Home > Oahu > Sailing Charters

Hawaii Sailing Charters

Name: Oahu Sailing Charters
Brand: Sailing Charters
Rating: 5.0 (25 reviews)

Oahu offers an abundance of sailing charters.

There are 30 tours in this category with adult prices that range in price from $29.90 to $4500.00 Skip Directly to Tours.

Oahu Sailing Charters

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 lots of water and by wind.
There are multiple Oahu sailing vessels on all coasts of the island..
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.
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.

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.

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

Sailing Charters Sorted by Specific Tour

Sailing Charters Sorted by Company

Recent Reviews

Hilton Waikiki Sunset - Port Waikiki Cruises on Oahu

Great way to spend a couple of hours - boat was nice, staff were friendly and helpful, we even.. Steve Byng

Sunset Cruise - North Shore Catamaran Charters

We had an amazing time!! Thank you for your kindness with my parents and letting my daughter steer! Loved the ride! Pamela Strabala

Reef Fishing Charter - Tradewind Charter

This was the best day of our trip. Captain Paul was fantastic and everything about the tour was.. Lilla Williams

Oahu Island Princess Sunrise Dolphin - Iruka Hawaii Experiences

This tour was fantastic! We absolutely loved it! We saw lots of dolphins and some turtles and other.. Karen Jensen

Rainforest to Reef- Bike, Hike, Sail and Snorkel Half Day - Bike Hawaii

Eland and Dave escorted us girls on a bike tour which was amazing and fun. Very professional and knowledgeable! The snorkeling was a blast! Thank you! Janet Doan

Hilton Turtle Snorkel Sail W/Lunch - Port Waikiki Cruises on Oahu

We had a wonderful experience! Stacy Smith

Sunset Cruise - North Shore Catamaran Charters

Perfect for a cruise. Not to long not to short! Crew was as friendly as could be and gave some cool.. Brian Shore

Sunset Cruise - North Shore Catamaran Charters

Outstanding! Captain Mark was very entertaining and we enjoyed his stories of Hawaii.. The crew was.. Sue Sykes

Snorkel Picnic Sail 4 Hour - North Shore Catamaran Charters

Loved every minute of this great tour. Captain Mark, Liam and Camilla were the perfect crew.. Vanessa Lynne

Snorkel Picnic Sail 4 Hour - North Shore Catamaran Charters

Fantastic trip! Wonderful crew! Would recommend highly! wendy bokota

Hilton Waikiki Sunset - Port Waikiki Cruises on Oahu

The best cruise ever. The crew was fantastic. Will do again. George Mason

Hilton Turtle Snorkel Sail W/Lunch - Port Waikiki Cruises on Oahu

The turtle snorkel sail with lunch was a wonderful experience for the eight of us. While I.. Michael Rothman

Reserve the Noon Snorkel Sail with Holokai Catamaran.

Turtle Canyon Snorkel Sail PM - Holokai Catamaran

It was a great trip. Crew was great helpful and knowledgeable. The only thing I would suggest would be to provide fins. Ann Dankworth

Snorkel Picnic Sail 4 Hour - North Shore Catamaran Charters

Great trip. Captain & crew were fantastic. Snorkeling was ok. No fault of captain. John Hollister

Sail & Snorkel - Tradewind Charter

Excellent charter. Captain Paul was great. Our group ages were from 10 to 98!. Paul handled everything perfectly. Dick Payne

Turtle Canyon Snorkel - Makani Catamaran

It was great. Got to see quite a few turtles. The sailing up around Diamond Head was a blast! Cheri Liddy

Top Activities
Customer Favorite Tours Based on Reviews

Let's face it. Sailing boats go way back in the history of human civilization.

Even here in Hawaii, without the sailboat, the Polynesians would have probably never found Hawaii. Columbus found America, on sailboats. Magellan sailed around the world. Sailboats are a part of our DNA as people, and in Hawaii we have lots and lots of sailboats to enjoy and to participate in.

We've got sailing on all of the islands, and Oahu is no different. Let's pull up a map. On Oahu we've got a lot of different boats that do sailing. There are a relatively small percentage of these boats that actually sail specifically for the purpose of sailing, a cruise that goes out only to sail. Usually the sailing is involved with other activities, like Snorkeling or a Dinner Cruise perhaps, maybe a Whale Watch. Just getting out on the water to do a number of things, and sailing is included if you're on a sailboat. Everybody likes to get the sails up and to enjoy them, enjoy the process of getting them up in the wind and having them billow and fill.

But that's usually just a portion of what we do on the sails that we have here on Oahu. There are some exceptions. There are a few Sunset Sails that go out, maybe 90 minutes, put up the sails and that's kind of the reason for that trip. Mai Tais might also fit into a part of that reason. There may be some boats that go out for a trade winds sail and just to see how fast they can go out in the channels and so on.

But most of the boats that you're going to find are going to include sailing with something else. Which is okay, the something else is good too. So there's a number of locations that we have throughout Oahu that you can catch boats that do sailing. Certainly off the coast of Waikiki and Honolulu. Ko Olina and Waianae are areas that we will also have sailboats. The North Shore, Haleiwa would be another place. Off the coast of Kailua in this area as well. So we're rich in boats that have sailing capacity here in Oahu. Just look through all the choices, see what you like. You might like a catamaran, you might like a mono hull, we've got a number of varieties, and we'll see what we can do.

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.

State Wide Sailing Charters

Sailing in Hawaii whether it be on a Hawaii sailboat charter, a Hawaii boat tour or a Hawaii yacht charter is simply a way of life in the islands. Keep in mind that the very first people to come to these islands came by virtue of a sail boat and so the sailing heritage runs deep in the waters surrounding Hawaii.

More Info / Buy Now

Sailing Charters on Kauai

Kauai sailing, with its sailing boats offering snorkeling trips, snuba adventures, snorkeling from shore, family snorkeling activities and various other tours involving sailing off Kauai are among the most interesting tours that Kauai has to offer.

More Info / Buy Now

Sailing Charters on Maui

The stiff Maui's trade winds provide for great Maui sailing trips. If the notion of Maui sails intrigues you, you've come to the right spot. The Maui sailing climate and prevailing winds provide the best possible sailing environment.

More Info / Buy Now

Sailing Charters on "The Big Island" of Hawaii

Sailing charters on the Big Island of Hawaii generally depart from the Kona side of the island. Because Kona is usually protected from the stiff tradewinds by the enormous volcanoes behind, these sails are often gentle in nature and are a great way to experience the beauty of Hawaii's ocean and sealife.

More Info / Buy Now

Hawaii Sailing Charters

Oahu Sailing Charters

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:

Where do Oahu sailing charters sail?

Sailing Charters Sorted by Specific Tour

Sailing Charters Sorted by Company

Recent Reviews

Hilton Waikiki Sunset - Port Waikiki Cruises on Oahu

Sunset Cruise - North Shore Catamaran Charters

Reef Fishing Charter - Tradewind Charter

Oahu Island Princess Sunrise Dolphin - Iruka Hawaii Experiences

Rainforest to Reef- Bike, Hike, Sail and Snorkel Half Day - Bike Hawaii

Hilton Turtle Snorkel Sail W/Lunch - Port Waikiki Cruises on Oahu

Sunset Cruise - North Shore Catamaran Charters

Sunset Cruise - North Shore Catamaran Charters

Snorkel Picnic Sail 4 Hour - North Shore Catamaran Charters

Snorkel Picnic Sail 4 Hour - North Shore Catamaran Charters

Hilton Waikiki Sunset - Port Waikiki Cruises on Oahu

Hilton Turtle Snorkel Sail W/Lunch - Port Waikiki Cruises on Oahu

Turtle Canyon Snorkel Sail PM - Holokai Catamaran

Snorkel Picnic Sail 4 Hour - North Shore Catamaran Charters

Sail & Snorkel - Tradewind Charter

Turtle Canyon Snorkel - Makani Catamaran

Top Activities Customer Favorite Tours Based on Reviews

Top Activities
Customer Favorite Tours Based on Reviews