The 3 Best Sailing Experiences in Big Island of Hawaii
Big Island of Hawaii is a destination that offers some of the most exhilarating sailing experiences in the Pacific. Unlike many places, it combines abundant marine life, impressive volcanic landscapes, and historic sites—all accessible from the water. Whether you’re eager to snorkel with dolphins, spot migrating whales, or explore the legendary Kealakekua Bay, there’s a cruise tailored for you. These tours showcase the island’s unique natural and cultural richness, making your time on the water truly unforgettable.
In this guide, we’ll explore three top-rated sailing adventures. Each offers a different approach—luxury, whale watching, or historic snorkeling—so you can pick the best fit based on your interests, budget, and schedule. From couples seeking a romantic cruise to families eager for a fun-filled day, you’ll find options that stand out for their quality and experience.
Quick Overview
For an all-around luxurious day on the water, the Deluxe Snorkel & Dolphin Watch aboard a Luxury Catamaran from Kailua-Kona offers a 4.5-hour cruise with excellent marine sightings and included meals.
If you’re interested in whale watching, the Kona Whale Watch from Honokohau on a Sailing Boat provides a shorter, more budget-friendly 1.5-hour trip with a whale sighting guarantee, especially suitable for peak migration season.
For a combination of history, snorkeling, and volcanic scenery, the Captain Cook Snorkel on a Power Catamaran with Lunch is a 4-hour tour that takes you to the iconic Kealakekua Bay, with the added bonus of seeing humpback whales in winter and enjoying a hearty onboard lunch.
1. Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona
At number one, this luxury snorkel and dolphin cruise stands out for its 5-star reviews and comprehensive experience. For around $189, you get about four and a half hours of sailing through protected marine sanctuaries, with chances to see dolphins, sea turtles, and other ocean mammals.
The tour begins with a safety briefing before jumping into crystal-clear waters equipped with all snorkel gear provided. The crew takes you to a site where you can expect about two hours of water time—a generous window for exploring vibrant coral reefs teeming with colorful fish. After snorkeling, you’ll relax with a premium cash bar and enjoy island-style breakfast and BBQ lunch, making it an all-day treat.
This cruise is popular for its friendly crew, excellent wildlife sightings, and high-quality amenities. Guests often mention the fun atmosphere and the well-planned itinerary, which mixes adventure with relaxation. The boat’s spacious layout and included meals make it a good choice for families and couples alike.
Bottom Line: If you want a balanced, luxurious day on the water with top-notch snorkeling and wildlife viewing, this cruise offers great value and a memorable experience.
2. Kona Whale Watch from Honokohau on Sailing Boat
During migration season, Big Island becomes one of the world’s best spots to see humpback whales. At number two, this Kona Whale Watch provides a straightforward, 1.5-hour sailing trip that’s perfect for a quick wildlife fix. Priced at just $117.75 per person, it’s an affordable way to experience whale migration up close.
The tour departs from Honokohau Harbor on a comfortable catamaran, with a focus on education. The guides share insights about whale behavior, migration patterns, and conservation efforts. The guarantee of whale sightings (or you can come back free) offers peace of mind, especially for visitors traveling during peak season.
Guests have praised the friendly staff and the boat’s comfort, with some describing it as a chance for intimate views and personalized attention with only six people aboard in some cases. While whales are seasonal, the company’s flexibility and focus on education make this a rewarding trip for families and singles alike.
Bottom Line: For a short and affordable outing with a strong focus on whale watching, this tour hits the mark, especially if you’re visiting during peak migration months.
3. Captain Cook Snorkel On A Power Catamaran With Lunch
At number three, this Captain Cook snorkel tour is a favorite among those interested in history and marine life. For about $85, you’ll spend roughly four hours exploring Kealakekua Bay—the site where Captain Cook was killed and a historic landmark for Hawaiians—and the surrounding volcanic coast.
The tour departs from Kona and offers a chance to see dolphins en route, which makes the journey itself exciting. Once at Kealakekua Bay, you’ll snorkel among stunning coral formations and vibrant reef fish. The crew provides all snorkeling gear and a hearty lunch, making it a convenient, all-inclusive option. During winter, you may also spot humpback whales breaching nearby.
Guests often comment on the knowledgeable crew and the personalized service—a small boat setting means fewer crowds and more attention. The mix of historical significance and marine exploration makes this tour appealing for history buffs and snorkelers alike. It’s a good value, especially with included meals and equipment.
Bottom Line: If you’re after both history and underwater beauty, this tour offers a well-rounded experience with excellent value and memorable sights.
How to Choose
When selecting a sailing experience in Big Island, consider your priorities. Budget travelers might prefer the Kona whale watch, which offers a shorter, more affordable outing focused on whale sightings. If you’re looking for luxury with food, drinks, and wildlife, the Deluxe Snorkel & Dolphin Watch is a top choice. For those interested in history and snorkeling in a scenic, less commercial setting, the Captain Cook tour hits the sweet spot.
Think about the season—whale watching is best during migration months—and your time constraints. For a day-long adventure with meals and wildlife, the luxury cruise is ideal. For a quick, focused trip, the whale watch or snorkel tour may suit your schedule better. Booking early is recommended, especially during peak seasons, to secure your preferred date.
Final Thoughts
Big Island offers diverse sailing options that cater to different interests and budgets. For a luxurious, all-inclusive experience, the Deluxe Snorkel & Dolphin Watch is hard to beat. If your main goal is to see humpback whales, the Kona whale watch provides an affordable, intimate chance to witness these giants during their migration season. Meanwhile, history lovers and snorkelers will appreciate the Captain Cook tour, which combines marine life with cultural significance.
Each offers a chance to experience Big Island’s marine environment in a different way. Whether you prefer a full-day adventure, a quick wildlife spotting, or a historic snorkeling trip, booking early will ensure you get the best spot on these popular tours. Now, all that’s left is to choose your water adventure and start planning your island escape.