Top Oahu Sailing Tours - page 2

Set sail and get up close with Waikiki’s majestic wildlife on this two-hour cruise. Board a spacious catamaran and glide across the water, admiring picturesque scenery of Oahu’s coast while searching for sea turtles, dolphins, coral, and vibrant fish. Stop to swim and snorkel in the turquoise water, or relax on the spacious deck.

This combination snorkeling and sailing adventure is perfect for families and nature enthusiasts. Swim with green sea turtles, tropical fish, and other marine life in Turtle Bay near Honolulu. Next, enjoy a cruise around Diamond Head in search of spinner dolphins, and in the winter months, humpback whales. Have some complimentary drinks and snacks as you savor the natural beauty that surrounds you.

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 at 95 Holomoana St, you can bring your own drinks or snacks.

Turtle Canyon lies just off Waikiki and is a top spot to snorkel with Hawaiian green sea turtles, but finding the best spots requires going with an in-the-know guide. This 2-hour catamaran tour includes snorkeling equipment and a professional guide to lead your adventure along the Waikiki coastline. Swim with turtles and tropical fish or relax on deck while enjoying ocean views.

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.

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.

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.

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.

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.

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.

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.

Snorkel with green sea turtles in Oahu—and leave the logistics to someone else—on this multi-watersport adventure. You’ll board a 45-foot catamaran and head out into the Pacific where you’ll have time to snorkel, use standup paddleboards, kayak, and try underwater electric sea scooters. After, enjoy snacks and drinks while you relax on the boat as it returns to Honolulu.

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.

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.

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and sail is the perfect combination of warm sun, refreshing salty water, and breezy adventure sailing. Snorkel equipment and drinks are all included.

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.

(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.

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.

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.

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.

You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine creatures that call the Hawaiian islands home.

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.

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.

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.