Top Maui Sailing Tours

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite sphere of color, surrounded by the islands of Maui, Lāna‘i, and Moloka‘i. Enjoy the best of performance sailing in Maui on our Conser 47' performance sailing catamaran. With spacious trampolines, shaded cabin seating, and a professional crew, this is the ultimate Maui sunset cruise. We invite you to relax, sip a cocktail, and watch the sky transform over the Pacific. Your sunset sail includes local appetizers and a full open bar with sparkling wine, white wine, and local beer. Experience the magic of Maui. This tour is perfect for all ages, with a limited capacity of 25 passengers ensuring a cozy atmosphere.

(103)

from $117

Paragon Lahaina Sunset Sail

Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

4.3

(6)

from $102

Likely to Sell Out

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

(19)

from $203

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buffet lunch is served and our complimentary bar is open after you are done snorkeling. We hoist the sails and return to Ka'anapali Beach while viewing the amazing coastline of Maui. Note: We are a beach loading catamaran and you might get wet up to your knees boarding.

5.0

(36)

from $216

Snorkel Sail Adventure off Ka'anapali Beach, Maui

4 hoursFree Cancellation

Day's End Cocktail Sunset Sail

(39)

from $192

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(80)

from $159

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

(116)

from $309

Experience an unforgettable catamaran cruise in Maui. Sail on a 65-foot boat along the Pacific Ocean where the professional crew takes care of everything—including photos (fee to purchase). Snorkel at a reef with guaranteed sea turtles, and after enjoy a taco lunch on the boat with margaritas and beer. Relax on the cruise back to Maui—look out for whales in season and beautiful views all year long.

4.4

(32)

from $142

Turtles & Tacos Luxury Catamaran Snorkel

3 hoursFree Cancellation

Experience the magic of a Molokini and Turtle Town on this catamaran snorkeling adventure, where you can swim inside a sunken volcano surrounded by vibrant marine life. Start your day cruising to Molokini Crater, then dive into its pristine waters to explore the coral reef teeming with colorful fish. Depending on the conditions, your next stop may be Turtle Town or Coral Gardens, where you’ll have the chance to search for sea turtles and create lifelong memories in Maui’s dazzling underwater world.

(124)

from $199

Maui Snorkeling Adventure to Molokini and Turtle Town

5 hours 30 minutesFree Cancellation

4.4

(2,325)

from $160

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Snorkeling in Molokini Crater is a frequent bucket-list experience for Hawaii visitors. Here in this submerged volcano off Maui’s southern coastline, more than 250 species of fish inhabit a world-class reef. Experience water so exceptionally clear you can see down 75 feet (23 meters), and swim with schools of tropical fish. This half-day tour from Maalaea Harbor takes care of all the logistics for you.

(50)

from $289

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Sunset Sail from Ma'alaea Harbor in Maui

(831)

from $203

Coral Gardens Coastal Snorkel & Sail

4.6

(217)

from $138

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kaho‘olawe. Guests can relax on trampolines or in shaded seating while enjoying locally-inspired appetizers and a selection of beverages, including cocktails, beer, and wine. From December to March, keep an eye out for majestic humpback whales as they migrate, often providing unforgettable sightings during the sail. - Enjoy a scenic 2-hour sunset sail aboard the 55-foot Akialoa catamaran. - Indulge in a selection of local appetizers and an open bar of drinks. - Limited to 48 passengers, ensuring a cozy and intimate experience. - Spot migrating humpback whales from December to March for a unique wildlife encounter.

(39)

from $122

Akialoa Mā’alaea Sunset Sail

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

(13)

from $108

Hawaii has a rich history of pineapple farming and this tour puts it all into perspective. Head to the historic plantation town of Hali'imaile to walk around a working pineapple field. Learn about pineapple growing cycles and cultivation from your guide and sample the fruit at its different stages. Best of all, each guest receives an 'airport-ready,' fresh pineapple at the end of the tour.

(217)

from $200

Maui Pineapple Farm Tour in Haliimaile

1 hour 30 minutesFree Cancellation

Leave the chaos of the mainland behind when you embark on this sunset cruise in Maui. An exclusive experience for up to six guests, this trip takes you through multiple natural landscapes, from the Molokini Crater to the Kahalewai Mountains and Lanai Island. Take in views of the coastlines and island volcanoes and relax as you watch the sun setting with your chosen group. You even have the chance to catch a glimpse of the green flash phenomenon.

(2,961)

from $99

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Enjoy a ‘front-row seat’ for Maui’s epic sunset accompanied by cocktails and snacks during this sailing cruise from Ka’anapali Beach. Enjoy views of nearby Lanai, Molokai, and Kahoolawe from your boat, drink and food in hand, as the Hawaiian sky puts on its nightly display. Plus, keep your eyes peeled for local marine life, including whales from mid-December to mid-April. Snacks, unlimited alcoholic drinks, and non-alcoholic beverages are all included.

(18)

from $279

Maui: Original Sunset Cruise with Open Bar from Ka’anapali Beach

Maui Premium Sunset Dinner Cruise from Ka’anapali Beach

(1,466)

from $127

Partake in a time-honored Hawaiian tradition during this private, outrigger canoe sailing experience along Maui's stunning Wailea coast. Learn about Hawaiian culture and history, including the ancient art of canoe construction, sailing, and navigation. Launch the boat from the beach using traditional methods. Spot sea turtles, reef fish, and seasonal humpback whales, with snorkeling equipment provided.

(949)

from $166

Hawaiian Canoe Sailing Experience in Maui

Dive beneath the waves to explore Maui’s colorful fish, vibrant coral, and graceful sea turtles on this 6-hour snorkel excursion to Honolua Bay. Experience one of the island’s most popular snorkel spots with the help of a certified marine naturalist before heading to a second site for more underwater adventure. An included breakfast, barbecue lunch, and periodic sightings of wild dolphins help add to the experience.

(60)

from $179

Honolua Snorkel Sail from Lahaina

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. Our warm, relatively shallow and protected waters make an ideal location for the humpbacks to mate and give birth to their calves. These whales are known for their acrobatics, and are often seen fully breaching out of the ocean! This charter is a seasonal opportunity, available from December 15th to March 31st annually.

(60)

from $199

Likely to Sell Out

Afternoon Sail With the Whales from Lahaina Harbor

Midday Whale Watch: Mā’alaea Harbor

5.0

(1)

from $100

Likely to Sell Out

'Alihilani Lahaina Sunset Sail

(104)

from $100

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Top Attractions in Maui

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Road to Hana from the above, Maui, Hawaii

Attractions

What are people saying about Maui

Linda_O, May 2026

Sailed out of the port in...

Sailed out of the port in Lahania. The crew was extremely grateful for everyone who boarded. The crew was very attentive to everyone. The trip was wonderful sailing down the coast of Maui for an hour one way then back with an Open Bar and tasty h'devours. The sunset was beautiful.

Turtles & Tacos Luxury Catamaran Snorkel

kurtweishaar, May 2026

Book It. You Won’t Regret It

We’ve done plenty of boat tours over the years, but the Ali’i Nui catamaran experience was on another level entirely. From the moment we stepped aboard, Captain Timothy and his crew: Ian, Lauren, and Emi, made us feel completely taken care of. They were professional, warm, and clearly love what they do. The energy on that boat was unmatched. The snorkeling was incredible. We were swimming alongside sea turtles within minutes of getting in the water. It really does live up to the guarantee. The reef was stunning and the crew made sure everyone felt comfortable and safe, whether it was your first time snorkeling or you were a seasoned pro. The tacos and margaritas on the way back were the perfect way to celebrate the experience. Fresh, delicious, and served with a smile by the crew. And a huge shoutout to Leo, the photographer, who captured moments we never could have gotten on our own. His shots were genuinely stunning and made great memories to bring home. The catamaran itself is gorgeous, spacious, smooth, and exactly what you want out on the Pacific. If you’re visiting Maui and debating whether to book this, stop debating. Just do it. Timothy and his incredible team will take care of everything else. 🐢🌊

Snorkel Sail Adventure off Ka'anapali Beach, Maui

kelsey_d, Apr 2026

Great snorkeling

We had such a great experience on this snorkel trip in Maui! The crew was super friendly, knowledgeable, and made everything feel easy and fun from start to finish. We didn’t spot any turtles during our trip, but they went out of their way to give us recommendations on other spots where we could go check them out, which we really appreciated. Overall, such a well-run excursion with an awesome team—we’d definitely recommend it to anyone visiting Maui!

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

Andrew_J, Apr 2026

Enjoyable time with Whales!

Enjoyable sunset cruise! Saw several whales and a turtle at the end. The snacks were pretty good and crew was very friendly. Parking at Outrigger was great with the validation. They dropped us at Whalers Village which is just a quick walk back to the Outrigger. We changed our cruise from Wed to Mon due to expected weather and process was easy.

Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

Danielle_M, Jan 2026

Great day on the water

We had a great day aboard the Teralani 5. Our crew (Joel, Josh, Quentin, and Captain Julia) made it a special day on the water with humor, great food, plentiful drinks, and information about the wildlife we saw. We had two great snorkel stops, and saw five turtles chilling together at our second stop. One turtle bobbed its head above water where we were swimming — a truly cool experience. We also got to see a mama and baby whale breaching on our way back. Highly recommend this snorkeling trip!

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

shirali_k, Dec 2025

This was a great...

This was a great experience. We saw at least 50 whales and had a magical experience snorkeling in the Molokini crater. The crew (AJ, Brandon, Jeff) were amazing and helped make sure that all of us were comfortable. Breakfast, lunch and coffee was provided, and we overall ended up having a very comfortable luxury adventure experience. I strongly recommend this for all travelers!

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Rachael_P, Nov 2025

Excellent and worth every penny!

What an amazing luxurious catamaran! Crew was amazing and top notch. From beginning to end, the entire experience was superb! Cannot recommend enough! Adult only was perfect. Drinks were rolling. 5 course meal was well timed. Food was to be expected for a boat trip- but worth it! Nothing beats a sunset view from the water. Best sunset we experienced during our entire trip!

Day's End Cocktail Sunset Sail

Lauren_C, Sep 2025

Memorable sunset sail between Maui, Lanai and Molokai

The Aliʻi Nui catamaran sunset sail was a highlight of our trip. Captain Jordan and her almost-all-female crew were not only warm and cheerful but also incredibly hard-working and skilled—raising sails and serving with seamless ease. The meal felt authentically local with pulled pork sliders and pineapple slaw, the drinks were generous and flowing, and the whole experience struck the perfect balance of relaxation and adventure. Notes: Plenty of inexpensive parking on the oceanside of the harbor. Interior and exterior seating options. Great professional photographer onboard - consider dressing accordingly if you intend to purchase (worth it!).

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Anne_J, Jun 2025

Wonderful Personal Experience!

We LOVED our experience, it was everything we hoped for. John and Walker were excellent. They were so engaging with us and our son with autism, who can take some time to warm up. We chose this boat because it was for small groups, large groups overwhelm our son. It was perfect! We had the most amazing view of the sunset and relaxed the evening away. Our sons favorite part was fishing with Walker and going fast! We really had a great time. This felt very personal unlike other tours where you are just one of many. HIGHLY recommend!!! Thanks guys!