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Sunset Sails & Cruises on Oahu

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There are 33 tours in this category that range in price from $42.90 to $2250.00.

Sunset Sails & Cruises

Oahu sunset sails or sunset cruises provide some of the most relaxing and romantic sunset sails in Hawaii.


Oahu cruise sunset sails are usually just a couple hours in length and occur during the most beautiful two hours of the day.


This is a 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 an Oahu sunset sail in the late afternoon as a preparation for a nice meal at a restaurant afterwards and the timing for this is perfect allowing for reservations at a restaurant at about 8 pm.


Sunset sails have always been a favorite in Oahu particularly out of Waikiki or Honolulu.


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 Waikiki is so popular for its sunset sails is the traditional Friday night fireworks display which occurs just after sunset and is great to see from the ocean looking back at the city from your sunset cruise.


Your choice of sunset sails and sunset cruises on Oahu is quite wide and there are any one of a number of sunset cruises and types of venues and programs to choose from.



  • Most sunset cruises 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 Oahu cruise sunset sail could be as few as just the two of you or could be with literally hundreds of others in a big sunset cruise party atmosphere.

  • Many Oahu sunset sails are referred to as a "booze cruise" and are just great for party time.

  • 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 full dinner on the Dinner Cruises.


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


We sell tickets to 33 items in the category Sunset Sails & Cruises on Oahu.

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Displaying 33 of 33 Results

$49.00

Join in for an unforgettable fireworks show along the Waikiki shoreline.

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$109.00
(2 Reviews, 5 Stars)

A Hawaiian evening on MAJESTIC's Island Style Buffet Cruise invites you to escape the crowds and enjoy an all you can eat Island style buffet, a sunset with spectacular views of Waikiki Beach, Diamond…

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$119.00

Celebrating Freedom on MAJESTIC's Friday Firework's Island Style Buffet Cruise invites you to escape the crowds and enjoy an all you can eat Island Style Buffet, a sunset with spectacular views of Waikiki…

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$79.00
(1 Review, 5 Stars)

A romantic Hawaiian evening on MAJESTIC's Sunset Appetizer Cruise invites you to escape the crowds and enjoy an Appetizer (Pupu's) buffet, a sunset with spectacular views of Waikiki Beach, Diamond Head…

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$89.00

Celebrating Freedom on MAJESTIC's Friday Firework's Appetizer Cruise invites you to escape the crowds and enjoy an Appetizer (Pupu's) buffet, a sunset with spectacular views of Waikiki Beach, Diamond Head…

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$68.90

Someone says "Hawaii" and almost subconsciously an image of the iconic landscape of our city on the sea, Waikiki, pops into mind. We're taking the traditional land based viewpoints of Honolulu and turning…

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$73.90

Experience a Friday Night Fireworks display outside of Waikiki. Join the Queen from 7 to 8:30 pm and you're sure to enjoy the Friday night city lights like you've never seen them before. Perfect for any…

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$89.00

This sunset sail departs from the Wai'anae Harbor on the west side of the island of Oahu. Enjoy appetizers and drinks as you watch the beautiful sunset. This tour's days and times can change seasonally.…

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$89.00

Enjoy a scenic cruise south toward Diamond Head, catch the moment the sun slips below the horizon and feast on some delicious appetizers and drinks. You may even see the green flash.

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$149.00

Come enjoy some time on the water and get great views of the fireworks while enjoying food and drinks. There is an array of gourmet, fresh selections, a fusion of the best Hawaiian, Asia -Pacific and Continental…

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$47.90
(4 Reviews, 5 Stars)

The beauty of a Hawaiian sunset can never be enjoyed more than when you are out on the ocean. Choose this tour and experience an afternoon sail on one of the newest boats in the Hawaiian Islands. Enjoy…

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$42.90
(1 Review, 3 Stars)

Friday night is fireworks night on Oahu, and seeing it from the water on the Holokai is a real treat! You are invited to enjoy a lovely evening under the stars and moonlight while watching a spectacular…

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$42.90
(21 Reviews, 4.9 Stars)

You'll board barefoot from Waikiki Beach and then sail into the sunset. This romantic journey offers golden views of Diamond Head, Waikiki and Honolulu's cityscape as the sun paints the sky and…

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$42.90
(5 Reviews, 4.8 Stars)

Shimmering water and twinkling lights make up the scenery as you glide across the deep blue sea with the mahina (moon) guiding the way. Enjoy a 90 minute sail, complete with an open bar, a spectacular…

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$89.90
(3 Reviews, 4 Stars)

Honolulu city lights and a sunset dinner. Escape and relax. Enjoy a sunset sail and open air dining on a beautiful catamaran. Watch the setting sun reflect off the Honolulu skyline and the famed Diamond…

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$98.90
(5 Reviews, 5 Stars)

Friday night is a wonderful time for a 2.5 hour cruise to enjoy a beautiful fireworks display, dinner and drinks. Enjoy views of the Honolulu and Waikiki skyline, Ko'olau Mountains and Diamond Head.

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$60.00
(4 Reviews, 5 Stars)

Cruise along the picturesque North Shore to the Waimea Bay area. Feel free to bring your own alcoholic beverages.For guests needing assistance with a walker please inform agent at time of reservation so…

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$60.00

Sunset, stargazing and full moon cruise. These trips are usually available two nights out of each month, most of the year. Tour is run in lieu of the traditional sunset cruise. Dates are determined by…

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$70.00
(2 Reviews, 5 Stars)

The North Shore of Oahu has more whale sightings than any other location on Oahu. Last season there were over 700 sightings and two double breeches in the Haleiwa Harbor Channel. Between December and…

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$142.30

Take in the sights, snorkel and catch a beautiful Hawaiian sunset. Travel 40 to 50 miles round trip, going all the way to beautiful Makua Valley, Yokohama Beach and even Ka'ena Point. Enjoy an hour…

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$89.00
(3 Reviews, 5 Stars)

There's nothing like a Hawaiian sunset and nothing beats seeing a sunset from sea. During this trip you will enjoy a scenic cruise from the Hilton Pier south towards Diamond Head. Normally the captain…

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$149.00

Set sail from Waikiki Beach onboard the 54 foot catamaran Spirit of Aloha to view the fireworks and eat dinner at sea. During the cruise you will be served an array of gourmet, fresh selections. The menu…

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$136.90

Where else would be better to watch fireworks? Watch as the incredible Hawaiian sunset paints color and vibrancy across the sky, the ocean and the lush green mountains. Relax and marvel as the city lights…

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$2250.00

On this Private Sunset in Paradise Sail feel the sea spray and look for dolphins on the bow while the sun sets slowly into the majestic Pacific Ocean! Relax Hawaiian style, enjoy tasty "Pupu's" (Hawaiian…

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$2250.00

Choose this Private Friday Night Firework Sail and get the Sunset and a Fireworks display! Guests can look for dolphins or whales on the bow while the sun sets slowly into the majestic Pacific Ocean!…

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$81.05
(4 Reviews, 4 Stars)

Enjoy the Pacific Star's buffet dinner with one welcome mai tai drink in the midst of a beautiful ever changing tropical backdrop filled with continuous enchantment that includes a welcome hula. During…

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$126.17

Save 10%
(3 Reviews, 5 Stars)

A champagne toast starts your three star sunset dinner and show aboard the Star of Honolulu. Feast on a 5-course whole Main lobster and tenderloin steak dinner complete with premium beverages. Four decks…

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$167.95
(3 Reviews, 5 Stars)

This is the ultimate in luxury and romance for special occasions or just to treat yourself. Be pampered at the exclusive Captain's welcome reception on the top deck with a champagne greeting. Also enjoy…

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$50.00 - $96.11
(8 Reviews, 4.3 Stars)

Enjoy casual elegance after a welcome aboard mai tai and explore four panoramic decks for breathtaking views of the Hawaiian sunset and coastline. Dine on all you can eat crab and sirloin steak dinner.…

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$104.45

Save 10%

Enjoy casual elegance after a welcome aboard mai tai and explore four panoramic decks for breathtaking views of the Hawaiian sunset and coastline. Dine on all you can eat crab and sirloin steak dinner.…

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$134.52

Save 10%

A champagne toast starts your three star sunset dinner and show aboard the Star of Honolulu. Feast on a 5-course whole Main lobster and tenderloin steak dinner complete with premium beverages. Four decks…

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$176.30

Save 10%

The ultimate in luxury and romance for special occasions. Be pampered at the exclusive Captain's welcome reception on the top deck with a champagne greeting. Also enjoy a seasonally inspired 7 course…

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$89.41

Enjoy the Pacific Star's buffet dinner in the midst of a beautiful ever changing tropical backdrop. Filled with continuous enchantment that includes a welcome Mai Tai drink, dinner, "Polynesian Journey"…

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Sunset Sails & Cruises Sorted by Company

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(6 Reviews, 5 Stars)

North Shore Catamaran Charters

3 Activity Options

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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(3 Reviews, 5 Stars)

Atlantis Adventures

4 Activity Options

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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(3 Reviews, 5 Stars)

Port Waikiki Cruises

2 Activity Options

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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(26 Reviews, 4.9 Stars)

Maita'i Catamaran

2 Activity Options

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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(8 Reviews, 4.6 Stars)

Makani Catamaran

2 Activity Options

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

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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(18 Reviews, 4.4 Stars)

Star of Honolulu

8 Activity Options

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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Aqua Zone

1 Activity Option

Aqua Zone is a great option if you are looking to take-in some diving while visiting Oahu. One and two tank certified dives are available to visit the numerous 'boat and airplane wrecks' located off the southern and eastern shorelines. One and two tank introductory dives are also available at bountiful sea life locations as are daily snorkel tours.
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Hawaii Nautical

3 Activity Options

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

1 Activity Option

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

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

1 Activity Option

Tradewind Charters specialize in private charters and can accommodate anywhere between just two to as many as twelve passengers on their 43 foot sailing yacht. Depending upon how many you may have in your party you just may be completely surprised in a favorable way by just how much money it will actually cost to charter a boat privately.
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Hawaii Glass Bottom Boat

2 Activity Options

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

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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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.


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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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