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Home > Oahu Shop All Sailing Tours on Oahu

Sailing Charters on OahuAside from the regularly scheduled sails we offer, don't forget that we also private group rates.Sailing Charters on Oahu

Sailing Charters on OahuSailing Charters on Oahu
Sailing CatamaransHawaii Nautical - Sailing Catamarans
Sailing ChartersIsland Magic Catamaran - Sailing Charters
SailingMaitai Catamaran - Sailing
65Makani Catamaran - 65' Sailing Catamaran
40North Shore Catamaran - 40' Sailing Catamaran
54Port Waikiki Cruises - 54' catamaran
52Royal Hawaiian - 52' Catamaran
Private Sailing, Sunrise Sails, Snorkeling Tours and Memorial ServicesTradewind Charters - Private Sailing, Sunrise Sails, Snorkeling Tours and Memorial Services
 Oahu Sails Tours and Charters Watch Videos - Click Here

Oahu Sailing Tours and Sailing Charters

(From: $26.74 - To: $474.90)

Oahu sailing charters can bring a gentle breeze into your Hawaiian vacation or an Oahu sailing trade wind adventure.


Let's get down to sailing basics. Oahu is an island that is surrounded by water and by wind. Sail boats are designed to catch the wind and sail on the water. There are lots of Oahu sailing vessels on all coasts of the island. All this equals a great sailing experience available for you and your family on one of Oahu's many sailing tours, sailing lessons or sailing charters.

As with all the Hawaiian Islands, Oahu is blessed, about 300 days of the year, with the prevailing "trade winds". These winds generally blow from out of the north-east and vary from 5 to perhaps 25 miles per hour which are excellent conditions for Oahu sailing charters. Mornings on Oahu are generally calm or have gentle winds suitable for light sailing but as the day progresses the trade winds usually become stronger and a stiff wind can become a consistent force for Oahu sailing vessels by mid afternoon. In the evenings and at sunset time the winds will usually die down again and return to a gentle breeze. This is probably an over exaggeration of the usual Oahu sailing day but it generally meets the overall daily template as it relates to sailing Oahu's coasts.


Where do Oahu sailing charters sail?

  • Kewalo Basin is by far the most departed from harbor for all Oahu sailing charters. The harbor is located in Honolulu just a stone's throw from Waikiki and most of your Oahu sailing charters will pick you up right from your Waikiki hotel and bring you to the departure point. The oceans off Honolulu and Waikiki are generally somewhat protected from wind by the mountains behind but can provide an excellent sailing experience particularly in the afternoon hours.

  • Oahu's North Shore off the coast line of Haleiwa is also a starting point for Oahu sailing charters and this coastline can often provide an even stiffer wind for your Oahu sailing adventure because of its less protected positioning on the island and can be in a direct line to the prevailing trades as they wrap around the island. Keep in mind however that the winter time can bring with it giant surf on this coastline and can sometimes alter, interrupt or even cancel your Oahu sailing adventure for the day.


Types of Oahu sailing boats

  • Many of the Oahu sailing vessels are catamarans and they vary in size and capacity greatly. Sailboat charter lengths can vary from 35' to 65' and capacities on these sailing catamarans can vary from a maximum of 20 passengers to a maximum of 80 passengers.

  • Charter sailing yachts can be very exclusive, carrying only 6 passengers and have amenities that can rival a penthouse condo.

Your Oahu sailing adventure can take the form of a short and gentle sunset sail off the coast of Waikiki with complementary cocktails and "pupus", it can include sailing with snorkeling off the coastline on a wonderful morning sailing charter or it can include an afternoon trade wind sail, a private sailing lesson or even a private inter-island sail taking you wherever you want to go.

Tom's Tips - Oahu Sailing Charters and Sailing Tours

  • An excellent idea for your Oahu sailing charter would be to bring a hat with a strong chin strap as the tropical heat and strong Oahu winds of an afternoon sail could provide the perfect conditions for a sunburn.

  • Keep one hand on some part of the sailing vessel at all times. Sometimes you'll need both.

  • Want to take the helm of your Oahu sailing charter? Don't be afraid to ask. Many captains will be happy to let you take over.

  • Looking to "really" sail on an Oahu sailing tour? Mid-afternoons are best --- check those out first.

 Oahu Sails Tours and ChartersSailing Tours and Sailing Rides in Oahu - Options Below:
Island Magic Catamaran

The Island Magic 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 25 people and in addition to its snorkel sails and sunset sails is available on a private charter basis as well. This boat is beautifully maintained and is an excellent choice for a sail off the Waikiki coastline.…(more info)
(From: $30.00 - To: $55.00)

Price Range:
(From: $30.00 - To: $55.00)
Maitai Catamaran

The forty-four foot , state of the art, sailing catamaran offered by Maita'i Catamarans provides a relatively inexpensive way to get out on the water, directly from its launch right in Waikiki, and do some sailing along the Waikiki Coastline or even combine sailing with snorkeling while taking in the majestic views on the ocean off Waikiki. The tours offered by Maita'i Catamaran that simply do the sail and sightseeing are about one-and-a-half hours in length and the ones that include snorkeling as well are about two-hours in length. The Maita'i Catamaran is one of the most popular on Waikiki beach and is also one of the most talked about. They can hold as many as forty-seven passengers so you are sure to be making friends on your choice of voyages. These sails and snorkels are suitable for the whole family from the young to the senior citizens and the pricing on these tours makes them affordable. The views alone are worth the price of admission as you will be able to see the entire Waikiki and Honolulu shoreline as well as have great views of Diamond Head Crater.…(more info)
(From: $26.74 - To: $39.90)

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(From: $26.74 - To: $39.90)
Makani Catamaran

The Makani Catamaran is a very special boat to sail on and is one of the newest and most beautiful boats available to you on a sailing charter off the coast of Oahu. The boat was built in St.Croix in the U.S Virgin Islands and was completed in 2005. It also arrived in Hawaii in 2005 and became ready for use in 2006. The Makani Catamaran is sixty-four feet in length and thirty-two feet in width. Capacity for the vessel is about eighty persons. The total sail area of its ample sails are a full 1,764 square feet providing sailing speeds of up to thirty knots. If you've never traveled that fast under sail you're in for a real treat. Should you run out of wind, do not fear, the boat is also equipped with Twin Yanmar 125 hp Turbo Diesel Engines In addition to the basics, the amenities provided on the Makani Catamaran are numerous. She has a thirty-two inch Flat Screen HDTV, a DVD player, a Bose surround sound audio system, for private charters they have a Power Point Presentation Compatible HDTV, two freshwater restrooms, dual bar stations, a semi-enclosed main cabin area, two forward sunbathing nets, duel swim ladders, helm station seating for passengers and open fore and aft decks. The Makani is an impressive boat and it is just perfect for a sail off the coast of Waikiki. Keep in mind however that the Makani can also be used as an inter-island vessel for any private use you may conjure up in your imagination.…(more info)
(From: $64.06 - To: $82.63)

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(From: $64.06 - To: $82.63)
North Shore Catamaran

If you're looking for a very exciting day sailing on the water why not spend a day visiting the North Shore of Oahu in conjunction with doing some sailing on the North Shore Catamaran. The North shore is special in so many ways. The little town of Haleiwa is picturesque and charming. There are great restaurants and beautiful views. A bit further up the coast you will find some of the most beautiful white sand beaches on the island and out at sea you will find the giant surf breaks that have made the North Shore famous all over the world. The names of surf breaks like Sunset Beach, Waimea Bay and Pipeline are probably names you have heard before. After cruising this magnificent coastline you will really enjoy boarding the North Shore Catamaran and going to visit the same coastline, this time from the perspective of being on the ocean. This coastline is a great place for sailing as there is beautiful reef life and fish and the views from the boat of the shoreline are spectacular as well. Keep in mind however that the conditions for sailing are generally better in the summer months as the winter season on the North Shore usually translates into "giant surf" and rough conditions.…(more info)
(From: $55.90 - To: $88.90)

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(From: $55.90 - To: $88.90)
Port Waikiki Cruises

If you would like to get out on the water and go for a sailing trip during your vacation on Oahu then you might want to consider looking at the offerings from Port Waikiki Cruises. There are a variety of different options that leave all throughout the day and evening. If you're staying in the Waikiki area then you will be pleased to find out that these trips all conveniently depart from the Hilton Pier (which is located right on Waikiki Beach). …(more info)
(From: $49.00 - To: $135.00)

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(From: $49.00 - To: $135.00)
Royal Hawaiian

Sailing charters are the strong suit on the sailing charters offered by the Royal Hawaiian Catamaran. Rudy Choy is a famous name in the boat-building business in Hawaii and the Royal Hawaiian is a boat especially designed by Rudy. This boat has been built for custom cruising and is capable of going on long ocean voyages and provide the ultimate in comfort. The Royal Hawaiian Catamaran rides high over the swells of the ocean and a calm and comfortable ride is assured. This boat will depart from Kewalo Basin near Waikiki and keep in mind that the best winds for sailing are generally in the afternoon hours. With only thirty persons on board you will enjoy the personalization that this small group will allow you. You will also enjoy the snacks of meats and cheeses, veggies and fruits that are included on many of the cruises.…(more info)
(From: $174.90 - To: $174.90)

Price Range:
(From: $174.90 - To: $174.90)
Tradewind Charters

Sailing cruises and sailing charters are available for you in Oahu on a private basis on Tradewind Charters. Your party could be as small as just a couple or as large as eighty people and you'll be treated with luxury and privacy on one of Tradewind Charters beautiful sailing yachts. There are a number of yachts available for your use ranging from forty foot sailing yachts to forty-five foot catamarans to sixty-five foot sailing catamarans. The intimate and relaxing ambience of these charters will make your visit to the islands all that more enjoyable. There is no question that taking a sailing cruise or having a sailing charter on a boat that is exclusively for your party, whether it be large of small, is the best way to go. The question always comes up however about the price. People often think that these costs would be prohibitive but in many cases the absolute reverse is actually the case. Tradewind Charters generally has their pricing based upon the number of hours that you would want the boat. The price charged could seem fairly expensive if there is just a few of you in the group but if you have larger amounts of people the pricing will get progressively better as your number of people grows. In many cases the actual price per person can become even lower than the price charged per person on other boats that are not a private. Tradewinds Charters is always worthy of consideration when viewed in this light as it might actually not only be your best choice for comfort, relaxation and overall ambience but it also might be your best choice regarding price as well. Keep in mind that Tradewinds Charters has many varied choices of cruises available including sunset sails, dinner cruises, a delightful Mimosa Sunrise Cruise, a champagne and chocolates cruise, private whale watching cruises, sailing cruises and even sailing lessons, memorial service and ash scattering, snorkel cruises, overnight and inter-island cruises, wedding and vow renewals at sea and even bachelor or bachelorette party cruises.…(more info)
(From: $468.90 - To: $474.90)

Price Range:
(From: $468.90 - To: $474.90)
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Sailing 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.

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