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Lahaina

Sailing trips & boat tours

Our most recommended Lahaina Sailing Trips & Tours

Lahaina: Turtle Town Snorkel and Whale Watching Cruise

1. 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. For beginners, there is an onboard snorkel demonstration before you set out. Enjoy an onboard lunch and drinks. Set sail from Lahaina Harbor towards Turtle Town, aka Mala Wharf (if weather conditions allow). In 1992, a powerful hurricane destroyed Mala Pier. The surviving posts have 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. All of these locations offer an excellent opportunity to see Hawaiian green sea turtles, brightly colored tropical fish, and beautiful coral reef formations. During the whale season (December to April), observe humpback whales as they enjoy the warm Hawaiian waters. This tour segment will include expert narration about the whales and provide a play-by-play commentary of the whales' behavior as you view them.

From Lahaina: Sunset Dinner Cruise with Live Music

2. From Lahaina: Sunset Dinner Cruise with Live Music

Departing from Pier One in Lahaina Harbor, enjoy a relaxing sunset cruise with a delicious three course meal, listen to island-style music, and watch the sun go down while cruising the waves on a state-of-the-art catamaran. Once aboard you will be seated by our crew to tables assigned based on the size of your party. Once you’ve settled in, our table side service will begin, and the crew will bring you warm breadsticks and water. Your dinner cruise includes two free drinks, once the catamaran has motored out of the harbor, we will take your drink order. We typically serve local beers from Maui Brewing Company, Cabernet and Chardonnay wine, cocktails such as Mai-Tai's, Pina Colada's, Margarita's, Tequila Sunrise, etc., soda, juice, and water. Your meal begins with a fresh spring mix salad with tomato, carrots, cilantro vinaigrette, and a taro roll with honey butter. For the main course, your options are rosemary garlic roasted prime rib, fresh Mahi-Mahi with lemon buttery caper sauce, or penne pasta with fresh Thai basil marinara sauce. On the side, enjoy sautéed vegetables and steamed white rice with shoyu sauce. For dessert, delight in delicious banana bread with homemade lilikoi frosting and cobbler topping. Relax as the sun sets behind the distant Maui mountains, and keep an eye out for humpback whales while you enjoy your delicious dinner cruise.

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

3. 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.

Maui: Deluxe Sunset Sail from Lahaina

4. 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. 

Maui: Dolphin Sailing Adventure with Lunch and Drinks

5. Maui: Dolphin Sailing Adventure with Lunch and Drinks

Get ready to experience the thrill of sailing alongside dolphins in the wild on a luxury sailing vessel. As you go, learn fascinating facts about the wild dolphins from your certified marine naturalist guide. Snap memorable photos when you catch a glimpse of the islands' acrobatic spinner dolphins, friendly bottlenose dolphins, and curious spotted dolphins. Enjoy an adventure great for all ages, and rest assured that dolphin sightings are guaranteed, else you can go again free on another Dolphin Watch within one year. During your sailing adventure, savor an included lunch and sip on 1 complimentary alcoholic drinks as you pass by the scenic shores of Maui.

Maui: Lanai Snorkel & Dolphin Watch from Lahaina Harbor

6. Maui: Lanai Snorkel & Dolphin Watch from Lahaina Harbor

Your eco-friendly wildlife adventure departs out of historic Lahaina Harbor aboard a 65 foot, double-deck powered catamaran. The journey over to Lanai takes approximately 60 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. 

Maui: Sunset Sailing Cruise with Champagne from Lahaina

7. Maui: Sunset Sailing Cruise with Champagne from Lahaina

A perfect Maui experience is not complete without witnessing the beauty of a sunset while out on the ocean. Board Paragon to experience a sunset sailing cruise and watch the sun dip below the horizon as you glide along the picturesque west cost of Maui. Beverages, including locally brewed beer, mai tais, wine, and champagne, are served as well as pupus (appetizers). This is as close as you can get to yachting, but make no mistake — when the wind is up it can be quite an exhilarating sail. During season from December to May, enjoy the thrill of watching the humpback whales that make their way to Hawaii each year.

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

8. Maui: Scenic 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.

Lahaina: 2-Hour Whale Watching Tours Aboard the Quicksilver

9. Lahaina: 2-Hour Whale Watching Tours Aboard the Quicksilver

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 Snorkel and Dolphin Adventure Cruise

10. From Lahaina: Lana'i Snorkel and Dolphin Adventure Cruise

Explore an entirely new island in Hawaii on a catamaran cruise from Maui to Lanai. Jump into the cool and clear waters to snorkel and swim with vibrant marine life and look up to towering cliffs above you. Enjoy a continental breakfast and deli sandwich lunch while you sail under the warm Hawaiian sun. Keep an eye out for spinner dolphins, who are known to frequent the area. Listen to music and your captain share his knowledge about this island paradise and the abundant sea life that makes this area their home. Arrive on the Lanai coast and explore the underwater world accompanied by a crew member throughout. Take advantage of the waterslide for extra fun. Marvel at the marine life as you snorkel beneath towering cliffs reaching up to 300 feet. Be among the few to snorkel at remote locations with great visibility, such as Shark Fin Rock and Manele Bay. See a spectacular view of the West Maui Mountains while enjoying a beverage and Quicksilver Crew Trivia on the trip back to Lahaina.

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Frequently asked questions about Lahaina Sailing Trips & Tours

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What people are saying about Lahaina

Overall rating

4.6 / 5

based on 231 reviews

We had a great night. The waters were a little rough but it didn’t affect our cruise. The staff was friendly and very attentive. We had great seats on the upper deck. I’m not sure the music was live but we enjoyed the selections. It was fun interacting with the other people. For me, I would rather have had a potato choice than rice. The veggies were sautéed cauliflower, broccoli, Brussels sprouts, carrots and potatoes. I liked them but my husband would rather have a different choice. The banana cake with cream cheese topping had good flavor but a little dry. But the prime rib was the BEST!! It was a great ending to our week in Mauai.

Crew was excellent - informative, helpful, funny, experienced. It was our first time snorkeling and they explained everything beautifully and we all felt safe.

Excellent snorkeling adventure with friendly crew, good food and drinks, and will definitely rebook on next trip to Maui! Big thumbs up!!!

Great experience ! Dinner was great! Prime rib and Mahi Mahi were prepared very well ! Staff was pleasant and accommodating and fun !

Enjoyed the ride, saw lots of dolphins and the crew was great and helpful. Lunch was good also