Top Hawaii Sailing Tours - page 4

Sail aboard a catamaran to Molokini crater, one of Maui’s best snorkel sites. The volcanic atoll off the south coast is a natural marine preserve, home to 250 species of tropical fish. Join the crew at the helm of “Paragon II” as Maui’s afternoon trade winds get the boat to this top destination.

Perfect for jetlagged early birds, this intimate morning yacht tour from Honolulu takes you to Turtle Canyon in a small group. Watch the sun rise over Diamond Head as you sail towards Turtle Canyon's reef, then jump into the water to snorkel in the company of sea turtles and colorful fish.

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.

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.

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.

Maximize your chances of seeing humpback whales by embarking on a catamaran cruise from Lahaina Harbor. In the company of certified marine naturalists and marine biologists who provide insights into whale behavior, head out onto the water in search of the gentle giants. Snacks and drinks are available on board upon purchase.

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.

The Kaneohe Sandbar is one of the best places around Oahu for swimming and snorkeling. But, without your own boat, it's tricky to get there. This boat trip does all the hard work for you so that you can relax on board as you cruise to the sandbar then spend your time as you please, whether by jumping into the water, spotting turtles or just soaking up the sun and scenery.

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.

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.

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.

Add some more outdoor adventure to your Maui itinerary with this Koa Kai whale watching trip at sunset. Get the chance to see humpback whales up close as they visit Maui to birth their young. Relax on deck, admire the natural scenery, and listen whale songs through the onboard hydrophone. Plus, you can enjoy alcoholic beverages and snacks throughout the journey.

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.

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.

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.

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.

The Au’au’ Channel is best known for its concentration of humpback whales. Hop on a boat in Maalaea Harbor to sip on a drink and spend time in the whales’ natural habitat. Your guide not only offers a trained whale-spotting eye but ensures you learn about the animals’ behavior and migration patterns. Don’t forget your camera: Lucky visitors get the chance to see the whales breaching in the open water.

Sail along the Maui coast on a humpback whale-watching excursion in the ʻAuʻau Channel—and leave the logistics to someone else. See these gentle giants spouting, tail-slapping, and maybe even breaching in their natural habitat from a comfortable boat, crewed by local experts. Enjoy the comfortable boat, ocean scenery and wildlife spotting, and look out for mother and whales and their calves because this is their winter breeding ground.

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.

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.

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.

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot catamaran 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 catamaran with 4 bean bag chairs as well as 2 small lounging nets on the back. 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 that 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 which you can connect to and play your own music. All snorkeling gear is provided. We are a USCG inspected and approved company.

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.

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.