Top Oahu Sailing Tours - page 3

Experience an important part of Hawaiian culture during your vacation and sail on a traditional Polynesian canoe. Join a small group and board the all-wood, double-hulled vessel for a sail along Waikiki's coastline at sunset. Hear myths, legends, and stories of native Hawaii and enjoy cultural activities like making food, clothes, and other traditional items.

Swap the crowded boat tours for the chance to explore the ocean your way with this private catamaran charter from Honolulu. Glide across the ocean in comfort on board a sleek 48-foot (15-meter) catamaran and take your pick from three activity options: snorkeling, swimming near Diamond Head, or sailing down the coastline to take in the island views and look for marine life.

Epic 34' catamaran sailing and snorkeling in Waikiki Bay. With Diamond as the back drop you lay back and enjoy the amazing views.

Cap off a day in paradise with a sunset cruise from Waikiki. Unwind as you glide across the ocean and soak in views of Waikiki and Diamond Head (Lē‘ahi) crater at golden hour, while looking out for turtles, dolphins, and (during migration season) whales Bring your own drinks (no glass) to enjoy your favorite beverage while cruising.

Friday Night Fireworks in Waikiki Beach is a major tourist draw each week. Avoid the crowds than congregate on the beach and surrounding streets by enjoying the spectacle from a boat as you cruise along the coast of Waikiki. You'll enjoy unobstructed views of the fireworks from the water and plenty of space to move around. The company provides light snacks and refreshments and you can bring your own beverages.

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales. Departing near Waikiki, enjoy a leisurely sail against the majestic backdrop of Diamond Head as you scan the water for majestic whales. Dolphins, sea turtles, and manta rays are often seen while relaxing aboard with your family and friends. The majestic Humpback whales migrate annually to the Hawaiian Islands between December and April. After a long crossing of the Pacific Ocean, the Humpback whales return to deliver their newborn calves off Hawaii’s warm, sheltered waters. Seeing these endangered species off Oahu is a true gift of nature!

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide along the iconic Gold Coast as the sun sets, painting the sky with vibrant colors that illuminate Waikīkī’s skyline. This tranquil evening experience is perfect for capturing stunning photos and enjoying the serene atmosphere of paradise. Whether you're a couple, family, or sunset enthusiast, this cruise offers a unique way to unwind and appreciate the beauty of Hawaii. Enjoy a refreshing swim in the crystal-clear waters off Waikīkī Beach. Sail along the iconic Gold Coast during the magical golden hour. Capture stunning photos of the sunset and Waikīkī skyline. Ideal for couples, families, and sunset enthusiasts alike.

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to accommodate groups wanting to do private charters in the morning to celebrate lives, scatter ashes, and conduct meaningful ceremonies. Capacity: 49 Guests Maximum Juices, sodas, and water are included.

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. You can go at the best time of day to snorkel (before 1pm) and see turtles, dolphins, eels, rays, octopus, big schools of tropical fish, and humpback whales (whale season is December - April). If you decide that you want to add to your trip, it’s no problem. It’s your boat and you decide the music, where you go, and rest assured you have the best crew to keep you safe at sea.

Experience Waikiki like the celebs do—from aboard a private yacht. With your captain at the helm, you’ll glide toward Diamond Head at sunset, you and your crew basking in the views, catching splashes of dolphins and whales in the distance. As the sun sets, the city lights begin to glow, and the views only get better and better.

On this exciting Oahu combo tour, start the day with a downhill bike ride with epic views of the coastline, before boarding a comfortable catamaran for a two-hour snorkeling adventure.  On this Oahu biking and sailing tour, all the necessary equipment is provided along with professional guides.

Explore Oahu's most popular spots all in one day on this tour, including transportation to and from your hotel. Travel comfortably around the island in an air-conditioned coach or minivan as you pass by Diamond Head and North Shore Surfing Beaches. Make stops at the Dole Plantation, Kualoa Ranch and a variety of lookout points.

Watch the sunset over Oahu from the comfort of a 46-foot chartered yacht during a 2.5-hour private dinner cruise. With space for up to six passengers, this evening excursion is the perfect opportunity to celebrate an anniversary, share a special family experience, or take your annual girls trip to the next level. Enjoy a freshly prepared dinner, plus an open-bar with unlimited prosecco, beer, spirits, and non-alcoholic drinks.

Set sail for beautiful Waikiki, the beachfront neighborhood of Honolulu, on this guided, 90-minute tour along the south shore of the island of Oahu in Hawaii. Beginning from the Kewalo Harbor waterfront, head down to Ala Moana Beach Park to Waikiki and the volcanic tuff cone Diamond Head. Along the way, look for Hawaii’s famous green sea turtles and other marine wildlife. Snacks, two free bar beverages and unlimited non-alcoholic drinks are provided.

Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a spectacular Hawaiian sunset on your private yacht. Get a chance to see whales, dolphins and sea turtles. Immerse yourself in a bucket list Adventure Today!

Get VIP views of Honolulu on this private sailing excursion out of Waikiki. With your captain and crew at your behest, you’ll cruise from Waikiki Beach to Diamond Head, spending time onboard however you wish. Choose between swimming or snorkeling with marine life, sunbathing on the deck, watching downtown Honolulu fade in the breeze—this is one travel memory to cherish forever.

Watch the sun glow over the Pacific Ocean and spot wildlife from whales and turtles to dolphins (if you’re lucky) with this exclusive catamaran snorkeling adventure. Relax onboard a comfortable vessel with padded seats and ample space, or hop into the water with the provided snorkeling gear, finding out what's below the surface—and seeing Hawaii's colorful underwater world.

Embarking on a sunset sail is the perfect way to end a day in Waikiki. With so many options, you'll want to be sure to make the best choice. This cruise promises comfort and relaxation by taking you out onto the ocean aboard a spacious twin-hulled catamaran. As the crews do the hard work, you can simply relax on board and feel the warmth of the setting sun.

Swap the crowded catamarans for the chance to soak up Hawaii's natural beauty from a spacious yacht, in the company of just your partner. This private Waikiki sunset cruise is the perfect romantic experience for couples and takes you along the Waikiki coastline, all the way past Diamond Head, in time to see the sun setting over the ocean.

Swap the hustle and bustle of Honolulu for a day out on the ocean on this relaxing afternoon cruise. Soak up the sun and sea breeze as you sail along the coastline, past Diamond Head, aboard a spacious and comfortable catamaran. Relax on board while looking out for spinner dolphins, Hawaiian sea turtles and (in season) humpback whales.

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. You can go at the best time of day to snorkel (before 1pm) and see turtles, dolphins, eels, rays, octopus, big schools of tropical fish, and humpback whales (whale season is December - April). If you decide that you want to add to your trip, it’s no problem. It’s your boat and you decide the music, where you go, and rest assured you have the best crew to keep you safe at sea.

Go whale-watching off the coast of Oahu on this excursion from Waikiki or Ko Olina. During the months from December to May, pods of humpback whales migrate through Hawaii's warm waters, and this tour guarantees whale sightings. With a small group of people, watch the gentle giants swim, feed, breach and play around your boat. In the rare event that you don't see any whales, you will be allowed to do the tour again for free. Snacks are included.

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. You can go at the best time of day to snorkel (before 1pm) and see turtles, dolphins, eels, rays, octopus, big schools of tropical fish, and humpback whales (whale season is December - April). If you decide that you want to add to your trip, it’s no problem. It’s your boat and you decide the music, where you go, and rest assured you have the best crew to keep you safe at sea.

Fit in a private kiteboarding, wind foiling, or wind surfing lesson while you’re in Oahu with this Kailua private lesson and learn the sport of your choice in class session that’s not packed with strangers. Plus, all your gear is provided for you, as well as an easy-to-use 2-way radio helmet.