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Hawaii Sailing trips & boat tours

Our most recommended Hawaii 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.

Lahaina: Turtle Town Snorkel and Whale Watching Cruise

2. Lahaina: Turtle Town Snorkel and Whale Watching Cruise

Spot Hawaii's native marine life in its natural habitat on a snorkel cruise to Turtle Town from Lahaina. Swim past green sea turtles, Moorish idols, and even humpback whales. Enjoy an onboard lunch and drinks. Set sail from Lahaina Harbor towards Turtle Town, aka Mala Wharf (if weather conditions allow). See where, in 1992, a powerful hurricane created an artificial reef and sanctuary where corals and other marine life thrive. Spot Moorish idols, green sea turtles, and saddle wrasse while snorkeling here. If snorkel conditions are not ideal at Turtle Town a.k.a. Mala Wharf, cruise to one of the other premier westside snorkel locations such as Honolua Bay, Airport Beach, or Launiupoko. See Hawaiian green sea turtles, brightly colored tropical fish, and beautiful coral reef formations. During the whale season between December to April, observe humpback whales as they enjoy the warm Hawaiian waters (time permitting). Learn from expert narration about the whales and provide a play-by-play commentary of the whales' behavior as you view them.

Kailua-Kona: Whale Watching Cruise

3. 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.

Maui: Molokini Snorkel & Performance Sail with Lunch

4. Maui: Molokini Snorkel & Performance Sail with Lunch

Discover Molokini aboard a fast-sailing catamaran, where your trip includes a continental breakfast on the leisurely sail across Ma’alaea Bay. Take in the stunning landscape that makes Maui special, and during whale season (December – May), spot the humpback whales as they swim nearby. While at Molokini, swim, snorkel, and rinse off with a freshwater shower. After snorkeling, indulge in a full lunch buffet and refresh with a variety of beverages, including wine and local beer. Maui’s afternoon trade winds can really get the boat going, so join the friendly crew at the helm and try your hand at sailing the high seas! 

Kaanapali: Sunset Dinner Catamaran Cruise With Drinks

5. Kaanapali: Sunset Dinner Catamaran Cruise With Drinks

This experience starts on Ka'anapali beach where you will hop aboard our luxury 65ft beach loading catamaran. Feel the mana beneath you as you cruise with the tradewinds along the shore of Maui and enjoy humbling panoramic views of Maui and its surrounding islands during the magic hours of sunset. Watch for ocean animals while you will enjoy a full open bar, and unforgettable elevated dinner by Chef Jai. At sunset we do a special champagne toast and cheers to the end of another incredible day in Maui.

Oahu: Shark Cage Dive on the North Shore

6. Oahu: Shark Cage Dive on the North Shore

Swim with the sharks during this tour that offers you the unique adventure of a shark dive, while ensuring your safety at all times. Discover the wonders of the sea on the North Shore of Oahu, Hawaii alongside a certified guide. Bring your own masks and snorkels or use the ones provided on board. Your guide will give you a safety briefing at the start of the tour and will answer all your questions concerning this special adventure. See up to 200 feet (60 meters) in the crystal-clear, cobalt blue water. Depending on the season, you will encounter such magnificent animals as the Hawaiian Green Sea turtles, playful dolphins, and Humpback whales. Admire the sharks from the ship's deck, or experience the rush of entering the shark cage which allows you to be only inches away from sharks that can grow up to 15 feet (5 meters) in length. Capture pictures with your underwater camera of their grace and majesty in the water. Have 20 minutes to marvel at the sharks and cherish this unforgettable moment. Up to 8 people can be in the cage at the same time, so you can experience the sharks with someone you love.

Lahaina: Maui Channel Whale-Watching Catamaran Cruise

7. Lahaina: Maui Channel Whale-Watching Catamaran Cruise

Travel via high-speed catamaran from Lahaina Harbor to the Maui Channel to see the humpback whales, who return to Hawaii for a few months each year to mate and give birth. Get up close to these creatures in their native environment from comfortable table and chair seating. Keep your eyes peeled for whales slapping the surface with their very long side fins, tails, or the strong muscles attaching the tail to the rest of the body. See them spy-hop, when humpback whales come high out of the water to have a look around at the world above. See the majesty of a breaching whale, if you are lucky. This is when a whale rises completely out of the water and crashes down again. Don’t forget to bring your camera and take memorable photos from the shade of a spacious cabin.

From Lahaina: Lana'i Coast Maui Sail and Snorkel Trip

8. From Lahaina: Lana'i Coast Maui Sail and Snorkel Trip

Start the tour by boarding a brand new luxury catamaran at the dock in Lahaina. Set off on your incredible adventure along the spectacular coastline of Lana'i. Onboard the vessel, enjoy a continental breakfast of tropical fruit, freshly baked banana bread, and locally roasted coffee. Head towards the pristine reefs along Lana’i’s south shores where you'll discover stunning sea cliffs, uncrowded snorkeling sites, and expansive island views. Get geared up with the snorkeling equipment provided and plunge into the warm waters to discover an array of local marine life.  This relaxed tour does not have a set destination, so the experienced crew can select the best locations based on sea conditions, and visit multiple snorkel sites when time and weather allow. After swimming and snorkeling, sit back with a drink and enjoy a full lunch while trying to catch a sighting of Lana’i’s famous spinner dolphins. Finally, return to the dock where your memorable day at sea concludes.

From Ma'alaea Harbor: Whale Watching Tours Aboard the Malolo

9. From Ma'alaea Harbor: Whale Watching Tours Aboard the Malolo

Depart from Maalaea Harbor, easily located off the highway with ample parking. This high-speed catamaran is located at Slip 87 near Coast Guard Station. While on board, enjoy complimentary juices and sodas, and a variety of alcoholic beverages. The optimal whale watching season starts in December and goes through April, during which thousands of humpback whales return to Hawaii for a few months each year to mate and give birth. Depending on the whales’ behavior during your two-hour whale watching trip, you may see any number of whale activity happening, from tail flapping to full body breaching. Keep your eyes peeled for whales slapping the surface with pectoral fins (their very long side fins), flukes (the tail), and the peduncle (the strong muscles attaching the tail to the rest of the body). Keep your fingers crossed for a breach - this is when a whale rises completely out of the water and crashes down again. And most importantly, don’t forget to bring your camera to capture a picture of these amazing animals.

Oahu: Afternoon Glass Bottom Boat Tour in Waikiki

10. Oahu: Afternoon Glass Bottom Boat Tour in Waikiki

If adventure is what you seek, join this daily boat tour. Enjoy the beauty of Hawaii’s South Shore as you head out from the slip in the Kewalo Basin Harbor and head toward Lē’ahi. Discover the underwater world while staying dry with the glass-bottom boat. Aboard the Haleiwa Queen, enjoy the clear view of the Pacific Ocean floor as you cruise over live tropical reefs and one of Hawaii’s shipwrecks. Keep an eye out for honu sea turtles, eels, reef sharks, dolphins, and schools of tropical fish, all from the deck of the vessel through the glass bottom boat viewports. Experience a unique perspective of Honolulu, above and below the surface.

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What people are saying about Hawaii

Overall rating

4.5 / 5

based on 1,221 reviews

The booking online was easy with a very clear calendar on what dates were available. From the start of the early morning boarding process (7:30am) til the end(about 11am) it was fantastic. There was an awesome breakfast of fresh fruit, breakfast sandwiches and banana bread PLUS drinks (and mimosas for adults). The catamaran is big and roomy with plenty of walk around space and my kids loved to sit up front on the netting. I will say we were lucky and had a half dozen whales breach (jumping out of the water) in front of us plus another 12/15 sightings of heads and tails. It was AMAZING!! granted we were there in late December which is start of the season but we will be back and book again on our next rip to Maui. Just a very relaxing, exciting adventure to share with my two sons and wife. Also it goes without saying the crew is the best and will answer literally every question you and your kids have, they are all the friendly and you can tell they love their job.

It was great!! enjoyed the atmosphere and saw lots of cool animals!! We saw turtles, dolphins, and lots of fishes. The view made it a 1,000 times better!! Definitely recommend!

great evening with Greg and crew. sunset was awesome and we got to see a whale. only shortcoming was the food. Though good, it was not what we perceived as advertised.

the driver of the boat kind of looks like Revolver Ocelot from the series Metal Gear Solid. You should get that guy to cosplay as the character for Halloween

Absolutely amazing! Crew did a great job. Lots of sharks to see.