian beef), Maui onion salad, penne pasta, tortilla chips with pineapple salsa, a vegtable platter, and taro rolls with lilikoi butter. Savor a cheese, grape and cracker plate, a selection of white wines and two free bar drink tickets per adult as you take in the breathtaking landscape of the Hawaiian coast. Sailing south toward Diamond Head, you may even be so lucky as to glimpse the green flash as the sun slips below the horizon. Enjoy this peaceful evening with the ocean breeze in your hair for an authentic Waikiki experience.

Oahu: Waikiki Sunset and Cocktail Cruise

5. Oahu: Waikiki Sunset and Cocktail Cruise

See a spectacular sunset and beautiful city lights views aboard Hawaii's only full-service bar and lounge on the sea. This will be an unforgettable yacht cruise experience with a spacious open-air top deck to experience Waikiki's lovely sea breeze and picturesque skyline. You will receive a complimentary welcome drink upon boarding. Additional drinks and packaged snacks are available for purchase. See iconic Hawaii landmarks, such as Honolulu Harbor, Diamond Head, and the Waikiki coastline from a unique vantage point. You can also sip on a cocktail in the modern air-conditioned lounge with floor-to-ceiling windows, perfect for taking in coastline views.

Oahu: Waikiki Undersea Adventure Submarine Tour

6. Oahu: Waikiki Undersea Adventure Submarine Tour

Climb aboard Atlantis XIV, the world's largest hi-tech passenger submarine which holds a whopping 64 passengers—that's 16 more people compared to the smaller 48-passenger submarines. Dive 100 feet below the surface and experience Waikiki’s marine mysteries. Being in a submarine and descending to 100 feet underwater is an adventure in itself. Also get to see real marine life up close. The Atlantis Waikiki dive site is home to many Hawaiian fishes, coral, and turtles. Known for its quality and safety, Atlantis is an eye-opening experience that takes you beyond the classroom as you learn about coral, reef life, and submersibles while visiting sunken shipwrecks, airplanes, and other artificial reefs. Atlantis has a spacious air-conditioned interior, large viewports, and comfortable seating. The hi-tech 64-passenger large submarine offers an enhanced amount of personal space and viewports. 

Kailua: 2-Hour Guided Kayak Excursion with Lunch

7. Kailua: 2-Hour Guided Kayak Excursion with Lunch

Perfect for beginners or travelers wanting to perfect their skills, this kayak tour has been designed to show off the very best that Hawaii has to offer. Follow a qualified guide to their favorite locations around the bay, visit secluded coves, discover Hawaii’s marine life, and find the best spots to snorkel. During the tour you’ll also protect the island by helping to collect marine plastics as well as learn how to positively interact with wildlife. The tour focuses on sustainable tourism and incorporates eco-friendly practices, such as the elimination of single-use-plastics at lunch. Get kitted out with all the necessary safety gear before hopping onboard your kayak and heading into the water. The first stop of the day is the beautiful Popoi’a Island, where you can admire and learn about the nesting sea-birds which are protected here. Next, follow your guide on an easy eco-hike around the island, and explore the tide pools that line the shore. Once you’ve worked up a bit of an appetite, replenish your energy with a snack break. While you eat, marvel at the magnificent landscapes of dormant volcanoes and the Ko’olau Mountain Range, which provide the perfect back drop to learn about Hawaii’s geologic history. Back on the kayak, soak up the tranquil atmosphere as you go in search of the green sea turtles that call these waters their home. Next, enjoy some free time to snorkel in search of colorful marine life, have a go at boogie boarding, or simply relax on the beach.

Oahu: Waikiki Sunset Cruise with Live DJ

8. Oahu: Waikiki Sunset Cruise with Live DJ

Board a modern boat at the Kewalo Basin Boat Harbor to begin your journey into the sunset. After a safety briefing and a group toast, you can explore the boat's two decks, wraparound seating, and Titanic-style front bow. Alcoholic drinks are available to purchase onboard and IDs will be checked prior to boarding. Take in the beauty of the iconic Diamond Head State Monument at the golden hour. Watch surfers glide along coastal waves and keep your eyes peeled for sightings of sea turtles, dolphins, and humpback whales. After the sun dips below the horizon, the boat lights up in a vibrant purple hue with twinkling lights overhead. A live DJ will entertain you with contemporary beats over the surround-sound speakers as you dance to the onboard light show. The unique Honolulu skyline will glitter for you in the warm twilight breeze. Finally, head back to the harbor where you will do one last group cheers with your new ohana.

Oahu: Morning Snorkel Sail along Waikiki Beach

9. Oahu: Morning Snorkel Sail along Waikiki Beach

Embark on a sailing tour, absorbing from a distance the Waikiki sights. Once far enough out at sea, you will have the opportunity to partake in a thrilling snorkeling experiences where you will be able to see Hawaiian Green Sea Turtles. If you don’t see turtles, you will be invited to come back and redo the tour free of charge. During whale season (December through April), you will also stop to watch these majestic mammals in their natural environment. Your guides will be onboard to facilitate your experience every step of the way. Departing from Kewalo Basin Harbor, Waikiki, you will board your 53-foot sailing catamaran, complete with a 49-passenger capacity.

Waikiki: BYOB Sunset Cruise with Snacks

10. Waikiki: BYOB Sunset Cruise with Snacks

See a majestic Hawaiian sunset from the comfort of a boat on a sunset cruise out of Waikiki. Bring your own drinks and sip on a cold one as you see Honolulu's city lights twinkle and Diamond Head proudly standing in the distance. Sit back and relax, enjoying the warm breeze and good company onboard. Depart Kewalo Basin and glide across the ocean's blue waters with beautiful views of the coastline. Watch as the sky turns from light blue to vibrant orange, red, and golden hues. During the summer months, see the sunset at the end of the cruise, and in winter, enjoy it at the beginning, marveling at Waikiki's twinkling lights for the remainder of your cruise.

Frequently asked questions about Oahu Sailing Trips & Tours

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Other Sightseeing Options in Oahu

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What people are saying about Oahu

Overall rating

4.5 / 5

based on 509 reviews

It was amazing to see turtles up close! You also got to see beautiful tropical fish. The guides were great at pointing them out and naming them. The experience was initially divided into the experienced swimmers and those who knew how to snorkel and the second group was those who were needing extra help either with swimming or snorkeling. That way they got more attention and help with skills if necessary. The guides also offered to dive down and take pics on our phones and gopros which was really nice! Overall 10/10!

Rikki was a great guide. The experience was well worth it. Plus, the options for lunch were great as well. Would highly recommend.

All the staffs were so passionate!!! Loved it!!! Great experience! And Jeremy is the best!!

Such a memorable experience! Book your tickets. You won’t regret.

Great service. Beautiful sunset. Awesome trip. Must do!