At sunset time the winds generally die-down and the sailing is gentle.
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Oahu Sunset Sails and Sunset Cruises
Perhaps the most romantic activities offered off Honolulu and Waikiki on the island of Oahu, Hawaii are the sunset sails or sunset cruises.
A variation of the dinner sunset cruise is what is fondly referred to in Hawaii as the "booze cruise". This usually includes just "pupus" (appetizers) and an open bar plus entertainment. These "booze cruises" are very popular and are a fun way to begin an evening in Honolulu.
You will be glad you arranged your evening 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 will be hard to find.
Alii Kai Catamaran - The Alii Kai Catamaran provides a "fun-filled romp" of a dinner cruise that is sure to have you dancing your sandals off. You will see a rainbow of sailboats, the lights of Waikiki, a majestic view of Diamond Head and a spectacular Hawaiian sunset from aboard the world's largest Polynesian catamaran. You will also enjoy a Polynesian show and dancing to a live band. You'll have a sense of the "old Hawaii" visited by generations of visitors over decades past and the experience will leave you panting as you exceed your "fun level" in the Waikiki of the old days. | ![]() Alii Kai Catamaran Price Range: (From: $66.90 - To: $102.18) |
Hawaii Nautical - Here's a boat company that does all things "nautical". How about a dolphin snorkel sail, a sunset cocktail cruise, a gourmet dinner cruise, an overnight interisland sail, a whale watch, a dive tour or a private boat charter. Hawaii Nautical is a family business and they pride themselves in being attentive to your every need. Their playground is the Waianae Coastline and their top-grade beautiful catamarans are designed for the discriminating Oahu visitor. | ![]() Hawaii Nautical Price Range: (From: $181.90 - To: $190.00) |
Hawaii Nautical Ko Olina Catamaran - Join the Captain and Crew of the custom power-cat "Pacific Passion" as they take an exhilarating cruise along the beautiful Waianae coastline in search of the wild Spinner Dolphins. Ko'Olina Ocean Adventures caters to small groups of up to 13 passengers. | ![]() Hawaii Nautical Ko Olina Catamaran Price Range: (From: $56.90 - To: $190.00) |
Island Dream Catamaran - The Island Dream Catamaran is the most photographed boat in the Hawaiian Islands. It is a jewel of Waikiki with its lovely pink sails that catch every eye. But don't let its beauty fool you. This catamaran has the speed to catch the fast flowing swells of Oahu. This "state of the art" twin hulled, catamaran is easily able to accommodate 30 people and in addition to its snorkel sails and sunset sails is available for charter on a private charter basis as well. This boat is beautifully maintained and is an excellent choice for a sail off the Waikiki coastline. | ![]() Island Dream Catamaran Price Range: (From: $23.00 - To: $45.00) |
Maitai Catamaran - Join MaiTai's friendly crew as you take in the picturesque beauty of Waikiki, the spectacular volcanic views, the cityscape of Honolulu and the breathtaking beauty of the ocean, all at once! This is great entertainment for the whole family. Come experience the MaiTa'i and find out why she is one of the most talked about catamarans on Waikiki Beach. | ![]() Maitai Catamaran Price Range: (From: $19.95 - To: $40.90) |
Makani - The Makani Catamaran is one of the newer catamarans in Oahu's fleet of boats having been built in 2006. This is one of the most beautiful vessels you will find on the island and has fantastic modern amenities. Their offerings include snorkeling tours, sailing adventures, sunset sails and whale-watching. This vessel is also ideal for private charters of all kinds and can accommodate up to 80 passengers. If you're looking for a special outing for your group that will be first class, the Makani is a fabulous choice. | ![]() Makani Price Range: (From: $32.90 - To: $65.00) |
Navatek I - Technology is the driving force behind the "Navatek 1" which revolutionized ocean travel by literally smoothing out wave action in rough seas. The Navatek’s SWATH technology (Small Water-plane Area Twin Hull design) offers guests a comfortable, stable and smooth ride. There are two air conditioned dining decks, each with its own bar, sound system and restrooms. Spacious outdoor decks, including a top floor observation deck which allows guests to take advantage of spectacular ocean and coastal views. Viewing the sunset lights from a dinner cruise aboard the "Navatek 1" is a sure-fire recipe for romance on your Hawaiian vacation. The "Navatek 1" is also available for large group private charters and we will be glad to arrange for the best pricing to accommodate your special requirements. | ![]() Navatek I Price Range: (From: $69.00 - To: $205.00) |
North Shore Catamaran - North Shore Catamaran Charters sails out of the quaint North Shore town of Haleiwa. This is the famous coastline you've heard about that has some of the biggest surf in the world at places such as Sunset Beach, Waimea Bay and Pipeline. During the winter months the surf is often enormous and conditions are too radical to allow for snorkeling off the coast. During this season the boat is mostly used to see our visiting humpback whale population and other marine animals. During the summer the coastline is ideal for snorkeling adventures and offers great visibility and fabulous reef-life. Sunset cruises are available all year long as are private charters for groups of 25 or less. This boat is beautiful and is a great choice for an intimate sailing, snorkeling or whale watch experience. | ![]() North Shore Catamaran Price Range: (From: $56.90 - To: $90.90) |
Royal Hawaiian - The Royal Hawaiian Catamaran is a boat that was especially designed to navigate Hawaiian waters by renowned boat builder Rudy Choy. Built for custom cruising on long ocean voyages she rides high over the ocean swells providing a calm and comfortable voyage. Snorkeling, sailing, sunset sails, whale watching and even star-gazing tours are in her repertoire and this is a magnificent boat to choose for your special private charter event. The boat features and amenities are outstanding and the captain and crew will give you the "royal" treatment on this truly "royal" vessel. | ![]() Royal Hawaiian Price Range: (From: $99.90 - To: $131.90) |
Star of Honolulu - http://www.tombarefoot.com/art/category_pages/oahu/dinner_oahu/star_of_honolulu___starlet1.jpg | ![]() Star of Honolulu Price Range: (From: $24.90 - To: $215.39) |
Starlet Dinner Cruises - The "Starlet" the smaller counterpart of the "Star of Honolulu". "STARLET" is a 128 foot, two deck motor vessel for 340 passengers. TRANSPORTATION from your hotel or condo is available. | ![]() Starlet Dinner Cruises Price Range: (From: $42.90 - To: $64.90) |
Tradewind Charters - Now if you really want to go exclusive, here’s your chance. Tradewind Charters offers fantastic private tours for your special occasion on a handful of boats. They do weddings and renewals at sea, bachelor and bachelorette parties, mimosa sunrise cruises, sunset dinner sails, sailing lessons, overnight and Inter-Island Cruises, Honeymooner’s Fireworks Cruise and just about anything you can make up on your own. All cruises are on a private basis so you’re guaranteed to be partying exclusively with your own group of friends and acquaintances. Obviously these cruises are more expensive than most if you are chartering the boat as a couple but you’ll be surprised how reasonable the rates are for such an exclusive service if you bring more friends to the event where the price per person goes way down. | ![]() Tradewind Charters Price Range: (From: $474.90 - To: $564.90) |
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Sunset Sails and Cruises in Oahu - Sailing on Oahu is rarely one of those activities that happens exclusive of itself. Generally sailing is accompanied by snorkeling as well to give you the full benefit of the ocean experience. If sailing is your primary objective however I would recommend taking a trip in the early afternoon when the trade winds are generally blowing the stiffest. We have some gorgeous sailboats on Oahu, many with some incredible amenities providing all your creature comforts and if you can afford the pricing, some of the most beautiful vessels are available on a private basis.





















