Top Big Island of Hawaii Sailing Tours

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Escape the hustle and bustle of land and soak up the sun and ocean breeze while taking in the sights of the Kona coastline on this sailing trip aboard a comfortable 53-foot catamaran. As you glide across the blue water, keep an eye out for marine wildlife such as dolphins and humpback whales during migratory season. Enjoy a full premium bar with tropical cocktails, beer, wine, soda, and juice on board.

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Kona Tradewind Catamaran Day Sail

1 hour 30 minutesFree Cancellation

Special Offer

Kona Signature Catamaran Sunset Sail

1 hour 30 minutesFree Cancellation

Afternoon Sail & Snorkel to the Captain Cook Monument

3 hoursFree Cancellation

4.9

(253)

from $136

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

4 hoursFree Cancellation

5.0

(718)

from $189

Special Offer

Waikoloa Signature Catamaran Sunset Sail

1 hour 30 minutes to 2 hoursFree Cancellation

Likely to Sell Out

Snorkel with Manta Rays Guaranteed

1 hour 30 minutesFree Cancellation

4.8

(757)

from $141

Sunset and Manta Ray Snorkel Adventure

2 hours 15 minutesFree Cancellation

4.9

(870)

from $155

Deluxe Sail & Snorkel to the Captain Cook Monument

This half-day boat cruise takes you to the two best snorkeling sites in Kealakekua Bay: The reef beneath Captain Cook's monument and the underwater lava formations of Red Hill. In addition to breakfast and lunch, your guides provide all necessary equipment, basic snorkeling tips, and identification charts to help you spot fish and dolphins in their natural habitat. Don’t forget your camera—the route showcases sweeping views of the Kona coastline.

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Deluxe Sail & Snorkel to the Captain Cook Monument

4 hours 30 minutesFree Cancellation

4.9

(574)

from $179

Special Offer

Waikoloa Catamaran Snorkel Sail Including Lunch

3 hoursFree Cancellation

Big Island Manta Ray Night Snorkel

2 hours 30 minutesFree Cancellation

4.8

(6,224)

from $94

Swim with giant manta rays in their nighttime habitat on this boat tour from Kona. Travel offshore to watch the colorful Kona sunset, then jump in to swim with the docile rays as they feed on microscopic plankton. Follow your guides around the manta habitat and watch as the animals are attracted to the bright lights. All snorkel equipment, including flotation devices and wet suits, is included.

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Glow of the Deep: Night Snorkeling with Manta Rays

2 hours 30 minutesFree Cancellation

4.6

(1,310)

from $80

Big Island Historical Dinner Cruise to Kealakekua Bay

Journey back in time — when ancient, powerful Kings ruled the rugged, fertile land of the Hawaiian Islands — on this half-day dinner cruise to Kealakekua Bay. Travel 12 miles (19 kilometers) down the Kona Coast to the Captain Cook monument. Learn the many secrets of the Big Island as a local historian points out numerous points of interest along the way, and enjoy dinner and live entertainment onboard.

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Big Island Historical Dinner Cruise to Kealakekua Bay

3 hoursFree Cancellation

4.7

(1,335)

from $189

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

4 hours 30 minutesFree Cancellation

4.8

(817)

from $184

Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch

4 hoursFree Cancellation

4.9

(2,473)

from $85

Manta Ray Night Snorkel at Kona, Big Island

1 hour 30 minutesFree Cancellation

4.7

(2,007)

from $30

Special Offer

Kona Snorkel Tour: Captain Cook Reef Snorkel, Dolphin & Sea Caves

2 hours 30 minutesFree Cancellation

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along the Kona coastline toward the Captain Cook Monument, where your adventure begins. Jump into the clear water to explore the vibrant reef of the marine sanctuary of Kealakekua Bay, which is home to schools of colorful fish and pods of spinner dolphins. Your tour includes breakfast, lunch, and equipment such as snorkeling gear and boogie boards.

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Deluxe Sail & Snorkel to the Captain Cook Monument

4 hours 30 minutesFree Cancellation

4.9

(479)

from $179

Easy access into the water with our two grand staircases.

Kealakekua Bay Afternoon Snorkel: Family Fun on the Kona Coast

4 hoursFree Cancellation

4.9

(700)

from $144

Kona Manta Ray Night Snorkel— Small Group - Wetsuit Included

Plunge into the waters off Kailua-Kona to swim with manta rays. During this sunset to moonlight tour, slip on the provided wetsuit and snorkel gear and follow your expert instructor into the water. Watch as the enormous vegetarian animals, some with wingspans of 20 feet (6 meters), swim in loops around you, taking in clouds of plankton for their evening meal. All gear and light snacks and refreshments are provided.

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Kona Manta Ray Night Snorkel— Small Group - Wetsuit Included

2 hoursFree Cancellation

4.8

(669)

from $123

Sail up the scenic Kona coastline, getting views of ancient lava flows and verdant cliffs, and stopping at the Captain Cook Monument, on this afternoon sail in Kealakekua Bay. Slip into the water using the provided snorkeling gear to see vibrant schools of fish, living coral, and even pods of spinner dolphins. Learn about the area's underwater flora, fauna, and ecosystem through guided commentary.

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Afternoon Sail & Snorkel to the Captain Cook Monument

3 hoursFree Cancellation

4.9

(738)

from $136

Special Offer

Indulge in a personalized sailing experience aboard the luxurious 51-ft Lagoon catamaran, No Wiki. This private charter offers an unforgettable journey along the stunning Kona Coast, where you can snorkel vibrant reefs or simply relax in comfort. With a professional crew dedicated to your enjoyment, your itinerary is fully customizable. Enjoy complimentary drinks and catering options for an enhanced experience. - Private luxury charter for up to 6 guests - Explore pristine snorkeling spots and scenic views - Comfortable shaded seating and onboard restrooms - Upgrades available for extended adventures to Kealakekua Bay

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Kona Coast Luxury Private Yacht Charter

4 hoursFree Cancellation

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. This all-inclusive trip features top-notch amenities: premium snorkel gear, gourmet lunch, and post-snorkel beverages from our full bar, including beer, wine, and spirits. Our local, experienced crew goes above and beyond to provide personalized service, guiding you to the best snorkel spots along the Kona coast based on daily conditions. With ample space for personal belongings, towels, reef-safe sunscreen, and complimentary parking, we make your comfort our priority. Plus, our unique itineraries avoid crowded areas, giving you a more intimate encounter with Kona's vibrant marine life, including dolphins, tropical fish, and seasonal whales. Choose the Afternoon Ali’i Adventure for a truly unforgettable and one-of-a-kind ocean experience!

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Afternoon Ali'i Adventure

3 hoursFree Cancellation

5.0

(6)

from $276

Top Attractions in Big Island of Hawaii

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Top Big Island of Hawaii Sailing Tours

22 results

Top Attractions in Big Island of Hawaii

Mauna Kea Summit and Observatory

Thurston Lava Tube (Nāhuku)

Hawaii Volcanoes National Park

Waimea

Kealakekua Bay

Kona (Kailua-Kona)

Mauna Kea Summit and Observatory

Thurston Lava Tube (Nāhuku)

Hawaii Volcanoes National Park

Waimea

Kealakekua Bay

Kona (Kailua-Kona)

Mauna Kea Summit and Observatory

Thurston Lava Tube (Nāhuku)

Hawaii Volcanoes National Park

Waimea

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