Maui’s coastline offers some of the most spectacular sailing opportunities in Hawaii. Its mix of calm, warm waters, vibrant marine life, and breathtaking scenery makes it a prime destination for boat lovers—and for those looking to see whales, turtles, or simply enjoy a relaxing day at sea. Whether you want the full luxury experience aboard a climate-controlled yacht, an intimate sunset sail, or a family-friendly snorkeling adventure, Maui delivers. The variety of tours means you can choose a trip that matches your budget, time constraints, and personal interests, turning your visit into a memorable maritime escape.
For those seeking a luxury cruise, the options range from private yachts to high-end catamarans, with some tours including gourmet meals and onboard amenities. Adventure seekers might prefer snorkeling excursions or whale-watching trips, especially in the winter months when humpbacks are in town. And if you’re interested in Hawaiian culture, a canoe sailing experience offers a chance to learn traditional methods of navigation and boat building. The list below highlights the 12 best sailing experiences in Maui, covering a broad spectrum of styles, prices, and experiences.
1. Maui Luxury Snorkeling Molokini aboard Air Conditioned Yacht Elua
At number 1, the Maui Luxury Snorkeling Molokini aboard Air Conditioned Yacht Elua stands out for its combination of comfort, luxury, and expertise. This yacht is the only one in Maui with air conditioning, making the trip especially appealing for travelers who dislike the heat or want to enjoy the ride in a climate-controlled environment. The 5-hour tour includes stops at Molokini Crater, a volcanic caldera known for its crystal-clear water and abundant marine life, as well as Turtle Town, where you can swim alongside Hawaiian green sea turtles.
What makes this trip unique is the modern Euro interior, plush sofas, and stunning fixtures, combined with professional crew with over 40 years of experience. They operate at just 60% capacity for added comfort, and reviews highlight the delicious food—including breakfast and BBQ lunch—and the friendly, knowledgeable staff. The snorkeling here is top-notch, and the scenery of Mt. Haleakala and West Maui mountains adds to the experience. With a 5-star rating from 189 reviews, this tour is ideal for travelers seeking a luxurious, relaxing day at sea with excellent marine encounters.
Bottom Line: If you prioritize comfort, high-end amenities, and a family-owned crew with decades of experience, this tour offers unmatched style and service for around $238 per person.
2. Maui: Snorkeling and Sailing Adventure with Buffet Lunch
Second on our list is the Maui: Snorkeling and Sailing Adventure with Buffet Lunch. For around $172, you get a 4-hour trip along Maui’s west coast, combining relaxation with marine exploration. The tour includes snorkeling among tropical fish and Hawaiian green sea turtles, with the added bonus of enjoying a hot buffet lunch and an open bar.
What makes this tour stand out is its versatility—guests can lounge on trampolines, relax indoors, or snorkel as much as they like. In winter, the chance to see humpback whales adds an extra element, though if whales aren’t in season, the sailing itself is still spectacular. The crew is praised for their organization and friendly service, and many reviews mention the excellent value for the included food and drinks. Plus, the boat is roomy and comfortable, making it suitable for families and groups of all ages.
Bottom Line: Perfect for those wanting a balanced mix of sailing, snorkeling, and delicious food, this tour offers good value at a reasonable price with the chance to see whales in winter.
3. Hawaiian Canoe Sailing Experience in Maui
Third on our list is the Hawaiian Canoe Sailing Experience in Maui. At just 2 hours and $179 per person, this tour offers a cultural twist on traditional Hawaiian sailing. This private outrigger canoe trip along the Wailea coast gives you the chance to learn about Hawaiian navigation, boat construction, and ancient sailing methods from experienced guides.
What makes this experience special is its personalized nature—it’s ideal for small groups or couples who want an authentic Hawaiian adventure. You’ll have opportunities to spot sea turtles, reef fish, and even humpback whales if in season, all while learning about the islands’ maritime traditions. Guests consistently praise the guide’s knowledge and friendliness, and the snorkel gear is included for underwater exploration.
Bottom Line: If you’re interested in Hawaiian culture and prefer a private, intimate outing, this 2-hour trip provides a meaningful connection to the island’s seafaring roots.
4. Luxury Catamaran Whale Watch
Fourth, the Luxury Catamaran Whale Watch offers a 2-hour journey from West Maui that’s all about getting close to the humpbacks. In winter months, the waters fill with these massive creatures, and this trip promises a chance to see them breaching, tail-slapping, and singing. The onboard hydrophone allows you to listen to the whales’ songs, adding an extra dimension to the experience.
This tour stands out because of its luxury feel—spacious deck, marine naturalist onboard, and a relaxed atmosphere. Reviewers love the attentive crew and the gorgeous views, calling it a memorable experience. Prices are reasonable at $159 per person, and guests report that the views of the whales are incredible, making it perfect for wildlife enthusiasts and those seeking a comfortable, scenic tour.
Bottom Line: For whale season, this elegant 2-hour cruise combines wildlife viewing with a premium experience, ideal for couples or small groups.
5. Turtles & Tacos Luxury Catamaran Snorkel
Number five is the Turtles & Tacos Luxury Catamaran Snorkel. This 3-hour tour at $169 per person combines snorkeling with delicious local food. The crew greets you with warmth and provides all the gear for a relaxed snorkel at a pristine spot famed for marine life and sea turtles.
What makes this trip unique is the tacos and open bar included, which isn’t just a snack but a highlight for many. Reviewers say the staff are friendly and attentive, and the boat is spacious with shaded areas. Snorkeling here provides opportunities to see many fish and even sea turtles, as well as the vibrant reefs. The crew also offers professional photos, making it easy to capture the day’s memories.
Bottom Line: If you want a laid-back, fun outing with excellent snorkeling, tasty food, and a friendly crew, this tour delivers for a reasonable price.
6. Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
At number six, the Luxury Catamaran Royal Sunset Dinner Sail offers a romantic, adults-only experience. For $289 per person, you’ll enjoy a 2.5-hour cruise with unobstructed sunset views, local cuisine, and tropical drinks. The boat’s spacious deck provides a perfect backdrop to watch the sky turn gold, while the fully licensed onboard bar keeps the drinks flowing.
Guests highlight the top-notch service, the quality of the food, and the stunning scenery. With a 5-star rating, this tour suits couples celebrating special occasions or anyone wanting a quiet, elegant evening on the water. The sunset views are considered some of the best, and the calm atmosphere makes it an ideal choice for a romantic night out.
Bottom Line: For a special occasion or a romantic getaway, this sunset cruise combines fine dining and scenic beauty in a luxurious setting.
7. Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
Seventh is the Sunset Sail on a Small Charming Hawaiian Catamaran. With a maximum of 40 passengers, this intimate cruise costs just $119 and offers a personalized experience. The small size means you can move freely, enjoy the golden sunset, and spot dolphins or whales in season.
Guests love the friendly crew, the good drinks, and the relaxed vibe. The boat is locally built, adding to its authentic appeal. Many reviews mention the opportunity to see whales breaching during the season and the overall friendly atmosphere. The captain takes care to find perfect spots for photos and sunset views.
Bottom Line: If you prefer an intimate sailing experience with personalized attention, this small-group sunset cruise provides excellent value and a cozy atmosphere.
8. Maui: Ma’alaea Catamaran Sunset Sail with Appetizers
Eighth on the list is the Maui: Ma’alaea Catamaran Sunset Sail with Appetizers. For $144, this 2-hour trip offers a combination of stunning sunset views, appetizers, and drinks. The boat features an open deck, trampoline, and covered seating, so you can choose your preferred spot as you glide past Maui’s coastline.
Reviewers praise the delicious appetizers and drinks, along with the friendly, attentive staff. The trip is ideal for those who want a relaxed, scenic experience with lots of photo opportunities. Many mention seeing whales or dolphins, especially during the season, making it a lively and memorable cruise.
Bottom Line: Perfect for a short, relaxed sunset sail with good food, drinks, and opportunities for wildlife sightings.
9. Lahaina: Private Sunset Sailing Trip & West Maui Mountains
Number nine is the Lahaina: Private Sunset Sailing Trip & West Maui Mountains. Priced at $1,936 for up to 6 people, this private charter is ideal for celebrating a special occasion or enjoying a more personalized experience. The trip lasts about 3 hours and offers stunning views of the West Maui Mountains as the sky turns to gold.
Reviews highlight the professional crew and the beautiful scenery. The private nature of this trip allows you to customize your experience, including a fruit, cheese, and cracker platter. It’s best suited for those seeking privacy, a romantic atmosphere, or a family celebration.
Bottom Line: If you’re celebrating a special event or want a private, scenic sunset experience, this yacht offers exclusivity and breathtaking views.
10. Maui: Alii Nui Whale Watch & Catamaran Sail
Tenth is the Maui: Alii Nui Whale Watch & Catamaran Sail. This 2-hour tour combines whale watching with a sailing adventure, offering a chance to see the whales in their natural habitat while enjoying a gourmet bar and appetizers. The waters around Maui are famous for humpback activity in winter, and this tour aims to give you a close-up view.
The ship is rated highly for its comfortable setting and the opportunity to observe whales singing and breaching. It’s suitable for those who want a quick but memorable wildlife encounter combined with a relaxed sailing trip.
Bottom Line: If whale season is on, this tour delivers excellent wildlife viewing coupled with a casual sailing experience.
11. Maui: Alii Nui Luxury Catamaran Day’s End Sunset Sail
Number eleven, the Maui: Alii Nui Luxury Catamaran Day’s End Sunset Sail, is a 2-hour cruise ideal for winding down. It features upscale hot and cold appetizers, premium drinks, and unobstructed views of the sunset. The setting is elegant, perfect for a relaxing evening with friends or loved ones.
Guests mention the “unforgettable golden glow” of Maui’s sunset, with many taking stunning photos. The crew is attentive, making this an excellent choice for those seeking a refined, scenic end to their day.
Bottom Line: For a quiet, luxurious sunset with quality food and drinks, this cruise offers a refined and memorable experience.
12. Maui: Private Yacht Snorkeling Tour with Breakfast and Lunch
Last on our list is the Maui: Private Yacht Snorkeling Tour with Breakfast and Lunch. Priced at $3,215 for up to 6 people, this luxury private yacht experience offers the ultimate in exclusivity. The 5-hour trip takes you to secluded reefs, where you snorkel with tropical fish and coral reefs guided by an in-water expert.
This tour is distinguished by its all-inclusive nature—breakfast, lunch, and the personalized service of a crew and captain. Many reviews emphasize the chance to see rare marine life, along with the high-end comfort of the yacht itself. It’s perfect for celebrating milestones or indulging in a high-end, private escape.
Bottom Line: If budget isn’t a concern and you want the most luxurious, personalized snorkeling experience possible, this private yacht trip delivers top-tier service and stunning marine encounters.
How to Choose Your Perfect Maui Sailing Experience
Choosing among these options depends on your priorities: Is comfort and luxury your main concern? Then consider the Maui Luxury Snorkeling Molokini aboard Air Conditioned Yacht Elua or the Luxury Catamaran Royal Sunset Dinner Sail. Want to see whales? The Luxury Catamaran Whale Watch and Maui: Alii Nui Whale Watch & Catamaran Sail are top picks. Looking for culture? The Hawaiian Canoe Sailing Experience offers a rare chance to learn traditional navigation methods.
Budget and time also matter—shorter trips like the Sunset Sail on a Small Charming Hawaiian Catamaran at $119 suit those with limited time or wanting a more personal experience. For those celebrating special moments, private charters like the Lahaina Private Sunset Sailing Trip offer exclusivity.
Booking early, especially during peak whale season or holidays, is highly recommended to secure your preferred date and ensure you get the best experience. Many tours include optional add-ons like professional photos or gourmet meals—consider these extras when planning your perfect day at sea.
Final Thoughts
Maui’s sailing scene is diverse, offering everything from luxurious yacht cruises and romantic sunset sails to family-friendly snorkel adventures and cultural voyages. The Maui Luxury Snorkeling Molokini aboard Air Conditioned Yacht Elua and the private yacht options stand out for their high-end amenities and exclusivity. Meanwhile, tours like the whale-watching cruises provide unforgettable wildlife encounters, especially in winter.
Whether you’re after a charming sunset, a cultural experience, or a luxurious day on the water, Maui has a sailing trip for you. To ensure a smooth trip, book early and consider what features matter most—be it comfort, scenery, or wildlife. With so many excellent choices, you’ll find the perfect sail to complement your Maui adventure.