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Oahu Sunset Sails & Cruises

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Sunset Sails & Cruises Sorted by Specific Tour

Your Oahu sunset cruise will be one of the most relaxing and romantic tours of your vacation. We offer many at discount pricing.

An Oahu sunset cruise will usually just be a couple hours in length and occur during the most colorful hours of the day. This is the time of the day to unwind and relax with a cocktail in hand and share in the day's adventures. Many people love to enjoy a Waikiki sunset cruise in the late afternoon in preparation for a nice meal at a restaurant later that evening. The timing for this is perfect allowing for reservations at a restaurant at about 8 pm.

A Waikiki Sunset Cruise has always been the favorite location for a sunset sail on Oahu. 

  • Your sunset sail sets the tone for the evening to follow and Waikiki is such a busy and happening evening location that the sunset sail will dove-tail just perfectly with whatever event my come next.
  • Another reason the Waikiki sunset cruise is so popular is because the traditional Friday night fireworks display, which occurs just after sunset, is great to see from the ocean looking back at the city from your vessel.

Your choices for an Oahu sunset sail are quite numerous.

  • Most of the Oahu sunset cruise options leave from Waikiki or Honolulu but we also have sunset sails departing from the Ko'Olina Resort Marina and from the North Shore at Haleiwa.
  • The size of your sunset sail could be cozy enough for just the two of you or you could be with literally hundreds of others in a big sunset cruise party atmosphere.
  • A close cousin to the Oahu sunset cruise is the Oahu Dinner Cruise, the difference being that instead of just serving 'pupus' on the sunset sails they serve a cull dinner on the Dinner Cruises.

Oahu Booze Cruise

  • The Oahu Booze Cruise is the name that has been adopted over the years to indicate that these sunset cruises are places where you can drink your fill and enjoy a 'party atmosphere' with others on board. Some Oahu sunset sails are more tranquil, and others really 'step up' the 'booze cruise' aspect. Take your choice.

You will be glad you arranged your evening sunset cruise entertainment off the coast of Waikiki and Diamond Head with its colorful sunsets and beautiful views of the Honolulu shoreline. A more romantic evening activity than a sunset sail will be hard to find.

Checkout Tom's Tips and Insights about Oahu Sunset Sails & Cruises

Tom Barefoot's Tips
  • Tom's Tips - Oahu Sunset Cruise

    Oahu has a bit of a 'step up' on the other Hawaiian islands regarding sunset cruises because on the most popular night of the week, Friday, many of the boats offer a sunset Fireworks cruise.  Each Friday, directly on Waikiki Beach right between the Sheraton Waikiki Hotel and the Haleakala Hotel fireworks are launched over the ocean during the 7 pm or 8 pm hour.  The sunset sails are beautiful enough without this added attraction but this simply adds to the fun.  These cruises do take a priority as people often opt for the Friday night cruise as an option over the other nights of the week.  As you can imagine, that means that Fridays fill up faster so please place your order for these sooner rather than later.



Sunset Sails & Cruises Sorted by Company

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(4 Reviews, 5 Stars)

Holokai Catamaran

1 Activity Option

Reserve a trip with the Holokai Catamaran

Go out on an adventure with Holokai Catamaran! Snorkeling, sailing, and great views of the island- we've got something the whole family will enjoy!
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(4 Reviews, 5 Stars)

Port Waikiki Cruises

2 Activity Options

54' Catamaran

If sailing is truly your ultimate objective in going out on a boat you will be thrilled with a ride on the sailing boat Paragon. The Paragon is a 47' sailing catamaran that is designed for these waters and designed for speed. There are not that many boats that pass through these waters that could go faster than this one.
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(3 Reviews, 5 Stars)

Atlantis Adventures

6 Activity Options

Submarine tours of Hawaii.

Atlantis Adventures will provide you with an opportunity to dive in absolute comfort in a 'state of the art', window filled submarine to a depth of about 100' for about forty minutes. Very spacious and air-conditioned these vessels hold just under fifty passengers as they are taken on one of the most unique rides of their lifetime.
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(29 Reviews, 4.9 Stars)

Maita'i Catamaran

2 Activity Options

Waikiki Sailing Charters and Booze Cruises

The 44' sailing catamaran, Mai Tai, has been one of the most popular boats we have ever had on Waikiki Beach. Leaving right from the sand between the Sheraton and the Halekulani this 47 passenger boat will take you out for a day sail, a snorkel or a sunset sail and a view of the Waikiki Coastline and Diamond Head.
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(7 Reviews, 4.7 Stars)

North Shore Catamaran Charters

2 Activity Options

40' Sailing Catamaran, 40' Catamaran

The beautiful North Shore of Oahu provides the seascape for one of the most majestic boats on the island, the Ho'o Nanea, operated by North Shore Catamaran Charters. This 19 passenger, 40' sailing catamaran is one of the fastest on the island and offers fabulous sunset cruises, picnic snorkel sails and whale watching in season.
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(23 Reviews, 4.6 Stars)

Star of Honolulu

8 Activity Options

Lunch and Whale Watch, Sunset Sails, Sunset Dinner Cruise

The 232' Star of Honolulu is the largest dinner cruise boat in Hawaii, has four levels and seats as many as 1500 people. Choose a dinner and show package from the 4 tiers of dinner options; Luxury 7-course, Deluxe 5-course, Casual 3-course or the Buffet dinner, all at varying prices. A smaller vessel, Starlite, seats only 149 passengers and provides dinner cruises as well. Each dinner option is served on its respective deck. In the winter months the Star of Honolulu also provides whale watches.
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(10 Reviews, 4.3 Stars)

Makani Catamaran

2 Activity Options

65' Sailing Catamaran

One of the most beautiful sailboats sailing the waters off the coast of Waikiki is the Makani Catamaran. This 64' x 32' Cat is one of the very fastest on Oahu often achieving speeds of over thirty knots. Flush with the most modern amenities you will be able to enjoy a wonderful sunset sail, a coastal daytime sail and a snorkeling excursion.
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Hawaii Nautical

3 Activity Options

Leid Back' Dinner Cruise, Snorkeling and Dolphins, Whale Watch off the leeward coastline,Oahu Scuba

Hawaii Nautical offers a large variety of boat tours throughout the island of Oahu and on the Big Island of Hawaii. Snorkel tours and dolphin watches are offered in the mornings and the afternoons and in addition they offer sunset sails, dinner cruises, scuba and snuba options, whale watching in season and private charters.
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Hawaii Glass Bottom Boat

2 Activity Options

Hawaii Glass Bottom Boat

The Haleiwa Queen is a new 49 passenger glass-bottom viewing boat offering day and sunset cruises as well as the ever popular Friday Night Fireworks Cruise for a wonderful display in the sky and in the sea.
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Ocean Joy Cruises

2 Activity Options

Kai Oli'Oli a 61' power catamaran

One of the most scenic coastlines on Oahu is the West Coast above Waianae near Ka'ena Point. Ocean Joy Cruises specializes in touring this area which is great for snorkeling but is extremely famous for its dolphin sightings. Their large and stable 61' power touring catamaran has all the comfortable features to make this outing a great day on the water.
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Paradise Helicopters

1 Activity Option

Scenic Helicopter Tours of Oahu, Pearl Harbor Flights, Door's Off Adventure Tours

Paradise Helicopters is one of the premier helicopter touring companies that services both the Big Island and Oahu. One of the biggest differences between this company and many others is the fact that they will offer you the opportunity to take a flight with the doors off. As nerve racking as that may sound, you are completely strapped in an just a secure as you would be in an enclosed helicopter. The big difference is that your view from this perspective will be absolutely amazing.
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Tradewind Charters, Inc.

2 Activity Options

Oahu Private Sail & Snorkel, Mimosa Sunrise, Sunset Dinner, Whale Watch Tours, Ash Scatterings

Tradewind Charters specializes in private charter tours. The maximum of only twelve passengers on the 43 foot sailing yacht or 40 foot sailing catamaran creating an intimate non crowded atmosphere. Our 50 foot motor catamaran for larger groups up to 49 guests. With additional options for catering or an on-board bar guests can really create their own adventure at sea. If you're on Oahu for a vacation or event check out Tradewind Charters.
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Hawaii Pirate Ship Adventures

2 Activity Options

Hawaii Pirate Ship Adventures - Sailing tours on the 85' Spanish Galleon

Featuring unique day and night sailing tours with the pirate theme on an 85 foot pirates galleon. Tours go out for approximately an hour and a half along the Oahu coast with opportunity to dress up and participate in on-board activities.
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And You Creations

1 Activity Option

And You Creations - 55-foot Luxury Tour Power Boat, Group and Private

And You Creations offers a an exclusive Dolphin Swim and Snorkel Tour, a Circle Island Sites and Food Tour and a Manoa Falls Hiking Adventure, all with Waikiki Hotel pick up. They offer Japanese translation on these exciting ocean and land adventures. Ideal for your family and friends!
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Mana Kai Catamaran

2 Activity Options

Waikiki Sailing Catamaran Charters

Come aboard the Mana Kai for an unforgettable sail that shows you the island of Oahu from a unique perspective. Standing 32 feet long and 16 feet wide, the Mana Kai Catamaran accommodates up to 26 passengers. Based in Waikiki Beach, our famous Hawaiian Rainbow sail, lounge net, restroom, and a pleasant sound system add to your sailing pleasure.
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North Shore Sailing Adventures

1 Activity Option

40' Sailing Trimaran Boat

North Shore Sailing Adventures sails out of Haleiwa Harbor to explore the beauty of the North Shore in a fast or leisure sail that is comfortable, and in a safe atmosphere. Areas we sail to: majestic Waimea Bay, the 7 Mile Miracle of the North Shore, Ka’ena Point and outside the Harbor depending upon the season.


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Recent Reviews


Video Transcript

Sunset sails are a very fun and relaxing activity to participate in on the island of Oahu.

One of the big questions that people have is what is the difference between a sunset sail or a sunset cruise and a Dinner Cruise? Well, they're out about the same amount of time. A Dinner Cruise can be out two hours, maybe two and half depending on the boat and variations there. Sunset sails are usually two hours but can be an hour and a half, so an hour and a half to two hours, a little bit shorter generally.

But the big difference is simply that they don't include Dinner on the sunset sails so they're markedly less expensive but they're an opportunity for you to get out onto the water and see the sunset and look back on the shoreline, look back on Waikiki and just relax with a cocktail, have some hors d'oeuvres, wine pupus they're referred to as, and just relax and enjoy your time.

This is something you might want to do before you actually go to Dinner, something like that. Any way you choose, it's a great night just to get out on the water. If you're going during Whale Season, you may have an opportunity to see some whales out there. If nothing else it just gives you an excuse to get on the water for a short amount of time to appreciate what the Hawaiian Islands are like from the water and that's part of what Hawaii is all about.

We have them, sunset sails that leave from all over the island. Certainly off the coast of Waikiki and Kewalo Basin here. In Honolulu we can get you out on some wonderful sunset sails. But up in Ko'Olina and Waianae we've got them, the North Shore and Haleiwa. We have some that'll be happening out of Kailua area on this side, the Kaneohe/Kailua side. So there's a number of locations you could go.

The boats are totally varied. We have huge boats that'll take lots and lots of people, hundreds in fact, and then they go in gradations down to smaller groups. We actually have them as private boats or smaller six-passenger boats that'll take you out. These can be Sailboats so you're actually able to put up some sails and you'll enjoy sailing as you're doing your sunset sail, or they could more in the variety that is like a cruise, a power boat, a power CAT or something like that. Not interested in sailing but just being out there to see the sunset and enjoy it from that perspective.

Cocktails are something that's always a part of what happens with regard to these cruises. Sometimes sunset sails or some sunset sails or cruises are referred to as a 'booze cruise' and I guess that's because one of the major aspects of those particular sails is the fact that you have a lot of cocktails and enjoy yourself that way in addition to being out at sunset. But there are so many varieties of sunset sails that we have. They all can be found on Oahu and it's a good way to spend an evening on Oahu.

So if you have any questions about Tours or Activities in Hawaii, just give us a call or check out tombarefoot.com. We're here to help.


Taking a Hawaii sunset cruise may prove to be the most romantic and relaxing moments of your vacation. Sunset cruises probably won't rank high on your list of adventure items on your trip but may instead be the simple ending to a perfect day.

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Kauai is amazingly beautiful from on the island but it is ridiculously beautiful off the coast from the vantage point of a sunset sail.

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This may turn out to be your most memorable two-hours of your vacation.

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A romantic sunset sail is one of the best ways to enjoy a sunset.

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