Honolulu’s location on Oahu makes it a prime spot for sailing adventures. The city’s stunning coastline, volcanic backdrops, and warm Pacific waters create the perfect setting for both relaxing and active days on the water. Whether you’re watching a spectacular sunset, snorkeling with sea turtles, or enjoying a luxurious day on a private sailboat, these experiences give you a chance to see the island from a different perspective. Unlike generic beach days, these tours focus on small groups, personalized attention, and in some cases, special activities like whale watching or paddleboarding. If you’re craving a memorable ocean experience, Honolulu offers a variety of options suited for all tastes and budgets.
For those who want an intimate, crowd-free experience, small-group tours are ideal. If luxury and customization are your priorities, there are premium options that combine sightseeing with fine dining. And if you’re after something unique—like fireworks under the stars or snorkeling with turtles—Honolulu’s sailing scene delivers. Below, you’ll find a curated list of the top sailing experiences with detailed insights to help you choose the one that fits your style and interests.
Quick Overview
Honolulu’s sailing tours range from simple sunset sails to elaborate luxury charters. For affordable yet intimate outings, check out Sunset sailing in small groups, which costs $104 per person for two hours with stunning views of Waikiki and Diamond Head. If snorkeling with sea turtles is your goal, the Waikiki Turtle snorkeling tour offers a 2-hour trip on a 45′ yacht, also just $104. For a more comprehensive experience, the Honolulu Sailing Tour features a 2-hour catamaran cruise spotting dolphins, sea turtles, and humpback whales in season. For those seeking luxury, the Luxury Day Sailboat Charter is a 2-hour customizable sail with high-end touches. Meanwhile, the Luxury 50′ Catamaran combines snorkeling, paddleboarding, and sunset views in a 3-hour private outing. Lastly, consider the festive Friday Night Fireworks Catamaran for a one-hour cruise with drinks and fireworks viewing.
1. Oahu: Sunset sailing in small intimate groups
At number 1, this Sunset sailing in small intimate groups offers a classic Hawaiian evening. For $104 per person, you’ll glide across tranquil waters while watching the sun dip behind the volcanic silhouette of Diamond Head. This tour emphasizes a cozy, personalized experience with small groups, making it perfect for couples, families, or friends who appreciate a quiet, scenic evening. As you sail, you’ll feel the gentle sea breeze and see the city lights flicker on as night approaches. The captain provides snacks and commentary, sharing insights about Oahu’s coastline and landmarks.
Guests consistently praise the friendly captain and the authentic feel of the tour. One recent review states, “Fabulous tour on the water with Captain Tony, wonderful recommendations, photos taken, and an amazing sunset!” The intimate size of the group means fewer crowds and more time to take photos or simply soak in the scenery. The highlight — watching the sunset with Waikiki’s skyline and Diamond Head as your backdrop — makes this a memorable way to end a day in paradise.
Bottom Line: This tour is ideal for those seeking a peaceful, beautiful sunset with a personal touch and no large crowds.
2. Oahu : Waikiki sailing turtle snorkeling in small groups
Number 2 on our list is the Waikiki sailing turtle snorkeling, priced at $104 per person for 2 hours. This tour takes you aboard a 45-foot sailing yacht with a maximum of six people—meaning plenty of space and personalized attention. The main draw: the chance to swim with sea turtles at Turtle Canyon and explore vibrant coral reefs full of tropical fish. The captain’s local knowledge significantly boosts your chances of spotting wildlife, and if no turtles are seen, they invite you back for a free redo.
The tour’s small group size means a relaxed atmosphere and excellent opportunities for photos and close-up wildlife encounters. During the trip, you’ll feel the sea breeze while taking in breathtaking views of Diamond Head. Guests often rave about the experience, describing it as “the highlight of the vacation” because of the up-close encounters with sea turtles and the colorful marine life. The combination of snorkeling and sailing makes this tour particularly suited for those who want both adventure and relaxation, with a focus on immersive wildlife encounters.
Bottom Line: This tour offers a personal, snorkel-focused experience that’s perfect for animal lovers and those wanting a memorable encounter with Hawaii’s marine life.
3. Oahu Hawaii: Honolulu Sailing Tour
At number 3, the Honolulu Sailing Tour gives you a 2-hour catamaran cruise around Oahu. For $141 per person, this trip offers the chance to see sea turtles, dolphins, and in winter, humpback whales. It’s a solid choice for those wanting to combine ocean wildlife spotting with stunning panoramic views of Honolulu, Waikiki, and Diamond Head. The boat’s smooth ride makes for a comfortable trip, and the semi-open deck lets you enjoy the sunshine and sea breeze.
The guide, with their local expertise, points out key landmarks and wildlife, making the experience educational as well as scenic. Reviewers mention the “beautiful coastline and great wildlife sightings” as highlights, and the chance to see dolphins or sea turtles is often cited as a memorable part of the tour. This trip is ideal if you want a balanced experience of sailing, wildlife, and city views, especially for travelers who prefer a shorter, more relaxed outing.
Bottom Line: Suitable for those who want a quick but lively cruise with chances to see marine animals and enjoy Oahu’s coast.
4. Oahu: Luxury Day Sailboat Charter
Number 4, the Luxury Day Sailboat Charter is a premium experience, offering a personalized two-hour sail tailored to your preferences. Costing $699 for up to six people, this experience is perfect for celebrating a special occasion or indulging in a private getaway. Starting from 1125 Ala Moana Blvd, you can customize your itinerary—whether it’s a scenic sail past Diamond Head, a wildlife viewing trip, or simply relaxing with snacks and drinks on deck.
Guests describe this as a “magical” experience where marine life and scenic landmarks are expected highlights. The captain’s flexibility allows for a tailored experience, including views of Diamond Head and Hawaii’s coastline. Many find the high-end, private atmosphere worth the price, especially if celebrating a special event. The calm waters and personal service make it suitable for travelers who prioritize privacy and luxury. One review calls the experience “very enjoyable and good value for money,” especially considering the exclusivity.
Bottom Line: Ideal for travelers seeking a private, customizable, and luxurious sailing adventure with a focus on comfort and exclusive access.
5. Oahu: Luxury 50′ Catamaran Cruise with Snorkeling and Sunset
Number 5 is the Luxury 50′ Catamaran Cruise with Snorkeling and Sunset, a 3-hour private charter that combines snorkeling, paddleboarding, and a sunset view for up to 12 people at $2,997 per group. Starting at the Ala Wai Small Boat Harbor, this tour is perfect for groups wanting a mix of active and relaxing activities. The boat is equipped for snorkeling, kayaking, and tubing, making it a full-on water day.
Passengers enjoy a gourmet charcuterie board and drinks aboard as they watch the sunset over Honolulu. The itinerary is flexible, allowing you to choose the activities that interest you most. Many guests appreciate the luxury amenities and the chance to customize their experience, with the captain providing guidance on marine life spotting and scenic landmarks. This tour is best suited for families or groups celebrating special occasions who want to maximize their water fun.
Bottom Line: This is a high-end, customizable experience for groups wanting a comprehensive day on the water with plenty of activities and comfort.
6. Waikiki: Friday Night Fireworks Catamaran Sail
Number 6, the Friday Night Fireworks Catamaran Sail offers a lively, one-hour experience for just $93 per person. It runs in the evening, giving you an up-close view of Waikiki’s fireworks with an open bar serving craft cocktails. The boat departs from Waikiki and offers panoramic nighttime views of Honolulu’s skyline and coast.
The tour’s highlight is the fireworks display combined with the gentle sway of the boat and drinks in hand. Included round-trip transportation from Waikiki makes it hassle-free. It’s a short but memorable option for those wanting a romantic or festive night out. Reviewers mention the “spectacular fireworks” and relaxed atmosphere as key positives.
Bottom Line: Perfect for an evening of celebration, especially if you want a short, party-style cruise with drinks and fireworks.
How to Choose
When selecting your sailing experience in Honolulu, consider your budget, the type of activity you prefer, and whether you want a private or group setting. For a romantic sunset or family outing, the Sunset sailing in small groups offers intimacy at an affordable price. If wildlife viewing is your priority, the Turtle snorkeling tour provides excellent chances for close encounters with marine animals. For larger groups or a more exclusive experience, the Luxury Day Sailboat Charter or the Luxury 50′ Catamaran deliver privacy and customization.
Timing is critical: book the sunset and fireworks cruises early, especially in peak seasons, to secure your spot. Reviews indicate that these experiences tend to fill up quickly, so plan ahead.
Final Thoughts
Honolulu offers a broad spectrum of sailing adventures suitable for different interests and budgets. If you’re after romantic views and a quiet evening, the sunset sail is perfect. For wildlife enthusiasts, snorkeling with sea turtles on a small yacht is a must-do. For those celebrating or seeking a luxurious escape, the private charters deliver style and exclusivity.
Ultimately, the best choice depends on what kind of experience you want—from relaxed scenic cruises to action-packed water activities. Whichever you pick, these tours promise a memorable way to see Oahu from the water. Be sure to book early and confirm availability, especially during busy travel seasons, so you don’t miss out on your ideal sailing adventure.