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WaikikiSailing trips & boat tours

Our most recommended Waikiki Sailing trips & boat tours

Oahu: Afternoon Glass Bottom Boat Tour in Waikiki

1. 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.

Oahu: Waikiki Glass Bottom Boat Sunset Cruise

2. Oahu: 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.

Oahu: Dolphin Swim and Snorkeling Trip

3. 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 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.

Oahu: Diamond Head Cruise with Drinks & Appetizers

4. Oahu: Diamond Head Cruise with Drinks & 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.

Oahu: Waikiki Beach Eco-Friendly Whale Watching Cruise

5. Oahu: Waikiki Beach Eco-Friendly Whale Watching Cruise

Enjoy a catamaran tour departing from Kewalo Basin Harbor and discover Humpback whales frolicking in their natural habitat on this cruise. Discover the Hawaiian Islands and enjoy snacks and drinks as you sail. Explore the shores of the main Hawaiian Islands, which are a favorite destination for humpback whales. See families of whales breach the water's surface, a spectacular sight to behold. As you ride along the waves, enjoy sodas, cookies, and chips as you watch for the whales. Enjoy the views from the double-deck power catamaran, a great vantage point for whale watching.

Oahu: Waikiki Sunset Cruise

6. Oahu: Waikiki Sunset Cruise

Step aboard the Island Princess and catch the beautiful sunset on the Waikiki horizon. Explore the Waikiki coast at sunset 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!

Honolulu: Waikiki Turtle Snorkeling Tour & 30ft Jump

7. Honolulu: Waikiki Turtle Snorkeling Tour & 30ft Jump

Experience the natural beauty of Hawaii's marine life on this snorkeling tour. Swim alongside majestic sea turtles, enjoy light refreshments while you cruise, and see panoramic views of Hawaii's coastline. Board your cruise and get a safety briefing and orientation before heading out to the best snorkeling spots to find sea turtles. In addition to the turtles, see a variety of local marine life as well, including tropical fish and colorful coral. Back on board, you can enjoy light refreshments, including water, juice, and snacks, while taking in the stunning views of Hawaii's coastline. All levels of snorkelers, from beginners to experienced swimmers can enjoy this turtle tour. If you prefer to stay on the boat and enjoy the scenery, you can book a discounted observer ticket. Turtle snorkeling, that's not all! Our travel offers unique experiences that set us apart from others. Get ready to take your adventure to the next level as you dive into the ocean from a dedicated 30-foot high jump platform. Experience the exhilarating feeling of flying through the air like a bird and take snapshots that will give you unforgettable memories and true freedom for a lifetime. Admire the beauty of Hawaii's coastline and panoramic views of the Pacific Ocean from our spacious multi-level decks while relaxing on the water.

Oahu: Morning Snorkel Sail along Waikiki Beach

8. 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 65-foot sailing catamaran, complete with a 80-passenger capacity.

Oahu: Waikiki Fireworks Catamaran Cruise with Music

9. Oahu: Waikiki Fireworks Catamaran Cruise with Music

Experience Hilton's fireworks show onboard our boat. Cruise along the Waikiki coast in Honolulu with music. Bring your own food and beverages, alcohol is allowed we kindly ask for no glass bottles. Experience views of famous Diamond Head and enjoy the city lights of Waikiki at night. Keep an eye out for local sea life as the sky is lit up by Hilton Hawaiian Village Hotel’s exclusive fireworks show. Only once a week, Hilton Grand Vacation sets off a firework display right off their beachfront. There’s no better way to come see it than out on the water aboard the Island Princess Catamaran with a drink in your hand and an aloha spirit surrounding you.

Oahu: Waikiki Sunset Sail and Swim

10. Oahu: Waikiki Sunset Sail and Swim

Board a pink-sailed catamaran and head for the seas during the beautiful golden hour. Marvel at the beauty of the sunset around you. See views of Diamond Head and world-famous Waikiki. Take a dive and go swimming, or enjoy the view from the deck.

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Frequently asked questions about Waikiki Sailing trips & boat tours

What are other things to do than Sailing trips & boat tours that are worth visiting in Waikiki?

The other unmissable things to do in Waikiki are:

Other Sightseeing Options in Waikiki

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What people are saying about Waikiki

This experience was amazing and I highly recommend it! I’ve told all of my friends and family that this is a must do activity for any vacation to Oahu. Our crew Brandon and Ford were so kind, knowledgeable, helpful, and made the entire experience that much better. They had complimentary water, they took photos, answered questions, and we even got the chance to see a turtle and a mother and baby whale. The boat was clean, safe, and had cool music and lights! It was also my boyfriend’s birthday and the crew made sure to go out of their way to make his day, everyone was so friendly, they even played a birthday song for him. I’m so grateful I booked this sunset cruise and will definitely be back! Thank you Brandon and Ford!

My daughter and I had a great time snorkeling with sea turtles and looking for dolphins. We did see some whales. We will return another day to see about those dolphins. The crew was fantastic!! Fresh pineapple was a treat! This was probably our best memory from the trip. We highly recommend.

This was a trip my daughter choose. It was so awesome. We actually got to see a breaching whale. The captains of our boat were great and very personable. I would recommend this trip for sure.

Wonderful experience Crew is very helpful and highly appreciated!!

Guides were great. Seen turtles, whales, fish. Great time.