Kailua-Kona Sailing trips & boat tours

Our most recommended Kailua-Kona Sailing trips & boat tours

Big Island, Hawaii: Night Manta Ray Snorkel Experience

1. Big Island, Hawaii: Night Manta Ray Snorkel Experience

Snorkeling with manta rays is a must-do while in Hawaii! Enjoy this amazing opportunity to see manta rays up close. Feed and interact with other ocean creatures on this cruise trip. After a safety briefing, gear up with the snorkeling equipment and wet suits provided. Relax and enjoy the cruise with drinks and snacks on board. Bring your underwater camera for photos and capture memories that will last a lifetime.

Kailua-Kona: Whale Watching Cruise

2. Kailua-Kona: Whale Watching Cruise

Hawaii is the only state in the United States where humpback whales mate, calve and nurse their young. Humpbacks may find Hawaii suitable because of the warm waters, the underwater visibility, the variety of ocean depths and the lack of natural predators. Mothers can be seen breaching alongside their calves and males can be seen competing with one another for females in fierce head-to-head battles. Join a 2.5-hour cruise as you follow these magnificent sea creatures and listen to their singing using the underwater hydrophones. Snacks and beverages will be available during your cruise providing a unique and memorable experience for the whole family.

From Keauhou Bay: Snorkel Cruise to Captain Cook's Monument

3. From Keauhou Bay: Snorkel Cruise to Captain Cook's Monument

Embark on an unforgettable day at sea from Keauhou Bay to Captain Cook's Monument on a guided Yacht trip. Enjoy scenic views of the Kona coast as you sail and indulge in tasty light snacks and tropical fruit juice. Meet your guide at the Keauhou Bay Pier. Hop aboard, relax and enjoy the ride. Cruise past rock formations, stop at beautiful coves, and soak in the views. Set sail along the beautiful Kona coast on a trip from Keauhou Bay, marvel at the ancient Kealakekua Bay, and see the Captain Cook Monument. Splash into the clear waters to swim, snorkel, or sunbathe onboard. Spot the colorful fish underneath the water, and take photos with your marine camera of the dolphins and other marine life. Enjoy site briefings and snorkeling tips from the crew members. Life jackets, floatation noodles, viewfinder boards, masks, fins, and snorkels are provided. Energize yourself with fruits and tropical juice. The crew will help you enter and exit the water if needed and will provide fish identification cards. They will even take you on a guided snorkeling tour.

Kailua Kona: Humpback Whale Watching Adventure Cruise

4. Kailua Kona: Humpback Whale Watching Adventure Cruise

See majestic humpback whales and listen to them sing on this whale watching cruise from Kailua Kona, Hawaii. Over 8,000 humpback whales journey over 3,500 miles to Hawaii every year. Between December and April, these incredible creatures gather to breed and raise their young. This 2.5-hour whale-watching experience in Kona offers you an incredible opportunity to view humpback whales up close in their natural habitats. Hear the whales sing with unique underwater hydrophones. Keep your eyes open for other marine creatures like spinner dolphins, pilot and sperm whales, manta rays, sea turtles, and more. Whale sightings are guaranteed or you can join the cruise again for free.

Honokohau: Kona Whale Watching Catamaran Cruise

5. Honokohau: Kona Whale Watching Catamaran Cruise

Take a trip to see humpback whales in the Pacific Ocean, with guaranteed sightings. Enjoy an up-close experience with these magnificent creatures. Head to Honokohau Harbor to board the 53-foot sailing catamaran and start your tour. Cruise along the Kona coastline as you admire the blue waters of the Pacific Ocean. Learn about the unique behavior of whales from your experienced captain and guides. Watch these gentle giants and they fluke, spy hop, and breach out of the water.

Big Island: 1.5-Hour Romantic Sunset Sail from Waikoloa

6. Big Island: 1.5-Hour Romantic Sunset Sail from Waikoloa

Explore the Waikoloa and Kohala Kona coastline aboard a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon while you enjoy the cruise with a loved one. You may even see the green flash.  Board from Anaehoomalu Bay to snorkel, sail, and relax. The custom-designed sunset-orange and maile lei sail is a stunning contrast to the azure Pacific as it sails along the blue Pacific ocean. Bask in the romance and relaxation of a stunning Kona-Kohala sunset cruise.  While you are on board, benefit from snacks and beverages served to you. Enjoy unlimited non-alcoholic beverages, two free bar drink tickets per adult, or purchase extra alcoholic beverages to feel at ease all night.

Kona: Dolphin Watch and Double Snorkel Boat Tour with BBQ

7. Kona: Dolphin Watch and Double Snorkel Boat Tour with BBQ

Discover the beautiful coastline aboard the Kibou zodiac vessel. Search for playful dolphins in the gorgeous blue Hawaiian waters, snorkel with exotic underwater species, and enjoy a hearty Hawaiian-style BBQ lunch. After meeting your crew and boarding the boat, begin by searching for majestic dolphins in the shimmering ocean surrounding Kona. Learn a bit about marine biology, Hawaiian history, and local traditions. Stop in a spectacular bay with a vibrant reef and enjoy plenty of time for snorkeling. Swim with wild turtles and exotic tropical fish as you explore the underwater world. After snorkeling, the crew will bring out the barbecue and cook up a delectable meal. Once finished snorkeling and with lunch, travel to a second snorkel spot to try and see more wildlife and potentially some manta rays, before heading back to the meeting point.

Big Island: Kailua-Kona Private Off-Shore Fishing Charter

8. Big Island: Kailua-Kona Private Off-Shore Fishing Charter

Join this private fishing charter in the beautiful Kona waters.  You'll depart at 7:30 AM on the 32 foot power catamaran from Honokohau Harbor. The local fishing guide will take you to the best fishing locations off of the coast including the (FADS) Fish Aggregation Devices. You'll also hunt giant Ono's or Wahoos on the 40-fathom line which is in Ono Alley. The Captain and fishing guides love to fish and are locals who know and understand the area. You'll only use the best fishing gear and equipment on the market including tackle from Black Bart and Tsumo which are local Hawaiian gear You may bring any food or drinks on the boat as you wish including adult beverages. However, complimentary beer is provided upon request. Water, juice and snacks are also provided.

Kailua-Kona: Catamaran Cruise with Hualālai Volcano Views

9. Kailua-Kona: Catamaran Cruise with Hualālai Volcano Views

Feel the wind in your hair as you sail along Hawaii's dynamic coast with this catamaran cruise from Kailua-Kona. Soak up some sun on the spacious deck or take in the views from the shaded seating area. Sail with a refreshing, chilled beverage in hand.  Check in at the activity provider's slip and hop aboard a comfortable ship in Honokohau Harbor. Feel the ocean breeze in your hair as you set sail past the western slopes of the Hualālai volcano. View where the volcano meets the ocean.  Watch turquoise waves crash upon the black lava rocks. Keep an eye out for local wildlife like sea birds and dolphins as you glide across the water. Relax aboard a ship that is maintained to the highest safety standards.  Snap pictures of the sweeping shoreline to share with your friends and family back home. Enjoy the good weather that this section of the island typically experiences. Return to your meeting point at the end of your cruise. 

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Frequently asked questions about Kailua-Kona

What top attractions are a must-see in Kailua-Kona?

What are the best day trips and excursions from Kailua-Kona?

The best day trips and excursions from Kailua-Kona are:

Hawaii Volcanoes National Park

Other Sightseeing Options in Kailua-Kona

Want to discover all there is to do in Kailua-Kona? Click here for a full list.

What people are saying about Kailua-Kona

Overall rating

4.5 / 5

based on 94 reviews

Simon and his crew were amazing! Was kind of scared to do this, but they were helpful, funny, kind & amazing! They made all my nerves chill & helped me have a blast! 100/100 would recommend! The manta rays were so cool & huge! One touched me on its way under the light! For anyone who thinks they might not like this or are iffy about doing it, do NOT hesitate! This is so far by far, the most amazing activity on our trip! Wish we could do it again during this trip!

For a relaxing evening with just adult company, this is the way to go. Not a full dinner cruise but a good simple meal with free drinks as you watch the beautiful sunset just let us have a peaceful time to really enjoy Hawaii.

Caring and knowledgable staff with safety at the forefront. Lots of history woven in. The area where we snorkeled had a diverse array of fish species. Lots to see!

It was such an awesome trip with many added bonuses not advertised!

Simon and his crew were tons of fun! highly recommend!