Hawaii’s Big Island sailing tours pack serious value for travelers seeking ocean adventures. The best outings combine snorkeling stops with wildlife viewing along the Kona-Kohala coast.

Morning catamaran trips offer prime dolphin spotting and snorkeling, while sunset dinner cruises deliver spectacular views and fresh local cuisine. During winter months (December-April), whale watching tours virtually guarantee humpback sightings.

We especially recommend Body Glove’s morning cruise for its roomy vessel and professional crew, and Fair Wind’s dinner sail for top-notch food and service.

Let’s explore the finest sailing tours available.

Key Points

  • The Deluxe Snorkel & Dolphin Watch offers a 2-hour adventure on a luxury catamaran with a 95% recommendation rate and inclusive amenities.
  • The Kona-Kohala Coast Sunset Sail provides a 1.75-hour evening cruise with a delicious dinner and complimentary alcoholic beverages.
  • The Waikoloa Catamaran Morning Snorkel departs from Anaehoomalua Bay, offering opportunities to spot marine life and a simple lunch.
  • The Kona Whale Watch guarantees a whale sighting during migration season or a free return on a different day.
  • These sailing experiences offer a range of personalized and inclusive options for exploring the Big Island of Hawaii.

Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran From Kailua-Kona

Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran From Kailua-Kona

Set out on a deluxe snorkel and dolphin watch adventure aboard a luxurious catamaran in Kailua-Kona, Big Island of Hawaii. With a 95% recommendation rate and a Badge of Excellence, this 2-hour tour offers the chance to discover Kona’s underwater paradise and spot marine mammals in protected sanctuaries.

You’ll enjoy island-style breakfast, lunch, and non-alcoholic drinks as you snorkel for approximately 2 hours, with all gear provided. The catamaran features a 20-foot waterslide, 15-foot high jump platform, freshwater showers, and is 100% wheelchair accessible.

The crew ensures your safety and enjoyment, with attentive support during snorkeling. Positive reviews highlight the excellent service, delicious meals, and engaging activities for all ages, including paddleboarding and swimming equipment for children.

While hotel pick-up isn’t available, free parking is provided, and the meeting point is a short walk to the pier. With a maximum of 85 travelers per tour and free cancellation up to 24 hours before, this is an unforgettable way to explore the Big Island’s marine wonders.

Read our full review: Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran From Kailua-Kona Review
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Kona-Kohala Coast Sunset Sail by Catamaran

Kona-Kohala Coast Sunset Sail by Catamaran

Sail along the stunning Kona-Kohala coastline and witness the breathtaking sunset over the Pacific Ocean on this evening catamaran cruise. With 93% of travelers recommending this tour, you’ll enjoy exceptional hospitality from the knowledgeable crew as they provide live commentary during the 1.75-hour journey.

Relax on the comfortable catamaran and take in the scenic views of the Waikoloa and Kohala-Kona coastline. Indulge in a delicious dinner of teriyaki chicken and enjoy two complimentary alcoholic beverages from the fully stocked bar.

The cruise’s maximum capacity of 49 travelers ensures an intimate and enjoyable experience. Departing from Anaehoomalu Bay, this tour is subject to favorable weather conditions, with options for rescheduling or a full refund if canceled.

As a barefoot cruise, you’ll be able to truly learn about the tranquil atmosphere of the sunset sail. Whether you’re a couple or a family, this Kona-Kohala Coast Sunset Sail is sure to be a memorable experience.

Read our full review: Kona-Kohala Coast Sunset Sail by Catamaran Review
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Waikoloa Catamaran Morning Snorkel Inluding Lunch

Waikoloa Catamaran Morning Snorkel Inluding Lunch

Typically, you’ll depart from the Anaehoomalua Bay at Waikoloa Beach Resort for this morning catamaran snorkeling adventure.

The knowledgeable, friendly, and safety-conscious crew will guide you through a scenic sailing experience, allowing you to spot marine life like fish, turtles, and even whales.

Once you’ve arrived at the snorkeling spot, you’ll have the chance to explore the vibrant underwater world, equipped with the provided snorkeling gear.

Refuel during the tour with a simple but appropriate lunch, complete with vegetarian options if pre-ordered.

The catamaran tour can accommodate up to 45 travelers, ensuring an intimate experience.

While some past guests have found the snorkeling locations could be improved, the majority had an enjoyable time, praising the beautiful boat, plentiful food and drinks, and opportunities to spot incredible marine life.

With a 4.5-star rating and a Badge of Excellence, this Hawaii Nautical excursion is worth considering for your Big Island sailing adventure.

Read our full review: Waikoloa Catamaran Morning Snorkel Inluding Lunch Review
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Kona Whale Watch From Honokohau on Sailing Boat

Kona Whale Watch From Honokohau on Sailing Boat

For those seeking a whale-watching adventure on the Big Island, the Kona Whale Watch from Honokohau on a sailing boat offers an exceptional opportunity.

With a 95% traveler recommendation and a 4.5-star rating from 38 reviews, this catamaran tour has earned a Badge of Excellence from Hawaii Nautical.

During the humpback whale migration season, you’ll have a guaranteed whale sighting or a free return on a different day. The tour includes soda, juice, and water, and while gratuities aren’t included, you can take advantage of the free cancellation policy up to 24 hours in advance.

The tour departs from the Honokohau Small Boat Harbor, where you’ll board the vessel Honi Olani.

Along With whales, you may spot false killer whales and dolphins, and the knowledgeable crew provides engaging commentary throughout the relaxing, scenic journey.

Read our full review: Kona Whale Watch From Honokohau on Sailing Boat Review
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Recap

Embark on an unforgettable sailing adventure on the Big Island of Hawaii. From deluxe snorkel and dolphin watching tours to sunset sails and whale watching excursions, you’ll discover the island’s stunning coastline and marine life in style. Whether you’re a seasoned sailor or a first-time adventurer, these premium sailing experiences offer an unparalleled way to explore the beauty of the Big Island.