Maui Sunset Cruises

Choose a Maui sunset cruise by where you are staying, then by cocktails or dinner. From Kāʻanapali, Teralani’s Luxury Sunset Cocktail Sail and Sea Maui’s Original Sunset Cruise board from the beach with an open bar, and both operators run dinner versions. From Lahaina, Sail Maui’s Alihilani sunset sail sails with the motors off. From Māʻalaea, Pacific Whale Foundation’s Maui Sunset Sail and three dinner boats serve South Maui. These trips run all year. Outside roughly December to April they are sunset sails, not whale watches, and even in winter most of them are not whale watches.

A sunset sail, not a whale watch

Every boat on this page sells the sunset first. Teralani says so directly on its cocktail sail: from 1 November to 15 April “we will focus on sailing during the sunset trip”, and “it will not be an official whale watch, although we will be in whale season”. Some operators add a whale element in winter. Sea Maui includes whale watching on its sunset cruise from 15 December to 15 April, Pacific Whale Foundation adds a whale-watch component and 30 extra minutes to its sunset sail from 20 December to 31 March, and Sail Maui says humpbacks may be seen on the Alihilani from December through March. From May to November humpbacks are scarce or absent, and you are booking a sunset cruise. If whales are the reason you are on Maui in winter, see sunset whale watching, where dedicated whale-watch departures are compared.

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Prices are per person, from the listings as checked October 2026.

Kāʻanapali: beach-loading sails

Kāʻanapali has no harbor, so the boats nose up to the sand. Expect to wade in, sometimes to the knees, with shoes off. That makes these sails easy if you are staying on the beach and awkward if you cannot walk on sand or climb a short boarding stair.

Teralani’s cocktail sail is the featured trip. The listing names the menu: a vegetable crudité platter, chipotle salsa, cheese and crackers, passed caprese skewers, teriyaki meatballs and edamame potstickers, and a coconut brownie pop. The open bar pours premium Hawaiian beer, wine, sparkling rosé, Mai Tais, vodka, rum and mixers. It costs from $135 per person on GetYourGuide, and the same sail is listed on Viator from $142, so compare both before you book. Our review has the details.

Sea Maui’s original sunset cruise is rated 4.8 from 1,588 reviews and costs from $137. It includes an open bar, pupus and live music on Tuesdays and Thursdays, and Sea Maui validates four hours of parking at Whalers Village. It is a barefoot sail, and departure times change through the year, so the operator asks you to call 24 hours ahead to confirm. Our Kāʻanapali guide explains the beach boarding in more detail.

Lahaina: the Alihilani

The Alihilani is a sailing catamaran that takes up to 49 guests. The crew raises the sails and turns the motors off for the run along the ʻAuʻau Channel, and guests sit on the forward trampolines or in the shaded cabin with light appetizers and an open bar. It costs from $127 and is rated 4.8 from 371 reviews. Sail Maui also lists a smaller Romantic Luxury Sunset Sail on its 47-foot Paragon, limited to 25 guests.

Sail Maui sells both from Lahaina Harbor, which reopened for limited, permitted operations in December 2025 after the August 2023 wildfire. County of Maui guidance as of August 2026 describes the harbor as daytime-only, with nothing after 6 p.m., so check the departure time and dock on your voucher before you go. See MauiRecovers for current access, and our Lahaina page for the harbor and parking.

Māʻalaea: for Kīhei and Wailea

There are no sunset cruises from Kīhei or Wailea in our data. South Maui guests drive to Māʻalaea, 15 to 20 minutes from Kīhei and 25 to 30 minutes from Wailea. Pacific Whale Foundation’s sunset sail runs on the Ocean Spirit, a sailing catamaran, with appetizers, island music and two included adult drinks. Its description says it departs from Māʻalaea, but its meeting notes refer to Lahaina Harbor, so confirm the departure point with the operator. On Friday and Saturday nights it is for adults 21 and over only.

For dinner from Māʻalaea, Quicksilver’s Sunset Dinner Cruise (from $140) and Calypso’s Prime Rib or Fresh Island Fish Dinner Cruise (from $150) serve at the table, and Pride of Maui’s Hawaiian Hula dinner cruise (from $168) adds hula and Hawaiian music. For a very small group, Hawaii Nautical’s Luxury Powerboat Sunset Cruise takes up to six guests on a 42-foot Boston Whaler, at $279 per person, with drinks on a bring-your-own basis in cans or plastic.

Dinner or cocktails

A cocktail sail is shorter and lighter: about two hours, appetizers and a bar. A dinner cruise adds half an hour or so and a full meal. Teralani’s dinner sail serves an assisted buffet, and Sea Maui’s Premium Sunset Dinner Cruise a buffet by Chef Jai with live music on Wednesdays and Saturdays. The dinner boats are compared in detail on our whale watching dinner cruise page.

Adults, children and price

The only adults-only rule in these listings is Pacific Whale Foundation’s: no children on Friday and Saturday sunset sails. On every boat with a bar, alcohol is for guests 21 and over with photo ID, and Teralani asks all guests for a valid picture ID. Families can book Quicksilver, which sells child tickets with a meal, or Pacific Whale Foundation’s sunset sail from Sunday to Thursday. Fares on the trips in the table run from $127 to $169 per person, before gratuities. Our price guide covers taxes and fees.

Sunset cruises after the whale season

From late April through November, a sunset cruise is the main evening trip on the water, and most of the boats above keep sailing. Our April guide covers what still runs as the season ends, and our snorkeling tours page covers daytime trips. For the whale-season picks, see the best Maui whale watching tours.

Ready for a sunset sail? Check dates for Teralani’s cocktail sail.