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Hawaii Sailing trips & boat tours

Our most recommended Hawaii Sailing trips & boat tours

Lahaina: Maui Channel Whale-Watching Catamaran Cruise

1. 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.

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.

Big Island, Hawaii: Night Manta Ray Snorkel Experience

4. 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.

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

5. 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

6. 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.

Maui: Deluxe Sunset Sail from Lahaina

7. Maui: Deluxe Sunset Sail from Lahaina

Enjoy stunning sunset on the coast of Maui on a catamaran cruise from Lahaina. Lay back on the forward trampolines or sit under the covered cabin space while savoring mouth-watering cold hors d’oeuvres and sipping on chilled drinks. Keep an eye out for whales as you sail.  Depart from Lahaina and set sail in the waters of Maui. Admire breathtaking views of the verdant and dynamic shores as the sunset paints the sea in a golden glow. Have a refreshing cocktail or snack on a delicious selection of hors d’oeuvres.  From December to May, enjoy the thrill of watching the humpback whales as they make their yearly journey to Hawaii. During the rest of the year, keep your eyes peeled for graceful seabirds and the black-finned Māui dolphin.  Return to your meeting point in Lahaina at the end of your cruise. 

From Ma'alaea Afternoon Snorkel to Molokini or Coral Gardens

8. From Ma'alaea Afternoon Snorkel to Molokini or Coral Gardens

Explore one of Maui’s most impressive sites on this relaxing afternoon catamaran cruise to Molokini Crater or Coral Gardens. Dive into the rich marine biodiversity of the reefs in this partially submerged volcanic crater. Head to the meeting point at Maalaea Harbor for your check-in before boarding the Malalo catamaran. Set sail and admire the beautiful Pacific coastal views as you cruise towards your snorkel site. Stop at the ideal snorkeling location for that day. Have the option to purchase food and drink aboard. Jump into the pleasant water and look for colorful fish like parrot fish, yellow tang, and cornet fish. Keep your eyes peeled for the elusive spotted eagle ray. Feel free to rent wetsuits, digital underwater cameras, and prescription masks on the day of your activity to enhance your aquatic experience. After your unforgettable swim, relax with a drink (available to purchase) on deck as you return to your boarding point.

Oahu: Shark Cage Dive on the North Shore

9. 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.

Maui: Molokini Snorkel & Performance Sail with Lunch

10. 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! 

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What people are saying about Hawaii

Overall rating

4.5 / 5

based on 1,221 reviews

Really liked this vessel.. very clean and great layout for whale watching. Was a super choppy day but the boat and Captain Carlos did a great job making it a comfortable trip. Saw some great activity and probably would have been even better if it wasn’t so choppy.

The sunset cruise was a perfect evening! The crew was very professional. The appetizers and beverages were flavorful. A professional photographer took photos during the evening. Good music and conversation among the guests. Highly recommend!

Saw whales up close. also spinner dolphins but they only breached the water, guess they were not in a mood to show off at the moment.

Best Excursion Ever!! Way better than expected. The sharks are 10-15 feet and you feel very safe.

Great crew and awesome adventure! Would definitely recommend