Big Island of Hawaii is a prime destination for sailing adventures. Its vast coastline, clear waters, and abundant marine life create perfect conditions for memorable boat trips. Whether you’re eager to snorkel with turtles and dolphins, watch a famous Hawaiian sunset, or go whale spotting during migration season, the Big Island offers options that suit all tastes. We especially love the Deluxe Snorkel & Dolphin Watch aboard a luxury catamaran for its combination of wildlife encounters and comfort, or the Sunset Sail for a romantic evening with breathtaking views. These tours give you a chance to see the island from a different perspective, enjoying the natural beauty and marine activity.
As you browse, you’ll find tours catering to different interests—whether you want a quick scenic cruise, a full-day snorkeling adventure, or a specialized whale watching trip. The list below highlights six of the best options, each with its own unique appeal.
1. Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona
This top-rated tour (5.0/5 from 772 reviews) combines snorkeling, dolphin watching, and a luxury experience on a well-equipped catamaran. Starting at Kailua Pier, it’s about a 4.5-hour trip that takes you through protected marine sanctuaries—hotspots for dolphins, sea turtles, and colorful coral reefs. The crew is known for being friendly and accommodating, and the boat features a premium cash bar, island-style breakfast, and BBQ lunch, making it a true treat for all senses.
What makes this tour stand out is the combination of wildlife sightings and comfort—all snorkeling gear is provided, and you can relax with non-alcoholic drinks or cocktails. The water time stretches for about two hours at the snorkel site, giving plenty of opportunity to swim with tropical fish and maybe even dolphins. The reviews rave about the excellent food, friendly crew, and overall fun atmosphere. For around $189, you get a balanced mix of adventure and relaxation.
Bottom Line: Perfect if you want a full, high-quality day on the water with guaranteed dolphin sightings and top-notch amenities.
2. Kona-Kohala Coast Sunset Sail by Catamaran
Rated 4.5/5 from 346 reviews, this 1.5-hour sunset cruise offers a more relaxed, scenic experience. Departing from Anaehoomalu Bay, you’ll sail along the Kohala and Kona coastlines on a 49-passenger power catamaran. The highlight is watching the sun set over the Pacific, with an optional glass of wine or beer included with your two drink coupons.
This tour provides live commentary, so you’ll learn about the coastline, the local environment, and the possibility of catching the elusive ‘green flash’ as the sun dips below the horizon. Many reviews mention how friendly and engaging the crew are, making it a comfortable and enjoyable experience. The price—about $153—includes drinks, making it a good value for a romantic or peaceful evening.
Bottom Line: Great for couples or anyone seeking a short, scenic escape into the evening with memorable sunset views.
3. Waikoloa Catamaran Morning Snorkel Including Lunch
This 4.5-star tour from Waikoloa offers an approximate 3-hour cruise perfect for morning adventurers. The boat, a spacious 54-foot catamaran, is ideal for snorkeling with dolphins, turtles, and a variety of reef fish. With onboard guides assisting with equipment, it’s especially suitable for first-timers or families.
One of the key attractions is the chance to spot humpback whales during December to April, adding a special touch during migration season. The tour includes snacks and drinks, ensuring you stay energized while enjoying the coastal scenery. Reviews mention the personable crew and the high-quality vessel, with many noting how much they appreciated the ample deck space and shaded areas for relaxing.
At around $174, this tour is a solid choice for those wanting a full morning of snorkeling and marine encounters without feeling rushed.
Bottom Line: Best for snorkelers wanting a comfortable, well-organized trip with wildlife viewing and scenic beauty.
4. Kona Deluxe Catamaran Whale Watch
Rated 4.5/5 from 49 reviews, this tour is the quintessential whale-watching experience from Kona. During migration season, humpback whales pass by in large numbers, and this tour takes you out onto the ocean in a luxury catamaran designed for whale observation. The trip lasts about 1.5 hours and is perfect for nature lovers.
What sets this apart is the learning opportunity—the crew shares insights about whale behavior, making it more than just a sightseeing trip. If no whales are seen, you’ll get a free return trip, which shows confidence in the experience. Reviewers mention seeing whales up close and the overall professionalism and friendliness of the crew. For just under $100, this is a cost-effective way to witness the giant mammals during their seasonal migration.
Bottom Line: Ideal for travelers wanting a focused whale-watching tour with a high chance of sightings and educational commentary.
5. Captain Cook Snorkel On A Power Catamaran With Lunch
This top-rated (5.0/5 from 1,827 reviews) tour is a favorite for its combination of history and marine exploration. Starting from Kona, it takes you to the historic Kealakekua Bay—famous for Captain Cook’s demise and Kamehameha III’s birthplace. The trip lasts about 4 hours and includes snorkeling, viewing dolphins, and a tasty onboard lunch.
The highlight is the visit to Kealakekua Bay, where the coral reefs teem with fish and the waters are clear enough to see plenty of marine life. The crew is praised for being knowledgeable and accommodating—many reviews mention how the captain, Aiden, was both funny and professional, and that the hot showers and hot meals added comfort after snorkeling. The tour offers excellent value at $85 per person, especially considering it includes snorkeling gear, lunch, and a visit to a historically significant site.
Bottom Line: Perfect for history buffs and snorkelers looking for a well-rounded, enjoyable day with cultural highlights.
$85.00 per person
6. Waikoloa Turtle Catamaran Snorkel Sail
Rated 5.0/5 from 1 review, this 2-hour trip from Waikoloa provides an intimate, relaxed experience. The focus is on snorkeling at a vibrant reef where you’re likely to encounter sea turtles, tropical fish, and colorful coral. The spacious catamaran offers plenty of room to sunbathe or enjoy the ocean breeze in the shaded areas.
While it’s a shorter trip, reviews highlight the personalized service and high-quality equipment. This tour is ideal for travelers who want a quick but satisfying snorkeling experience without large crowds or long hours.
Bottom Line: Best suited for those wanting a brief, comfortable snorkel with a high chance of turtle encounters.
$149.00 per person
How to Choose Your Perfect Big Island Sailing Experience
When choosing your ideal tour, consider your interests, budget, and schedule. If wildlife like dolphins and whales is your main goal, the Deluxe Snorkel & Dolphin Watch or the Whale Watch are excellent options. For those seeking romantic sunsets, the Sunset Sail offers a shorter, scenic trip. Budget-conscious travelers might prefer the Captain Cook Snorkel, which combines history, great snorkeling, and good value.
Timing also matters: whale watching is best during migration season (December to April), while snorkeling is great year-round, with humpback whales visible in winter. For family trips or those new to snorkeling, the Waikoloa Morning Snorkel offers comfort and simplicity.
Final Thoughts
The Big Island offers a wide array of sailing adventures that cater to different interests and budgets. Whether you want a luxury dolphin cruise, a romantic sunset sail, or an educational whale watching trip, there’s an option for you. The Deluxe Snorkel & Dolphin Watch is our top pick for a full day of wildlife and comfort, while the Sunset Sail offers a quick, magical evening. For history and snorkeling, the Captain Cook tour hits all the right notes.
No matter which you choose, booking early is wise—especially during peak seasons. These tours tend to fill fast, and giving yourself a seat ensures a smoother, more enjoyable experience. Dive in, enjoy the ocean, and make your Big Island trip truly unforgettable.