The Island of Hawaii offers some of the most exciting sailing experiences in the Pacific. With its diverse coastline, abundant marine life, and warm waters, it’s a sailor’s paradise. Whether you’re after a relaxing day on a luxury yacht or an energetic snorkel cruise, Hawaii’s waters promise unforgettable moments. The islands’ crystal-clear waters and impressive marine sightings make sailing not just a pastime but a must-do activity for visitors. These tours showcase the island’s natural beauty and marine diversity, giving you a chance to see dolphins, sea turtles, whales, and more in their natural habitat.
Hawaii’s sailing options range from casual snorkel trips to intimate luxury yacht charters and seasonal whale watches. Each offers a unique perspective on the island’s coastline and marine life, making it easy to find a tour that matches your interests and budget. To help you decide, we’ve put together a list of the best sailing experiences, carefully selected for their quality, reviews, and distinctiveness.
Quick Overview
Our list features three top-rated sailing experiences on the Big Island: a 3-hour snorkeling and sailing adventure on the Spirit of Aloha, a luxurious private yacht trip along the Kona Coast, and an exciting whale-watching cruise from Honokohau. Each tour offers something special—whether it’s snorkeling with tropical fish, enjoying privacy on a boutique yacht, or spotting humpback whales during their seasonal migration. For more details on each, visit the linked experiences.
1. Big Island: 3 Hour Waikoloa Snorkeling & Sailing Adventure
At number 1, this snorkel and sail trip on the Spirit of Aloha combines comfort with marine exploration. The 3-hour trip runs either in the morning or afternoon, making it easy to fit into your schedule. The boat is a classic catamaran, providing stability and space, perfect for relaxing while sailing along the Waikoloa and Kohala-Kona coastlines. The focus here is on snorkeling in warm Hawaiian waters, where you’re likely to see sea turtles, tropical fish, eels, and even octopuses, according to reviews.
What makes this tour stand out is its balance of comfort and adventure. The crew is described as fun and informative, keen on safety while sharing insights about marine life. The reviews highlight this trip as one of the best snorkeling experiences, with many praising the helpful crew and beautiful snorkeling spots. The included lunch—simple but tasty—adds to the relaxed vibe. Some mention the boat feeling crowded, but overall the small-group feel and marine encounters make it worthwhile.
Bottom Line: This tour is perfect if you want a straightforward, enjoyable snorkeling trip with knowledgeable crew and some dolphin sightings, all aboard a comfortable boat.
2. Big Island: Luxury Catamaran Trip along the Kona Coast
For around $506 per person, the Luxury Catamaran Trip offers a much more upscale experience. This is not your average sailing trip. With a maximum of 6 guests, each person enjoys private quarters for seating and dining, making it an intimate adventure. The vessel is a spacious yacht, designed for comfort and privacy, and is ideal for travelers seeking a luxurious escape.
What sets this tour apart is the personalized service—you might even see wild dolphins and snorkel with Hawaiian green sea turtles. The tour includes a fancy lunch, either a picnic or a bento box with fresh-caught grilled fish, adding a gourmet touch to your day. The reviews are glowing, emphasizing the helpfulness of the crew and the quality of the boat. Some users note the experience didn’t exactly match initial advertising, but overall, the yacht’s comfort and exclusivity make this a top-tier choice.
This tour suits travelers who are willing to spend more for a private, luxurious experience, perhaps celebrating a special occasion or seeking a quiet, elegant day at sea.
Bottom Line: Ideal for those wanting a high-end, intimate sailing experience with superb service and privacy, especially if you’re comfortable with the higher price point.
3. Honokohau: Kona Whale Watching Catamaran Cruise
If whale watching is on your Hawaii bucket list, the Kona Whale Watching Cruise is a solid choice. Priced at $116 per person, this 1.5-hour cruise from Honokohau offers a quick, affordable way to see humpback whales in their natural environment. The tour is seasonal, typically running during the whales’ migration months, from December to April.
The highlight here is the chance to see humpback whales in the wild, often breaching or tail-slapping—if you’re lucky. Even if whales aren’t sighted, the crew is praised for their friendly approach and knowledge about marine life. The scenery along the Kona coastline provides a beautiful backdrop, and the smaller boat size ensures a more personal experience.
This trip is best suited for travelers with limited time or those primarily interested in whale sightings. It’s a budget-friendly option that still offers a memorable ocean experience. Reviews note that, while whales aren’t always visible, the crew’s effort and the scenic cruise make it worthwhile.
Bottom Line: A great pick if you’re after a short, affordable whale-watching adventure during the season.
How to Choose
When deciding between these options, consider your budget, time constraints, and interests. If you’re looking for a full-day adventure with snorkel gear, the Waikoloa snorkeling trip offers excellent value with marine encounters. For travelers wanting a luxury experience with exclusivity, the luxury yacht trip fits the bill. If whale watching is your priority, the Honokohau cruise provides a quick, budget-friendly chance to see these giants in season.
Booking early is advisable, especially for the luxury yacht, which has limited availability. Also, check the seasonality of whale watching—peak from December to April—if whale sightings are your main goal.
Final Thoughts
Hawaii’s waters provide a broad spectrum of sailing experiences, from casual snorkeling to upscale private charters and seasonal whale watches. For budget-conscious travelers, the Waikoloa snorkeling trip offers plenty of marine life at a reasonable price. Those seeking privacy and a touch of luxury will find the luxury yacht perfect for a special occasion. And if you’re eager to spot humpback whales, the Honokohau cruise is a quick, affordable choice during winter months.
No matter your preference, these tours promise memorable days on the water, showcasing Hawaii’s natural beauty and marine wonders. Be sure to book early, especially during peak seasons, to secure your spot on these popular trips.