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The 3 Best Sailing Experiences in Island Of Hawaii
Hawaii isn’t just about lounging on the beach or hiking volcanic trails; it’s also a fantastic place to sail. The island’s warm, clear waters and scenic coastlines make for memorable boating adventures. We’ve looked at three top options, each offering a different way to experience the ocean—whether that’s snorkeling with sea turtles, enjoying a private yacht, or spotting humpback whales. One thing’s certain: the Island of Hawaii offers more than enough variety for every sailor at heart.
From the family-friendly Big Island: 3 Hour Waikoloa Snorkeling & Sailing Adventure to the upscale Luxury Catamaran Trip along the Kona Coast and the exciting Kona whale watching cruise, there’s a sailing experience suited to nearly every traveler. We’ll walk through what makes each special, so you can pick the one that fits your style and budget.
1. Big Island: 3 Hour Waikoloa Snorkeling & Sailing Adventure

This three-hour adventure aboard the Spirit of Aloha catamaran is a wonderful way to combine sailing and snorkeling without overdoing it. Starting from Waikoloa, the tour offers a relaxed, comfortable cruise along the Kohala and Kona coastlines, where you’ll likely see dolphins, sea turtles, and a host of colorful fish. The boat’s design emphasizes comfort, making it suitable for families, first-time snorkelers, or anyone who wants a laid-back ocean experience.
What sets this tour apart is the combination of scenic sailing and underwater exploration. You’ll hop in the warm Hawaiian waters to snorkel at prime spots, with all necessary gear provided. Plus, the marine life here is quite active, so spotting dolphins and turtles is common. The reviews are solid, with a 4.6 out of 5 rating from 36 travelers, praising the crew’s friendliness and the quality of the snorkeling. The price is around $169 per person, which includes all equipment, making it good value for a half-day on the water.
Bottom line: This is an excellent choice if you want a relaxed, family-friendly introduction to Hawaii’s marine environment with a comfortable boat and flexible schedule.
2. Big Island: Luxury Catamaran Trip along the Kona Coast

For those seeking an upscale, intimate experience, the Luxury Catamaran Trip along the Kona Coast offers a 4-hour escape aboard a spacious yacht, with a maximum of 6 guests. This tour is all about comfort and personalized service—each guest gets their own private seating and dining areas, making it perfect for a romantic getaway or a small group celebrating a special occasion.
The trip features snorkeling with Hawaiian green sea turtles, wild dolphin sightings, and spectacular views of the Kona coastline. The boat’s luxury amenities include a freshly prepared lunch, with options like a picnic or bento box with grilled fish, along with plenty of space to lounge or chat with your companion. The guide’s 25 years of experience ensures a smooth, informative trip, and the reviews consistently praise the high level of service and the exclusivity of the experience. At $449 per person, it’s a premium experience, but many say it’s worth every penny for the privacy and quality.
Bottom line: This tour is perfect for travelers wanting a personalized, luxurious day on the water with plenty of opportunities for wildlife viewing and relaxation.
3. Honokohau: Kona Whale Watching Catamaran Cruise

If your timing aligns with whale season—generally December through April—the Kona Whale Watching Cruise is a must. This 1.5-hour cruise offers a chance to see humpback whales in their natural habitat, often breaching and tail-slapping just off the Kona coast. It’s a shorter trip but packed with action, making it ideal for travelers with limited time or those mainly interested in whale encounters.
The boat is a custom-built sailing catamaran, providing a stable and comfortable platform for viewing. The captain and guides are knowledgeable, sharing insights about these majestic creatures and the ocean environment. The reviews are positive, with a 4.4-star rating from 18 travelers, many emphasizing how close and memorable the whale sightings can be. The price is $119 per person, making it an affordable, family-friendly option.
Bottom line: Perfect for whale enthusiasts or those looking for a quick, scenic ocean experience during the right season.
How to Choose Your Perfect Hawaiian Sailing Tour
When deciding between these options, consider your budget, interests, and available time. If you’re new to snorkeling or want a laid-back, family-friendly outing, the Waikoloa adventure offers good value and fun. For a more luxurious, private experience with gourmet food, the Kona luxury yacht is ideal—though it’s pricier. If you’re visiting during whale season and want a quick wildlife fix, the Kona whale cruise is a smart, affordable pick.
Think about how much time you have—if only half a day, the snorkeling or whale-watching tours fit perfectly. For a full, leisurely day on the water, splurging on the luxury catamaran could be a highlight. Booking early is wise, especially during peak season, as these tours fill quickly.
Final Thoughts
Hawaii’s waters provide a fantastic backdrop for boating adventures, whether you want to snorkel alongside sea turtles, enjoy a private yacht experience, or witness humpback whales breach. The Big Island: 3 Hour Waikoloa Snorkeling & Sailing Adventure offers a great, affordable introduction for families or first-timers. The Luxury Catamaran Trip along the Kona Coast is best for those seeking exclusivity and comfort, while the Kona whale watching cruise provides a quick, exciting glimpse at Hawaii’s most majestic marine mammals.
No matter which you choose, these sailing experiences will give you a different perspective on Hawaii’s natural beauty. For the best experience, book early and choose a tour that matches your interests and schedules—Hawaii’s ocean adventures are well worth planning ahead for.
