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Oahu Sailing trips & boat tours

Our most recommended Oahu Sailing trips & boat tours

Oahu: Shark Cage Dive on the North Shore

1. Oahu: Shark Cage Dive on the North Shore

Swim with the sharks during this tour that offers you the unique adventure of a shark dive, while ensuring your safety at all times. Discover the wonders of the sea on the North Shore of Oahu, Hawaii alongside a certified guide. Bring your own masks and snorkels or use the ones provided on board. Your guide will give you a safety briefing at the start of the tour and will answer all your questions concerning this special adventure. See up to 200 feet (60 meters) in the crystal-clear, cobalt blue water. Depending on the season, you will encounter such magnificent animals as the Hawaiian Green Sea turtles, playful dolphins, and Humpback whales. Admire the sharks from the ship's deck, or experience the rush of entering the shark cage which allows you to be only inches away from sharks that can grow up to 15 feet (5 meters) in length. Capture pictures with your underwater camera of their grace and majesty in the water. Have 20 minutes to marvel at the sharks and cherish this unforgettable moment. Up to 8 people can be in the cage at the same time, so you can experience the sharks with someone you love.

Oahu: Afternoon Glass Bottom Boat Tour in Waikiki

2. Oahu: Afternoon Glass Bottom Boat Tour in Waikiki

If adventure is what you seek, join this daily boat tour. Enjoy the beauty of Hawaii’s South Shore as you head out from the slip in the Kewalo Basin Harbor and head toward Lē’ahi. Discover the underwater world while staying dry with the glass-bottom boat. Aboard the Haleiwa Queen, enjoy the clear view of the Pacific Ocean floor as you cruise over live tropical reefs and one of Hawaii’s shipwrecks. Keep an eye out for honu sea turtles, eels, reef sharks, dolphins, and schools of tropical fish, all from the deck of the vessel through the glass bottom boat viewports. Experience a unique perspective of Honolulu, above and below the surface.

Honolulu: Waikiki Sunset and Whale Watching Cruise

3. Honolulu: Waikiki Sunset and Whale Watching Cruise

It is finally that time of year where the beautiful humpback whales make their return to the Hawaiian islands after migrating from Alaska! Step aboard the Island Princess and catch the beautiful sunset on the Waikiki horizon while searching for our seasonal humpback whales! Explore the bay of Waikiki and see Diamond Head Crater (Lē‘ahi Crater), check out the gorgeous turquoise waters, and learn about the majestic creatures and the local area with our experienced and knowledgeable crew! Bring your own beverages, sit back, and enjoy the view!

From Honolulu: Oahu Dolphin Swim and Snorkeling Trip

4. From Honolulu: Oahu Dolphin Swim and Snorkeling Trip

Explore the remote Wai‘anae coast of O‘ahu and experience an adventure of a lifetime. Step aboard the beautiful double-decker catamaran, the Eco, and perform a Hawaiian ‘Oli (chant) with the crew to permit safe passage on your journey. Start the adventure by looking for Hawaiian Spinner Dolphins close to the majestic and mountainous coastline. Learn about the marine and local culture. You'll explore deeper chartered waters to drop in and swim with bottlenose and spotted dolphins. Voyage back inland and moor the boat in the absolutely stunning and pristine Makaha bay. Here, you'll participate in ocean activities such as the waterslide, rock climbing wall, floating mat, and paddle boards, put on some good local tunes, snorkel with turtles and exotic fish, and enjoy a delectable locally crafted lunch. Finish the tour by traveling back to the harbor with the chance to try out the optional photo packages of your adventure.

From Honolulu: Waikiki Glass Bottom Boat Sunset Cruise

5. 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 fascinating 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.

Honolulu: Diamond Head Cruise with Drinks and Appetizers

6. 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 delicious local food and the fresh ocean air as you sail on a 65-foot catamaran.  Board the Honu Lani and sail out into the water. Enjoy unlimited non-alcoholic drinks and 2 alcoholic drinks. Take in the breathtaking landscape of the Hawaiian coast as you cruise along the shores of Waikiki.  Admire views of the Diamond Head volcanic cone and savor a delicious bento-style dinner with chilled beverages. 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.

Honolulu: 5 in 1 Turtle Snorkeling Tour with Transfers

7. Honolulu: 5 in 1 Turtle Snorkeling Tour with Transfers

Get your adrenaline pumping with a range of thrilling water sports in Honolulu. Board a catamaran for a cruise that combines snorkeling, a water slide, kayaks, a water trampoline, and stand-up paddle boards. After boarding, take your pick on which activity to do first. You could use the snorkel equipment provided to discover Hawaii's breathtaking marine life. Alternatively, get your adrenaline pumping by climbing to the top of the island's biggest onboard waterslide for a splash in the sea. Make use of the kayaks and stand-up paddle boards to explore the area or bounce to the sky on the water trampoline. If you're feeling brave, dive into the sea from the catamaran's second deck. When you’re not enjoying yourself in the water, enjoy a peaceful cruise and stunning panoramic views of Waikiki and the Pacific Ocean from the multi-level deck. Help yourself to snacks and juice before the journey back to the meeting point.

West O'ahu: Swim with Dolphins Catamaran Cruise

8. West O'ahu: Swim with Dolphins Catamaran Cruise

Go on an exciting cruise on the lookout for dolphins. Board a double-hulled catamaran and enjoy a comfortable and stable ride as you enjoy the scenery and look for the sea creatures. Relax aboard the vessel and take in the breathtaking views of the ocean and the mountains. Luxuriate on the clear waters of West O’ahu, and look for the wild dolphins swimming gracefully in small or large groups Search also for Hawaiian green turtles, tropical island fish, and other rare wild sea creatures. During the winter months, you also might catch sight of the annual migration of humpback whales as they playfully swim the West O’ahu ocean waters. On your return journey, view the majestic cascading views of the Waianae Mountain range as you voyage back towards port.

Oahu: Go City All-Inclusive Pass with 40+ Experiences

9. Oahu: Go City All-Inclusive Pass with 40+ Experiences

The Oahu All-Inclusive Pass provides free admission to the island's top activities, attractions, and tours, offering the ultimate in convenience, savings, and flexibility. Choose between a 1- to 7-day pass at a low, pre-paid price and pay nothing at the gate. Save up to 60% compared to full retail admission prices. The more you do, the more you save. When you buy a 3-, 4-, 5-, or 7-day pass, you’ll also receive free admission to one premium activity. Simply check your digital guide for any instructions, including how to make advanced reservations for selected activities, then show your pass on your mobile device or in printed format at each attraction for admission. Included activities, attractions, and tours with the Oahu All-Inclusive Pass (for all pass durations): Cultural and Historic Sights • Polynesian Cultural Center • Battleship Missouri Memorial at Pearl Harbor • Pacific Fleet Submarine Museum at Pearl Harbor • USS Arizona Memorial Narrated Tour at Pearl Harbor • Pearl Harbor Aviation Museum • Bishop Museum • Iolani Palace • Honolulu Museum of Art • Queen Emma Summer Palace Tours and Cruises • Makani Catamaran Sail • Secret Island Beach Activities at Kualoa Ranch (choice of 1 Kualoa Ranch activity per day) • Ocean Voyage Adventure at Kualoa Ranch (choice of 1 Kualoa Ranch activity per day) • Aloha Aina Tour at Kualoa Ranch (choice of 1 Kualoa Ranch activity per day) • Malama Experience at Kualoa Ranch (choice of 1 Kualoa Ranch activity per day) • Pearl Harbor & Honolulu City tour (including tickets to Arizona Memorial) • Guided Hike on the North Shore • North Shore Soap Factory Tour • Taste of Hawaii: two bars of delicious Manoa Chocolate Outdoors • Diamond Head Hike: Shuttle & Self-guided Hike • Rainforest, Waterfalls, and Movie Sites: Shuttle & Self-guided Hike • Makapuu Lighthouse & Halona Blowhole: Shuttle & Self-guided Hike • Waimea Valley • Wet ‘n Wild Hawaii including Da Flowrider • Sea Life Park Hawaii • 3-Hour Kayak Rental • Stand Up Paddle Board 3-Hour Rental • Full-day snorkel rental near Hanauma Bay • SUP Morning Yoga by Yoga Floats • Morning Yoga under the Palms • Shoreline Fishing Experience on the North Shore • 8-Hour Bike Rental (choice of 1 rental per day) • 3-Hour Moped Rental (choice of 1 rental per day) • 3-Hour E-Bike Rental (choice of 1 rental per day) • Coconut Palm Basket Weaving on Sunset Beach • Shell Pendant Making on Sunset Beach • Hawaiian Lei Making on Sunset Beach • Lyon Arboretum • Waikiki Surfboard Rental Premium Activities (3+ day passes only) (choose 1): • Makani Catamaran Sunset Sail with Drinks • Private Group Surf Lesson (for 2+) • Hidden Gems, Byodo-In Temple & Turtle spotting • North Shore Dole Pineapple Farm Tour • Moana Splash Luau • Dolphin Aloha + Hawaiian Reef Encounter + Sea Life Park Admission Please note attractions and tours are subject to change. Check your digital guide for an up-to-date attraction line-up including instructions before you go.

Oahu: Eco-Friendly West Oahu Snorkel Sail with Dolphins

10. Oahu: Eco-Friendly West Oahu Snorkel Sail with Dolphins

Experience Hawaii's unparalleled snorkeling with this cruise from Oahu. Look for Hawaiian spinner dolphins and tropical fish. Savor a mouth-watering breakfast and lunch onboard and relax with two beverages from the bar and unlimited sodas and juices.  Board the boat and set sail for the turquoise waters of the Ko Olina coast. Keep your eyes open for playful dolphins that like to jump and play in the wake of the boat. Enjoy a tasty continental breakfast on your way to your snorkeling spot. Ride on an eco-friendly sailboat, geared towards dolphin preservation and equipped with the finest of amenities, including 2 large restrooms and a fresh-water shower. There's plenty of shade on the deck, as well as tables and seating at the bar. Sip on two complimentary drinks from the bar and have the chance to purchase more as you go. Stay hydrated with unlimited non-alcoholic drinks all day long. Hop into the crystal-clear water and uncover a hidden world of vibrantly colored fish and corals. Work up an appetite and sit down to a picnic lunch on the boat's comfy deck tables. Return to your meeting point at the end of your cruise.

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What people are saying about Oahu

Overall rating

4.5 / 5

based on 509 reviews

This was a great experience for a great price. I was a little skeptical at first that we would see any whales, as the ocean is so large and there’s no knowing when and where exactly they will show, but I booked anyway to see the beautiful Hawaiian sunset on a boat. We ended up seeing a couple of whales tails come above the water 4 different times! I appreciated that the boat captain would quickly drive the boat to any location that we saw whales off in the distance. Would definitely recommend this to anyone who wants to see whales and a beautiful sunset at the same time!

It was great!! enjoyed the atmosphere and saw lots of cool animals!! We saw turtles, dolphins, and lots of fishes. The view made it a 1,000 times better!! Definitely recommend!

great evening with Greg and crew. sunset was awesome and we got to see a whale. only shortcoming was the food. Though good, it was not what we perceived as advertised.

the driver of the boat kind of looks like Revolver Ocelot from the series Metal Gear Solid. You should get that guy to cosplay as the character for Halloween

Absolutely amazing! Crew did a great job. Lots of sharks to see.