Top Hawaii Sailing Tours - page 3

Escape the hustle and bustle of land and soak up the sun and ocean breeze while taking in the sights of the Kona coastline on this sailing trip aboard a comfortable 53-foot catamaran. As you glide across the blue water, keep an eye out for marine wildlife such as dolphins and humpback whales during migratory season. Enjoy a full premium bar with tropical cocktails, beer, wine, soda, and juice on board.

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.

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along the Kona coastline toward the Captain Cook Monument, where your adventure begins. Jump into the clear water to explore the vibrant reef of the marine sanctuary of Kealakekua Bay, which is home to schools of colorful fish and pods of spinner dolphins. Your tour includes breakfast, lunch, and equipment such as snorkeling gear and boogie boards.

Experience the ultimate Friday night in Waikiki aboard a fireworks cruise! After sunset, get ready for a spectacular show as fireworks light up the city skyline. Sip on premium drinks from the onboard bar and enjoy the illuminated night sky. This party promises unforgettable views and a vibrant atmosphere that will make your evening truly special. Book now and experience an amazing night on the water, surrounded by the magic of fireworks and the beauty of Waikiki.

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.

Discover all the vibrant marine life that calls Turtle Canyon’s reefs home—and enjoy an accessible way to snorkel and explore—on this family-friendly catamaran trip. Make your own way to the Kewalo Harbor, and hop aboard your well-appointed catamaran: snorkels, fins, masks, and more are all provided on board. Once you make it to the reefs, dive in, spot sea turtles and other marine life, and admire the underwater scenery.

Sail along Oahu's beautiful coastline and immerse yourself in Hawaiian culture on this sailing trip aboard a Polynesian canoe. Join a small group and board the all-wooden vessel to begin your journey. Listen to local stories and enjoy hands-on activities such as making food, clothes, and tools using local items, with the beautiful coastal scenery serving as your backdrop.

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.

Discover a side of the Big Island of Hawaii that very few other travelers get to see on this one-of-a-kind submarine tour. Choose from multiple start times, head to the Kona coastline, and board the submarine. As you descend towards the colorful reef, peer through the portholes and spot fish and other marine life. Along the way, your on-board naturalist guide provides in-depth commentary about the aquatic sights.

Escape the crowds of Waikiki Beach and enjoy the magic of a Hawaiian sunset on board a spacious double-decker catamaran. Roomy decks provide panoramic views of the Oahu coastline and a submerged glass-bottom viewing room offers the chance to observe marine life such as dolphins, whales, sea turtles, and native fish.

See the Waikiki coastline like never before on a sunset dinner cruise on board a 65-foot (20-meter) catamaran. Set sail from Waikiki and enjoy unobstructed views of the beach with a backdrop of the Ko`olau mountains. As the sun sets and the Honolulu skyline lights up, toast your day in paradise with two included drinks and a delicious dinner.

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.

Cruise to Oahu's Turtle Canyon in a 65-foot (20-meter) catamaran that departs from the only pier in Waikiki. Learn about the life, behavior, and cultural significance of Hawaiian green sea turtles (known locally as *honu*) then jump into Turtle Canyon's protected tropical waters to swim among them.

Set sail down the Kona coastline aboard a trimaran, arriving in the Kealakekua Bay Marine Preserve for an afternoon of snorkeling. Splash into the turquoise waters near the Captain Cook Monument, and search for pods of spinner dolphins that frequent the bay. All equipment is provided along with light snacks and reef-safe sunscreen to make the trip convenient.

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and unforgettable views in one trip. We reach Turtle Canyon quickly, giving you more time in the water to swim with Hawaiian green sea turtles in clear, warm conditions. Beyond snorkeling, enjoy kayaking, stand-up paddleboarding, sea scooters, and swimming—all included at no extra cost. The highlight is the timing. After your activities, relax on board as the Waikiki sky fills with vibrant sunset colors, with Diamond Head as your backdrop. The experience ends with a peaceful sunset sail, complemented by charcuterie and cocktails. With a friendly, attentive crew and beginner-friendly guidance, this tour is perfect for everyone—from first-time snorkelers to experienced ocean lovers. More than just a tour, it’s a memorable Waikiki experience you won’t forget.

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kaho‘olawe. Guests can relax on trampolines or in shaded seating while enjoying locally-inspired appetizers and a selection of beverages, including cocktails, beer, and wine. From December to March, keep an eye out for majestic humpback whales as they migrate, often providing unforgettable sightings during the sail. - Enjoy a scenic 2-hour sunset sail aboard the 55-foot Akialoa catamaran. - Indulge in a selection of local appetizers and an open bar of drinks. - Limited to 48 passengers, ensuring a cozy and intimate experience. - Spot migrating humpback whales from December to March for a unique wildlife encounter.

Snorkel with green sea turtles in Oahu's Turtle Canyon on this tour departing from Waikiki. Board a power catamaran and sail along the shore of Oahu towards the island's best place to spot the resident turtles. Turtle sightings are guaranteed; if a turtle is not sighted, you will be given a free second cruise. The midday tour includes lunch and complimentary alcoholic drinks, while the morning tour offers unlimited soft drinks.

Explore Oahu's waters on this submarine-style ride aboard the Atlantis Submarine. During this family-friendly adventure, learn about the local fish, coral, and other animals in this marine habitat through your guide's informative commentary. Descend 100 feet (30 meters) under the surface of the water without getting wet in a vehicle that is quiet and pollution-free, so marine life is undisturbed.

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.

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.

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.

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.

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.

Every Friday night, catch the weekly Hilton Hawaiian Village fireworks display from the water on this evening cruise off Waikiki Beach. The cruise includes an open bar, making this a fun and affordable way to kick off the weekend. This is a great option for families and group celebrations such as birthdays and bachelorette parties.