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Sailing Trips & Tours

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Our most recommended Oahu Sailing Trips & Tours

Honolulu: Turtle Snorkeling Tour

1. Honolulu: Turtle Snorkeling Tour

Enjoy a peaceful cruise off the coast of Honolulu complete with a snorkeling experience where you'll get the chance to swim with turtles. (Disclaimer: Marine life can't be guaranteed and every trip is different. Thank you for your understanding!) Board your catamaran at the Kewalo Basin Harbor and set out to explore the waters off the coast of Oahu. As you cruise, sit back and relax on the multi-level deck and admire panoramic views of Hawaii's tropical scenery. Water, soft drinks, and snacks are provided on board. Then, hop into the water and swim within a safe viewing distance of the tropical fish and turtles that regularly frequent these waters. If you visit between December and April, you may even be lucky enough to spot humpback whales and dolphins.

Honolulu: Turtle Canyon Guided Snorkeling Adventure Tour

2. Honolulu: Turtle Canyon Guided Snorkeling Adventure Tour

Snorkel over coral reefs with green sea turtles on a guided boat tour from Honolulu. Look beneath the waves and have the chance to see sharks, stingrays, octopus, and colorful fish. Experience beautiful views of the Waikiki coastline on the way. Make your way to the dive shop and meet your guide and group for the day. Briefly go over the different snorkeling spots before cruising off the coast towards Turtle Canyon and enjoying the views of Oahu disappearing behind you. Warm up with a light surface session and see how many fish you can spot in the crystal clear water. Move on to one of the favorite reef sites in Honolulu and have the chance to swim alongside green sea turtles in their natural habitat at a safe distance. Get back into the boat and share your experience with your crew as you relax on deck and stare out into the stretching sea. Watch the shoreline of Waikiki coming quickly into view and return to the dive shop.

Waikiki: Turtle Canyons Snorkel Excursion

3. 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.

Honolulu: Waikiki Sunset and Fireworks Cruise with Drinks

4. Honolulu: Waikiki Sunset and Fireworks Cruise with Drinks

Discover the beauty of Diamond Head from the water as the sun sets on this cruise from Honolulu. Watch a brilliant display of colors as fireworks go off over the golden sands of Waikiki beach. Sip on 2 alcoholic drinks, water, and juice and enjoy some snacks along the way.  Show your voucher at the ticket booth and board a comfortable boat. Cast off and make a toast with your drink as you admire views of the coast. Capture pictures of the Diamond Head volcanic cone in the glow of the setting sun.  Cruise along the palm tree-lined Waikiki beach and watch a stunning fireworks display after the sun has set. Admire views of the city as it lights up for the night. On clear nights, see the moon rising above the water. Return to your meeting point at the end of your cruise. 

Oahu: North Shore Snorkeling Tour from Haleiwa

5. 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.

From Honolulu: Waikiki Glass Bottom Boat Sunset Cruise

6. 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.

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: Waikiki Sunset and Cocktail Cruise

9. 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.

Honolulu: Diamond Head Cruise with Drinks and Appetizers

10. 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.

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

We had an amazing time sailing. Our captains, John & Toby, were a wealth of information about the history/cultural significance of “the Mokes”. This activity included a bit of everything…beach time, wildlife (monk seal, birds & crabs), paddling, sailing, hiking and playing in the waves. The wa’a (canoe) was very stable and none of us felt in danger, even with the wind and big waves. Paddling the canoe was easier than we thought. We did get wet, but our stuff didn’t! They supplied quality dry bags for our items. Once at the island, we hiked up to Queens Bath. Even though John and Toby hiked up barefoot, you’re going to need no slip shoes of some sort. It’s very rocky, but easy if you follow the guides. I have double knee replacements and didn’t have a bit of trouble. It has an amazing view and well worth it! Not once did we feel rushed and were so relaxed the entire time. It was a great way to end our vacation. This was by far my 13-year daughter’s favorite activity.

I loved it! My tour was filled with divers so I had the snorkel instructor to myself!!!! She was amazing and helpful. They provide snacks and drinks on the boat for free! The staff was amazing. I would book another trip with them.

Jim was an incredible boat captain. My family had a wonderful time. I strongly recommend this for anyone traveling to Waikiki. The sunset was beautiful thanks to captain Jim

Very much enjoyed the excursion. Captain and guide were both wonderful; very nice, informative, and created a great experience. Glad we did it for sure!

It was my first time ever. The experience was incredible, I was able to get close to many turtles and even got to see an eagle ray along with many fish.