Top 12 Sailing Trips on Maui

1.Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

★★★★★★★★★★4.6 · 979 reviews · 2 hours · from $49Our pick

Cruise from Ma’alaea Harbor aboard Quicksilver’s double-deck power catamaran. Your captain and crew explain whale behavior while hydrophones bring their songs onboard. Look for calves, spy-hops, tail slaps, and breaches, with shaded seating, restrooms, and drinks included.

“The staff and Captain were extremely pleasant, informative and competent. The boat was very safe and comfortable with both open and under awning seating, bathroom and some snacks/drinks for sale. Plus they shared water during the sail. We saw whales immediately on leaving the harbor and the Captain did a great job of safely following blows and sightings. We saw breeches, flukes and fin waves, mommas and a baby. Additionally, the company worked with my husband and I when we had to reschedule due to some weather issues that affected our original date. Very gracious and accommodating. I would definitely recommend and definitely book this cruise again!!”

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2.Molokini and Turtles Luxury Yacht Snorkel

★★★★★★★★★★5.0 · 477 reviews · 5 hours (approx.) · from $263Top rated

Board Pride of Maui’s modern, air-conditioned yacht at Maalaea Harbor for a five-hour snorkel trip to Molokini and Turtle Town. Captain Justin and his crew provide gear, breakfast, an onboard barbecue lunch, warm showers, and drinks after snorkeling. The route depends on weather and sea conditions.

“This was from beginning to end an amazing experience. The captain and crew early on guided us gently with safety and put all uneasiness quickly to rest. Really enjoyed the luxury yacht and all the amenities including such pristine and clean conditions. A very super friendly crew with knowledge and also genuine niceness towards us. We got to do everything listed but in a non hurried and enjoyable way. This outfitter is very lucky to have such an outstanding crew representing them. There are not enough words to share how pleased we were”

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3.‘Alihilani Sunset Sail Catamaran Tour

★★★★★★★★★★4.8 · 348 reviews · from $114

Sail Maui’s Alihilani carries you through the Auau Channel from Maalaea Harbor for a two-hour sunset sail. Expect open-deck seating, trampoline nets, drinks, cold hors d’oeuvres, English-speaking crew, and possible dolphins or humpback whales from December through March.

“Absolutely amazing experience! Jamie, Nicholas, and Steven were a fantastic crew, and we would recommend this to anyone coming to Maui!”

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4.West Maui Snorkeling & Sailing Day Trip with Lunch

★★★★★★★★★★4.8 · 210 reviews · from $200

Sail from Maalaea Harbor toward Lanai aboard a comfortable catamaran, with snorkel gear, breakfast, a buffet lunch, reef-safe sunscreen, and an open bar included. Captain Patrick, Captain Ron, James, Dan, and other crew members are noted for clear safety briefings and friendly help, while conditions decide the final snorkel stop.

“We had a great experience including my husband and boys aged 15 and 17. We are very happy to be able to participate in this catamaran trip, where we were snorkeling on Lanai and seeing dolphin herds and whales. Thanks to the captain and crew members.”

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5.Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea

★★★★★★★★★★5.0 · 194 reviews · 2 hours 30 minutes (approx.) · from $85

Spend about 2½ hours aboard Winona, a Hawaiian-built catamaran departing Maalaea. From December through March, watch humpback whales with Capt. Sam, Spencer, Meghan, or the crew, listen through underwater hydrophones, and enjoy snacks, drinks, music, and views of West Maui, Molokai, and Lanai.

“Excellent trip, good information, good weather, good drinks, good snacks, remember sun screen and fun friends to bring with you”

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6.Snorkeling and Sailing Adventure with Buffet Lunch

★★★★★★★★★★4.8 · 115 reviews · from $172

Spend four hours aboard Gemini Sailing Charters off West Maui, snorkeling at Honolua Bay or another sheltered site, then enjoying a hot buffet and open bar. The crew provides instruction, quality gear, prescription masks, and kid-size equipment. Winter trips look for humpback whales, while summer sails may spot spinner dolphins.

“Great crew, friendly and attentive. Loved that they had gluten free options.”

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7.Turtles & Tacos Luxury Catamaran Snorkel

★★★★★★★★★★4.5 · 103 reviews · 3 hours (approx.) · from $199

Sail from Maalaea Harbor on Alii Nui’s spacious catamaran for about three hours of turtle snorkeling, tacos, margaritas, and local beer. The crew handles the gear and safety briefing, while onboard photographers capture above and below-water moments for purchase. Captain Bre, Josh, and Tim have all earned warm praise.

“One of the best days I’ve had in Maui!! Fantastic attentive staff, open bar with delicious island cocktails, snorkel gear, mineral sunscreen and towels provided, great tacos. And…swimming with turtles was just amazing!! Beautiful sail to a spectacular snorkel spot. I would do this again for sure!”

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8.Ka’anapali Whale Watching Cruise on Luxury Sailboat

★★★★★★★★★★4.8 · 89 reviews · from $108

Leave Ka’anapali Beach on a spacious Teralani catamaran with a marine naturalist, live whale songs, breakfast snacks, Kona coffee, tropical juices, soft drinks, and an open bar. You may hear crew members such as Bama, Bri, Sammy, Tylie, or Julia share the work of finding Maui’s humpback whales.

“We had a great time whale watching! The crew was knowledgeable and we saw lots of whales. The boat was comfortable with easy access and there were snacks provided. I would recommend this whale tour.”

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9.Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

★★★★★★★★★★4.5 · 87 reviews · 2 hours (approx.) · from $119

Board Winona in Maalaea at 4:30 pm for a roughly two-hour sunset sail along Maui’s coast. You’ll get Hawaiian snacks, local beer, seltzers, cocktails, soft drinks, music, and two restrooms. From December through April, keep watch for humpback whales.

“It was fun for rverone, they allowed you to walk all over the sail boat barefoot, it was a beautiful sunset, we were lucky and seen whales and dolphins”

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10.Luxury Catamaran Whale Watch

★★★★★★★★★★5.0 · 66 reviews · 2 hours (approx.) · from $119

Sail from Maalaea Harbor aboard a comfortable catamaran for two hours of West Maui whale watching. A marine naturalist explains humpback behavior, a hydrophone lets you hear whalesong, and the bar serves premium drinks. Crew members may include Ryan, Logan, and Johanna.

“This is a super fun booze cruise style whale watching. The captian and crew are fantastic. The bartender mixes very tasty cocktails”

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11.Hawaiian Canoe Sailing Experience in Maui

★★★★★★★★★★4.5 · 59 reviews · 2 hours (approx.)

You’ll sail the Wailea coast in a private 32-foot Hawaiian outrigger canoe with a guide such as Sage, Brody, or Kira. Expect island stories, sea turtles, reef fish, and a chance to snorkel at quiet spots. Groups are limited to six, with gear and water included.

“Vine’s Hawaiian lore and singing were amazing. Turtles and snorkeling was great too! Sailing on the canoe and being in a quiet setting on the water was so peaceful.”

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12.Sunset Dinner Catamaran Cruise With Drinks

★★★★★★★★★★4.8 · 55 reviews · 2h 30m · from $153

Board Sea Maui’s 65-foot beach-loading catamaran from Kaanapali Beach for 2.5 hours of sunset views, dinner, and an open bar. Crew members such as Carrie, Luke, and Quinn have helped make this a warm, social cruise, with possible whale and dolphin sightings in season.

“Fantastic. Carrie, Luke, and Quinn were top notch and friendly.”

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