Top Hawaii Sailing Tours - page 4

Hop aboard The Universe, or your sailboat, to watch the sunset in Waikiki on this small-group tour. Your captain navigates, so you just need to relax. Sip on provided soda and water and snack on chips and crackers as you cruise along the water. Check out Diamond Head as the sun goes down and get some awesome photos.

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.

Eat, drink, and be merry on a sunset cruise aboard a luxury catamaran. Sail the waters off Maui as you experience the ho’okipa (hospitality) of the crew and panoramic views. Enjoy an array of premium appetizers, unlimited non-alcoholic beverages, and 2 complimentary adult beverages as you cruise around. From December to March, the tour includes a whale watch to see humpback whales and extends by 30 minutes.

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.

Humpback whales migrate to Hawaiian waters between December and April to give birth and breed, and seeing them from shore is hit-or-miss without knowing where the pods are concentrated each day. This whale-watching tour sails from Honolulu to the areas where the humpbacks are active, with sightings of dolphins and green sea turtles also possible across the route.

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.

Get a front-row seat for Waikiki's famed Friday night fireworks display. This evening cruise from Honolulu provides a romantic experience to remember. Enjoy a complimentary alcoholic welcome beverage as you embark, then settle in and enjoy the scenery as the sun goes down and the fireworks light up the sky.

The waters off the coast of Maui are often home to majestic humpback whales. Set sail from West Maui on this catamaran whale-watching tour as you attempt to catch a glimpse of the marine giants in their natural habitat. The onboard hydrophone will even let you listen to the whales’ song as you travel.

Leave the chaos of the mainland behind when you embark on this sunset cruise in Maui. An exclusive experience for up to six guests, this trip takes you through multiple natural landscapes, from the Molokini Crater to the Kahalewai Mountains and Lanai Island. Take in views of the coastlines and island volcanoes and relax as you watch the sun setting with your chosen group. You even have the chance to catch a glimpse of the green flash phenomenon.

The Big Island of Hawaii has a diverse ecosystem unlike anywhere else on the planet. On this small-group day-long nature tour with hotel pickup, experience the beauty of its black-sand beaches, thundering waterfalls, and Hawaii Volcanoes National Park. If you’re lucky, you spot Hawaiian green sea turtles basking on the coast.

Experience the joys of whale watching in Honolulu during this two-hour tour that guarantees sightings. Hop onto a modern trimaran boat with spacious seating, unobstructed views, and protective shade. Learn from onboard naturalists as you watch humpback whales breaching against the backdrop of Diamond Head. Conveniently located near most Waikiki hotels, you can bring your own drinks or snacks.

Enhance your chances of spotting whales in Hawaii. Discover the lives of the magnificent mammals on this whale-watching boat tour departing from Waikiki. Enjoy stunning views and photo opportunities while traveling along Oahu's coastline and get insights into whale behavior, including their breaches, flukes, and tail slaps, from the crew.

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.

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, laid-back vibe perfect for couples, families, and small groups. Sail along the Waikiki coast beneath our iconic rainbow sail—bold, colorful, and instantly recognizable. It's the perfect backdrop for stunning photos and unforgettable memories. Choose General Boarding (includes one complimentary drink) or upgrade to Mana Premium for early boarding and all-inclusive island-style cocktails. With a closer-to-the-water design, friendly local crew, and relaxed pace, this isn’t just a sunset cruise—it’s an authentic aloha experience. Feel the ocean breeze, soak in golden skies, and sail into the magic of Waikiki like a true islander.

Wake up in the morning and enjoy a sail around Oahu aboard a traditional, all-wood Polynesian canoe. This small-group tour has a strong focus on Hawaiian heritage and guests can learn about the stories and history of the tropical state. While onboard, guests also enjoy hands-on activities like making food, clothing, and tools with traditional items.

This afternoon sail in Maui offers a chance to see humpback whales in the ‘Au ‘au channel. Enjoy snacks, water, sodas, and alcoholic beverages aboard a small boat for an intimate experience focused on whale watching. Chat with your crew along the way and learn all about whale behavior as you keep an eye out for the majestic marine mammals.

Avoid large, crowded cruises in Hawaii and book this Diamond Head Private Sunset Sail from Honolulu. Cruise the water with awesome views of Diamond Head and Waikiki. This private tour offers an intimate atmosphere for just your group. Plus, you can bring food or drinks on board to make your experience even more special.

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.

Partake in a time-honored Hawaiian tradition during this private, outrigger canoe sailing experience along Maui's stunning Wailea coast. Learn about Hawaiian culture and history, including the ancient art of canoe construction, sailing, and navigation. Launch the boat from the beach using traditional methods. Spot sea turtles, reef fish, and seasonal humpback whales, with snorkeling equipment provided.

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.

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawaiian Style have lots of room for lounging in the sun, but it also has plenty of seating in the shade as well. We have two coolers we fill with ice for whatever food and beverages you choose to bring aboard. Stainless steel eco-friendly cups are also provided. We have bluetooth surround sound you can connect to and play your own music. We are a USCG inspected and approved company.

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.

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!