Sailing in Maui

Sailing in Maui comes in three versions in my data: a winter whale watch under sail, a sunset sail from Ma’alaea, and a four-hour snorkel and sail from Ka’anapali. All three are catamarans, all have 4.8 or higher, and the prices run from $113 to $192. For the wider list of cruises, see my guide to boat tours in Maui. Prices are in US dollars, checked in October 2026, and booking links are affiliate links, as I explain on my about page.

My pick for sailing in Maui is the Sail Maui sunset sailing cruise at $124: 4.9 from 142 reviews, a 54-foot catamaran, two hours. If I wanted to snorkel as well, I’d take the Gemini at $192.

Sailing Maui Hawaii

Sailing in Maui, Hawaii means a catamaran in almost every case, because the island’s tour boats are built around the wide, stable hull. The three trips differ in what you do once the sails are up.

Trip	Operator	Price	Duration	Boat	Rating	Cancellation
Ka’anapali Whale Watching Cruise	Teralani Sailing Adventures	$113	2 hours	Luxury sailing catamaran	4.8 (170)	2 days ahead
Sunset Sailing Cruise from Ma’alaea	Sail Maui	$124	2 hours	54-foot sailing catamaran	4.9 (142)	24 hours ahead
Snorkeling and Sailing with Buffet Lunch	Gemini Sailing Charters	$192	4 hours	Sailing catamaran	4.8 (137)	24 hours ahead

The Sail Maui cruise is the one I would call a true sunset sail. The Akialoa departs daily from Ma’alaea Harbor and crosses the inter-island channel with views of Maui, Lanai and Kahoolawe. The listing says to stretch out on the forward trampolines or sit in the shaded cabin, and that the crew raises the sails as the sun sets.

Night tour

Sail Maui

Maui Sunset Sailing Cruise from Ma'alaea Harbor

• ★ 4.9 (142 reviews)
• 2 hours
• Free cancellation

My pick: My pick for sailing: $124, two hours, 54-foot catamaran, open bar, 4.9 from 142 reviews.

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Maui Catamaran Trips

Maui catamaran trips are not all sailing trips, and I’d separate them. The power catamaran on my whale watching page runs on engines, while the three trips here are under sail. The Teralani whale watching cruise is the sailing version of that outing. It costs $113 for two hours and boards from the sand at Ka’anapali Beach, so you skip the harbor. The listing includes breakfast snacks, Kona coffee, tropical juices, soft drinks and Pogmosas, and it has 4.8 from 170 reviews.

Check-in is at the Aqualani Beach Activities Kiosk along the beach walk, oceanside of the Outrigger Ka’anapali Beach Resort. Wheelchair users are listed as unable to join. I’d choose it over the Quicksilver power catamaran when I wanted a quieter boat, and over the small group trip when I wanted to board from the beach. Pick the winter months, because the whales are not here all year.

Teralani Sailing Adventures

Ka'anapali Whale Watching Cruise on Luxury Sailboat

• ★ 4.8 (170 reviews)
• 2 hours
• Free cancellation

My pick: A sailing whale watch from the beach: $113, two hours, 4.8 from 170 reviews, snacks and Pogmosas included.

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Maui Sailing Canoe

A Maui sailing canoe trip is not in my data. Every listing I compared is a catamaran, and I’d rather say that than describe a canoe I can’t price. If a traditional outrigger sailing canoe is what you want, look for a Hawaiian cultural operator and read their listing for group size, season and cost. What the catamarans give you is space: the Sail Maui listing mentions forward trampolines and a shaded cabin, and the Gemini lists an open bar and a hot lunch.

The Gemini is the closest to an adventure on the list. It is a snorkel and sail that costs $192 for four hours, with 4.8 from 137 reviews. The primary snorkel site during most of the year is Honolua Bay Marine Reserve, according to the listing, with Cliff-house, Lanai and Turtle Town in Olowalu as alternatives. The complimentary bar serves Mai Tais, Chardonnay and Maui Brewing beers.

Gemini Sailing Charters

Snorkeling and Sailing Adventure with Buffet Lunch

• ★ 4.8 (137 reviews)
• 4 hours
• Free cancellation

My pick: The sail-and-snorkel option: $192, four hours, hot buffet lunch and bar, 4.8 from 137 reviews.

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Sail Maui Reviews

Sail Maui reviews are worth reading, because the operator has two trips in my full list and both score well. The Akialoa sunset cruise has 4.9 from 142 reviews. The Alihilani sail from Lahaina, which belongs on my sunset cruise page, has 4.8 from 371. Reviewers of the Akialoa call the sail the highlight of their Maui trip and describe a crew that was knowledgeable, friendly and fun.

Both trips cancel for a full refund up to 24 hours ahead, which is tighter than the 2-day window on Teralani. The Akialoa meets at slip 72, toward the far end of the jetty side of Ma’alaea Harbor, and the listing says reef-safe sunscreen is on board.

Maui Boat Trips

Boat trips in Maui under sail share some points. First, the listings give no departure times, so look at the times on the booking page for your date. Second, each includes a bar of some kind, which keeps the price per person higher than a power catamaran. Third, parking is separate, and at the Ka’anapali trips the listing points you to the Outrigger Ka’anapali Beach Resort at 2525 Kaanapali Pkwy, or to the Whalers Village garage for the Gemini.

For stable boats compared by price, my catamaran page includes the Quicksilver, and for the meal trips my dinner cruise page shows the three options. For snorkeling without a sail, see my snorkeling page.

How I’d Choose Sailing in Maui

Sailing in Maui is easy to choose once you ask what you want from the water. For whales in winter, I’d take the Teralani under sail and look at the other whale trips on my whale page if I wanted to compare. For a sunset, the Sail Maui Akialoa. For a half day with a reef stop, the Gemini. Each Maui sailing trip here lasts between two and four hours, and the price rises with the hours: about $57 an hour on the Teralani, $62 on the Sail Maui and $48 on the Gemini, which is the best value per hour if you want to be on the water longer.

Group size matters too. None of the three listings states a maximum number of guests, so I can’t tell you how crowded a Maui sailing trip will be. A Sail Maui reviewer says the boat did not feel excessively full on the Alihilani, which is a different trip, and the Teralani reviewers mention a family of eight on the cocktail sail. If a quiet deck matters, book the earliest slot you can and read the latest reviews. Whichever boat you pick, read the exclusions in the listing too: wheelchair users are listed as unable to join the Teralani, and the Gemini and Sail Maui listings give you a clear check-in spot to find before you board.

Sail Maui Sunset Cruise

The Sail Maui sunset cruise is the trip I would send most people to, and the data supports it: the highest rating of any sailing trip, a clear meeting point and everything included. The listing names appetizers, non-alcoholic drinks including water and soda, an open bar with local beer, wine and assorted cocktails, and a gratuity. The route crosses the channel as the sun sets over the Pacific, and you see Maui, Lanai and Kahoolawe.

The weather is what I can’t tell you. The listing doesn’t state sea conditions, and neither will I. Book a date with a 24-hour refund window and watch the forecast. When you are ready to compare the whole set, return to my guide to every Maui boat tour I compared, or go to the home page for the other cities.