Introduction
From the dock, most Hawaii sunset sails look like the same evening.
The difference is what the ticket puts in your hand once you are aboard, and on these eleven sails it runs from water and juice to a full dinner.
Blue Hawaiian Activities books eleven sunset trips across O’ahu, Maui and the Big Island that are sold as sails or cocktail cruises rather than as dinner cruises or whale watches.
Sorting them by what comes aboard is the fastest way to find the right one, from a soft-drinks ticket to an open bar or a full dinner.
Key Takeaways
- Blue Hawaiian Activities books eleven Hawaii sunset sails on three islands.
- One ticket includes only water, soft drinks and juice.
- Three sails include two drink tickets per adult.
- Three sails load from the beach rather than a harbor.
- One Maui sail motors rather than sails during whale season.
The ticket that includes the least
The Waikiki Sunset Sail sells two tiers of the same trip.
It runs daily for 1.5 hours on a new catamaran called Hawea, departing at 5pm or 5:30pm depending on the season, with check-in 30 minutes before.
The standard ticket includes water, soft drinks and juices. The VIP ticket adds an open bar of local beers, wines, mai tais and cocktails.
Prices below are per person before taxes and fees, from each tour’s booking calendar in October 2026. The standard ticket is $65.00 and the VIP ticket $85.00, so a celebration with cocktails suits the VIP.
The Oahu Gold Coast Sunset Cruise adds one included drink, and its page lists food as available to buy rather than included.
It is two hours, daily, at $100.00 per traveler, with bottled water and your first alcoholic drink included for guests 21 and over. Additional drinks and all food are available to buy rather than included.
Departure is 5:00pm from November 1 to March 1 and 5:30pm from March 1 to November 1, and the page notes the chance of humpback whales from November to May.
Two drink tickets and a light bite
Three sails share nearly identical drink terms, two on O’ahu and one on the Big Island.
The Waikiki Sunset Cocktail Cruise leaves Kewalo Basin Harbor and runs 5pm to 6:30pm in fall and winter, 5:30pm to 7pm in spring and summer.
It includes a charcuterie slider box, unlimited non-alcoholic drinks and two bar drink tickets per adult, with extra beer at $1 and mixed drinks at $2. Gluten-free and vegan options need advance notice.
Adults are $99.95, or $119.95 with transportation.
It is a barefoot sail, so you check your shoes before boarding, and a light sweater is a good idea because it can get cool on the water.
The Hilton Sunset Cocktail Cruise carries the same two-ticket terms and the same $1 and $2 extras aboard the Spirit of Aloha, at $139.95 for adults.
It checks in between 4:40pm and 5:10pm depending on sunset, at the Port Waikiki Cruises kiosk near the Hilton Pier, and runs daily except Fridays. Guests need to be able to climb the boat’s stairs, and the cruise is not wheelchair accessible.
The Kona Sunset Cocktail Sail brings the same model to the Big Island aboard the Honi Olani, a 53-foot catamaran for 49 passengers with restrooms and shade.
Check-in is 4:40pm in fall and winter and 5:10pm in spring and summer, for a sail of 1.5 to 2 hours. Snacks, unlimited non-alcoholic drinks and two bar drink tickets per adult are included, and adults 13 and older are $139.00.
Open bar and appetizers
Three sails include an open bar in the base ticket.
The Ka’anapali Holo Holo Sunset Sail on Maui runs about two hours, with an October start of 4pm and a return at 6pm. Its open bar lists a house sunset cocktail, white wine, sparkling rosé, beer on tap, mai tais, vodka, rum and mixers, with chef’s appetizers.
During whale season the boat motors rather than raising its sails. Adults 13 and older are $119.95.
Check-in is behind the beach activities kiosk at the Outrigger Ka’anapali Beach Resort, with parking there at $8 plus tax for up to five hours with validation.
The Catamaran Sunset Sail Waikoloa on the Big Island runs about 1.5 hours from Anaeho’omalu Bay on the Kohala Coast, with a premium open bar and light island-style appetizers, at $139.95 for adults 13 and older.
It is listed for all ages and includes a complimentary shuttle from Hilton Waikoloa Village, which needs an advance reservation. Check in 45 minutes before departure, and expect to board directly from the beach.
The Sunset Dinner Sail Adventure on Maui is the third, and the most generous with food of the three.
It runs two hours, Monday to Friday, with live music, an open bar of local spirits, beer, wine and champagne, and a sparkling rosé toast at sunset. The page lists three plated courses it calls appetizers, from hummus and charcuterie to seared ahi and baked pasta, then chocolate cake.
Adults 13 and older are $189.00. It loads from the beach at Maluaka in Makena, with a free shuttle from the Wailea resorts to check-in.
The two Trilogy sails on Maui
The Deluxe Ka’anapali Sunset Sail and the Ma’alaea Sunset Sail share one operator, one menu and one schedule.
Both are two hours and serve the same pupus. A pulled pork slider, BBQ chicken satay, tomato and mozzarella caprese, hummus with vegetables and a seasonal dessert.
Both list a premium bar of a Molokai Mule, a Lanai Tai, local beer, prosecco, pinot noir and sauvignon blanc for guests 21 and over. Both are $122.00 for adults.
The departure point is what separates them.
The Ka’anapali sail loads from the Sheraton’s beach lawn, so expect to get wet up to your knees as you board. For guests with mobility issues, the operator recommends the Ma’alaea departure instead.
The Ma’alaea sail leaves from slip 99 in the harbor, with parking paid by QR code at $1 an hour, and it adds a whale watch during whale season.
Departures move with sunset through the year, between 4:00pm and 5:15pm. Blue Hawaiian Activities can confirm your exact time when you book.
The one that includes dinner
The Hawaiian Cultural Sunset Sail is the only sail here whose page lists dinner as an inclusion, and the only one built around Hawaiian storytelling rather than the view.
It runs about two hours off Waikiki aboard a traditional voyaging vessel, with cultural practitioners sharing mo’olelo, the stories and history of the places you pass, along with music and a ceremonial sunset ‘oli.
Refreshments and dinner are included, and adults 12 and older are $250.00. The page asks guests to check in no later than 4:30pm.
Trilogy also runs a Ka’anapali Sunset Whale Watch from December 15 to April 15, with the same menu. For sunset trips where dinner is the point, our comparison of sunset dinner cruises by island covers the full set.
Conclusion
The best Hawaii sunset sail for your evening depends on what you expect to be handed once the boat leaves.
Choose the Waikiki Sunset Sail standard ticket or the Gold Coast cruise for a lighter evening, the two-ticket cruises for a drink and a bite, and the Holo Holo, Sunset Dinner Sail Adventure or Waikoloa sails for an open bar.
Blue Hawaiian Activities recommends the Hawaiian Cultural Sunset Sail as the best Hawaii sunset sail for a first evening on O’ahu, because it is the only one here that lists dinner as an inclusion and puts Hawaiian storytelling at the center of the trip.
Ready for the water? Book your Hawaii sunset sail with Blue Hawaiian Activities and our island concierges will confirm the departure time and what your ticket includes.
Frequently Asked Questions
What is included on a Hawaii sunset sail?
It ranges from water and juice to dinner across the eleven sails Blue Hawaiian Activities books. The Waikiki Sunset Sail standard ticket includes soft drinks, the Gold Coast a first drink, three cocktail cruises two drink tickets, three sails an open bar in the base ticket, and the Hawaiian Cultural Sunset Sail dinner.
Which Hawaii sunset sail has an open bar?
Three of the eleven Blue Hawaiian Activities books state an open bar in the base ticket, the Ka’anapali Holo Holo and Sunset Dinner Sail Adventure on Maui and the Catamaran Sunset Sail Waikoloa on the Big Island. The Waikiki Sunset Sail offers an open bar only on its VIP ticket, and the two Trilogy sails on Maui serve a premium bar for guests 21 and over.
How long is a sunset sail in Hawaii?
Between about 1.5 and 2 hours on the sails Blue Hawaiian Activities books. The Waikiki Sunset Sail and the Catamaran Sunset Sail Waikoloa run about 1.5 hours, the Kona Sunset Cocktail Sail runs 1.5 to 2 hours, and the Gold Coast, Holo Holo, Hawaiian Cultural, Sunset Dinner Sail Adventure and both Trilogy sails run about 2 hours.
What time do Hawaii sunset sails leave?
Between about 4pm and 5:30pm, moving with the season, on the sails Blue Hawaiian Activities books. The Gold Coast cruise departs at 5:00pm from November to March and 5:30pm the rest of the year, while the two Trilogy sails on Maui leave between 4:00pm and 5:15pm, depending on the month.
Can you see whales on a Hawaii sunset sail?
On some, in season, according to the pages Blue Hawaiian Activities books. The Gold Coast cruise mentions humpback whales from November to May, and the Ma’alaea Sunset Sail includes a whale watch during whale season. The Ka’anapali Holo Holo Sunset Sail states it motors rather than sails during whale season.
Prices shown are before taxes and fees, and can change by date. Contact Blue Hawaiian Activities for your total.
