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Hawaii Sunset Sails & Cruises

The Oahu Sunset Cruise is a tradition on the island.

There are 36 tours in this category with adult prices that range in price from $42.90 to $2250.00 Skip Directly to Tours.

Oahu Sunset Sails & Cruises

Your Oahu sunset cruise will be one of the most relaxing and romantic tours of your vacation.

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.

Look for this symbol in the tour descriptions below to indicate if it is Pride of America compatible.

Sunset Sails & Cruises Sorted by Specific Tour


Sunset Sails & Cruises Sorted by Company

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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

4 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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(28 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

3 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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(9 Reviews, 4.7 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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(5 Reviews, 4.6 Stars)

Holokai Catamaran

2 Activity Options

Reserve a trip with the Holokai Catamaran

Go out on an adventure with Holokai Catamarans! Discover colorful tropical fish, green sea turtles, exotic coral reef and more of Hawaii's undersea life. Dolphins are also possibilities on this incredible adventure. Snorkeling in Hawaii is very fun and easy.
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(19 Reviews, 4.5 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. You will have your choice of various tiers of dinner options varying between 7 course, 5 course and 3 course meals, all at varying prices. A smaller vessel, Starlite, seats only 149 passengers and provides dinner cruises as well. In the winter months the Star of Honolulu also provides whale watches.
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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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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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Royal Hawaiian Catamaran

1 Activity Option

52' Catamaran, 52' Catamaran - Sunset Excursions, 52' Sailing Catamaran, 52' Catamaran - Sunset Excu

One of the most beautiful catamarans to ever grace the waters off the coast of Waikiki is the 52' Rudy Choy designed custom cruising catamaran, the Royal Hawaiian. This famous boat builder built this specific boat with the expressed purpose of sailing Hawaiian waters. The boat is used for snorkel and sailing trips as well as private charters which can include dinner, sunset, star watching and whale watches.
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Tradewind Charter

2 Activity Options

Sail Oahu, Private Sail and Snorkeling, Private Sailing, Sunrise Sails, Snorkeling Tours and Memoria

Tradewind Charters specializes in private charter tours. The maximum of only twelve passengers on the 43 foot sailing yacht creating an intimate non crowded atmosphere. 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 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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Sail Oahu

2 Activity Options

SV Shalimar is a 67 foot Mega Yacht

Experience Hawaii and the Pacific Ocean aboard your private yacht, Shalimar. The meaning of Shalimar in Sanskrit is "Home of Love on the Water".
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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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Recent Reviews


Top Activities
Customer Favorite Tours Based on Reviews

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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A Kauai sunset sail or Kauai sunset cruise is a good call for any evening of your vacation but perhaps the very best time would be your last evening on the island for a fond farewell.

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Many vessels on Maui can take you on a sunset cruise, most leaving from Lahaina harbor. Catamarans, sloops, schooners, and even power vessels - no matter what boat on Maui you take, one thing is certain, it will be the beginning of an evening you will remember for a long time to come.

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Sunset Sails off the coast of the Big Island of Hawaii provide the ultimate in relaxation. The beauty of the ocean and the colors of the sunset provide a remarkable experience to conclude your Hawaiian day.

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