Sailing in Maui combines practicality with unforgettable ocean experiences. The best tours operate from Lahaina Harbor, offering 3-hour to full-day excursions that typically cost $100-300 per person. For the money, catamaran dinner cruises deliver exceptional value with chef-prepared meals and guaranteed sunset views. Whale watching trips (December-April) stand out for their expert naturalists and hydrophone equipment – you’ll hear these giants sing. My favorite remains the Molokini Crater snorkel sail: crystal-clear waters and abundant marine life make this a must-do adventure. For families or small groups, private charters provide flexibility and personalized service, though they run $1000+. Let’s look at our carefully selected top sailing tours in Maui.
Key Points
- Explore Maui’s stunning coastline and witness breathtaking sunsets on luxury catamaran dinner cruises, offering upscale amenities and exceptional service.
- Experience exhilarating whale watching adventures aboard comfortable catamarans, complete with knowledgeable crew, hydrophones to listen to whale songs, and opportunities for close encounters.
- Discover the vibrant marine life of Molokini Crater and West Maui’s pristine reefs through guided snorkeling excursions, with delicious meals and gear provided.
- Enjoy peaceful and scenic sailing adventures along Maui’s shoreline, ranging from intimate sunset sails to private charters for special occasions.
- Enhance your sailing experience with unique offerings, such as full-service bars with premium drinks, knowledgeable naturalists, and special events like 4th of July fireworks cruises.
Luxury Royal Catamaran Sunset Dinner Cruise in Maui
Embarking on the Luxury Royal Catamaran Sunset Dinner Cruise in Maui transports you to a world of unparalleled elegance and breathtaking vistas.
Departing from Maalaea Harbor, you’ll set sail at 5:30 PM, surrounded by a maximum of 40 fellow travelers. The 3-course buffet dinner and full bar with premium drinks ensure an exceptional dining experience, complemented by the attentive crew who consistently deliver exceptional service.
Though not wheelchair accessible, the boat offers two restrooms accessible via a few steps, and crew assistance is available.
With a rating of 4.9 out of 30 reviews and a 97% recommendation, this cruise is a must-do for an unforgettable evening under Maui’s picturesque sunset.
Read our full review: Luxury Royal Catamaran Sunset Dinner Cruise in Maui Review
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Maui: Molokini Crater Luxury Catamaran Sail
Sail to the captivating Molokini Crater aboard a luxurious catamaran and experience Maui’s underwater wonders.
This 5.5-hour tour takes you to the crescent-shaped volcanic crater, renowned for its vibrant marine life. Snorkel through the crystal-clear waters, teeming with tropical fish, sea turtles, and the occasional friendly dolphin.
Refuel with a delicious meal and relax on the boat’s spacious deck as you cruise back to shore.
With its 4.5-star rating and affordable price, this snorkeling excursion is a must-do activity during your Maui vacation.
Explore the island’s natural beauty and discover the magic beneath the waves on this unforgettable Molokini Crater adventure.
Read our full review: Maui: Molokini Crater Luxury Catamaran Sail Review
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Maalaea Harbor: Whale Watching Catamaran Cruise
Escape the crowds and embark on a whale watching adventure at Maalaea Harbor. From $49.95, you’ll cruise aboard a spacious double-deck catamaran for 2 hours, spotting humpback whales in their natural habitat.
Listen to their songs through underwater hydrophones and observe their captivating behaviors like fin slaps and breaches. The friendly and knowledgeable crew will provide insightful narration throughout your scenic tour.
With restrooms, comfortable seating, and a shaded cabin, you’ll experience the best of Maui’s whales in comfort. Convenient parking is available at the Maui Harbor Shops, just a short walk from the departure point.
Don’t miss this chance to witness the wonders of these majestic creatures.
Read our full review: Maalaea Harbor: Whale Watching Catamaran Cruise Review
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From Maalaea: Whale Watching Catamaran Cruise With Drinks
Depart from the serene Maalaea Harbor for an unforgettable whale watching adventure aboard a spacious catamaran.
This 2-hour cruise offers an intimate experience with a small group, led by a knowledgeable captain and crew. You’ll enjoy safety briefings, refreshments, and insights into the fascinating behavior and biology of humpback whales during their annual migration.
Relax to island-style music as you take in scenic views of West Maui’s mountains, Molokai, and Lanai.
Don’t forget to bring motion sickness prevention and sun protection.
With free cancellation up to 24 hours in advance and the ability to reserve now and pay later, this whale watching excursion is a must for your Maui vacation.
Read our full review: From Maalaea: Whale Watching Catamaran Cruise With Drinks Review
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Lahaina: Sailboat Cruise With Snacks and Drinks
When you’re ready to trade the crowds and bustling streets of Lahaina for the tranquility of the open waters, hop aboard a luxurious sailboat for an unforgettable cruise.
Enjoy the gentle breeze and panoramic views as you sail along the Maui coastline. This 2-hour excursion includes complimentary snacks and drinks, allowing you to sit back, relax, and soak in the island’s natural beauty.
Whether you’re seeking a romantic sunset sail or a leisurely afternoon on the water, this sailing tour offers an idyllic way to experience Maui’s stunning scenery and laid-back island vibe.
With a 4.7-star rating from 38 reviews, this cruise is a must-do for any visitor.
Read our full review: Lahaina: Sailboat Cruise With Snacks and Drinks Review
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Maui: Alii Nui Whale Watch & Catamaran Sail
For a whale-watching excursion unlike any other, set sail aboard the Alii Nui catamaran.
You’ll cruise through Maui’s warm, shallow waters, spotting humpback whales in their natural habitat. The 2-hour tour runs 7 days a week from mid-December to when the whales depart.
On board, you’ll enjoy gourmet appetizers and access to a premium bar. A marine naturalist provides fascinating facts about the whales, and you can even listen to their songs through a hydrophone.
With free cancellation up to 24 hours in advance and a convenient departure from Maalaea Harbor, this whale watch is a must-do Maui experience.
Read our full review: Maui: Alii Nui Whale Watch & Catamaran Sail Review
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Maui: Luxury Alii Nui Catamaran Royal Sunset Dinner Sail
Elevate your Maui experience with the Alii Nui Catamaran’s Royal Sunset Dinner Sail.
Cruise along the picturesque South Maui coastline as you savor a delectable 4-course dinner with drinks.
Bask in the warm glow of the setting sun and take in the breathtaking views.
This 2.5-hour tour earns a stellar 4.7 rating from 60 reviews, making it a must-try for an unforgettable evening.
Priced at €168.25, it’s a premium experience that’s worth every penny.
Don’t miss this unique opportunity to indulge in Maui’s natural beauty and culinary delights during your stay.
Read our full review: Maui: Luxury Alii Nui Catamaran Royal Sunset Dinner Sail Review
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Maui: Maalaea Catamaran Sunset Sail With Appetizers
Set out on a captivating Maui adventure with the Maalaea Catamaran Sunset Sail. For $144.28 per person, you’ll enjoy a 2-hour sail as the sun dips below the horizon.
Savor premium appetizers like furikake-crusted ahi and BBQ kalua pork quesadillas, complemented by unlimited beverages. Relax on the open deck or trampoline, capturing stunning photos of Maui’s coastline.
Certified Marine Naturalists are on hand to share their expertise. With a 4.7/5 rating based on 15 reviews, this is an experience not to be missed.
Just be sure to check in 45 minutes early and leave the smoking at home. Secure your spot and get ready for an unforgettable sunset sail.
Read our full review: Maui: Maalaea Catamaran Sunset Sail With Appetizers Review
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Maui: Alii Nui Luxury Catamaran Makani Sunset Sail
Escape the crowds and learn about Maui’s unparalleled beauty aboard the Alii Nui Luxury Catamaran Makani Sunset Sail.
This 2-hour premium experience showcases Maui’s iconic sunset from the water, complete with upscale appetizers and a full bar.
You’ll enjoy seating in the cabin or on the spacious deck, with access to two clean bathrooms.
The cruise departs from Slip #56 at Maalaea Harbor, with parking available nearby.
Guests must be 18+, and those over 21 will need a valid ID to access the open bar.
At just €160.51 per person, this is a luxurious way to witness Maui’s natural splendor at sunset.
Read our full review: Maui: Alii Nui Luxury Catamaran Makani Sunset Sail Review
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Lahaina: Private Sunset Sailing Trip & West Maui Mountains
Indulge in a private sunset sailing excursion along Lahaina’s scenic coastline and witness the West Maui Mountains transform against the vibrant sky.
From Kč 45,864 per group, you’ll board a private sailboat and set sail around 4 pm. Delight in a platter of fruits, cheeses, and crackers as you relax with family or friends, and bring your own alcohol for an extra touch.
Spot Hawaiian marine life during the 3-hour cruise and admire the magnificent sunset views.
The experience isn’t suitable for those with mobility issues, but the excellent crew and 5/5 customer ratings ensure an unforgettable sunset sailing adventure in Maui.
Read our full review: Lahaina: Private Sunset Sailing Trip & West Maui Mountains Review
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Maalaea: West Maui Snorkeling & Sailing Day Trip With Lunch
Set sail for an exhilarating West Maui snorkeling and sailing adventure from the picturesque Maalaea Harbor.
Aboard a luxury catamaran, you’ll explore pristine reefs and spot marine life like sea turtles and vibrant coral. During whale season, you might even get close to majestic humpbacks.
Enjoy a continental breakfast and deli-style lunch, plus an open bar with local beer, wine, and cocktails.
With snorkel gear, reef-safe sunscreen, and towels provided, you’re all set for a hassle-free day on the water.
Flexible snorkeling spots ensure an optimal experience based on daily conditions.
This highly-rated tour offers incredible value, with glowing reviews praising the knowledgeable guides and personalized service.
Read our full review: Maalaea: West Maui Snorkeling & Sailing Day Trip With Lunch Review
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South Maui: 4th of July Fireworks Harbor Cruise by Catamaran
Experience the vibrant 4th of July celebrations in Maui with a captivating fireworks harbor cruise aboard a luxurious catamaran.
Enjoy the festive atmosphere as you sail through the tranquil waters of South Maui. Enjoy a front-row seat to the dazzling pyrotechnic display over the harbor, complemented by a delicious 4-course dinner and an open bar.
This 2.5-hour cruise is the perfect way to celebrate Independence Day in style, offering stunning views and unforgettable memories.
Book your spot on this unique South Maui adventure to make the most of Maui’s 4th of July festivities.
Read our full review: South Maui: 4th of July Fireworks Harbor Cruise by Catamaran Review
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Maui: Snorkeling and Sailing Adventure With Buffet Lunch
Explore the vibrant underwater world of Maui’s west coast on this captivating snorkeling and sailing adventure. Encounter Hawaii’s iconic state fish, the Humuhumunukunukuapua’a, and endangered green sea turtles as you snorkel along the coastline.
Sail to stunning locations like Honolua Bay Marine Reserve and Turtle Town, where you can relax on the trampolines or in the spacious cabin. Savor a delicious hot buffet lunch and complimentary open bar as you take in the seasonal sights of whales or spinner dolphins.
With high-quality gear, professional instruction, and a friendly crew, this experience promises an unforgettable day on the water. At just $172.01 per person, it’s an exceptional value for your Maui adventure.
Read our full review: Maui: Snorkeling and Sailing Adventure With Buffet Lunch Review
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Maui: Private Yacht Snorkeling Tour With Breakfast and Lunch
Set out on a private yacht snorkeling adventure in Maui, where you’ll learn about the vibrant undersea world along the island’s western coast.
This 5-hour tour, priced at $3,215.47 for up to 6 participants, lets you explore secluded reefs and spot tropical fish and coral with the guidance of an in-water instructor.
Enjoy a light breakfast and catered lunch on board, featuring local cuisine.
The luxury sailing yacht, Kainani, departs from Kaanapali Beach, offering pickup and drop-off for your convenience.
This all-inclusive experience earns rave reviews for its exceptional boat, attentive crew, and unique wildlife sightings, including sea turtles and sharks.
Read our full review: Maui: Private Yacht Snorkeling Tour With Breakfast and Lunch Review
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The Sum Up
You’ve got plenty of amazing sailing experiences to choose from in Maui. Whether you’re looking for a sunset cruise, a snorkeling adventure, or a whale watching tour, there’s something for all. With luxury catamarans, private yachts, and more, you’re sure to find the perfect sailing excursion to make your Maui vacation unforgettable. So don’t hesitate – book your sailing adventure today and get ready for an incredible time on the water!