Plain-speaking travelers visiting Maui have excellent sailing options worth every dollar. For the best value, book a whale watching expedition from Maalaea Harbor on the Winona Catamaran, where expert biologists share fascinating details about marine life. The sunset cruises, particularly aboard luxury catamarans, serve quality meals with premium drinks in a classy yet relaxed setting. I’m especially fond of the traditional Hawaiian canoe experiences – they’re intimate and culturally rich. Private sailing charters, while pricier, give you the freedom to snorkel and explore at your own pace.
Let’s check out the stand-out sailing tours that deliver memorable experiences on Maui’s waters.
Key Points
- Luxury Catamaran Whale Watch offers an intimate and educational experience, accommodating up to 65 travelers with an open premium bar and high-quality amenities.
- Sunset dinner cruises like the Luxury Royal Catamaran Sunset Dinner Cruise provide a serene and upscale experience, featuring a 3-course buffet and premium bar service.
- The Hawaiian Canoe Sailing Experience offers a unique culture with a small group size, snorkeling opportunities, and knowledgeable guides.
- Private sailing charters, such as the 5.0-rated Full Day Private Catamaran Sailing and Snorkeling Charter, provide personalized experiences with snacks, meals, and equipment.
- Snorkeling and sailing adventures, like the Maalaea: West Maui Snorkeling & Sailing Day Trip, offer a well-rounded experience with breakfast, lunch, and an open bar.
From Maalaea Harbor: Whale Watching Tours Aboard Winona Catamaran
From the picturesque Maalaea Harbor, travelers can embark on captivating whale watching tours aboard the Winona Catamaran. The approximately 1.5-hour excursions offer the chance to spot majestic humpback whales, accompanied by insightful commentary from an onboard biologist.
With a maximum of 40 guests, the small-group tours provide an intimate and memorable experience. Amenities include light snacks, beverages, underwater hydrophones to hear whale songs, and island-style music.
While the tours aren’t wheelchair-accessible, they’re suitable for travelers with moderate fitness. With a 95% recommendation rate and a Badge of Excellence, these Maui whale watching tours deliver an engaging, enjoyable sail for nature enthusiasts.
Read our full review: From Maalaea Harbor: Whale Watching Tours Aboard Winona Catamaran Review
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Maalaea Harbor: Whale Watching Catamaran Cruise
For those seeking an unforgettable whale watching experience in Maui, the Maalaea Harbor: Whale Watching Catamaran Cruise offers a captivating 2-hour adventure.
Priced from $49.95 per person, this popular tour is likely to sell out, so booking early is advised. Guests will cruise the Maui coastline aboard a comfortable double-deck power catamaran, guided by a knowledgeable crew who provide live narration.
Highlights include witnessing whale behaviors and listening to their songs via underwater hydrophones.
With spacious seating, free water and soft drinks, and an overall 4.7/5 rating, this whale watching excursion delivers an educational and breathtaking experience.
Read our full review: Maalaea Harbor: Whale Watching Catamaran Cruise Review
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Hawaiian Canoe Sailing Experience in Maui
Nestled along the picturesque Makena coastline, the Hawaiian Canoe Sailing Experience in Maui invites travelers to embark on an authentic cultural journey.
This highly-rated activity, operated by Hawaiian Sailing Canoe Adventures, offers an intimate group experience for up to 6 participants. Priced from $179 per person, the tour provides snorkeling equipment, bottled water, and outdoor amenities.
Travelers praise the knowledgeable guides, such as Sage and Brody, and highlight the incredible sightings of turtles, dolphins, and excellent snorkeling conditions.
While not wheelchair accessible, the experience requires moderate physical fitness. Families and first-time snorkelers will find this a delightful adventure, especially when visited early in the day for calmer winds.
Read our full review: Hawaiian Canoe Sailing Experience in Maui Review
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From Maalaea: Whale Watching Catamaran Cruise With Drinks
Departing from the picturesque harbor of Maalaea, the From Maalaea: Whale Watching Catamaran Cruise With Drinks invites guests to embark on a captivating 2-hour adventure.
Priced from $115 per person, the cruise offers the chance to observe humpback whales, hear insights from a marine biologist, and listen to whale songs via underwater hydrophones.
Aboard the small, charming Hawaiian catamaran “Winona,” passengers can enjoy refreshing beverages and island-style music.
With free cancellation up to 24 hours in advance and the option to pay later, this experience provides excellent value and flexibility.
Guests have consistently praised the transportation and overall value, making this whale watching cruise a must-do activity in Maui.
Read our full review: From Maalaea: Whale Watching Catamaran Cruise With Drinks Review
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Luxury Royal Catamaran Sunset Dinner Cruise in Maui
The Luxury Royal Catamaran Sunset Dinner Cruise in Maui invites visitors to embark on an enchanting evening voyage.
With a 5.0 overall rating based on over 30 reviews, this cruise boasts a 97% recommendation rate and a Badge of Excellence. Guests will enjoy a 3-course buffet dinner, a full bar with premium brands, and exceptional crew service, all while taking in the stunning sunset views from the well-maintained catamaran.
While the cruise isn’t wheelchair accessible, it offers accessibility via public transportation and crew assistance for boarding. The only potential limitation is the 2-4 steps down into the cabin for the restrooms.
Read our full review: Luxury Royal Catamaran Sunset Dinner Cruise in Maui Review
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Maui: Alii Nui Whale Watch & Catamaran Sail
Exploring the waters of Maui, the Alii Nui Whale Watch & Catamaran Sail offers an immersive adventure for travelers.
The 2-hour excursion sails through warm, shallow waters, providing opportunities to observe humpback whales in their natural habitat. Guests can enjoy gourmet appetizers and a premium bar while taking in the views from the spacious cabin and deck areas.
A marine naturalist on board shares facts about the whales, and a hydrophone allows for listening to their songs.
With a departure from Maalaea Harbor, this whale-watching experience operates seven days a week from mid-December to the whales’ departure.
Read our full review: Maui: Alii Nui Whale Watch & Catamaran Sail Review
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Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
Travelers seeking a tranquil sunset sail can embark on a charming Hawaiian catamaran adventure from Maalaea Harbor. The locally built vessel, Winona, offers Aloha hospitality to a maximum of 40 passengers, ensuring personalized attention.
The 42 reviews boast a 93% traveler recommendation, praising the friendly crew, beautiful views, and relaxing atmosphere. Passengers can enjoy non-alcoholic beverages, an open bar, and Hawaiian snacks as they witness the sunset and potentially spot whales.
While the experience isn’t recommended for those with mobility issues or serious medical conditions, it presents an opportunity to soak in the island’s beauty from the comfort of a small, intimate catamaran.
Priced from $119 per person, this sunset sail is a must-try for visitors to Maui.
Read our full review: Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor Review
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Maui: Alii Nui Luxury Catamaran Makani Sunset Sail
Soaring along the scenic Maui coastline, the Alii Nui Luxury Catamaran Makani Sunset Sail offers an unparalleled experience for discerning travelers.
This 2-hour excursion, priced from $169.95 per person, departs from Slip#56 at Maalaea Harbor. Guests will enjoy a delightful culinary experience, with upscale hot and cold appetizers and a full premium bar.
The catamaran provides comfortable cabin seating or spacious deck dining, and two oversized clean bathrooms are available. Guests must be 18 or older, and those over 21 will need a valid government-issued ID to consume alcohol.
With free cancellation up to 24 hours in advance, this sunset sail is a must-try for those seeking a luxurious nautical adventure in Maui.
Read our full review: Maui: Alii Nui Luxury Catamaran Makani Sunset Sail Review
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Catamaran Private Morning Snorkel And Sail in Maui
This private morning excursion aboard a spacious catamaran offers an intimate and immersive exploration of Maui’s captivating marine life.
Guests are provided with all necessary snorkeling gear and guided by an experienced in-water reef tour guide, ensuring a safe and enriching experience.
The tour includes a light breakfast of local fruits and baked goods, as well as a deli-style lunch served onboard after snorkeling.
While alcoholic beverages aren’t included, guests may bring their own.
With a maximum group size of your party, this tour provides a personalized and flexible adventure to enjoy Maui’s beautiful waters and vibrant underwater world.
Read our full review: Catamaran Private Morning Snorkel And Sail in Maui Review
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Maui: Snorkeling and Sailing Adventure With Buffet Lunch
Maui’s west coast offers an unparalleled snorkeling and sailing adventure, providing visitors the opportunity to enjoy the island’s captivating marine ecosystem.
For $172.01 per person, this 4-hour tour allows you to snorkel in the warm waters of Honolua Bay Marine Reserve, renowned for its abundant sea life, including tropical fish and endangered Hawaiian green sea turtles.
The tour also includes a hot buffet lunch, an open bar, and the chance to spot seasonal highlights like spinner dolphins and humpback whales.
With quality snorkeling gear and professional photography available, this excursion delivers an unforgettable experience amid Maui’s stunning natural beauty.
Read our full review: Maui: Snorkeling and Sailing Adventure With Buffet Lunch Review
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Mauis Best Private Sunset Sailing Charter
Nestled along Maui’s picturesque western coastline, Maui’s Best Private Sunset Sailing Charter offers visitors an enchanting opportunity to experience the island’s breathtaking natural beauty from the comfort of a private yacht.
This highly-rated tour boasts a 5.0 overall rating based on 9 reviews, providing guests with a charcuterie board, non-alcoholic beverages, and the option to bring their own alcohol.
Departing from Slip #83 near the public bathrooms and coast guard station, the tour returns to the same meeting point after a leisurely sail.
With accommodations for all ages, including infants, this private sunset sailing charter is an ideal way to witness Maui’s stunning landscapes and vibrant sunsets.
Read our full review: Mauis Best Private Sunset Sailing Charter Review
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Maalaea: West Maui Snorkeling & Sailing Day Trip With Lunch
One of Maui’s premier snorkeling and sailing adventures, the Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch offers visitors an unforgettable opportunity to explore the island’s stunning underwater world.
Priced from $200 per person, this 5-hour excursion departs from Maalaea Harbor, providing guests with snorkel gear, a continental breakfast, deli-style lunch, and an open bar.
Sailing along the West Maui coastline, participants can snorkel at pristine reefs, spot whales during the season, and observe abundant sea turtles.
With an overall rating of 4.8/5 from 209 reviews, this flexible and well-organized tour delivers exceptional value, knowledgeable guides, and a memorable day on the water.
Read our full review: Maalaea: West Maui Snorkeling & Sailing Day Trip With Lunch Review
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Maui: Maalaea Catamaran Sunset Sail With Appetizers
Although visitors to Maui have a wealth of sailing and sunset cruise options, the Maui: Maalaea Catamaran Sunset Sail with Appetizers offers a unique and memorable experience.
Priced at $145.59 per person, this 2-hour tour allows guests to sail on a comfortable catamaran while enjoying stunning sunset views, premium appetizers, and unlimited refreshments – including three complimentary alcoholic beverages for those 21+.
The experience also features live music, the possibility of whale sightings, and the opportunity to capture beautiful photos.
With an overall rating of 4.7/5 based on 15 reviews, this activity provides a relaxing and enjoyable way to experience Maui’s natural beauty.
Read our full review: Maui: Maalaea Catamaran Sunset Sail With Appetizers Review
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Luxury Catamaran Whale Watch
The Luxury Catamaran Whale Watch offers visitors a unique opportunity to witness the majestic humpback whales that frequent Maui’s waters during the peak winter season.
Departing from Maalaea Harbor, this 5-star rated excursion accommodates up to 65 travelers and features an open premium bar, hot and cold appetizers, and two restrooms.
While not wheelchair accessible, the crew provides assistance for those needing help boarding the vessel.
With a 100% recommendation rate from past guests, this 5.0-rated tour is a must-do activity for those seeking an unforgettable whale watching experience on Maui.
Read our full review: Luxury Catamaran Whale Watch Review
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Maui: Luxury Alii Nui Catamaran Royal Sunset Dinner Sail
Frequently, travelers to Maui seeking an unforgettable dining experience opt for the Luxury Alii Nui Catamaran Royal Sunset Dinner Sail.
This 2.5-hour tour includes a 4-course dinner and drinks while sailing along the picturesque South Maui coastline. With a 4.7 rating, this sunset cruise is a top pick among visitors.
The catamaran offers ample space and stability for an enjoyable sail, while the gourmet meal and stunning ocean views create a truly memorable experience.
Priced at $178.14, this dinner cruise is a popular choice for those looking to elevate their Maui vacation with a touch of luxury and romance under the setting sun.
Read our full review: Maui: Luxury Alii Nui Catamaran Royal Sunset Dinner Sail Review
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Full Day Private Catamaran Sailing and Snorkeling Charter
For those seeking a day of adventure and exploration on the open waters of Maui, the Full Day Private Catamaran Sailing and Snorkeling Charter offers an unparalleled experience.
Rated 5.0 out of 5 stars, this full-day private tour provides guests with a variety of amenities, including a breakfast of local fruits and baked goods, a deli-style lunch, and non-alcoholic beverages.
Snorkeling equipment and a reef tour guide are included, allowing guests to enjoy the vibrant underwater world.
The charter departs from Maalaea Harbor, with a check-in at Slip #83, and returns to the same location at the end of the day.
This private tour is suitable for all ages, though it isn’t wheelchair accessible.
Read our full review: Full Day Private Catamaran Sailing and Snorkeling Charter Review
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Lahaina: Private Sunset Sailing Trip & West Maui Mountains
A private sunset sailing trip from Lahaina offers an unparalleled opportunity to witness the stunning natural beauty of the West Maui Mountains as the sky transforms into a breathtaking canvas of golden hues.
Priced at $1,935.88 per group of up to 6 people, this 3-hour experience allows you to relax on the private sailing yacht while enjoying light appetizers and your own alcoholic beverages.
Throughout the journey, you may spot Hawaiian marine life and celebrate special occasions with family or friends.
The trip includes a knowledgeable captain and crew, non-alcoholic beverages, and gratuity, making it an all-inclusive and exceptional sunset sail.
Read our full review: Lahaina: Private Sunset Sailing Trip & West Maui Mountains Review
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Maui: Private Yacht Snorkeling Tour With Breakfast and Lunch
This private yacht snorkeling tour in Maui offers an unparalleled opportunity to explore the island’s secluded reefs and tropical waters.
Priced at $3,215.47 for up to 6 participants, the 5-hour excursion includes a live English-speaking guide, free cancellation, and complimentary breakfast and lunch.
Guests will board the luxury yacht Kainani, where they’ll snorkel with a trained guide, observe marine life, and enjoy panoramic sea views.
The tour provides snorkeling gear, an onboard shower, and towels, while guests over 21 can bring their own alcohol.
With an impressive 5/5 customer rating, this tour promises a unique and memorable Maui experience.
Read our full review: Maui: Private Yacht Snorkeling Tour With Breakfast and Lunch Review
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Frequently Asked Questions
Can I Bring My Own Food and Drinks on the Cruise?
Most cruise lines allow passengers to bring their own food and drinks on board, though they may have restrictions on items like outside alcoholic beverages. It’s best to check the specific cruise company’s policies before setting sail.
Do the Tours Accommodate Travelers With Disabilities?
Many sailing tours accommodate travelers with disabilities, providing specialized equipment and assistance. It’s best to check with the tour operator in advance to ensure they can meet the needs of any passengers with mobility challenges or other special requirements.
What Is the Maximum Capacity of the Catamarans?
The catamarans typically accommodate up to 49 passengers, though the exact capacity may vary between tour operators. Travelers should check with the specific company they’re booking with to confirm the maximum capacity of the vessels used for their sailing experience.
Are the Tours Suitable for Young Children?
The tours are generally suitable for young children, though parents should consider the child’s age, attention span, and tolerance for being on the water. Most operators welcome families and provide life jackets and other safety gear for kids.
Can I Book a Private Charter for a Special Occasion?
You can book a private charter for a special occasion. Many sailing companies offer customizable charters that accommodate groups of various sizes. This allows you to create a personalized sailing experience tailored to your needs and preferences.
Recap
Maui’s sailing experiences cater to a variety of interests, from whale watching and Hawaiian canoe sailing to luxury sunset dinner cruises. Visitors can choose from group tours or private charters, whether they want to go snorkeling, enjoy the sunset, or simply take in the island’s stunning coastline. With so many options, there’s something for every sailor, making Maui a top destination for unforgettable water-based adventures.