Big Island of Hawaii offers some of the most memorable sailing experiences in the Pacific. Unlike many destinations, the Big Island boasts clear waters, abundant marine life, and dramatic coastlines that make every trip on the water feel special. Whether you’re after a lively snorkeling adventure, a romantic sunset cruise, or whale-watching in season, you’ll find options that fit your mood and budget.
We especially love the Deluxe Snorkel & Dolphin Watch aboard a luxury catamaran (see details here), thanks to its combination of wildlife sightings, gourmet lunch, and onboard relaxation.
On the Big Island, sailing isn’t just about the ocean — it’s a way to see the island from a new perspective. From the calm waters along Kona’s coast to the open ocean during whale migration, each tour offers a unique view of Hawaii’s natural beauty. Our favorites blend comfort, adventure, and opportunities to see marine life, making it easy to find the perfect match for any kind of traveler.
- 1. Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona
- 2. Kona-Kohala Coast Sunset Sail by Catamaran
- 3. Waikoloa Catamaran Morning Snorkel Including Lunch
- 4. Kona Deluxe Catamaran Whale Watch
- 5. Captain Cook Snorkel On A Power Catamaran With Lunch
- 6. Waikoloa Turtle Catamaran Snorkel Sail
- How to Choose Your Perfect Big Island Sailing Experience
1. Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona
At number 1, this 4.5-hour cruise takes you through protected marine sanctuaries along Kona’s coast, where hundreds of ocean species flourish. The tour includes a brief safety briefing, followed by about two hours of snorkeling at prime sites, with all gear provided. What sets this trip apart is the chance of dolphin sightings—the crew actively seeks out these playful mammals during the cruise.
The boat itself is a luxury catamaran with a premium cash bar, making relaxing with a cocktail during the return trip a highlight. Included are island-style breakfast, lunch, and non-alcoholic drinks, so you won’t go hungry or thirsty.
Reviewers praise the crew’s friendliness and the high-quality food, with one saying, “The food they provided was amazing, and the boat was so much fun.” Given the combination of wildlife, comfort, and great food, this tour offers excellent value at around $189 per person. It’s perfect if you want a well-rounded experience that combines adventure with comfort.
Bottom Line: A top pick for families and anyone wanting a full day of snorkeling, marine life, and island scenery in style.
2. Kona-Kohala Coast Sunset Sail by Catamaran
Number 2 features an approximately 1.5-hour sunset cruise that captures the magic of Hawaii’s evening light. Setting sail from Anaehoomalu Bay, this barefoot cruise on a 53-foot power catamaran offers stunning views along the Kohala and Kona coasts. The highlight, of course, is watching the sunset over the Pacific, with a glass of wine in hand.
Onboard, there’s live commentary, and two drink coupons are included to enjoy cocktails or white wine. Guests appreciate the captain’s engaging narration, and the relaxed atmosphere makes it suitable for couples, friends, and families alike. Reviewers often mention the “unbelievable sunset” and friendly crew as particular positives.
At around $152, the trip is a bit shorter but still offers exceptional value for those seeking a romantic or scenic experience.
Bottom Line: Ideal for travelers wanting a quick, comfortable way to enjoy Hawaii’s famous sunset with light drinks and engaging commentary.
3. Waikoloa Catamaran Morning Snorkel Including Lunch
Number 3 offers a 3-hour morning cruise departing from Waikoloa, perfect for those who want to combine snorkeling with a relaxed start to their day. The 54-foot catamaran provides plenty of shaded deck space, making it comfortable even on warmer days. This trip provides opportunities to spot dolphins and turtles while cruising along the coast, with onboard guides assisting in the water.
The experience is praised for its knowledgeable crew and the chance to see humpback whales during season (December through April). The included snacks and drinks keep everyone fueled for adventure. One reviewer notes, “The crew was personable and knowledgeable, and we had plenty of time to enjoy the water.” For $174, it offers good value considering the combination of scenic cruising and snorkeling.
Bottom Line: Great for families or solo travelers wanting a balanced mix of wildlife sightings, snorkeling, and relaxed coastal scenery.
4. Kona Deluxe Catamaran Whale Watch
Number 4 is a whale-watching trip during migration season, taking about 1.5 hours out into the Kona waters. This tour specializes in humpback whale sightings, with a money-back guarantee if no whales are seen. During the season (December to April), whales are abundant and actively migrate past the island, making this a prime opportunity.
The tour’s comfortable catamaran includes educational commentary about whale behavior, helping you understand what you’re seeing. Several reviews mention seeing whales up close, with one traveler saying, “We saw whales and had a wonderful day with a friendly crew.” The tour runs at about $99.96 per person and is an excellent choice for whale enthusiasts.
Bottom Line: Perfect for nature lovers and those visiting in whale season who want a guaranteed chance to see these giants.
5. Captain Cook Snorkel On A Power Catamaran With Lunch
Number 5 is a 4-hour journey to the historic Kealakekua Bay, where Captain Cook was killed. This trip is highly praised, with over 1,800 reviews and a 5.0 rating, making it one of the most popular options. It includes snorkeling gear, lunch, and searches for dolphins on the way there.
What makes this tour stand out is the combination of history and nature. The bay is famous for its clear waters, vibrant fish, and coral reefs. The crew is known for being engaging and helpful, ensuring everyone gets the most out of the snorkeling.
One reviewer said, “The snorkeling was fantastic, and we saw dolphins on the way back.” The inclusion of lunch and snorkeling gear makes it a good value at $85.
Bottom Line: A top pick for history buffs and snorkelers wanting a comprehensive tour that blends culture with marine exploration.
6. Waikoloa Turtle Catamaran Snorkel Sail
Lastly, this 2-hour trip is perfect for a shorter, relaxing experience. Setting sail from Waikoloa, it takes you to a vibrant reef with sea turtles and tropical fish. The boat offers lots of space for sunbathing or enjoying the ocean breeze in shaded areas, making it ideal for those seeking a laid-back activity.
While only one review is available, it’s glowing, describing a “beautiful snorkeling experience with plenty of turtles.” The focused duration and intimate setting make it suitable for families, couples, or anyone looking for a quick escape on the water for about $149.
Bottom Line: Best for travelers short on time who want a peaceful, scenic snorkel trip with a chance to see turtles.
How to Choose Your Perfect Big Island Sailing Experience
When selecting the right tour, consider your priorities: If wildlife, especially dolphins and whales, is your main goal, the Deluxe Snorkel & Dolphin Watch or the Whale Watch are great options. Those seeking a romantic sunset should opt for the Sunset Sail, while families or casual snorkelers will enjoy the Waikoloa Morning Snorkel or the Turtle Sail.
Budget also plays a role. The Captain Cook Snorkel offers excellent value with its combination of history and marine life, while full-day cruises with gourmet food, like the first tour, come at a higher price but include more amenities.
Booking early, especially during peak whale season (December–April), ensures you get your preferred date. Check each tour’s cancellation policy and consider whether a guarantee (like the whale tour’s) is important for peace of mind.
In summary, Big Island offers a variety of memorable sailing experiences tailored to different interests and budgets. Whether you want an all-inclusive day on the water with dolphins, a quick sunset cruise, or a whale-watching adventure with a guarantee, you’re in for a treat.
For the best experience, book early and choose the tour that best matches your adventure style. Now, all that’s left is to get your swimsuit ready and enjoy Hawaii’s incredible ocean!