Maui’s reputation as a premier Pacific island isn’t just about its lush landscapes and volcanic craters; it’s also about its prime sailing conditions. Thanks to consistent trade winds, calm waters, and a scenic coastline that seems to go on forever, Maui is a sailor’s paradise. Whether you’re eager to spot humpback whales during winter, enjoy a romantic sunset sail, or snorkel at volcanic crater sites, Maui offers a wide variety of sailing experiences. Among the many options, the Ma’alaea Harbor Whale Watching Tour stands out for its affordability and family-friendly vibe. Meanwhile, the Sunset Dinner Sail offers a luxurious, adults-only evening perfect for couples craving romance. We love the variety—each tour provides a different way to experience Maui from the water.
From intimate private outings to large-group adventures, Maui truly has a lot to offer. Whether you’re interested in whale watching, snorkeling at volcanic calderas, or enjoying a sunset with drinks in hand, this list covers the best options for every budget and interest.
Quick Overview
Our list of the best sailing experiences in Maui includes a mix of whale watching, sunset sails, luxury snorkeling trips, and cultural sailing adventures. For example, the full-day Maui Luxury Snorkeling aboard Air Conditioned Yacht Elua offers a high-end experience at Molokini Crater, rated a perfect 5.0 with rave reviews. If a romantic evening is your goal, the Hawaiian Sunset Dinner Sail provides a five-star dinner with unobstructed sunset views. For those on a tighter budget, the Ma’alaea Harbor Whale Watching Tour at just $50 per person is a great chance to see whales in their natural habitat.
Below, you’ll find detailed descriptions of each experience, helping you decide which best suits your interests and style.
1. Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran
This whale watching cruise is a top-value option, especially during whale season (Dec – Apr). Aboard a double-deck power catamaran, you’ll get excellent vantage points to see humpbacks breaching, fin slaps, and tail slaps. The cruise is fully narrated, with a marine hydrophone allowing you to listen to whale songs—a magical experience. The spacious deck with comfortable seating makes it easy for everyone to see and take photos. With a 4.7-star rating from over 830 reviews and a price of just $50, this tour offers a fantastic introduction to Maui’s marine life without breaking the bank. This tour is perfect for families, first-time visitors, or anyone wanting a reliable, fun, and educational experience.
Bottom line: A budget-friendly, family-oriented whale cruise that offers great views and lively whale action. Book early, whale season is popular!
2. From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour
For around $114, the Sunset Sail hits the mark for a romantic, picture-perfect evening. This deluxe cruise departs from Ma’alaea Harbor, where you can relax on the open deck, trampoline, or covered seating. As the sun dips below the horizon, you’ll sip on tropical drinks and enjoy cold hors d’oeuvres, making the experience feel truly special. Wildlife sightings like dolphins and seabirds add to the magic, and the gentle breeze enhances the romantic atmosphere. The boat’s spacious design ensures comfort, and the 4.8-star reviews reflect high satisfaction among couples and solo travelers alike.
Bottom line: Ideal for couples seeking a relaxed, romantic sunset with light refreshments and stellar views—an experience to cherish.
3. Maui Luxury Snorkeling Molokini aboard Air Conditioned Yacht Elua
The Air Conditioned Yacht Elua stands out as Maui’s only luxury yacht dedicated to snorkeling tours, rated a perfect 5.0 with glowing reviews. This 5-hour tour takes you to the crystal waters of Molokini Crater—an ancient volcanic caldera teeming with marine life—and Turtle Town, where you can swim alongside Hawaiian green sea turtles. The yacht offers plush seating, modern interiors, and clean restrooms, making it a true floating oasis. Included are breakfast, a BBQ lunch, and drinks, all served onboard. The crew’s 40+ years of experience shines through as they share their knowledge while ensuring comfort and safety.
Guests praise the quality of food, the boat’s luxury, and the chance to see turtles up close. This tour is best suited for those looking for a luxurious, all-inclusive snorkeling experience.
Bottom line: A high-end, all-day adventure perfect for snorkelers who appreciate comfort and top-notch amenities.
4. Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch
This 5-hour sailing trip combines snorkeling, wildlife watching, and scenic coastline views. Starting from Ma’alaea, the luxurious catamaran explores West Maui’s reefs, with special spots selected for their clarity and marine life. During whale season, you might see humpbacks breaching close to the boat. The included continental breakfast and deli lunch make it easy to relax and focus on the surroundings. An open bar with local beer, white wine, and island cocktails further enhances the experience.
Rated 4.8, this tour offers a good balance of activity and relaxation, making it ideal for families or groups wanting a full day on the water without sacrificing comfort.
Bottom line: Great for snorkelers and wildlife lovers, this trip offers a mix of adventure and scenic beauty at a reasonable price.
5. Maui: Snorkeling and Sailing Adventure with Buffet Lunch
This 4-hour sailing adventure is perfect for those who want a combination of snorkeling, sailing, and good food. You’ll glide along Maui’s west coast, where the warm waters are teeming with fish and sea turtles. The spacious boat features trampolines for sunbathing and indoor space for relaxing. The included hot buffet lunch and open bar make this a well-rounded day at sea. In winter, there’s a chance to see humpback whales, adding to the excitement.
Rated 4.8, it’s a favorite for travelers seeking a lively, social atmosphere with plenty of marine encounters.
Bottom line: Excellent value, especially if you love snorkeling combined with a hot meal and drinks.
6. Hawaiian Canoe Sailing Experience in Maui
For an authentic Hawaiian experience, the Hawaiian Canoe Sailing ranks highly. This private outrigger canoe trip along Wailea’s coast takes only about 2 hours but offers a deeply cultural perspective. Learn traditional canoe construction, sailing, and navigation from guides with deep local knowledge. You might see sea turtles, reef fish, and even humpback whales in season. The small size allows for a personalized outing, and snorkeling gear is included.
Rated 5.0, guests love the hands-on experience and the chance to connect with Hawaiian traditions directly. It’s best suited for travelers interested in culture, history, and nature conservation.
Bottom line: A unique, culturally rich, and intimate way to experience Maui’s waters, especially for those wanting a personalized adventure.
7. Maui: Ka’anapali Whale Watching Cruise on Luxury Sailboat
This 2-hour whale watching cruise departs from Ka’anapali Beach on a luxury sailboat, combining naturalist commentary and underwater hydrophone listening. It guarantees whale sightings or you can go again for free—making it a reliable choice for whale season (Dec-April). The tour’s sleek design and attentive service make it a memorable outing for families and couples alike. Snacks are provided, and the naturalist’s narration adds educational value.
Rated 4.8, this tour is great for those who want a short, comfortable, yet informative whale watch.
Bottom line: An excellent choice for whale lovers wanting a reliable, upscale experience with guaranteed sightings.
8. Luxury Catamaran Whale Watch
Rated a perfect 5.0, this Luxury Whale Watch from West Maui offers a premium experience. The spacious catamaran is equipped with a hydrophone to listen to whale songs, and a marine naturalist narrates the whales’ behavior. The boat’s modern design and relaxing amenities make it ideal for travelers who want comfort and a high likelihood of seeing humpbacks.
Guests mention the attentive crew and gorgeous views, making this a top pick for whale season. It’s best for those looking for a luxury yet educational outing.
Bottom line: An upscale, immersive whale-watching trip that combines comfort with excellent chances of seeing Maui’s giants.
9. Turtles & Tacos Luxury Catamaran Snorkel
This 3-hour snorkel adventure combines marine life, cultural food, and fun. Anchored at a prime snorkeling spot, you’ll see abundant fish and Hawaiian green sea turtles. The crew is friendly and attentive, offering delicious tacos and an open bar. The vessel is roomy with shaded areas, making it suitable for families or groups who want comfort and a lively atmosphere.
Rated 5.0, travelers rave about the crew’s hospitality, the quality of food, and the snorkeling experience. It’s perfect for those who want a relaxed, immersive day on the water.
Bottom line: A lively, culturally flavored snorkeling trip with great food and friendly service.
10. Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
This adults-only sunset cruise offers an elegant evening with dinner crafted from local ingredients. Glide over the water, taking in the stunning sunset views from the spacious deck. You can sip tropical drinks, listen to soft music, and enjoy a gourmet meal. Rated a perfect 5.0, it’s ideal for romantic couples or those celebrating special occasions.
Guests describe this as a “top-notch cruise,” noting the attentive crew and beautiful scenery. It’s best suited for travelers seeking a luxurious, intimate experience.
Bottom line: The perfect sunset dinner for couples and adults wanting a refined, scenic evening.
11. Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
This intimate sunset sail hosts a maximum of 40 passengers, providing a personalized experience. The boat’s handcrafted design and friendly crew make it a favorite among those seeking a less crowded, more relaxed cruise. Look for dolphins, whales (in season), and enjoy Hawaiian snacks and drinks onboard.
Rated 4.5, travelers appreciate the friendly atmosphere and the opportunity to get closer to nature in a small-group setting.
Bottom line: An ideal choice for travelers wanting a quiet, authentic Maui sunset with personalized attention.
12. Maui: Ma’alaea Catamaran Sunset Sail with Appetizers
This 2-hour sunset cruise from Ma’alaea features premium appetizers and refreshing drinks in a comfortable environment. The boat’s open deck and trampoline offer great views of the sunset, while the onboard bar keeps your drinks topped off. Its relaxed pace and scenic route make it a favorite for couples and small groups.
Rated 4.8, it’s a solid choice for those wanting a combination of good food, drinks, and scenery.
Bottom line: A relaxed, appetizing way to enjoy Maui’s sunset with friends or loved ones.
13. From Maalaea: Whale Watching Catamaran Cruise with Drinks
This 2-hour whale-watching cruise is very accessible, with a focus on up-close whale encounters and informative narration by a marine biologist. The small catamaran allows for an intimate experience, and you can sip drinks while watching whales splash and breach. The tour’s affordability (just $69) makes it great for budget-conscious travelers.
Rated 4.7, it’s ideal for those who want a short, personal, and educational whale adventure.
Bottom line: Budget-friendly, intimate whale watching for those eager for personal sightings and learning.
14. Maui: Luxury Catamaran Whale Watch & Sail
This luxury whale watch offers a premium experience with guaranteed sightings, hydrophone listening, and naturalist narration. The panoramic decks and shaded areas ensure comfort, and the focus on humpback behavior makes it ideal for whale enthusiasts. The reviews emphasize the “unforgettable” nature of this trip, especially during whale season.
Bottom line: For travelers seeking a high-end, educational, and reliable whale watching tour, this is an excellent choice.
15. Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks
This 2-hour afternoon sail combines cultural storytelling with scenic cruising. The onboard host shares Hawaiian legends and history, complemented by handcrafted cocktails and local snacks. It’s a laid-back way to learn about Maui’s traditions while enjoying the ocean view from a luxury 65’ catamaran.
Rated 5.0, travelers appreciate the blend of culture and relaxation.
Bottom line: An engaging, culturally rich way to experience Maui’s coast in a comfortable setting.
$159.00 per person
16. Maui: Afternoon Catamaran Sail w/ Local Culture & Cocktails
Similar to the previous, this afternoon cruise offers storytelling, local spirits, and beautiful scenery. Although ratings are not available, the focus on Hawaiian legends and ocean views makes it appealing for those wanting a cultural experience combined with leisure.
Bottom line: For those interested in local stories and island flavors, this sail offers a relaxed, immersive afternoon.
$159 per person
How to Choose Your Maui Sailing Experience
When selecting a tour, consider your budget, interests, and the experience you want. If whale watching is your main goal, the Ma’alaea Harbor Whale Watching Tour offers a reliable, budget-friendly option. For a romantic sunset, the Sunset Sail or Royal Sunset Dinner Sail provide luxurious atmospheres. For those wanting top-tier snorkeling, the Air Conditioned Yacht Elua stands out with its high ratings and comfort.
Also, think about seasonality—many tours focus on whale viewing from December to April, while snorkeling and sunset sails are available year-round. Booking early is advisable during peak seasons to secure your preferred date.
Final Thoughts
Maui offers a stunning array of sailing experiences—from whale watching and snorkeling to romantic sunset cruises and cultural outings. For a family-friendly adventure, the whale watching tours provide close encounters with humpbacks. Couples craving romance might prefer the elegant Sunset Dinner Sail. For those seeking a luxurious day on the water, the Yacht Elua offers top comfort and superb marine encounters.
Whatever your preference, Maui’s calm waters and spectacular scenery make it a sailing capital you shouldn’t miss. Remember to book early, especially if visiting during the busy winter whale season or summer months, and prepare for unforgettable ocean adventures.