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MauiSailing trips & boat tours

Our most recommended Maui Sailing trips & boat tours

South Maui: Molokini and Turtle Town Snorkeling Tour

1. South Maui: Molokini and Turtle Town Snorkeling Tour

See Maui from a new perspective as you swim and snorkel alongside its marine life at Molokini and Turtle Town. Cruise to these famous snorkeling destinations by catamaran, and enjoy breakfast and lunch onboard. Meet your captain and crew near Maalaea Harbor for your check-in. Board the comfortable catamaran and enjoy a continental breakfast of pastries, muffins, fresh fruits, coffee, tea, juice, soda, and water as you head towards Molokini. Arrive at Molokini and admire the scenery of the extinct volcanic cone, home to around 250 different local species. Jump into the water and snorkel with native wildlife such as black triggerfish, yellow tang, and parrotfish. Continue onto Turtle Town, where you’ll swim with protected Hawaiian green sea turtles among the underwater lava formations. Rest assured a lifeguard will be in the water at all times as you snorkel around the beautiful coral gardens. Enjoy a deli lunch with Turkey and ham Hawaiian sweet roll sliders with Mediterranean pasta salad, soft drinks, juice, and water. Choose to purchase beers or a Mai Tai, and relax in the shade of the cabin. Or top up your tan on the bow of the boat as you return to Ma'alaea Harbor, where your unforgettable activity will come to an end.

South Maui: Sunset Prime Rib or Mahi Mahi Dinner Cruise

2. South Maui: Sunset Prime Rib or Mahi Mahi Dinner Cruise

Watch the glow of the sunset on the Kahalawai Mountains, Lanai Island, and the Molokini Crater on this sunset catamaran cruise from Ma’alaea. Keep an eye out for humpback whales while listening to Hawaiian music. Savor a gourmet dinner and relax with two drinks from the bar. Depart from the Ma’alaea Harbor and set off into the waves on a catamaran. After exiting the harbor, enjoy a complimentary drink before the dinner service kicks off. Explore the alcoves of the boat, gaze out over the ocean, and snap photos. While soaking up the tropical views, listen to island-style music. For dinner, chef Keoni will serve the succulent Hawaiian prime rib, Mahi Mahi, teriyaki chicken, ribs, steamed vegetables, white rice with soy sauce, and more. As you dine, take in views of Kaho’olawe and Lanai in the distance, as well as the top snorkeling location, Molokini Crater. Gaze out at the Kahalawai Mountains of Maui extending toward the sky. You are likely to see humpback whales visiting the islands from Alaska along with other marine mammals.

South Maui: PM Snorkel to Coral Gardens or Molokini Crater

3. South Maui: PM Snorkel to Coral Gardens or Molokini Crater

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.

South Maui: Sunset Cruise with 4-Course Dinner and Drinks

4. South Maui: Sunset Cruise with 4-Course Dinner and Drinks

Make some unforgettable memories on this once-in-a-lifetime cruise experience, gazing at the colorful Maui sunset from the water while you enjoy a lovely meal at your private outdoor table on the deck, accompanied by your family or friends. All entrees are freshly grilled on board. Dinner includes appetizers, locally grown salad, a choice of entrées, dessert, and an array of drinks and cocktails. Island-style music and open sea views of Maui’s scenic coast add to the ambiance of this memorable experience. Have a peek at the delicious menu waiting for you on the cruise:-Appetizer -Salad: Greens and vegetable salad with mango-passion vinaigrette -Choice of grilled entrée: choose between the lemongrass-curry marinated shrimp with lilikoi butter sauce, the teriyaki boneless chicken breast with Big Island papaya salsa, the chimichurri flat iron steak with wild mushroom demi-glaze, or the grilled portobello mushroom marinated in chimichurri over Molokai purple sweet potato mash. -Dessert: triple chocolate chip brownies with fresh Kula strawberries, Maui coffee, and hot tea.

Maui: Breathtaking Sunset Cocktail Cruise in Ka'anapali

5. Maui: Breathtaking Sunset Cocktail Cruise in Ka'anapali

Come on board this state of the art catamaran and enjoy an evening cruise between the islands of Maui, Molokai and Lanai. What better way to end a day than on board Teralani’s Original Sunset Sail. The journey begins on Kaanapali Beach where the catamaran's helpful crew and experienced Captain take you out to see to enjoy Maui’s magical sunset. While on board you can relax and sip on refreshing beverages, surrounded by breathtaking West Maui coastal views. Enjoy delicious appetizers prepared for you by an experienced chef. A perfect way to end your day, or start your night, relaxing in comfort and embracing an incredible Maui sunset.

South Maui: Lanai Snorkel & Dolphin Watch from Maalaea

6. South Maui: Lanai Snorkel & Dolphin Watch from Maalaea

Your eco-friendly wildlife adventure departs out of Maalaea Harbor aboard a 65 foot, double-deck powered catamaran. The journey over to Lanai takes approximately 70 minutes as the captain passes by known wild dolphin habitats before heading to your snorkel destination. Discover an underwater oasis and world-class snorkeling with warm crystal clear waters and vibrant reefs teeming with marine wildlife. Lanai is also famous for its large populations of wild dolphins, plus toothed whales, sea turtles, and the occasional Hawaiian monk seal. On the trip over, be treated to a continental breakfast of fresh island fruit, bagels and cream cheese, and apple danishes along with hot coffee, tea, hot chocolate, and juices. Take part in a guided reef tour with a certified marine naturalist and enjoy a leisurely snorkel. Feast on a barbecue lunch which includes chicken breasts, hot dogs, garden burgers, potato salad, veggie salad, and chocolate chip cookies. There's also all-you-can-drink water, sodas, juices and 1 complimentary alcoholic drink for those 21 and over. 

South Maui: Molokini Snorkel and Performance Sail with Lunch

7. South Maui: Molokini Snorkel and 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! 

South Maui: Molokini Snorkeling Adventure

8. South Maui: Molokini Snorkeling Adventure

Embark on a half-day snorkeling adventure on a glass-bottomed catamaran, with breakfast, lunch, and a professional crew included. Look out for all types of Pacific marine life, from dolphins to turtles and coral reefs, in 2 snorkeling spots — the Molokini Crater and Turtle Town.  Begin your tour at Maalaea Harbor to board your boat. Join the crew aboard the Calypso, Maui's newest addition to the fleet, where you can even view the ocean from its glass bottom. Calypso is the only 3-deck catamaran in Hawai'i. Benefit from an easy-to-use stairway in and out of the water, lots of shade, and plenty of Jimmy Buffet music.  Start the day off right with a continental breakfast that includes mixed muffins, pastries, fruit, coffee, tea, and juice. Next, be dazzled by Molokini Crater, located off the south shore of Kihei. Expect pristine conditions as Molokini is a protected marine preserve and bird sanctuary.  See how the extinct volcanic cone provides a home for native Hawaiian marine life such as manta rays, fish, urchins, and sharks, who all swim around the coral through the clear water year-round. Use the provided snorkeling equipment to explore the underwater world.  Take advantage of the 2 water slides to make it more fun, especially for kids. And fret not— a lifeguard is always in the water watching over the snorkelers to ensure their safety. After leaving Molokini, your second snorkeling spot of the day is Turtle Town, where you will swim with Hawaiian green sea turtles amid the calm water and coral. Then, return to the boat for a relaxing deli sandwich lunch. Some of the tour’s top amenities include 2 slides, a jumping platform, 2 freshwater showers, use of snorkeling gear, flotation devices, and restrooms on the boat. There are 11 stair points to get into the water for easy and comfortable access. Wetsuits and underwater digital cameras are available to rent once onboard.

Big Island: Morning Snorkel Sail to Captain Cook's Monument

9. Big Island: Morning Snorkel Sail to Captain Cook's Monument

The Hoku Nui sets sail from Keauhou Bay at 8:30 am. Keep a watchful eye out for Hawaiian Spinner Dolphins, Hawaiian Humpback Whales (seasonal Dec-April), and other marine life while you sail down the beautiful Kona Coast. As you enjoy your tropical style breakfast, entering Historic Kealakekua Bay, you will observe the World Famous Captain Cook Monument (sail time approx. 45 min.) Your snorkeling adventure will begin in the pristine waters and the vibrant reef of the Marine Sanctuary of Kealakekua Bay. Your captain will select the best snorkeling sites in Kealakekua Bay, as the friendly and professional crew members provide site briefings and historical facts. The crew members will provide snorkel tips and basic instructions to guests of all ages and experience levels. Life jackets, floatation noodles, and viewfinder boards as well as masks, fins, and snorkels are provided aboard the Hoku Nui. The crew members 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 and have lunch ready when you have snorkeled up an appetite. Snorkel time is approximately one hour at each location. Make sure to bring an underwater camera to capture the colorful schools of fish, pods of spinner dolphins that are also commonly spotted in the bay, and the landscaped ledges of ancient lava flows. You will then have a moment for another breath taking view of the bay while you enjoy a sumptuous lunch with beverages. Exiting the bay, you set sail for “Red Hill” (weather permitting). The Red Hill area is home to unique underwater lava formations such as archways and lava tubes, and more snorkeling with schools of vibrant sea life. As your snorkel adventure comes to an end, you will set sail back to Keauhou Bay arriving by 1 pm (approx.), with majestic memories of your Sea Paradise trip that will last a lifetime.

South Maui: Sunset Dinner Cruise Aboard the Malolo

10. South Maui: Sunset Dinner Cruise Aboard the Malolo

Come join us aboard the Malolo and experience the world-famous Maui sunset as we cruise gently along the coastline. Enjoy the Aloha as our friendly crew serves up a delicious meal and refreshing cocktails. Sit back, relax, and listen to island music as you take in the spectacular panoramic views of the islands of Kahoolawe and Lanai and beautiful Maui mountains and coastline. We depart from Ma'alaea harbor and once aboard you can choose a comfortable seat inside the cabin or outside for better viewing. Once outside the harbor you can order a refreshing cocktail, a cold beer, or glass of wine and get yourself a plate of from our buffet style serving stations. Three alcoholic beverages per adult are included at no additional cost.

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What people are saying about Maui

Overall rating

4.5 / 5

based on 596 reviews

We booked before we arrived in Hawii and on the day of our excursion all we had to do was check in and when it was time to board they called our name and on board we went. The staff was very friendly and answered all of our questions. One person in our party got sick and while we were in the water they kept an eye on her. We would definitely recommend this excursion. We even got to see a momma whale and her baby.

The crew took great care of us from the moment we boarded until we deboarded. Seats and equipment (including graded goggles for us wearing eyeglasses) are more than adequate making everyone enjoy. The captain knows where to position the boat to get great possibility of successfully seeing whales. The whales put on a show, even breaching from the water. Highly recommended!

Wonderful crew made for a wonderful experience! Very friendly and hospitable, would highly recommend this excursion. The sunset was unreal and the sighting of whales just topped it off!

Snorkeling was okay)))) But !!But!!!on a way back home we saw so many Whales and they was just next to our boat!!!Crew are super fun and nice!!!Recommend

Our second year going with this company and LOVED it!!!